someone or something is deleting our work emails

by Alison Green on April 10, 2023

A reader writes:

My coworker, Jane, and I share a common Outlook mailbox and the emails get sorted out to each team member chronologically. Example: first email gets assigned to me, second email gets assigned to Jane, third email gets assigned to me, fourth email gets assigned to Jane. And so on. We can tell who each email is assigned to, as the person sorting adds the appropriate initials to the subject line.

Anyone can do the sorting of the emails, but I find that I do it the majority of the time. And because I do it, I also see follow-up emails that come in — people asking for a status update on email sent in a week or more ago. When these come in, I do a quick search through the mailbox to see if Jane or I have started processing this email and are just waiting on some more information before it’s completed. This does happen sometimes and, in those cases, I reply that the issue is being worked on and what is needed before completion. But more often I have been finding the first email in the deleted folder, having been untouched.

For example, Joe Smith emails on 3/22 asking for the status of a request submitted 3/6. And I find the 3/6 email in the deleted folder, with no replies or forwards and no work having been processed in our systems. And the pattern I am noticing is that all of these emails found in the deleted folder were originally assigned to Jane. I let my manager know when I find these scenarios and then reassign them out as appropriate.

This has been happening for years now, and it happens more frequently in our busy periods. We have had other team members come and leave the department and the only time an email is found in the deleted folder not having been worked on, that email was originally assigned to Jane. We have had team meetings to discuss how this might be happening. My manager suggested once that it’s possibly a system error but IT is unable to tell who or what is deleting these emails. And Jane is just as seemingly baffled as the rest of us.

I have my suspicions that this is not a systems error, because emails seem to disappear a few times a week for a month, we have a team meeting about it, no more emails disappear for three or four months, and then it starts up again. I, of course, have no way to tell if Jane is intentionally deleting emails. Maybe her computer has a serious bug that randomly deletes emails in Outlook. But a lot of red flags are being raised.

I have come to realize that this is somehow not as big of a deal to my manager as I believe it is, so I’m not really expecting anything to change. But it did make me wonder what my options would be if I was the manager.

Could Jane actually face disciplinary action for this if she maintains that she is not intentionally deleting emails and there is no way to determine how these emails are being deleted? How would this even be addressed from an issue of how to make it stop? I can’t imagine she could be put on a PIP if there is the possibility of a systems error, let alone outright fired. What are your thoughts?

Also, does it ever get to be my responsibility to raise this to someone above my manager seeing that it keeps happening?

It seems really unlikely that this is a systems error, given that it’s only happening to emails assigned to Jane, and especially given that it stops for a few months after it’s addressed with you both and then starts up again. (I’m assuming only you and Jane have access to this mailbox.) I would bet money that Jane is deleting emails to avoid having to deal with them.

It’s bizarre that your manager doesn’t seem terribly concerned about this when not only are work requests going ignored (a big problem in itself), but it’s potentially due to the deliberate negligence (and cover-up) of a staff member.

I’m curious who the requests come from. If they’re internal requests from other teams, this has the potential to harm your team’s (and therefore your manager’s) reputation. If they’re coming from the public, maybe she thinks there won’t be real consequences since each sender will think it’s a one-time fluke … whereas if they’re internal, word will start to get around that your team is unreliable.

But I wonder if your manager actually spoke to IT about this or if she told you they can’t resolve it without actually checking with them — because IT should indeed be able to track down some useful data on how items are getting deleted. And they’re unlikely to want people to just accept “oh, we have a bug that randomly deletes emails.” If such a bug existed and they didn’t act, that would reflect badly on them. So my hunch is that she didn’t talk to them, or she did and she’s misrepresenting what they said because she doesn’t want to deal with it.

You asked what your options would be if you were the manager. First, you’d talk to IT, who could probably help you. If for some reason they couldn’t, you could consider ways to build more oversight into the system (for example, more frequent spot-checks, a weekly check of the deleted folder, or a different way of assigning tasks). But there’s also enough here to warrant a manager having straightforward conversation with Jane, pointing out that the deleting stops for a few months every time you address it, it’s only with her emails, and what’s going on? I’d also be looking more closely at Jane’s work generally — is her workload too high? Is she cutting corners in other places? Is she good or bad at follow-through with other tasks? If she’s really deleting emails on the reg to avoid answering them, it’s highly likely that you’d find other problems with her work, and it could make sense to focus there rather than getting sidetracked on having to “prove” this piece of it.

What shouldn’t be an option is just throwing up your hands and saying “oh well,” as your manager seems to have done for years now.

You asked whether Jane could face disciplinary action if there’s no way to prove she’s deleting emails. I remain skeptical that IT can’t help but for the sake of argument, if they couldn’t, you could certainly require her to do things like a regular check of the deleted box to fish out anything that “got deleted on its own.” But also, that’s where the look at the rest of her work comes in — if she’s deleting emails to avoid work, you’re probably going to find other problems.

As for whether it’s your responsibility to raise this to someone who’s not your manager … it depends on the content of the emails and how much your organization would care. If they’re really low-stakes emails (like feedback from the public on something that doesn’t really require a response), it might not rise to that level of escalation. If they’re higher-stakes, I’d look for a way to bring it to someone’s attention, although whether and how to do that will depend on the internal politics there.

Read an update to this letter.

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  1. Hills to Die on*

    I will throw out the possibility that she could be doing it on accident – not likely but still. A lot of people, myself included, make more mistakes when they are in a hurry. My guess is that it’s deliberate though.
    IT should absolutely be able to tell you.
    What about a spreadsheet tracker for these as well to prevent the emails from getting lost? It could be a duplication of effort in tracking and not worth it if your boss isn’t super concerned. However, in G sheets you can see who edited a cell and know for sure that it was Jane or not.

    1. Siege*

      I’ve been known to delete an email by accident for one reason or another. Sometimes another email comes in and my cursor is on the wrong email, sometimes my cat steps on my keyboard, sometimes I’m not paying close attention.

      I have never been known to accidentally selectively delete only emails assigned to me, in a shared inbox, for a period of weeks or months, and then stop when I am aware that others have noticed.

      OP, you used a lot of hedging language in your letter, and it’s good to not leap to accusing someone right away, but Jane is deleting the emails because she is choosing not to deal with them, and not to deal with a larger problem like a workload issue, that takes up her time. If this “bug” is plausible, it would happen to everyone, or else it would happen to her 100% of the time in a way where her initials actually trigger some strange Outlook command, and there would not be gaps where it doesn’t happen. Things don’t not-work like this. And she will continue doing it for as long as your manager prefers to prioritize Jane’s failure to do her job over literally everything else. I hope you follow up on this.

      1. Ellie*

        It’s still possible, she could have her Outlook sorted or filtered to only show emails that were sent to her. OP said she does the initial sorting. She could also have a rule to auto-delete anything with a certain subject or key words and it is that that’s doing the deletion.

        The most suspicious part of it is that it stops for a while when brought to her attention, but even then… she could be going slower or paying more attention while its fresh in her mind.

        Does OP have any access to her deleted items? I’d start periodically checking that folder, then bring it to her attention every time, as soon as it happens. And push for an ‘IT’ solution (the IT solution could be to actually start using a proper ticketing system such as Jira or similar to track tickets properly, instead of relying on email.) The weirdest thing about this is, if it is intentional, that she hasn’t started clearing her deleted items yet.

      2. MCMonkeyBean*

        I agree that OP is coming at it from the right way of technically hedging that it could be somehow a crazy error but still suspecting what is really happening–but my question then is does the boss actually know it is only affecting emails assigned to Jane or do they potentially not realize that aspect because of the hedging language that may be getting used in meetings?

      3. just some guy*

        Deliberate deletion seems like the most likely cause, but there are cases where things do not-work like this. Even when everybody is using the same system to do the same job, they’re not always going to use it identically. If Jane’s using keyboard shortcuts to activate functionality when everybody else uses point-and-click, if Jane’s using a Mac when everybody else is on PC, if Jane has a slightly glitchy mouse that occasionally registers two clicks instead of one, or if Jane just holds the delete key down a little longer than her co-workers – any of those things can cause “nobody else gets that bug” bugs.

        Some of those causes can be sporadic, and can be correlated with other factors – maybe Jane only holds the delete key down long enough to cause problems when she’s tired, maybe she only uses the Mac when she’s working from home and she only works from home when things are busy, yada yada.

        It seems most likely to me that she’s doing it on purpose, but the consequences of making that call incorrectly are drastic, so it’s worth pausing to look at other explanations first.

    2. Butterfly Counter*

      This is what I came here to suggest.

      How many emails have I “Archived” in this past month alone because if I click on an email and move my mouse at all to one side (idk if it’s right or left) the email is “Archived” and a pop-up at the bottom of the screen lets me know what I’ve done, but there have been times I’ve missed that pop-up.

      There are also times, especially when logging into Outlook for the first time in a day that the system lags. I clear out my spam and advertising emails first, using the trash bin icon, and the emails just stay there until the system catches up, then suddenly those emails disappear, the screen jumps, and I’m clicking a trash icon next to an email that was important instead of the spam I was trying to get rid of.

      Therefore, the fact that this happens when things are busy makes it more, not less likely to seem accidental. Some of us get a little to slap happy with that trash bin icon when our inboxes are bursting.

      1. Lavender*

        I’ve accidentally deleted emails too—it happens. But if my job involved answering a lot of emails, and my coworker pointed out that a lot of emails were getting deleted when they weren’t supposed to, *and* the majority of those emails were assigned to me, I’d be taking extra steps to figure out what was going on. Maybe that means checking my trash folder at the end of every workday, or getting rid of keyboard shortcuts so emails have to be manually deleted, or talking to IT about creating a pop-up message that makes it obvious when an email gets deleted. If I did all of that and emails were still disappearing, then I could use that as proof that it was a glitch and not my fault.

        1. Butterfly Counter*

          Oh, I definitely agree, but it doesn’t sound as though the OP or ANYONE has made this Jane’s problem.

          From Jane’s perspective, she has a meeting every couple of months to remind her to be careful about deleting emails, but doesn’t have to deal with following up on the deleted emails (OP takes care of that) and isn’t singled out as the person with the problem as it’s brought up as a team issue. She’s not being told this is happening to her exclusively and specifically and it’s causing more work and problems for her coworker.

          When I accidentally delete or archive an email, I have to solve the problem it creates, which helps curb my quick trigger finger on the delete button.

          1. Lavender*

            My impression from the letter is that Jane knows this is mostly happening to emails assigned to her, although it’s possible I’m misreading. Regardless, I agree that it sounds like Jane isn’t having to deal with the resulting issues so probably doesn’t have much motivation to fix it.

        2. BatManDan*

          It’s not a majority; it’s ALL. From the LW “And the pattern I am noticing is that all of these emails found in the deleted folder were originally assigned to Jane.”

            1. Peppermint Petty*

              A few of things I would try as not-the-manager (I personally would go with #2):
              1) CC Manager on all of Jane’s emails? Iffy at best since Manager doesn’t seem to care, and could cause more issues with Jane.

              2) When someone follows up on the deleted email, send to Jane and Manager with the follow-up and the original deleted email, along with “so strange – another one of Jane’s found in the deleted folder!” (I am petty.)

              3) …Nothing? Not saying it’s right, but since OP handles it, Jane has no consequences and manager doesn’t care. Maybe doing nothing solves both of those?

              1. Lavender*

                At the very least, I feel like the “deleted” emails should be forwarded back to Jane for her to deal with. It’s not fair to anyone involved if OP has to pick up the slack.

        3. Worldwalker*

          Exactly.

          If important emails were landing in my trash because I deleted them, or because a weird bug deleted them, or because space aliens from the planet Xyzzy deleted them, I’d make a habit of checking my email for them daily. It’s like if you know your spam filters have a fixation on the monthly all-staff update from the CEO, you check your spam box for it. You don’t just let it ride.

          1. Lavender*

            Yep. If you’re not receiving emails you’re supposed to receive, that’s an issue you need to solve—or at least figure out where it’s coming from, if the issue turns out not to be on your end. The solution isn’t to just say, “Huh, that’s weird, guess I won’t read those emails.”

        4. WillowSunstar*

          It may depend on where you work, but my job literally says we can never delete any work-related emails. They all have to be put into an archive folder. This is for legal reasons, I guess.

          1. Lavender*

            My last job involved a lot of email correspondence, and I don’t think we had a policy like that. I almost always archived emails instead of deleting them though, on the off-chance I would end up needing them later.

          2. Vio*

            Personally I find this useful to do anyway. If I ever need to refer back to something from ages ago, I still have some email records of it to help my memory. The only time I’d delete work emails is if there’s extremely sensitive information (rare but not unheard of in my role), in which case I’ll forward it to the relevant parties and/or put it on our password protected database/sharepoint then delete the email and empty trash.

      2. cabbagepants*

        Yes, I could see something like this.

        What’s weird is that it keeps happening. Jane should have taken a serious look at her email handling practices and made changes so this stops happening.

        Accidents happen but patterns are avoidable, and it’s a pattern.

        1. Butterfly Counter*

          Yes, but as I state above, it doesn’t seem that JANE knows it’s a pattern she has to address. She just sits in a meeting every couple of months and is told that people need to be careful about deleting emails.

          1. Observer*

            Yes she does. She knows that this only happens to her. And she’s been asked about it, which is why the OP knows that “Jane is just as seemingly baffled as the rest of us.”

            So even in the unlikely event that it’s a real accident, it’s still something Jane knows is happening to her.

            1. Artemesia*

              If she had a manager which apparently she doesn’t, that manager would be reviewing the delete file themselves every week and then would insist if it continues that Jane do this. IT can certainly identify who is deleting these emails; the manager just doesn’t want to deal with it.

              What the LW should not do it fix this for Jane. If she uncovers deleted emails, she needs to forward the info to Jane to fix cced to the non manager not managing this team.

              1. Anonymosity*

                Yes, absolutely. Return the ball to her court but make sure the the bug also bugs the manager. I’m not sure I trust this manager, so it’s also a CYA move for the OP.

            2. Butterfly Counter*

              Why is this a team-wide meeting when the problem is only with Jane. I’m suspicious that they’re softening the message to something like, “Y’all watch out because important emails are in the deleted folder.”

              Jane’s problem needs to become Jane’s problem.

              1. Lavender*

                Yeah, if Jane is claiming that the missing emails are caused by a glitch, then addressing it with the whole team only reinforces that. If she is deleting emails (which seems…very likely), then this isn’t a “this could happen to anyone” scenario.

        2. Venomous Voice*

          Not sure if anyone else has suggested this, or if IT has looked into it, but you should also check to make sure you don’t have a mail rule that is somehow inadvertently picking these up and deleting them. For example, if you get a lot of emails you don’t need to deal with from the ITH team and have set up a mail rule was set up that if it includes the letters ITH anywhere in the subject or body, then it would delete those. However that would also mean that if anybody typed the word “with”, then then those emails would also get deleted.

          1. Just Another Zebra*

            Yeah, if I was to be charitable in this situation, I’d say it’s possible something like this was going on. But I think by this point Jane should have realized something was up and corrected the issue.

            Which, to me, means it’s most likely deliberate.

          2. WillowSunstar*

            Good point, and also take before screen shots to be able to make sure there isn’t a commonality to the emails being deleted.

            1. Lexi Lynn*

              Or set up a rule to copy every email to a folder Jane doesn’t know about. If the email is in that folder and not the inbox then there is a high chance that the emails are being deleted intentionally.

              But if you and Jane keep a clean email box and delete the original when its been worked, Jane may have it set that hover marks email as read do it gets deleted with all the others that have been worked

              1. Observer*

                But if you and Jane keep a clean email box and delete the original when its been worked, Jane may have it set that hover marks email as read do it gets deleted with all the others that have been worked

                Except that the OP says that these emails are untouched.

      3. Katie*

        No. It’s ONLY JANE all the time. She’s doing it on purpose. Sometimes a duck is a duck. And it’s magically fixed when it’s brought up. I’m

        1. elle *sparkle emoji**

          but according to the letter it has been brought up. I’m suspicious that the manager wasn’t clear about the issue, but if they were and the problem has accurately been addressed with Jane the issue should have resolved.

    3. OneTwoThree*

      Using Zapier, you can automatically create new entries/ rows for emails received. I’ve used this function and it was very easy to set up and helpful for tracking.

      1. azvlr*

        Thank you for this suggestion! I think this is something that may help me with a dilemma I have had for a while:
        I submit Help Desk tickets to request updates from other teams. I receive an email when the ticket is created and when the status changes, but I do a lot them. If I don’t remember the details, it takes a while to find the information. Sometimes, I need that item complete before I can check something else off my list, and every once in a while, they get cancelled or forgotten. So I definitely need a way to track them. Currently, I manually add them to a spreadsheet, but I would love to automate this.
        I’m definitely going to explore this product more!

      2. I GOTS TO KNOW!*

        I think Zapier or something like it is absolutely the way to go here. Since it can automatically populate a Google Sheet and assign tasks out, I think even linking the email, it should eliminate the issue. It was also leave a trail of who did what if any rows mysteriously start disappearing.

    4. Observer*

      I will throw out the possibility that she could be doing it on accident – not likely but still.

      SOOO unlikely that I’m not sure that it’s worth even dealing with. Beyond that, I don’t think it matters at this point. This is not one or two emails per year. This is a consistent and noticeable problem, and the issue is not minor. Either her workload is really out of line, in which case her boss needs to fix that, or she’s just sloppy. Even when you are in a hurry when you are on notice, as Jane is, that this is a regular issue, you take steps to counter it.

    5. Observer*

      IT should absolutely be able to tell you.

      On a separate note, no this is not likely. IT should be able to give you some information about when, where and who. But not about WHY.

      1. Artemesia*

        They should be able to tell the manager WHO is deleting those emails. That is the operational information. the manager is just a crappy manager.

        1. Wintermute*

          they may or may not be able to, leaning towards probably not able to, actually.

          A shared mail account will have everything in it done by “shared@workplace” it doesn’t know “this instance of the shared box is owned by Jane, that one on that other PC is owned by Sara”

            1. Wintermute*

              not usually as far as I know. I’ve been down this rabbit hole with someone that was creating rules that were having unintended consequences. The TL:DR of what Microsoft support told me is that it’s just not possible to link actions to a specific user unless you want to get really, really deep in the weeds and turn on forensic logging normally associated with highly regulated industries or highly confidential information (e.g. biglaw firms probably have those settings enabled, or defense contractors) or have Microsoft support do it (if they can and will, and at no small expense), and even then it’s likely you’ll just be told when it happened.

              For moving emails it’s even less logged because outlook doesn’t really “move” them anywhere it just uses a tags system.

              If you have on-premises Exchange servers you might have more options but those are considered a legacy product and most companies except the very largest are going to be on Office.com (formerly Office 365) in which case you have even less information.

          2. Jack of Shadows*

            it takes enabling extra logging above and beyond typical, but IT can absolutely tell you who actually deleted the email, actions in shared mailboxes are done by the people who have access, not the shared mailbox itself, which typically isn’t a ‘real’ login – assuming it’s set up per best practices anyway.

            1. Wintermute*

              that’s fair, what I meant was that they would not be able to look into the past because it’s unlikely they have that kind of logging enabled.

              And frankly, unless you have some kind of special pull, most IT people I know wouldn’t do that and their managers would back them on that.

              Jane’s deleting emails to avoid work, simple answer, there’s no good business case for spending hours enabling logging and debug messages, asking the server team to allocate more drive space to fill with logs, configuring drive space alerts in Solarwinds for the ops center so those new logs don’t fill up the disk and crash your email system, creating runbooks for those new alerts for the ops technicians grepping through gigs worth of logs and so on when the answer is SO OBVIOUS.

    6. LR*

      I wouldn’t find this super surprising. Sometimes when Office is being super laggy (which is at least one day a month), I often wind up accidentally deleting a few emails when I only mean to delete one. If I was being publicly called out I’d prob be more careful for a few weeks. The fact that it’s then happening again and again is also an issue but I would assume malice vs stubborn refusal to get better at using outlook.

    7. Lulu*

      My Outlook periodically has a glitch where if I delete 1 email, the adjacent email will also be deleted. I usually notice when I can’t find an email I read and then left to respond later. At which point, I’ll discover several other accidental deletions for that or a few previous days. After a week or two, the problem go’s away for awhile only to pop up again. I’ve been blaming our excessive security protocols for lack of any other Google-able cause. It could be user-error, though I’d think it would be less clustered if that’s the case. Anyway, from my experience I would totally believe system error. But, that doesn’t mean Jane shouldn’t be proactive I creating a regular trash checking process since it’s clearly a problem linked to her, one way or the other.

    8. JSPA*

      Yeah, some sort of two step verification for the deletion might help–the recipient has to first check off a read-receipt box, or re-initial, before they can delete.

      That will help in terms of deniability. It’ll also help if when she’s rushing, her finger hits delete on two messages instead of just the one she intends to delete. They can’t both just go poof with a single keystroke.

      It might also be worth checking if there’s a pattern of whom the messages are from, or the specific topic, of the ones she manages to skip, if you have regular clients. Maybe there’s a task she’s undertrained on, or someone she’s ducking, or an entire company or group of people she’s ducking. And the outcome could be very different, depending.

    9. ZugTheMegasaurus*

      Yeah, I’ve definitely had some bizarre email errors. I’ve had ghost messages where I’m certain I read something, but later it’s inexplicably missing from my inbox, trash, or archives, never to be seen again. I once sent an email at the exact moment another one was coming in, and I still do not understand to this day how this happened, the highly-sensitive confidential document attached to the incoming email somehow attached itself to the outgoing one, sending it to a dozen external addresses who weren’t authorized to see it.

      But those things are really hard to re-create. I have to agree that it’s not super likely that Jane is somehow managing to do it by accident over and over and over, and if she was, it seems like she would say something (like “I have a weird glitch deleting emails”) rather than just allowing it to make her look bad.

    10. Katie*

      It’s a 100 percent Jane. Intentional or not. Jane should be assigned the responsibility of checking deleted emails EVERY DAY.

    12. Dragon_Dreamer*

      There’s also the remote possibility that the boss is doing it, and/or covering for Jane. I’d open a ticket with IT myself, expressing concern that this could start happening to MY emails. That would be a way to find out if the boss even told IT it’s been going on.

  2. Pool Noodle Barnacle Pen0s*

    Maybe your manager isn’t concerned because there hasn’t been any demonstrable negative impact on workflow or customers, due to you going in and following up/fixing it. You should stop doing that for a while and let something bigger fail. I bet your manager will be more motivated to take a harder look.

      1. The Rafters*

        Exactly. I had to do this for a while and called the person out on it several times. I also notified my supervisor each time. Nothing changed, but at least they all stayed off of my back.

    2. Peanut Hamper*

      Yes, this. If it isn’t your responsibility, then it shouldn’t be your problem. Make it the problem of the person who is supposed to be managing all of this.

    3. Sylvan*

      +1

      Or, if you get follow-up emails related to things Jane deleted, don’t handle them yourself. Send them to Jane.

      Stop letting Jane’s problem become your problem to the extent that you can.

      1. Just Another Zebra*

        I agree with this. Send it with the original “Jane, this was assigned to you on 3/6. Please follow up with the customer.” CC your boss. Do it enough and maybe the pattern will become (more) apparent.

        1. Jessica Fletcher*

          Exactly, this is the obvious solution. When OP says she finds the deleted email and reassigns it out…does it go to someone other than Jane, so Jane avoids having to do the work?

    4. Not Tom, Just Petty*

      This.
      I copied this, “It’s bizarre that your manager doesn’t seem terribly concerned about this,” from Alison’s answer to comment, that it’s not bizarre. It’s simple. OP is cleaning up the mess. Manager doesn’t care, because OP is making it her own problem.
      When you check your own emails and discover you never had one to begin with, don’t go digging through deleted. You know what happened.
      Forward the message to Jane. Let her dig through deleted to find it and confirm if it is hers or not. If she has a problem and loops in manager, explain that with the history of technical problems Jane has while using the SHARED PROGRAM, you are going to err on the side of technical difficulties and let Jane handle it.
      After all, wouldn’t it be better for Jane to have a tangible event to share with IT to show the issue.
      Stop doing Jane’s and manager’s job.

      1. me just me . . .*

        This!! Just forward to Jane — along the lines “this must be yours because I don’t know anything about it” and let her handle it. Don’t redistribute it as if it’s the first time being triaged. It’s already been assigned to Jane and so Jane needs to follow up. And then let things fall as they may. I bet that once Jane knows that she’s going to have to handle all the work assigned to her, she’ll quit deleting these emails.

      2. danmei kid*

        YES this, stop covering for the issues, and let the people responsible either take it up or fail and suffer the consequences.

    5. AnonInCanada*

      Exactly this. This isn’t OP’s battle. Let Jane deal with the repercussions of her actions (or apparent lack thereof shove-them-under-the-carpet-and-hope-no-one-notices way.) She should’ve done a better job permanently deleting those emails.

      But now that the cat’s out of the bag, just keep copies of the forwards to Jane as proof you did originally forwarded them, and let the proverbial chips fall where they may.

    6. goddessoftransitory*

      This, 100%. You are unfortunately the plank over the Missing Jane Stair, and the manager probably thinks along the lines of “well, they end up getting dealt with, so I don’t have to worry.”

      One thing I’ve noted in my time reading AAM; a failing of shaky or bad managers tends to be allowing that one reliable team member to “just handle” XYZ and letting that to stand in for actually managing. And the longer it goes on, the harder it is for them to go y’know, this really isn’t cool, because it’s BEEN cool for such a long period of time.

      So just–stop doing the part of your job that isn’t your job.

      1. RVA Cat*

        So many of us were that student who did all the work on the group project because we couldn’t stand to get a bad grade, and it is so hard to train ourselves out of that mentality.

  3. Alton Brown's Evil Twin*

    OP, this shouldn’t be a mystery. Sherlock Holmes, Columbo, and the entire cast of every iteration of Law & Order is looking at this and saying “Well of course Jane deleted them.” Whether that’s out of incompetence or work-shirking is yet to be determined.

    The fact that you are trying to find other reasons why this is happening, no matter how outlandish, is an indication that the poor work habits of Jane and your manager are starting to affect your sense of norms, too.

    1. Czhorat*

      Wanting to look for an alternate explanation than “my coworker is lying” is a positive thing.

      1. Siege*

        After a problem has persisted for years, it really isn’t. At that point you’re being willfully credulous.

          1. Siege*

            Agree – in my comment on the first reply, I commented on that, and I think it’s appropriate to a point. I also think that it’s okay to follow up on possible options, give serious time and consideration to them, and eventually conclude your coworker is the issue if that’s where the evidence leads. If it’s been happening for long enough that a multiple-incident 4-to-5 month pattern is visible, it’s okay to stop looking for zebras because you can see the horses.

            1. JustaTech*

              Yes to this: follow the data and see where it leads.
              Goodness knows my work email system has done enough really weird stuff like bouncing all emails from France, or deleting emails out of the boss’s inbox (which no one believed until several people watched it happen).

              But computer systems rarely get better after the humans who don’t control those systems have a meeting. So you’ve got to follow that data as well.

          2. Yorick*

            She probably also knows that if she doesn’t, commenters are going to speculate that the coworker isn’t doing it

    2. Destra N.*

      I’m thinking of this in terms of “if the system currently isn’t working for us, how do we work around that to not miss emails using the system as it is until a permanent fix is in place?”

      My solution here is to ask Jane to start checking the deleted emails folder for anything that was missed be part of her daily workflow. That should be a formal request from her manager.

      I’m betting that one of two things happens:
      1) Emails magically stop disappearing, or
      2) Jane is held accountable when email requests that she is supposed to be checking for are still not being addressed.

      1. Tangochocolate42*

        I think if Jane is given the responsibility of checking the deleted items folder, the emails in there are going to get permanently deleted so that they don’t show there either.

    3. I'm Just Here for the Cats!!*

      There could be one alternative. Is there someone else who somehow still has access to the email, who may have a grudge against Jane. Like did Sally used to do those emails but she was removed and the task went to Jane, but no one removed Sally’s access or changed the password so she can still get in and mess things up. I know is a leap but it could be a reason.

  4. negligent apparitions*

    Was really hoping the “something” was going to allude to a mischievous spirit. Spooooooookyyyyyyyyy

    3. Wintermute*

      to be fair, sendmail for unix systems is basically as close as you get to real black magic.

  5. NeutralJanet*

    I’m guessing that the paragraph, “ It seems really unlikely that this is a systems error, given that it’s only happening to emails assigned to Jane, and especially given that it stops for a few months after it’s addressed with you both and then starts up again. (I’m assuming only you and Jane have access to this mailbox.) I would bet money that Jane is deleting emails to avoid having to deal with them.” is meant to be the beginning of Alison’s answer and not the end of OP’s question?

    In any case, whether it’s some bizarre IT issue or not, y’all need to figure out a way to work around this. If Jane is deleting emails on purpose (which she almost certainly is), then maybe putting in a policy that means she has to do MORE work will make her stop? Or possibly make it even more clear that she’s the problem, which is good in its own way, I suppose.

    1. Not Tom, Just Petty*

      I think that any “strays” that come in should be sent to Jane to research. OP has done enough. It won’t be unfair to say that the onus for the extra work should go to the person causing it. If Jane is deleting them, well, deal with the fallout. If Jane’s computer is deleting them, then IT can have examples straight from her, dates, times, senders…
      OP, step back. Stop making this your problem to fix.

  6. Lea*

    I guess I wonder why care more then your boss? If you’ve raised the issue, there’s been multiple meetings on it and no traction – why keep trying to escalate? Just ignore and mind your business would be my advice. Getting this caught up in a job is usually not worth it. Also, don’t mean this harshly- just in terms of self preservation.

    1. Loulou*

      But it makes OP’s work more difficult because now she has to deal with the people whose emails were originally deleted by Jane — some of whom are likely now disgruntled.

      1. cabbagepants*

        nah, Jane doesn’t have to deal with it. She e could just forward the follow up emails to the manager and be done.

      2. Iconic Bloomingdale*

        If this occurs, then OP should refer the disgruntled customers to the manager to deal with.

        When this happens too many times, the manager will finally decide to take action to remedy the issue.

        In my experience, I have found that management is more likely to act on a work problem when it directly inconveniences or negatively impacts them.

        1. Michelle Smith*

          Exactly this. Make it the manager’s problem.

          If I were in this situation, I would also email IT myself, copying Jane and Manager, and explain the situation in a way that does not hint at or accuse Jane at all. Something like “Hi IT Professional, I believe this issue has been raised with you before, but we are still having persistent problems with emails from the shared inbox being deleted. Can you please look into this again to see if we can figure out why it might be happening? Appreciate anything you can do.” And then see what happens.

      3. jomny*

        Agreed, and if Jane is this purposeful about shirking her work she may be that purposeful about shifting the blame to OP in some way.

        OP, something similar happened at my workplace. I couldn’t get my boss to care about even though we work in a field that sounds like it has higher risk/liability than yours. When I realized I cared more about fundamental things than the higher ups did, it no longer felt like a safe work environment and I knew I had to find an exit strategy. It might be worth reflecting on whether this is the kind of workplace you want to continue in, and whether this thing with Jane may point to larger problems you or others have been conveniently ignoring. Best of luck to you!

      4. Samwise*

        No she doesn’t. Forward them right on to Jane. Make a little template: Jane, not one of mine so it must be yours. Looks like that weird IT problem!

        And cc the boss.

    2. Code Monkey, the SQL*

      We are currently having an issue with one of our opposite team members who doesn’t seem to know what to do with any task that doesn’t exactly fall within his narrow conception of First A, then B, then C, then close.

      My manager has been made aware of the issue, but she wants us to document every time we need to do extra work, so that when she speaks with his manager, she can speak to exactly how much time we are spending saying: “Yes, I know B didn’t work, there’s an A2 step, it’s in the document. Please try again. Yes, you did A and B, but your instructions also say to do Q before you move on to C.” Meetings are one thing, but documenting time spent fixing is integral to getting managers to invest in solving the problem.

    3. delazeur*

      I would add to this that no competent manager will every tell you: “yes, this is a problem and your coworker is being terminated on Friday afternoon. [Please keep this to yourself.]”

      Something could be in the works, for all LW knows. I’ve had frustrating coworkers who seemed to be getting away with incompetence for years before management suddenly dropped the axe. Of course, it was sudden to me but the process had been working for a long time.

  7. EBStarr*

    Even with a great team this system of “assign emails by hand by entering initials to the subject line” seems both laborious and unreliable. If I were the manager I’d start by improving the system, maybe creating actual tickets from each email in a task management system like Jira. I’m sure there are ways to automate the assigning of work, etc., and as a bonus it becomes a lot easier to audit what work is getting done (or ignored) by whom. But it would probably also make the whole team’s life easier.

    1. Siege*

      They assumes that you are a manager who cares that Jane has chosen not to do part of her job, which this manager isn’t. I mean, I agree, but the manager isn’t interested in solving the terribly complicated case of Jane Is Deleting Her Emails Full Stop.

      1. ecnaseener*

        Yeah, manager clearly does not care about these balls being dropped. My work has a shared inbox and we don’t have any fancy tools, but we at least have the person triaging emails respond with “I’m copying in Jane who will assist you” so if Jane never answers the person can follow up with her.

    2. Professional Button Pusher*

      Agree, this sounds like a truly awful system. In my office, we use Front (https://front.com) connected to a shared inbox as a lightweight alternative to a full-fledged ticketing system. It works great for automatically assigning emails and tracking response status (and I’m sure there are other similar products out there that could help).

    3. KToo*

      This is what I was going to say. Although even a ticketing based system wouldn’t be able to divide the work 50/50 as the OP is saying it has been, since whoever is quickest will close more tickets faster and therefore end up taking on more work. But it also sounds like OP is already taking on more work by being the person who primarily sorts the emails, and if they’re really doing more that also needs to be acknowledged.

    4. Erin*

      100%, that would be my first act as manager in this situation. Get a tool like Jira and get rid of this home grown email system. It’d make seeing status and history of every ticket 100x easier.

      1. Observer*

        Do you think that the manager WANTS to see this?

        Let’s face it, they are ignoring some pretty strong evidence. Why would they want to do something that might force them to act?

      2. goddessoftransitory*

        Agreed. Right now this is like a mom and pop operation that won’t admit it’s outgrown checking inventory with a clipboard and having Billy Smith come by after school to make deliveries. It’s time to integrate some modern and trackable sorting/assigning systems.

    5. TechWorker*

      Kanban is another option, some of my team use that to track emails/tasks coming into a shared inbox.

    6. AnonForThis*

      My reaction to this “system” was WUT. I understand that humans can get used to lots of strange and awkward things, but this probably shouldn’t be one of them. What reactions do you get when you introduce the “system” to new team members? Given my terrible poker face, I wouldn’t be able to hide my horror.

    7. Observer*

      Even with a great team this system of “assign emails by hand by entering initials to the subject line” seems both laborious and unreliable.

      Agreed. The system makes me cringe SO hard.

      On the other hand, I don’t think that it’s really going to make a difference to THIS problem. Because the manager does NOT care. Even in a great ticketing system there are ways to make tickets “disappear”. And if the system is not set up WELL, with a good audit trail AND the manager actually CARES to deal with it, tickets are still going to disappear.

    8. Pangolin*

      We had something very similar happen recently at the nonprofit where I work – emails in a shared inbox were ending up in the deleted folder (and there’s evidence some emails were removed from that too). It was starting to cause reputational damage and material harm to our clients. it also transpired the emails thing was the tip of the iceberg. Turned out one team member had a second fulltime job and was deleting things to cover up that they simply hadn’t been doing any of their nonprofit job. They got dismissed.

      That was just a related anecdote, not speculation on what’s going on here, but it seems unlikely as Alison said that there are no other issues with Jane’s work. Also emails being assigned turn about seems a lot – having people responsible for the inbox on a day to day rota or similar might take some of the work out of the system and improve accountability.

    9. Hannah Lee*

      EBStarr, I agree. This “shared email inbox” where things are accessed, managed, updated manually by multiple people within the one email inbox pool of messages just seems like a problem waiting to happen even if everyone is pulling their weight and working on good faith.

      As folks have mentioned, there are easily opportunities to accidentally lose items through keystroke or mouseclick errors, system lags, mail processing rules with unintended consequences that could cause problems.

      Then add in the layer of no systemic visibility to the volume of requests, how they are assigned, how they are resolved, the volume of cases each person is handling, resolving successfully, has to escalate, if/when they’ve fallen through the cracks, etc etc. and you’ve got a really bad system with no opportunity to streamline, manage, learn from. (for starters, are there common categories of requests a simple MECE analysis could find – maybe a good % of these “issues” are things that could be headed off with improved pipeline filters, better training, clearer system prompts, an FAQ page or plugging a hole in some other process)

      There are likely a gajillion ticket/case management applications available out there in the world, off the shelf, easily implementable for the kind of workflow it sounds like this company is trying to patch together via email, inbox management and manual editing. And it’s highly likely that those have out of the box capability to see what’s happening with individual tickets.

      And if they’re aren’t any that are what this manager, company wants, there are likely ways to organize the tools they have today to streamline and possibly automate the majority of the “ticket” assignment in such a way as to have visibility into who cases were assigned to and where they stand.

      But for any of that to be an option, the manager and company would need to care about having visibility to the volume, nature of, resolution of whatever these issue emails involve and that “emails go missing, possibly randomly, possibly not” is an actual problem that needs to be solved. Because if not, there is going to be no interest in expending any time, money, effort to change things. And LW should just accept that and go from there.

      For the LW, I’d advise trying to take One Giant Step back from the minutia of The Mystery of the Deleted Emails and consider what the actual business purpose is of this entire process.

      One way to think about it is to imagine that whole process just disappeared – If this email inbox ceased to exist today, right this second; if any prior emails, their subject lines, just went POOF!, if no one was there to look at these emails and act on them –
      Big picture:
      – what would happen?
      – who would care?
      – what downstream processes would fall apart (not just “we couldn’t print the weekly internal TPS reports anymore” but “we couldn’t pay our employees on time” or “the order processing, fulfillment processes would break or be slowed down from 7 day delivery to 2 month delivery”)
      – how would it impact the company’s ability to function, compete, stay profitable (or fulfill its mission if a non-profit)
      – how would it impact customers’ or other stakeholders’ ability to do what they do well, are looking for this company to help them do?

      If the answer to any/all of that is hmm, not much or stops at stuff like “no more TPS reports” or “no one can tell that LW does more than Jane, or that their department is too busy/not busy enough” LW should just let it go. yes even if it’s annoying and means that things fall through the cracks.

      But if there are bigger impacts, LW could pick 1-2 big impacts, summarize them and talk with manager about them. Not focused solely on the missing emails, but more generally about how a manual, proven to be error-prone process that provides no systematic visibility to case volume, status, resolution or unactioned issues isn’t the right choice for a business critical process and whether that should/could be addressed and how. How manager or if needed skip-manager responds to THAT conversation will give LW an idea of whether this is a job they want to stay in.

      1. Hannah Lee*

        Ah, yeah, seeing the length of that post, I’d be willing to bet money that I, and pretty much any person commenting here, have already spent more time and effort thinking about this than LW’s manager.

    10. Chutney Jitney*

      Hahaha! I like this idea that a manager can just tell their company to buy and implement new software. I used to share a team Outlook inbox with 5 coworkers and we color coded them to know who was following up. We couldn’t get an update to software that was no longer being supported by the developer (for over 5 years), we certainly weren’t going to get a “nice to have” like Evernote or whatever.

      1. EBStarr*

        Lol, good point, but they could at least use a spreadsheet! Anyone with Outlook presumably has Excel, no?

        1. Observer*

          Or even separate email boxes with access to a group box where these customer emails come. Gives a LOT more visibility.

  8. Peanut Hamper*

    My coworker, Jane, and I share a common Outlook mailbox

    Well, there’s your problem right there.

    You really do need a ticketing system that can handle these sorts of requests (and auto-assign them as necessary), and will also keep a log of who moves what where and when they move it. If work isn’t getting done because you’re using Outlook for something it’s not really designed to do, that is a serious issue. (And the fact that the manager isn’t concerned? Oh, my.)

    1. Tracker*

      This. You need a real ticketing system.

      You can still accept requests by e-mail and it will look roughly the same for customers.

      1. ferrina*

        Exactly. You need a ticketing system. That will also add a layer of accountability- you need to be able to show who the ticket was assigned to, and give the follow ups to that person (Jane might do more when you say “oh, that was assigned to Jane. She’ll follow up with that).

        Ideally, a ticketing system would also include difficulty degree, time, or effort. It’s possible that by pure happenstance, Jane gets the harder requests (or possibly assigning easier ones to herself). You should be able to reassign work based on availability so no one person is getting overloaded with work, and have that easily on the record.

    3. Lacey*

      Yeah, I’m sure they don’t want to pay for a ticketing system, but it would be a better method.

      Though, Jane could still just click “closed” on tasks she doesn’t want to deal with and say. “Weird! I don’t know how that happened!” And it sounds like that wouldn’t raise a single red flag for your boss.

      2. lilyp*

        But any real ticketing system would have some sort of audit log of actions on each ticket (in jira at least that log is also public) which would clearly show that Jane had done that.

        1. Lacey*

          If mine has it, I don’t know about it, but I guess I’ve never needed to. I know on a lot of applications you can see which user did any given action, so I wouldn’t be surprised.

          A friend of mine had a coworker change the due date for a project on their shared calendar so that he wouldn’t be late with his deliverables. He insisted he hadn’t done it… until she brought up the activity log and clearly he had done it the night before.

    4. Siege*

      A real ticketing system isn’t going to magically solve this problem when the actual problem is the person who is choosing not to do their job. I worked as the manager of a maintenance ticketing system at a retirement community in one of my jobs; it was amazing how many tickets the guy who was reported as sleeping in the laundry room of a building on more than one occasion could clear. (Before anyone asks, the only thing I managed was the ticketing system. I was the department receptionist, in my second job, and had exactly zero personnel authority.)

      1. Peanut Hamper*

        Nobody’s going to claim that its magic, but it will add a layer of accountability and tracking that is not there currently.

        1. Observer*

          I doubt it’s going to matter. The reality is that there is currently a clear pattern – there is really no credible way to claim that this is a “glitch”. There are only two possibilities here – Jane is doing this (whether accidentally or deliberately) or someone else is doing this deliberately. The manager doesn’t care. They still won’t care if there is a better log.

    6. CanRelate*

      I was also coming in to say this, ticketing systems were built for this purpose and many of them are cheap if just to or three people are in it.

      This sort of accountability is too essential to jobs that handle outward communication to leave it to a system that you cant check basic logs.

      1. Observer*

        This sort of accountability is too essential to jobs that handle outward communication to leave it to a system that you cant check basic logs.

        True. But the fundamental problem is that that kind of accountability starts with people who CARE about accountability. All the tools in the world won’t help if the people using those tools can’t be bothered.

        The bottom line, in my opinion, is that this system is a SYMPTOM, *not* a cause of a deeper problem.

        1. CanRelate*

          I agree with you, for sure.

          In this case it seems like there is someone who cares (The OP) but they are in a system that buries the ability to dig into this behind a team that doesn’t (IT). Something like Fresh Desk or Intercom makes that accountability super forward, making it a little easier to put in the hands of users who are looking to follow up on these things.

          I can guess at how deep the problem runs, but its speculation based on the information given. A help desk solution could aid solving the problem at hand if it can be implemented, at the very least.

    7. Dust Bunny*

      Seriously.

      This alone is ridiculous and raises for me some big questions about how your workplace operates. An actual ticketing system won’t necessarily solve it but it should make it easier to figure out what’s going on because fewer people will have their fingers in the same pie.

      (I’m betting Jane is deleting them, although I guess it’s sort of possible that someone else is deleting them to sabotage her.)

      1. Observer*

        This alone is ridiculous and raises for me some big questions about how your workplace operates

        I agree. This is not a system that has ever made sense, and it’s even less sensible today. The fact that the evidence of a problem – ie work emails that are getting deleted when they shouldn’t has not caused anyone to move to a better system speaks volumes.

    8. candyhearts*

      Maybe the emails are coming from outside the business and sent to a single email as a point of contact, examples would be accounts receivable/order entry etc. where a ticking system would not be put into place

      1. A million cats walking across a million keyboards*

        Most ticketing systems have email interfaces (e.g., email sent to grooming-help@llamainternational.com would be entered into the llama grooming ticketing system, assigned a ticket number, and auto-replied to; the auto-reply would include the ticket number in the subject line, and all subsequent replies to it would be attached to the original ticket).

    9. goddessoftransitory*

      It might be time to suggest a meeting with the Grandboss or whoever is her manager’s manager and look into revamping how these things are handled in general, especially since everybody seems so keen on avoiding saying Jane, quit deleting the emails already.

      Framing it as “more efficient and up to date so our workload is better handled by all of us! (JANE)” could help solve at least part of the problem. (And if it means Jane can’t keep plausibly denying her share of the workload, good.)

    10. A person*

      We have an admin group that has a shared mailbox like this (with the intent that if the person that would normally assist us out, others can). But the assignment of tasks isn’t random. The emails follow a subject line and they each grab their set of subject lines on their own. I don’t know all the inner workings of it, but they seem to have it under control 98% of the time. It’s pretty rare that an email in that group gets dropped (it happens occasionally but for the volume of emails they deal with it’s not bad). It does seem like a system of manually assigning emails at random might not work well.

  9. DisneyChannelThis*

    In terms of what *you* can do , you can check the deleted items folder regularly as part of your inbox check. You can also propose a different system, like automatically forwarding emails into a ticketing system or other tracker. There’s also parsers to move emails from outlook into excel automatically and similar things.

    If your boss doesn’t care that Jane is accidentally or deliberately deleting emails then you can’t really do anything as Jane’s peer.

    1. EPLawyer*

      What she can do is if these when these requests come in and they are for things assigned to Jane, just forward them to Jane. Full stop. Not her problem to solve. Unless she has the authority to manage Jane — which she does not — taking on more responsibility to fix the Jane problem is not the solution. Right now the manager doesn’t care because OP is solving the problem and the work is getting done, even if not timely. The only way to make this a problem for the MANAGER who will act is for OP to stop covering for Jane.

      OP, someone said this a week or so ago here (I can’t remember who) that was brilliant — you do NOT need to prove beyond a reasonable doubt that someone did something. This is not a court of law, this is an office. If Jane is suspected of deleting the emails, you can do more (if you are a manager) than just say oh darn Jane says its not her and I can’t prove it so nothing can be done. You can address it with Jane and expect improvement in this area. You don’t need to walk in with reams of evidence to do this.

    2. Snow Globe*

      My first thought was that I’d be reviewing the deleted items folder regularly, then forwarding any emails I find back to Jane. But I suspect at that point, Jane would just delete the emails from the deleted items folder. (I’m actually surprised that she hasn’t figured that out already.)

      1. H*

        That’s what is puzzling to me. If Jane is purposefully doing this, why hasn’t she removed emails from the deleted folder as well?

  10. Llama Llama*

    FWIW, my company has gone away from using emails for requests. When we can, we require people to log a ticket so everything can be tracked. when emails are sent, it creates a ticket. It’s not perfect, but it does prevent things from disappearing and you know if a request has been actioned.

  11. Lilo*

    I have worked on a shared inbox and I’m questioning this system because of the accountability issues. When I’ve had inbox duty we assign a specific person to the mailbox for a specific time period. While the responses come from the mailbox address the person who answered the question also signs the email so they can be contacted for follow up.

    I think alternating here is pretty confusing and easy to mess up. Is it possible to alternate days instead? What about creating a spreadsheet where incoming work is logged and assigned?

    1. Baby Yoda*

      We used to alternate grabbing incoming email requests, but found it’s better to set up rules in Outlook so certain emails are directed to certain team members. Then it would be obvious if emails going into her folder are ignored.

    2. doreen*

      When I’ve worked with shared mailboxes, there was one person who actually checked the mailbox most of the time. The reason it was shared was so that other people had access when that person was not available – before we had shared mailboxes, emails sent to individual mailboxes might not be read for weeks if someone unexpectedly went out sick. And we had the person responding signed the email as well.

    3. It is what it is*

      I worked a job where two of us worked a shared mailbox. The company was not interested in any program that assigned incoming emails.

      My coworker and I set up a schedule, we rotated weekly, where one person was in charge of the shared mailbox in the morning and the other in the afternoon. The one who was not in charge of the shared box was in charge of the phones.

      When you worked the shared box you distributed the new email requests between the two of you to work. If an email came in about something already handled (usually a follow up question) it was assigned to the person who worked the original request.

      Every Monday morning an email went out to the boss and others in our department who was working the shared box mornings and who had afternoons.

      Not a perfect system but we worked with what we had.

  12. Essess*

    Has anyone looked at Jane’s Outlook settings to see if she has some ‘rule’ on her mailbox that deletes emails based on a keyword that she created for another purpose and these emails are getting filtered out because of it?

    2. Janet Pinkerton*

      Yup, this is my guess! If the organization is so tech-averse that they’re using a shared mailbox for work assignments in this manner, it wouldn’t surprise me if this sort of problem has gone undiscovered.

    3. Sylvan*

      I was thinking about that, because of how I manage my personal, non-work email inbox.

      But this makes me think Jane is deleting things manually:

      I have my suspicions that this is not a systems error, because emails seem to disappear a few times a week for a month, we have a team meeting about it, no more emails disappear for three or four months, and then it starts up again.

      If she were toggling a setting on and off, and turning it off solved the problem, she would just leave it off, right? But if she were doing something manually, she might return to old habits after a few months.

      1. Siege*

        Plus, I’m not an expert on shared boxes but since the email is being manually sorted that suggests that any rule would apply to all emails. If the receiving email is info@companyX, there’s no way to set the rule that wouldn’t hit all of them equally. You could theoretically set the rule to apply once the initials were applied but then I think OP would be able to watch the emails disappear when they were sorted, and it would affect them consistently.

        1. Essess*

          You are correct. I forgot the original email would have been in the same inbox and wouldn’t have been seen to assign initials if it was a rule firing. Nope, back to manual user deletion scenario.

    4. Wintermute*

      it’s a shared mailbox, which means any rule she’s set up would affect everyone that uses that shared box.

    5. Frog&Toad*

      We had a virus or security issue a couple of years that created a rule to send emails to trash…go onto the web page version of Outlook and check there as the settings are different than those on the client.

  13. scandi*

    IT should definitely monitor it. I wouldn’t dismiss the idea that it is a weird bug – I’ve attracted a few weird Outlook ones, including a bug that somehow made emails I sent not arrive to the recipient. It happened with several different recipients, and the email would send from my side with no error and show up in my sent folder but never arrive. And it displayed a weird periodic behaviour (it happened to five or six emails in two weeks, and then nothing for a few months before starting up again). However, when I notified IT that it started up for the second time, they did a very thorough check and eventually discovered some problem and fixed it (something about a special character in my name not being coded correctly in their system and interfering with something else). It took them until the third time it started happening to figure it out, but I at least had the chance to develop a real rapport with George the IT support guy.

    1. London Calling*

      *IT should definitely monitor it. I wouldn’t dismiss the idea that it is a weird bug – I’ve attracted a few weird Outlook ones, including a bug that somehow made emails I sent not arrive to the recipient*

      Agree with this. A few times at exjob I’d open my inbox and watch a new email or two just disappear without me touching anything. Not in the deleted folder, not anywhere.

      And that method of assigning emails sounds incredibly laborious and time consuming.

  14. Rainbow*

    I’m a tech person working with non-techies. Would recommend you set up some automation – if you have access to Power Automate, which is sometimes bundled with Office, that looks scary at first but is actually a very accessible way anyone can use to make things happen to emails. You could make it work on all incoming emails, or with particular tags in the title, or you could target any deleted items only. You could alternatively use Quick Steps directly within Outlook. This could make the assignment process easier in any case (or maybe it would not; I don’t know your workflows).

    Much as it’s not fixing the core behaviour, assuming it’s a Jane problem, that’s your managers responsibility and she seems to be burying her head in the sand. So maybe you can smoke out the issue by forcing people to do their jobs properly. It’s a nice way to find out about the “system issue”.

    1. Bee Eye Ill*

      IT person here as well. They are basically “doing it wrong” and need a better way of tracking requests than this mess.

  15. Akcipitrokulo*

    Yeah, IT, if asked, said “Jane’s deleting them.”.

    Because if they didn’t think that, then it would have been top priority for every dev that something was deleting emails.

    So either your manager is lying that they consulted IT, they are lying about what IT said or you have the worst IT department in the history of IT departments (real and fictional).

    1. Rainy*

      See my comment below for details, but I think my org must have the worst IT department in the history of IT departments. I don’t even bother opening tickets anymore, because I’m tired of being told I’m a liar.

    2. Observer*

      I agree with everything that you said except for “worst IT department”. Even here we’ve seen some truly bizarre stuff. The one that sticks in my head is the IT Department that changed someone’s email without telling her because SOMEONE ELSE asked them to – and not even her manager! This was in the discussion on some post or other, so I doubt I could find it.

  16. Llama with a haircut*

    It’s not clear from the letter, but when you get a request asking for follow-up and find the deleted email, is someone then doing an audit to see if there are other deleted emails that no one bothered to follow-up on, so they just never got a response? It seems likely that if Jane is deleting the emails to avoid having to do the work, there must be a benefit in that at least some of the times she never has to address the email at all, it just gets deleted and no one is the wiser.

    But I agree with the commenters above that the weird shared email box is likely part of the problem. I don’t even share an outlook box across my own different roles because it’s too messy.

  17. Keymaster of Gozer*

    I could find out who deleted emails on our Exchange server in under a minute. There is a slight possibility that someone with access to the inbox has set up a badly coded rule that sends stuff to deleted items if it contains x y or z – and if that’s client side it’s slightly harder to find.

    Not impossible. If your IT have admin access to the systems and you all have distinct logons then they can see what’s going on. It’s an absolute faff to do it (server administration tools are never user friendly) so they may have said they can’t because they don’t have time/can’t be bothered.

    Having said that, I’d strongly recommend an actual ticketing system because every single implementation of ‘we’ll just use a shared mailbox’ I’ve seen generates issues like a spilled lorry of maple syrup generates flies.

    1. Zofran*

      Could you tell who was deleting emails if they’re both logging in directly rather than accessing the email through individual delegate accounts?

  18. Rasberry*

    To me, it looks more like they are accidents, since Jane seems baffled and it happens mostly in busy times. There are plenty of people who are careless when they delete emails. They can mix up emails and delete the wrong one, they can assume the email was a repeat request, they can get heavy handed in mass deletion, they can accidentally press the wrong button or shortcut. Weird though that your boss isn’t addressing it when it has become a problem, though.

      1. Mostly Managing*

        I agree.

        Also, if Jane is deliberately being deceitful by deleting emails, it’s not hard to also “appear baffled” when called on it. Part of lying effectively is not caving when someone asks if you’re the problem.

    2. Not Tom, Just Petty*

      That may well be true, but OP does not say that Jane is so freaked out/embarrassed or concerned that she suggested something like “hey, OP, when a “stray” comes in, let me know and I’ll research/dig through deleted since it’s my issue.” She just suddenly either pays more attention or figures she’ll give it time. And manager is letting her do it. I’m not saying that manager should be punitive and Jane penitent, I’m saying that they are taking two steps back, and making OP handle the entire situation. And that is unfair and unsustainable

      1. ecnaseener*

        That was my thought too. She seems bemused whenever it comes up, but has no apparent interest in stopping it from happening or even in proving it’s not her? She’s either so clueless she doesn’t realize her integrity is in question, or she doesn’t care (because said integrity doesn’t matter to her, because she’s doing it on purpose).

        Obviously you can’t base conclusions off her emotional performance, that’s not fair, but the *action* of a person with integrity would be to check that deleted folder religiously.

    3. Observer*

      Seriously? It’s so simple to appear “baffled” that using that as a significant argument is just not even close to reasonable.

      Sure, people can get careless. But when it’s a pattern like this, it’s definitely willful. Even if the individual deletions are not intentional, the patter IS. Because Jane *knows* that this is happening, and she *knows* that it’s related to her – and she IS capable of keeping this from happening.

    4. Moose*

      Acting baffled isn’t necessarily a sign she’s not doing it on purpose–she’s not doing any follow-up to figure out what the problem is. If she’s been doing this for years, of course she’d not be honest about it. Not to mention that the problem stops for a while after the manager brings it up to the team, like she’s covering her tracks. This does not read as a random mistake to me.

    5. Kella*

      If you are regularly making a mistake like this, you don’t just randomly stop making them for 2-3 months after every time someone talks to you about it. And, even if it is a repeated mistake, that’s still a performance problem that Jane needs to fix. She needs to put a system in place to double-check her work to make sure she’s catching any of these emails that fall through the cracks.

  19. Rainy*

    It really would not have occurred to me to just…delete non-spam emails if I didn’t want to deal with them. I might procrastinate a bit, but I’m not going to just delete them and pretend it never happened. Gonna be honest, this one is a bit croggling to me.

    I agree with all above that the most likely explanation is that Jane is deleting them. Her big mistake is that she stops when she’s talked to about it. If she just kept doing it, it would look a lot more like some kind of system bug.

    (My entire bleeding organization is using a CRM software product for a purpose it was not intended for, and as a result there are some really obnoxious bugs, and support’s default response if you email them to open a ticket for one of those bugs is to tell you that you’re a liar, so my faith in internal support is currently hovering somewhere in Dante’s eighth circle of hell, but even we don’t have issues this frequently with the software product we are abusing.)

    1. Dust Bunny*

      Right? Because that only works until disgruntled clients email again and again to ask what’s going on with their job order. I guess some of them might give up and go away, but not all of them, and I would assume that it would catch up with me after awhile.

      But the manager here is so weak that maybe there aren’t any consequences.

    2. Rekha3.14*

      And I thought my org was the only one misusing a CRM!! hah I don’t feel so badly now about it.

      unless we work for the same org and have no idea, but I doubt it…

  20. BellyButton*

    If LW is the one who does the majority of the sorting and assigning I would suggest checking the deleted folder every afternoon and moving them back to Jane’s assigned folder (and keep track of how many you are doing a day).

    1. Not Tom, Just Petty*

      Or is this a new phase in the process that OP created/adopted because Jane’s deleted emails created an problem, OP discovered it and is fixing it because she hasn’t put it on Jane and manager to handle?

  21. Potato*

    It absolutely sounds like Jane is deleting emails, but I’m curious if there’s any pattern to the content of the deleted emails? If you get emails on subjects A, B, and C, for example, are all the deleted items only related to topic A? Do the deleted emails seem spammy at all?

    In my time doing similar work in a shared inbox, I definitely deleted a few emails that I thought were not real requests because the person wrote in a particularly phishing-sounding sort of way, only to find when they re-emailed that it was a real request.

    1. mlem*

      My more cynical immediate question was related to yours. Do the deleted emails all seem to be from ($minority / $identity) senders? Are they always for a particular annoying-to-handle service?

  22. a clockwork lemon*

    I…don’t really understand how this system works. How are you going in and changing the subject headline of a received email in a shared inbox? If emails are being assigned to Jane and you can literally see her name on the assignment in the trash bin, wouldn’t that mean that someone had to go in and add her name? Who is actually assigning these things? Why is your default practice not to forward the initial message to the person who is responsible for managing the inquiry?

    I manage a shared inbox for my entire team via Outlook and off the top of my head I can think of a few things happening:

    1) There’s an Outlook rule running a background process that everyone has forgotten about, and the reason it stops for a couple of months then starts back up again is that the process only runs as long as the rule is being executed–it won’t self-execute if the action has already been completed manually

    2) Someone accessing the inbox via mobile app is accidentally swiping a notification away and their phone is configured to automatically delete messages that are swiped–Jane (or whoever else) thinks she’s dismissing a notification on her phone but the inbox is actually sending these emails to the trash;

    3) These messages have a meeting invitation attached. Some Outlook configurations automatically delete calendar invitations once you’ve accepted a meeting, and there’s usually no workaround except to manually move the message with the original invitation

    OP it sounds like what you’ve identified is a system with a ton of failure points, which your team is collectively bumping up against. Maybe Jane is intentionally sabotaging some of her work and is just a super convincing actress, and maybe you’ve got wildly incompetent IT, but it’s clear your boss isn’t fussed about it. If you focus on fixing the system as a whole, it won’t matter whether you’re dealing with malice or gross incompetence or normal human fat-finger error.

    1. ThatGirl*

      I don’t know what the LW’s system is, but I helped manage a shared inbox for a customer service team for awhile; it was an Outlook folder with sub-folders for each CS person. We had color coded tags for each person, and would tag each email as needed and move it to that person’s folder where it showed up as unread. (Additional replies would go straight to the person’s folder generally, because we had rules set up for each one’s name.) I don’t quite understand the deleted folder part, because I don’t think those are shared between computers, but I’m not an IT person and clearly the LW has access to it somehow.

      1. EvilQueenRegina*

        If it’s a shared mailbox, if it’s anything like the one I use, anyone with access to the mailbox can access the deleted folder and recover it as necessary, unless/until someone double deletes it. I know I was able to recover something from ours recently that my coworker had mistaken for a duplicate and deleted in error.

    2. Pizzazz*

      I recently was having an issue with items disappearing from a shared inbox, and it turned out that the culprit was a rogue rule that I apparently configured myself…whoops!

      If Jane is genuinely baffled, but it’s only ever her assigned tasks that get deleted, I’m wondering if something like #2 is happening here, and Jane just lacks the attention to detail to be cognizant of it.

  23. Colette*

    I’m not at work today, but I’m pretty confident that if I delete an email from my shared mailbox in Outlook, it goes to my deleted items, not the deleted folder for the shared mailbox. Maybe there’s some setting we don’t have enabled?

    But, assuming a ticketing system isn’t an option, I’d start proactively checking the deleted items and moving anything that hasn’t been handled back into the main mailbox.

    1. SharedInbox*

      Hmm, not for my shared inbox — two different deleted folders, sent folders, drafts, etc.

      Somewhat related to the larger question, a previous job I did have a shared mailbox where search just… didn’t work well. In retrospect I should’ve asked IT to look into it but at the time it seemed to be accepted that this inbox of many years just didn’t pull up everything you wanted easily. So while this all sounds suspicious, I do think Outlook can sometimes have a mind of its own.

        1. All Het Up About It*

          Same set up here. If someone deletes/archives something from a shared email, it goes to that individuals personal email trash/archive. Same with “sent” emails. Now there could be different configurations, but if there ARE that feels even more like IT could figure out what is going on.

          Jane sounds vexing because yes, even if she is truly not doing this, and there is a ghost rule or some other bizarre system gremlin, that she is not continuously checking for these emails feels wrong. Also – I’m not clear on the “assignments.” Where are those tracked? How can you tell that those are Jane’s assignments? If there is an easy way to track who is assigned items, it feels like there should be an easy way for a person to keep track of their assignments. Soooo…. what does Jane think happens to those assignments?

          There is much to be frustrated about here OP and I sympathize. Particularly because it’s possible that this is a case where not only does your boss suck and they aren’t going to change, but your IT sucks and your co-worker sucks.

          1. SharedInbox*

            Oh interesting! Yes definitely different setups — someone I share the inbox with recently was able to find a deleted draft related to a conversation with search while not pulling up the actual email (which was in a subfolder of the inbox).

  24. Warrior Princess Xena*

    I’d go for the tactic of pushing for a more formalized ticketing system myself, especially since then you’re targeting the client-facing problem. Be it deliberate, accidental, whatever, the end result is that client emails are being deleted and as a result client work isn’t being properly done. Focus on that when you go back to your manager. This will completely abrogate the “is Jane deleting the emails” loop, which has a chance of making you look like you’re picking on a coworker (not true, but always good to prevent any such issues), and focus on the actionable client problem.

    In terms of what to do in the short term (assuming that your manager won’t go back to IT), it sounds like it’s time to institute a weekly audit of the deleted folder.

  25. N*

    Having worked with a shared inbox system like this, I think there are lots of other non-malicious user-error possibilities, like the filter-gone-wrong someone mentioned above . Or just a misunderstanding of different work styles (for example, I have a coworker who saves all important emails to neatly organized folders on her hard drive and then deletes them from her inbox. Nothing wrong with that system but to an outsider it would look like she just deletes all of her emails.)

    The good news is that it doesn’t matter if she’s doing it maliciously or not, the solution is the same – you need a better work assignment system.

    1. Warrior Princess Xena*

      This is what I was thinking – Outlook is sometimes a persnickety beast and there’s a possible nonmalicious cause. Approaching it as if it’s an uncurable Outlook bug and the solution is a better ticketing system will have the double advantages of making OP look like the sensible employee, earning competence cred, and make it so this doesn’t happen again.

    2. Cthulhu's Librarian*

      … there’s actually quite a bit wrong with the “save it on my computer and delete it from the server” style of workflow. Lack of recoverability in the event of a catastrophic coffee spill, for instance, and we had a whole saga about an architect doing this with their work products on this site. What if a global pandemic locks people in their homes and you can’t access the past communications because of no one is allowed to go into the office? Or her computer gets stolen on a business trip (possibly by a guest in their suite?)

      The system may not have failed so far, but that doesn’t make it a good one. It’s like not having health insurance in the US. Sure, it seems great when you’re healthy, but eventually you’re going to get sick, and then it’s really going to bite you.

      1. N*

        I abbreviated for brevity because it was not the point of my comment, but she was actually saving the emails in multiple formats to multiple shared drives which made them much more accessible to all staff across several different offices, not just those who have access to the shared Outlook inbox.

    3. Observer*

      Two thoughts.

      1. If that’s what she were doing it would me more consistent and she would not be baffled – she would explain what she is doing. And these would not be untouched emails, either.

      2. for example, I have a coworker who saves all important emails to neatly organized folders on her hard drive and then deletes them from her inbox. Nothing wrong with that system but to an outsider it would look like she just deletes all of her emails.)

      Actually, it’s a terrible system and your employer should not allow it. You’ve got no backup, no recoverability, no audit trail, etc.

      1. N*

        1) It doesn’t hurt to give people the benefit of the doubt when the solution is exactly the same either way. And the emails were not “untouched” – the subject line was changed to indicate who should handle them, and they were deleted. Many other things could have happened to them in between, even if they were marked as “unread” at the end.

        2) I’m sorry I declined to write a full essay about how one person I know works with emails since this is such a sticking point but she does have backup, and recoverability, and an audit trail. Far more than a shared Outlook account that only two people can access.

        1. Observer*

          In that case, you are talking about more than a “difference in work style” and a situation that is so different than the one described here that there is no basis for any sort of comparison.

          And the emails were not “untouched” – the subject line was changed to indicate who should handle them, and they were deleted.

          Yes, they were untouched between the time they were assigned and the time they were deleted. Why are you claiming otherwise?

          It doesn’t hurt to give people the benefit of the doubt when the solution is exactly the same either way.

          Not true. There are two possibilities here and neither of them include a well thought out workflow that keeps people in the look and gives them access to all of the information they need. (If that were the case, there wouldn’t be missed emails, the OP wouldn’t find the emails ONLY in the deleted folder and Jane would not pretend to be puzzled.) Either Jane is doing this, deliberately or through extreme sloppiness, or someone is trying to sabotage Jane. Assuming that it might be something else keeps gives the manager an excuse to not do anything about the problem.

        2. Kella*

          The solutions are not exactly the same either way. If this is an issue of mistakes, systems, and workflow, then it’s a performance problem that needs to be addressed with Jane. If it’s a bug, then IT needs to work on the problem and fix it. And if Jane is intentionally deleting emails to avoid work and lying about it, she needs to lose her job.

  26. FG*

    A) This assignment & tracking system sucks. As someone else mentioned, a formal request/ticketing system – where assignees can’t delete items – would help. If you use SharePoint a simple one is fairly easy to build.

    B) Failing that, it is possible that things are being deleted by mistake, and after conversations with Jane, she gets extra diligent, but then slides. I would also look for other patterns, mostly because it’s possible – I’ve seen it happen many times – that she has a rule set up to auto delete emails from certain addresses (i.e., a Do Not Reply address) or with certain keywords, meant to handle one type of email but these legit ones are getting caught. The intermittent improvements make it less likely, but still. The thing about deliberate deletions is, if that’s the case, Jane isn’t bright enough to permanently delete rather than just send to Deleted Items.

    1. MissCoco*

      To me the biggest piece of evidence in Jane’s favor is that she’s *not* permanently deleting the emails. First time, sure maybe she isn’t tech savvy and didn’t realize it was a thing that they get sent to a deleted folder, but after multiple occurrences, the fact that she hasn’t improved her MO at all is baffling me! On the other hand, even permanently deleting the emails would still make this a pretty bad scheme

  27. ThisIsNotADuplicateComment*

    As others have mentioned above you need to move from a shared inbox to a ticketing system. Here’s how you can make that an option if your manager rejects it when you first suggest it:

    1. Make sure everyone, and I mean EVERYONE, knows there’s a ‘bug’ deleting emails. If Joe Smith follows up on his request reply to him, CC Jane and your manager, and say “Oh no! It looks like your original request was deleted by our mysterious system bug! Jane, it was assigned to you before the system ate it can you get Joe a response asap?”. Do this every time. Heck this alone might solve the problem if it annoys Jane/your manager enough.
    2. Start telling people you think your team needs a ticketing system, specifically because of this mysterious bug. If you have any sort of process improvement process/team make the suggestion there. Mention roughly how many requests are being mysteriously deleted. Mention that your manager has checked with IT and they can’t help you.

    Your manager clearly doesn’t see this as an issue right now. Give it enough visibility that they can’t just have a 30 minute meeting and then forget about it. Give it enough visibility that someone above your manager looks at the current system and says it needs to be fixed. It won’t even be that much more work than you’re already putting into it.

    2. bighairnoheart*

      Just wanted to say, I love both of these suggestions. Especially #1 because it suits my petty nature and calls out the issue to all relevant parties in a reasonably professional way.

    3. Ginger Baker*

      I absolutely think Weaponized Earnestness is a great approach and would couple that strongly with Return Problem To Owner: every time you get a follow-up email that does not show up in an actual folder (IE shows up in Deleted Items) I would forward to Manager ONLY with a screenshot from your search and “Hi Boss! We have a follow-up email on an email not in any active queue. It does appear to be in Deleted Items. Sending to you so you can follow-up and resolve, thanks!” STOP OWNING the responsibility for solving this issue: you don’t, you don’t get paid to, and you can hand this off to the real owner (your manager) with zero qualms.

  28. LJK123*

    An easy way to make this process ( a tiny bit easier ) without having to get a full blown ticketing system (I agree with that btw). Is to use the categories feature in Outlook. You can make the categories any color and any heading that you want and then sort your inbox by categories so that you know what is assigned to who or if you wanted to go by what stage the request is in. I do this with my emails and it makes it so much easier then having to search for everything! Personally, I have a category for each project I’m working on, emails to follow up on, things to do and things to keep. It’s so helpful to stay organized.

  29. Wintermute*

    I work in IT, and have dealt with not this but things like it.

    No there is no way to tell who is doing what in a shared mailbox, oftentimes. Microsoft does not recommend shared boxes be used in place of a proper ticketing system and that’s not just to sell more ServicePro subscriptions it’s because they’re fundamentally unsuited to it.

    IT isn’t going to be able to hand you a smoking gun here but they can point out the obvious: this is not affecting everyone, it’s affecting one person. If it were a systems bug it would affect EVERYONE, and while bugs can be intermittent they usually don’t stop when the boss chastises the team. In addition if it were something in the mailbox settings itself (say, a misconfigured rule) it would affect all emails constantly.

    Now is it possible Jane made some kind of rule that has specific filtering based on her name and whatnot? yes, I guess so, but you would be able to see that in the shared box in the list of rules/filters. Plus does it really matter? doing it by hand or doing it via a rule, it still smells like work avoidance to me.

    Y0ur boss doesn’t seem to care, and you probably can’t make them. But if you want to make another go at it, sometimes using blunt language like “work avoidance” “sabotage” and “refuses to serve clients/users/customers/etc” can get through.

    1. STG*

      Yea, I agree. I don’t think IT is going to be able to tell you much in this instance. Shared mailboxes shouldn’t be used for something like this.

      1. Wintermute*

        “mailbox as a ticket queue” is an antipattern that has probably replaced “database as IPC” in terms of relevance and prevalence. But yeah, it leads to exactly these issues.

    2. Observer*

      IT isn’t going to be able to hand you a smoking gun here but they can point out the obvious:

      Probably true on the smoking gun. But in addition, the should be able to provide some additional information. I doubt that they will though, because no one seems to care about this existing issue, plus all of the other issues (bot existing and potential) to invest in any resources to mitigate any of the problems.

      1. Wintermute*

        in a shared mailbox all IT can say is “some user did this” they can’t tell you WHO, which is sort of the important thing here. That’s why shared mailboxes are such a bad idea, because any issue could be anyone.

        I am in IT and we had an issue with a shared alerts box where someone was creating rules for sorting things that they clearly felt strongly about having (they were recreated when deleted, repeatedly, even after we were told no new rules without management approval) but were stepping all over legitimate alerts and hiding them. There was no way of telling you who made those rules, whatsoever.

        They could tell you what time which helps narrow down (e.g. if it happened at 3am US central, so it was probably offshore’s doing, if it’s 6am central time it’s probably not the LA office, etc) but that’s about all

        1. Observer*

          So time makes a difference. In many cases it’s also not so hard to track what computer the work was being done on, so that also helps. And if they have separate system log ins, that’s something IT can give you. So, actually potentially some useful information.

          A group email box that is accessed by people’s individual email accounts is a much better system when you really need multiple people to be able to access one box.

  30. Carol the happy elf*

    Coming here, with my teeth grinding, because yes, it’s Jane. Of course it’s Jane.
    (Jane has a LOT of gall, by the way. A lot of people aren’t technically adept.
    This means that when they lie, they don’t have a clue as to why other people know they’re lying. So they try the ‘Lie With Authority”, or “Lie With Emphasis!”

    Think of little Tommy. He’s four. Little Tommy is bored at home, so he works himself up into an enthusiastic fantasy and he tells his Mom that there’s a tiger in the back yard.

    Mom doesn’t have to channel “Occam of Razor”, or have ever read Sherlock Holmes. She doesn’t have to be a Veterinarian, a meteorologist, a child psychologist or a mind reader.

    Mom just has to have a brain.

    1+1 only = 6 in sci fi, and Jane needs to be fired, or at least out on a PIP by a competent manager and a working chain of authority.

    In my business as in many others , Jane could be arrested and spend time in jail. She isn’t stealing from the petty cash drawer, but Jane is stealing time, stealing goodwill, and messing with company assets.

    There’s no tiger in the backyard, but there’s a snake in the grass.

    1. Moana*

      Um, are you okay, hon? There’s just…A Lot going on here. Maybe take a screen break for a bit?

    3. RagingADHD*

      I would love to know what country you live in where “stealing goodwill” is a criminal offense, much less one with jail time attached.

  31. JustMe*

    Something similar-ish happened at my OldJob and I felt it was important enough to bring up to the managers. (Also, tbh, I really just didn’t like my coworker in general and his work performance sucked.) I privately brought it to our direct manager and the second in command by saying, “I’m concerned about [thing] because after the conversation that Fergus had with you all, I went into the system and saw [whatever thing] with this timestamp, and I wanted to bring it to your attention.” In this case, there were internal policies about why Fergus wasn’t supposed to do the thing that he did, and when the managers looked into it, they found he’d been sharing some confidential legal documents with a third party that was not supposed to have them. He was fired that day.

    If it keeps happening and the stakes are high enough, loop in a higher up if you can.

  32. ohinnwe*

    Check to see if any rules have been set up for the mailboxes that might be filtering those emails. It’s unlikely given that this only happens to Jane’s but there is a slight possibility that someone set one up and it is now unexpectedly keying on something in those emails. I had a similar thing happen where I was filtering “Go [team]!” emails where I wasn’t in the “to” field to trash (Uni so lots of sports-related emails cluttering my mailbox). But someone had “Go, [team]!” in their email signature and cc’d me so it got filtered as well.

  33. Northbayteky*

    I don’t think your IT department will be much of a help. This is happening on a client that two people have access to. We’ll assume for simplicity sake that there is a single username/password to access that email client. Unless there are two separate accounts to access that one email account, there’s no way to be certain who deleted anything. All it will look like on the IT end is SharedEmailAccount@askamanager had 33 deleted emails in the month of March.

    Unless it’s a shared account that two different accounts have permission to access, it will always appear to have been accessed by the name on the account.

    I might suggest a free help desk type software for people to submit their requests to and the manager can assign them accordingly. The manager will have full access to all the requests and the software will keep track of all the steps in any given ticket/issue.

  34. A lawyer*

    Is there a chance OP’s manager isn’t taking it too seriously against Jane because they aren’t sure if maybe OP is causing the problem? I know OP knows she isn’t the one doing it, but OP’s manager doesn’t know that for sure and we’ve seen other posts about people sabotaging co-workers in shared documents/systems.

    1. Redaktorin*

      It’s 100% this, and Jane is 100% hinting to the boss that it’s all OP’s fault in order to get away with deleting important work on a regular basis. The more you push this issue, the higher the odds are that Jane will start telling lies about you to anybody who will listen.

      Watch your back.

  35. Michelle*

    In the absence of a ticketing system, my team would copy the person it’s assigned to, and actually respond to the original inquiry with something like:

    Thank you for your (email/inquiry/ whatever. My copy of my response, PERSON X will review and respond to you (within X/by Y).

    The person who it was assigned to had to copy the shared box on their acknowledgement. Perhaps this has already been suggested above and I missed it. Our volume was not high so it worked well for us.

  36. OP*

    Thank you, everyone for confirming what I’ve been thinking for years now, Jane is most likely intentionally deleting these e-mails. Ticketing systems have been suggested, but because our team is so small, our company won’t approve the expense. So as frustrating as it is, I have to just accept that this situation isn’t going to change. My manager and Jane are not going to change. If by some miracle, something does, I will be sure to send in an update. Appreciate everyone’s help. I was starting to feel like I was living in the twilight zone, but Jane and my manager were not.

    1. Warrior Princess Xena*

      OP, huge sympathies. You are not wrong and this situation is wild. In absence of a ticketing system, may I suggest a regular email audit? Once a week, check the deleted folder. If all the finished tickets end up in the deleted folder, then pick a sample of them and check that work was done. If emails aren’t supposed to be deleted from there, then just check all of the emails for work. It’ll let you keep up if anything else gets deleted AND show a pattern.

    2. Peanut Hamper*

      Just an FYI for anyone else looking at this down the road: there are open-source ticketing systems available that cost nothing. It does require an IT person who knows how to install and upgrade it, so it’s not as simple as just paying for a Jira account, but it’s definitely a possibility.

    3. Malarkey01*

      We all have something at work that is super frustrating but just won’t change. It can be helpful to reframe the question a little and think since no one else cares about this what can I do not minimize my annoyance.

      Maybe it’s sending each status update to Jane and manager to say hey here’s another missing request, maybe it’s leaving all follow up requests in the email for Jane to deal with since the majority of the time it’s hers, maybe it’s asking manager for a script to respond.

    4. goddessoftransitory*

      Honestly, talk about penny wise and pound foolish on the part of your company! They won’t approve X amount for a very basic and required piece of software, but they don’t mind the X+1000 amounts of money, clientele and reputation they’re losing by allowing Jane and your manager to just shuffle client requests off to Buffalo because they don’t want to be bothered?

      I’d start updating your resume, OP; I wouldn’t bet more than a dollar that your employers are on solid financial ground.

    5. Observer*

      I agree with the others.

      In the meantime, can you suggest a smaller, but useful change?

      Each one of you has you own email account. Then use a shared email box that is a “group” type account. The two of you, and anyone else that needs access can have it. What that does is to insure that every action is attributed to the person who did it.

      Also, with this set up it becomes easier to do some organizing the emails in ways that are easier to see and track.

    6. Generic Name*

      You can’t make your boss or Jane change, but you can change how you respond to this. Stop picking up the balls that get dropped. After you determine that you didn’t miss something assigned to you, I suggest you email your boss and maybe IT as well when someone follows up why something didn’t get done. Make is your boss’ problem to manage the situation. Right now you are doing: 1) your job, 2) the work assigner’s job, 3) Jane’s job, and 4) Boss’ job. Do you get paid to do 4 people’s jobs?

    7. Northbayteky*

      There are ticketing systems that are free. Granted, there’s not a lot of features to them. But what you need don’t require a lot of features. Before we purchased a ticketing system, we tried 0ne from SpiceWorks. I just did a google search on free ticketing system software (because I forgot which one we tried) and there are different options available.

      If that doesn’t work, the manager should be the one to read and assign the emails and forward them to the assigned person, leaving all the shared messages untouched by either employee. How the manager hasn’t figured out that a disinterested 3rd party is really the answer, if a ticketing system is too much to handle, has escaped me.

    8. Sourdough Bread*

      OP, I went through this exact same thing! Shared email box, unanswered emails, and disinterested manager. It isn’t a perfect solution and ideally requires 5 team members, but we ultimately assigned days and everything that came in that day was your responsibility. If it’s only you two, you could switch off MWF and TR every week.

      If suddenly only Tuesday emails aka Jane’s day disappear, even more evidence that it’s Jane.

      FWIW, my Jane acts dumbfounded anytime things were deleted or unread/unanswered. They are a good actor.

  37. Xakeridi*

    IT can set the permissions in the shared email account preventing Jane from being allowed to delete things. They don’t want to.

  38. Just me, Vee*

    She could accidentally be clicking “ignore”, and all emails relating to that conversation will automatically go in the deleted folder as unread. I’ve found that out the hard way.

  39. Lalitah92*

    I’d recommend that the OP requests to their IT department that the shared mailbox not allow deletion of emails sent to that group box (that security setting is housed in MS Outlook folder-level permissions). You can also setup a rule to forward new emails to another address to create an audit trail, if you have a personal box (but that depends on the setup you have with Outlook).

  40. AnneSurely*

    Wait, am I the only person so far who wonders if there might be someone trying to sabotage Jane? (Apparently I’m trusting enough to believe it’s possible Jane really is surprised about what is happening, but suspicious of humanity enough to also believe it’s possible that someone is trying to fork with Jane.) I mean, if there aren’t any obvious beefs between Jane and someone else, this seems really unlikely. But if Jane really seems to honestly not know WTF is happening here and also doesn’t have other red flags in her work, it feels worth considering, assuming there are others who might have access to the shared inbox.

    I’m not clear on exactly how these are getting assigned (like, how do you edit the subject line of a received email in an inbox?), but would it be possible to update the procedure such that when you or Jane are assigned to a “ticket”, the person who sent the email is also notified which of you has been assigned? That way, if something is deleted or not addressed for whatever reason, the requestor knows specifically who to follow up with. And it also adds a layer of “I know you know” to the situation. Jane (or whoever) can’t make the work just disappear by deleting it, because they know that someone else already knows they’ve been assigned to it.

    1. AnneSurely*

      Is there a setting to prevent deleting contents of the deleted folder? If not, I also wonder about the intelligence of whoever is doing this, if they doing it on purpose. Why would you just leave the evidence right there in the deleted folder? This feels like when a toddler gets into the chocolate, and then denies it with a chocolate smeared face. Did they not think through their end game with this?

        1. irene adler*

          Me as well.

          If the intent is to get rid of an email, you gotta do more than simply send it to the deleted items file. Need to take that next step and permanently delete it.

          I know sometimes I hit the wrong thing and an email ends up somewhere else. But not with any regularity like the OP’s situation.

    2. Redaktorin*

      My initial hot take scenario was that Jane has ticked off someone in IT and that’s the real culprit. Would explain why they’re just throwing up their hands about solving the issue!

  41. Healthcare Manager*

    We had this at my work place. Shared mailbox between several different users. It was an IT issue causing the emails to disappear, in our case it was the server being overloaded due to the high volume. IT weren’t able to resolve it and gave us short term solutions that would work for a couple of weeks/months and then pick up again.

    As a side note, wouldn’t assume Jane’s manager isn’t trying to deal with it, but as a manager I most certainly wouldn’t be accusing Jane without a confession or IT confirming it.

  42. Magenta Sky*

    Were I the IT guy on this, the first thing I’d check would be filters in Outlook on every computer that has access to the email account. It’s possible there’s a misconfigured filter somewhere that’s moving things to the trash.

    If not, yeah, there should be logs somewhere that IT can dig out.

    1. Captain dddd-cccc-ddWdd*

      > It’s possible there’s a misconfigured filter somewhere

      A filter misconfigured in such a way that it spontaneously fixes itself for a while after the manager happens to mention to OP and Jane about emails going missing…? Sorry, that is a step too far to be believable in this scenario.

      1. Magenta Sky*

        Without seeing details on the deleted messages, it’s impossible to even guess at what such a hypothetical filter might be filtering on. It could be a particular sender, a particular subdomain, a particular sending server, a particular public IP address for a particular office, messages send during a particular time or date window, or a thousand other things. I wouldn’t rule out the possibility that whatever process of assigning messages to Jane is involved. Outlook’s filters are *very* sophisticated, and sometimes, very easy to misconfigure.

        I’m inclined to agree that’s not it, but I’ve seen far weirder (and more unlikely) things in 30 years of IT work.

  43. Observer*

    If you guys share a log in to both email and the general system, then your IT really cannot tell WHO deleted it, but they can probably tell WHEN they were deleted and maybe even which machine it was deleted from. If they can’t, it’s probably a matter of set up, and they should be able to set up the audit trail to show that information.

    Based on what you say in your letter, I’m guessing that you share an email log in. But if you do have separate system log ins, and people are careful about this, then they can almost certainly set up the audit trail to get some information.

    Now, it’s possible that IT simply doesn’t have the capacity to do this at this point, and they don’t have the budget and capacity to set this up.

  44. Ms. Chanandeler Bong*

    I’d be reaching out to IT to let them know that the situation is unresolved – polite, matter of fact, “We flagged an issue with our shared inbox in MONTH, and I wanted to let you know that it’s still happening. Here are some recent incidents, with dates. Would it be possible to investigate further? Happy to assist in any way possible”.

    Lots of good CYA advice here in the comments, but if it was happening in your own private inbox and wasn’t resolved, or if it was another piece of shared tech acting up, I suspect that you would open/re-open an IT ticket. It’s not sneaky or underhanded, because you’re not accusing anyone of anything! You’re asking them to solve a tech problem, that’s what they’re there for, and you don’t need your boss to action it to get an answer.

  45. Lily Potter*

    I would be super curious from the OP about the content of the messages that get deleted. Are they regularly things that you could think “yeah, that’s a stinker….I can see why Jane might want to not deal with that?” Or are there super random “easy” requests in there too?

  46. koala*

    There was someone we worked with who was not great at their job AND was notoriously bad at technology, and they would constantly try to blame their computer for all the balls they dropped. Once they claimed not to have received an email they should have acted on. My boss used one of Alison’s favorite techniques and took them completely at their word; she immediately looped our head of IT into the thread and asked him to look into whatever problems were going on with our mail server that caused this person to not receive all their emails. The head of IT replied pretty quickly with timestamps of when exactly the email had landed in that person’s inbox and when it had been moved. (I forget now if it had been deleted, archived, or moved to another folder, but whichever it was, IT knew.) I was cc-ed in the whole thread and it was delicious. I don’t think the person ever tried lying about email again.

  47. Peanut Hamper*

    Honestly, if a ticketing system isn’t going to happen, then the obvious solution is to have three email accounts: one for incoming tickets, one for LW, and one for Jane.

    All the incoming tickets can get then get forwarded to either LW or Jane. But it’s important that only one person (ideally somebody else, but probably going to be LW) have access to the incoming tickets account. Jane should not have access to that account. (Because no email account should have two people who can access it.)

    If Jane decides to delete emails after they are forwarded to her, then that’s on her. But at least you can pinpoint where it is happening.

  48. Team PottyMouth*

    First of all, stop with the initials thing and add categories to your emails. Everyone gets assigned a color, each incoming email gets assigned to a person’s color and then they’re automatically sorted by assignment with the unassigned items on top.

    Second, to be as generous as possible to Jane, I wonder if she has a Quick Step or an Ignore filter set up that accidentally catches emails it shouldn’t?

  49. ijustworkhere*

    I would reply to the person asking for an update, copy Jane and the boss, and say, this situation was assigned to Jane, here is her direct email/phone number so you can contact her directly to discuss.

  50. kina lillet*

    LW, I wouldn’t be so sure that your manager actually knows about this pattern and how it is absolutely pointing toward Jane. If your manager is a bit in denial and also you’ve been hinting here, I can see her saying to herself, “yeah it’s not great but I don’t want to freak out on my employees over this kind of mistake.”

    You’re seeing it all the time and being really annoyed by it all the time—is it possible that your boss just isn’t really seeing the pattern? If she’s otherwise pretty good, would it make sense to go back to her and say something like, “this has been happening for a long time, and it’s awkward to say but I really think Jane is deleting these emails due to this pattern that I’ve seen for years. I don’t want to be adversarial about this and I’m going to drop it now that I’ve brought it more explicitly to your attention, but it’s concerning to me.”

  51. Cindershade*

    OP, I have been in a really similar situation to this. Shared inbox, coworker(s) with sometimes questionable ethics or willingness to take responsibility, and odd but periodic errors of emails disappearing into the trash that happened infrequently, but in clusters.

    In the end, I never got a true answer, but based on conversations with IT and the coworker(s), I actually fell on the side of “non malicious” and unintentional errors… especially once it happened to me too! The reason being, shared inboxes really are not great, and things go wrong on accident that are mostly untraceable.

    The posters above that mentioned some of these errors are spot on! Rules interacting oddly, notifications being dismissed that delete the whole email with them, emails with meeting requests that delete when accepted…I can verify all of these! And want to add a couple more:

    – Shared inboxes, even on the same network, don’t always update/synchronize at the same time. This can mean that if you delete a trash email, it may not vanish immediately on another user’s inbox. Then if they press delete even a little later, it can take the next email in the inbox instead when the inbox synchronizes again. Because the server knows the trash email should already be gone, so it deletes the next in line. This sucks, but it happened to us several times.

    – If users are on different OS (Mac vs. PC) Outlook and shared inboxes can operate differently. This leads to latency issues like above, but also just to other weird settings that can be tough to assess. I had a situation after a system update where anything I sent from the shared inbox was not recorded in Sent Items, either in the shared inbox or my personal inbox (on Mac these conflate slightly depending on settings). This made it look like I was not responding in a timely fashion, but the users did receive the emails I sent! So as a precaution, every email I sent from then on included the shared inbox email in the CC, and this became standard operating procedure going forward for the team. Annoying, but at least addressed the tracking problem.

    So in the end, while it can be really tempting to just blame the other person, there are DEFINITELY things that can lead to your exact situation that are hard to pinpoint but not intentionally being done. Good luck, and good for you trying to give the benefit of the doubt!!

    1. Peanut Hamper*

      They are logged in as the same user, so…probably not. But I’d love to hear how it could be done in this case.

      1. OrigCassandra*

        IP address. With an in-office desktop machine, this would probably be a static IP tied to the machine. Wifi, there’s an authentication trail.

        1. Inkognyto*

          They could be walking up to a static machine and using the shared account that way.

          1 workstation 1 shared account.

          I’ve seen just about everything with bad ways to handle accountability in 25 years in IT.

          my guess is someone else knows the credentials and is doing it.

  53. Khatul Madame*

    OP, you may want to look at the Deleted folder every week or so, just to make sure there haven’t been any new “accidents”. Like others have noted, this should be your manager’s concern, but apparently manager prioritizes protecting Jane over timely and responsive customer service in her department.

  54. Olivia*

    This is absolutely Jane’s doing and it’s absolutely on purpose. A lot of people are commenting that they sometimes accidentally delete emails. The fact that this can happen is not really relevant, though, because things that are being done accidentally don’t suddenly stop for a short period after the person gets talked to about them, only to resurface later, in an endless cycle. If Jane couldn’t help it, then she would be just as unable to help it after it was brought to her attention this time. I’m all for giving people the benefit of the doubt, but Jane is clearly acting like someone who knows they’re doing something wrong.

    What I’d do is find a way to casually mention it to someone in IT. They’ll either look into it or they won’t (but don’t ask them to). If they do look into it, they’ll confirm it’s Jane. If they don’t look into it because they haven’t been explicitly asked to do so, they’ll tell you that it sure sounds like it must be Jane deleting the emails. Either way, you can take that back to your manager. You didn’t go over their head because it was just you making conversation with someone in IT.

    1. Just me, Vee*

      The OP could be reading the email, accidentally hitting “ignore” (which I’ve done) causing all further emails in that conversation to go to the deleted folder.
      So, yes it could be Jane’s doing, but to say it’s absolutely on purpose is not something you can be certain of.

      1. Moose*

        Of course we can’t say anything for sure, but it’s so, so deeply unlikely that it’s just user error based on the info the OP has here. This is a recognizable pattern–it’s been a repeated problem over years, it completely stops for a bit after the boss asks the team about it but then starts again, it’s worse during busy periods. If it was happening consistently or more randomly, it could be a user error or a mistake, but this is plenty of evidence that someone is doing this on purpose and covering their tracks for a bit once it gets noticed.

  55. Where’d Jane’s Initials Go?*

    OP, are Jane’s initials still on the subject lines of the deleted emails? If not, then I don’t see how a systems error could be responsible (moving the emails AND erasing her initials but leaving the original subject line.)

    If so, then every time you assign out new emails, also go to the deleted folder and reassign anything you find there, if you don’t mind having to spend an extra five minutes or so each day. Maybe send an email to her, drily summarizing the reassignment.

  56. Choggy*

    Unfortunately, if the manager does not care to change the process to prevent this from occurring, there is not much you can do except work your own emails and ignore the ones that are being deleted and unhandled. It’s odd that you would still be finding these deleted emails, and Jane is not even looking for them to see if she “accidentally” deleted them? Why are you doing this extra work when it should fall squarely on Jane to follow up?

  57. Lizziabna*

    As a manager, you don’t need to have iron-clad proof to raise an issue. You shouldn’t throw accusations out willy nilly, but if you note a pattern, you can raise it and ask the employee if there is a logical explanation other than the one you’re seeing.

  58. Lizzianna*

    Also, LW, I would start making this Jane and your manager’s issue. If you get a request for a follow up and it’s not one that was assigned to you, send it to Jane. Don’t do the work of finding the original email. If it happens more than a couple times, copy your boss.

    1. Captain dddd-cccc-ddWdd*

      I’m not sure about that, because I expect Jane would just delete that request as well… which, “not my problem” perhaps, but on the other end of these emails is someone actually needing the answer, they don’t just come into existence out of nowhere. If there’s an unhappy customer (or whatever the relationship is) the priority is to resolve the situation on behalf of the team at that point, and then reconcile it internally.

      1. I'm Just Here for the Cats!!*

        Yes, but it might be the boost that the manager needs to get to the bottom of this and fix the issue. The reason why the manger doesn’t think its a big deal is because work is still being done. By the OP assigning the emails back to Jane, without replying they are showing that they are not going to do extra work anymore.

  59. KatieP*

    OP, I was in a similar situation. Using Outlook to track purchase requests for ~500 people.
    When I got promoted to manage that area, I used the MS Power Suite to build a homegrown ticketing system. It took me a week, but it fixed 98% of the problems.
    That being said, I agree with Allison, it’s weird that your manager told you that your IT department couldn’t figure out what was going on. Our IT department was always able to tell us, “Oh, yeah, it shows Jane deleted that email at 12:27 PM on April 10, 2023.”
    In our case, it was usually someone misclicking and moving the email to a random folder.

    1. H3llifIknow*

      But if Jane did NOT delete those messages, then there is no trail for them to follow. I have had up to 13… THIRTEEN legitimate emails (within the DoD) go to either Junk or Deleted with NO action from me. IT has checked my rules. They’ve had me add to contacts and safe senders lists etc… but randomly emails just… go there.

  60. House On The Rock*

    Lots of other people have covered the tech side as well as whether Jane is doing this intentionally or is just bad with Outlook. FWIW I totally agree that this systems is a horrible way to handle user requests and also that LW should stop trying to “fix” things by re-sending deleted emails to Jane, “reminding” people not to delete emails, and/or following up with people whose requests have been deleted.

    But it’s also possible that the boss does see this as a problem and is working to resolve it, but isn’t able to share details about what’s going on. What sounds to LW like “I don’t see this as serious” could be the boss’s attempt to avoid disclosing a performance problem that’s in the process of being addressed. If the boss is working with IT to prove that Jane has been deleting emails, that’s not necessarily something to share with others. Granted, she shouldn’t outright lie about IT’s ability to track this down, but she also shouldn’t say “yes indeed, Jane is being dishonest and we are building a case against her”. What boss should do is let LW know that she’s handling it and any instances of possible deletion should be shared directly with boss and then let go.

    1. Moose*

      If this has been going on for *years,* I’m not sure I’d believe the boss has something going on behind the scenes. It shouldn’t take that long to build a case or get to the bottom of the issue.

  61. Jamie*

    If Outlook keyboard shortcuts are enabled, it’s all too easy to delete accidentally without realizing you’ve done so. You just have to hit “d” with the mouse arrow in the wrong spot, and poof.
    –Signed, The Person Who Recently Disabled Keyboard Shortcuts Because Oops

  62. Captain dddd-cccc-ddWdd*

    Regarding “can this be treated as a disciplinary issue even though there is no proof” – in my experience yes – the “standard of proof” for a disciplinary action isn’t the same as convicting someone of a crime i.e. beyond reasonable doubt. For a disciplinary process to be considered acceptable it’s often just a “more likely than not” standard of proof, which I think based on the information given in the letter, this certainly meets.

  63. Moose*

    100% on everyone who’s suggested it’s time to upgrade to a ticketing system–Jira is, I think, the most widely used but there are other cheaper/simpler/etc. ones. Something that creates a record of the request automatically once an email is received, at least, so that the only place these requests exist isn’t a regular email inbox where things can be overlooked, mis-sorted, or accidentally deleted even without the bizarre situation you have going on here. I know you likely don’t have the standing to implement that, LW, and it may be a big ask at a small company depending on where you work. But this doesn’t seem like a sustainable way to do this business even without the Jane issue. Worth suggesting as a process improvement without even bringing up Jane since your boss doesn’t take the issue seriously…

    although if she’s not willing to dig into this issue, I doubt she’d be willing to do a process overhaul. Ugh. I’m sorry your manager is dropping the ball on what should be a pretty big deal! I also agree with the people suggesting that you do a regular audit of the deleted folder to catch missed requests before someone has to follow up; what if there are other requests that you are never catching if the person never follows up? But I wouldn’t trust Jane to do this, so it would create more work for you–not fair.

    The fact that this seems to happen more during your busy periods is the most telling, aside from the fact that only Jane’s assignments are the ones disappearing. She must have learned over the years that the deleted emails are caught eventually, but if she’s feeling overwhelmed, she can buy herself time on some tasks by deleting them and not having to return to them until the person follows up. And of course she’s learned that there won’t be consequences as her manager won’t pursue the matter after an initial convo. Really frustrating.

  64. Let’s get visible*

    I’d monitor the deleted box daily and pull janes deleted emails out and resend them to her. Seems like a decent solution.

  65. M*

    At my office, some of us started to notice that every once in a while, a seemingly random email would move itself from our Inboxes to Deleted Items. It wasn’t super-frequent and there wasn’t any particular pattern, but sometimes we would literally see the email disappear from the inbox while reading it. Our IT was able to determine it was a glitch in the firewall and fix it. It certainly sounds here like there’s something else going on, but it’s worth asking IT to specifically rule out a firewall issue before escalating.

  66. Peonies*

    It doesn’t sound like it is the case here, but before I took any action as a manager, I would want to make sure to consult IT to be very sure it isn’t a bug. I had a situation when I was new at a job where my manager assumed I was ignoring certain emails from an automated system, but I actually was not receiving them. The pattern was perplexing, but when I took the initiative and went to IT, we were able to confirm that I was not receiving all emails from the automated system and my manager had accused me of something that was not at all my fault. It really stung and left me feeling pretty anxious for a long period of time that she would assume the worst about me and not bother to confirm it.

  67. Generic Name*

    I’m reading tons of suggestions about the tech issues that could be behind this, Outlook tips and tricks to make the process smoother, and suggestions of ticketing and task management systems. All cool suggestions. FOR MANAGEMENT. None of this is your problem to solve. The reason your boss is unconcerned, is the work is getting done. He doesn’t care that it’s you who is doing it and Jane is maybe/probably not doing her fair share. So stop filling in the gaps and solving management’s issue yourself. When someone follows up wondering why something didn’t get done, make sure it wasn’t assigned to you. AT MOST you can forward the email to your boss and let them handle it.

  68. H3llifIknow*

    Do NOT assume it is Jane! I am having a weird Outlook issue the past few months where important emails, even from those in my contacts, end up in either Junk or Deleted–and I DO NOT share an Inbox. It’s allllll MINE. I’ve not seen them. I’ve not touched them. I don’t know they exist until I get asked for a follow up. I’ve contacted IT and done all their steps “add them to your contacts and safe senders, blah blah” but it STILL happens. Outlook is a weird, weird flaky, glitchy beast. Unless you really have reason to think Jane is that lazy and unreliable, I would place the blame squarely on MS Outlook!

  69. I'm Just Here for the Cats!!*

    “I have my suspicions that this is not a systems error, because emails seem to disappear a few times a week for a month, we have a team meeting about it, no more emails disappear for three or four months, and then it starts up again.”
    I wonder if there is a pattern to when the disappear. Like do they only get deleted on days when Jane is super busy? On Friday when she doesn’t want to work, etc.

    My other thought, and this is a long shot, is that someone else besides Jane and OP has access to the email. Is there someone who is backup for when Jane or the OP are out so the other person doesn’t have to do all the emails? Is there someone who used to do the emails but the task was given to Jane and now that person has it out for Jane and is deleting the emails?

  70. Manic Pixie HR Girl*

    This sort of reminds me of how so many scientists had very complicated explanations for how and why planets and starts went “retrograde,” when in fact the simplest answer is that Earth was not, in fact, the center of the universe.

    It’s definitely your colleague doing this. If it wasn’t, she’d be all over IT to fix this because she would not want to be blamed for something she wasn’t intentionally doing.

  71. Orange You Glad*

    I’m going to second (or third) what others have said – stop making this your problem. If a follow-up comes in that is related to Jane’s assigned messages, just assign it to Jane and move on. If she deletes it again and the user gets upset – let them and then escalate that issue to your boss.

    If you’re really invested in the situation, what is stopping you from going to IT directly? As a user of the inbox, this issue affects you. It doesn’t sound like you need to or you could do anything with the info when they come back to tell you Jane deleted it on x date but at least you’d know. Again, I’d recommend just not making it your problem, but if it needs to be for some reason it doesn’t sound like your boss or Jane will do anything about it.

    I also work in a shared inbox that requires a lot of triage every day. It took years to iron out a good system to make sure everyone was doing their fair share of the work. My coworkers wouldn’t just delete something, but anything that required more than the most basic of responses was pushed off on me to do 90% of the time. A big part of changing that was putting the person that ignored or forwarded the request on the spot to explain why they were unable to do it. Luckily my boss is supportive of the actions I’ve taken and is helping me hold everyone accountable.

  72. Peon by choice*

    We encountered a similar issue at my workplace and it led to the employee being terminated. The items were not worked out of Microsoft Dynamics and the same person would continually have “system issues” where requests were closed without any action. The employee never admitted it was intentional. Anyway, this comment is to say that if management makes enough noise to IT, this is absolutely something that can and should be investigated. Either scenario (Jane is deliberately deleting there OR it’s a genuine bug) requires action. Also, moving things to deleted could potentially impact the retention period for the item which can cause issues if the emails could be required in the future.

  73. Jay*

    Quite a few years ago I worked (for about a year or so) for a department of a state agency in a Southern state known for not really liking the existence of it’s state government (as in, if you were in a state vehicle, you needed to check your tires whenever you left it in public because people would unscrew your lug nuts while you were gone). There was an employee in another group (I’m fuzzy on the Org Chart). No one seemed to know EXACTLY who he worked for or EXACTLY what he did. He just sent out these emails, trying to get other people to do things. Often things that were completely unrelated to their jobs. Mind you, he had no actual authority to do this. He was none of these people’s boss. He just seemed to spend his whole day bothering everyone else about random tasks. We called him The Pest. One of the first things new hires were told (unless we REALLY didn’t like them) was to delete any email they got from The Pest. Don’t even bother opening it. DEFINITELY don’t do anything he tells you to do. That just encourages him to focus on you, and then he will literally fill your in-box daily with dozens upon dozens of requests that everyone else was smart enough to ignore.
    Ignoring emails from The Pest and several other sources was a survival trait. It was literally the only way to get anything done. Our bosses did the same thing. Their bosses pretended they had no idea what was going on. The next level up really DID have no idea what was going on. About anything, really.

    I bring this up, because it might be worth looking into the possibility that you have a situation where an employee is getting emails that she can’t outright refuse, but should not actually be spending their time on. Are they all from the same source or about the same subject? It could be worth asking quietly about.

    1. Observer*

      Since the OP is the one assigning these emails, don’t you think they would be aware of this. According to what they say, these are perfectly normal requests.

    2. RagingADHD*

      Since the manager has been discussing the situation with Jane and the LW for *years* it strains credulity to imagine that such an issue would never have been mentioned, if it were the case.

  74. Starfox*

    This would be my cue to start going through the deleted emails every day & sending them straight back to Jane. “Oops that thing is happening again but I caught it, here you go!”
    But I’m petty.

  75. RagingADHD*

    It seems like the logical response is to have a tracking system of who each email is assigned to on the front end, and then have each person responsible for checking / following up on the results of their assignments, with the manager holding them accountable for completing their list.

    Whether or not Jane is doing it on purpose is not the problem that needs solving. The fact that nobody knows the request came in until the customer complains, and it’s been going on for *years* means that this needs a practical solution, not a series of meetings to talk about it.

    And if Jane is doing it on purpose, it will make it pointless for her to try, because she will still be accountable for following up on the requests, no matter what folder they are in.

  76. Goody*

    This definitely sounds like a PICNIC issue. The question is whether it’s deliberate or accidental. I’m gobsmacked that this has been going on for years, though.

  77. Kuzco’s Llama*

    “I let my manager know when I find these scenarios and then reassign them out as appropriate.”

    1. Have you told your manager that all of the missing requests were for Jane? Or do you just inform her one-off when it happens? It’s possible manager hasn’t put the puzzle together, which is why the whole team meets to figure it out. If you haven’t discussed the trend with your manager, you need to do so!
    2. I do hope you are cheerfully re-assigning the work to Jane. “Oops, another mystery deletion! Jane, it looks like this one was initially assigned to you. Can you still take it on?”

  78. Megan*

    As the person who was sabotaged at work, I really do encourage you to verify no one else has access to the account, though it seems she’s deleting them herself.

  79. Bazzalikeschasingbirds*

    Most people would wonder where their emails had disappeared to, if they were there one day but not the next. What work does Jane actually do? or is it confined to those months after the meetings. Jane and her boss are very happy with you, you’re doing your own work and picking up the slack for Jane.

  80. IdiotSavant*

    A few people have mentioned that IT should be able to work out who’s doing the deletion. But, this isn’t necessarily the case – not everything is logged and what is logged varies from system to system. For example, for this shared mailbox they may have information on who has logged in/out when, and when emails were deleted, but nothing about what buttons people clicked whilst logged in.

  81. Bazinga*

    Maybe stop deleting?
    Make a “Jane” folder and an “OP” folder.
    Move emails into these, depending on who it was assigned to.
    Then Jane can’t say she missed it when she could look in her folder.

  82. Inkognyto*

    LW1 – This email is setup to fail.

    Multiple people are using this mailbox and it does NOT need to be this way.

    There’s different mail systems and it’s possible to give people their own account (because you are sharing an account), and yet still access a shared account/email access.

    I’d really approach IT and ask if there was a way to have separate emails but still access and used the shared one that way you would have some accountability. When you access another mailbox from a personal one there should be some tracking. Here you are both using the same credentials to login thus they cannot tell the difference. It shows that they didn’t really have a concern in this either as they didn’t find a solution.

    I’ve handled email access before in IT and we’d never let this fly for this reason.
    It harms the company or team reputation and lacks any accountability.

    If people involved don’t want a different solution stop fixing it. If they try and blame you for doing it say that you have brought it up multiple times and they are not concerned.

  83. Theo*

    This exact issue got our admin fired pretty much immediately — they were indeed deleting emails, with this exact same chain of evidence. This isn’t a mysterious bug!

  85. Gravey*

    I have a personal hotmail address, and any email I get sent from one particular email address from one particular company goes immediately into the deleted folder.
    It took me MONTHS to find these and figure out what was happening. I never set up any rules or anything like that, outlook just doesn’t like those emails.

    Things like this do happen, however because Jane’s problem stops for a little while after each meeting and then restarts I doubt that is the case here.

  86. Betsy S*

    I’m an email admin, although I do more Unix/Linux than exchange. I’ve spent more than three decades chasing down email anomalies.

    What everyone else said about a ticketing system – there are free ones even – but if you can’t get one:

    1) Ask your IT admins to check how many different devices/IP’s are checking the mailbox. It is *possible* that one device, but not the others, is set to delete on check, or to use ‘POP’ instead of ‘IMAP’. (your email admin will know what this means). It’s even possible that Jane is only checking her email from this second device during busy times. Dunno about likely, but possible.

    2) *IF* what Jane is doing is deliberate, most of these suggestions are just going to teach Jane to go into the trash and do a permanent delete. Depending on how your Outlook is set up with Exchange, you may or may not be able to see this. So I suggest:

    Set up a forwarding rule that automatically copies email sent to this account, to your personal mail box. Ideally, have the admins do this at the system level by making the alias you use into a ‘distribution group’, so it happens before the email ever hits the shared mailbox. That way you’ll have your own copy of the emails that can’t be deleted by anyone else and you can run reports.

    Also make a rule between yourselves that requests are never deleted, only saved in a folder (perhaps by month?). That will help make accidental deletions more obvious.

    But seriously, ticketing system. It will save you time and really, money, because you will spend less time tagging work or updating users. I’m not an expert but here are a few links. You’ll probably want a paid plan and for two users it will cost less than the cost of a lunch a month.

    https://blog.hubspot.com/service/free-help-desk-software
    https://www.helpscout.com/help-desk-ticketing-system/

    (not on the above: if your outlook is connected to o365, as most small companies are, there’s some free-forever-for-one user thing called Microsoft Helpdesk Plus . I haven’t tried it. My $sidegig uses something called Groove.)

    You’ll probably want to check for a feature that doesn’t allow deleting requests without a trace, many helpdesk programs will do this.

  87. Annonymous*

    I really hate it when companies decide to use a shared inbox instead of a real service management software. They’re cheap, they aren’t that hard to set up, and then stuff like this doesn’t happen.

    Yes, your coworker sounds like she’s doing something shady, but the system enables her.

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