employee thinks I’m sending “secret messages” about time off, coworker is annoyed I won’t stay late, and more

by Alison Green on October 9, 2024

It’s five answers to five questions. Here we go…

1. My employee thinks I’m sending “secret messages” about how much time off she has

I’m a new manager with less than a year of experience, and I manage one direct report, Sally. We’re both based in the U.S., while our director is in the UK.

Recently, one of Sally’s collaborators reached out to me, mentioning that Sally has been telling people I’m sending her “secret messages” about having unlimited PTO. This is inaccurate — our team gets 200 hours of PTO per year.

However, our department does have a flexible approach when it comes to things like half days, childcare issues, or doctor’s appointments, partly due to having team members in the UK who follow different guidelines. While I’ve encouraged her to take time off when she’s had childcare or medical issues, I’m beginning to feel that she may be taking advantage of this flexibility. I’ve never suggested anything like unlimited PTO. In fact, I recently made it clear by saying, “That’s what PTO is for. Use it!”

I plan to address this with her this week. While I’m obviously concerned that she may be taking advantage of the flexibility, the idea that I’m sending “secret messages” is more alarming. Could this be a sign of a potential mental health issue?

I wasn’t expecting your last line — that’s a big leap! It’s much more likely that Sally simply misunderstood something. It’s also possible that something got lost in the retelling — like that Sally didn’t actually tell the colleague that you were sending “secret messages” but rather said “Jane doesn’t say it openly, but she’s signaled I can take whatever time I need,” the colleague relayed that to you as “secret messages,” and you thought those were Sally’s literal words when they weren’t. Or maybe Sally did say “secret messages” but meant it as shorthand for something more like this.

Flexibility is a good thing, but it can also lead to people being confused about exactly what is and isn’t okay … and sometimes managers hesitate to spell things out explicitly because they feel that adds rigidity to something intended to be the opposite … but when you have an idea in your head about what is/isn’t okay, it’s a kindness to make sure everyone is on the same page, particularly once you see signs that they’re not. So just talk to her and clarify the expectations, and it will likely be fine.

2. Using a water flosser at work

I have adult braces, so I have to be very diligent about dental hygiene, and your previous answer about teeth-brushing at work assured me that it was not weird. However, sometimes food gets stuck in a way that is not conducive to braces. I have a small travel water flosser — is it weird to use it in a bathroom where other people can see? Something about flossing feels weird!

It’s fine to floss your teeth in the office bathroom. The bathroom is the right place for flossing to happen! Water flossers can be messier than regular floss, so just make sure you’re cleaning up any mess (not leaving water spray all over, etc.). If the area is clean for the next person, you’ve handled it appropriately.

3. Coworker in a different time zone is annoyed I won’t stay late

I’m having an issue with a coworker in another time zone. I work remotely in Eastern Standard and my coworker works in a time zone 2 hours behind me.

Lately, she’s been sending me requests to stay after hours at end of day (4:40-5:15). She consistently waits until my work hours are almost over to ask that I work late. I have classes three times a week at 5:30 and have told the team that I log off by 5:05. So, I’ve been saying no to her a lot.

I also know my coworker has made the request to my higher-ups that I change my working hours to accommodate her working hours, but thankfully they said it wasn’t necessary.

I don’t want to keep saying no, but I do not appreciate being asked to work late last minute so frequently. I would like to confront my coworker about this habit but as a remote worker, I don’t want to rock the boat too much. I feel like I’m expected to get the short end of the stick because I don’t have to commute in.

Is there a way to do this where I don’t come across as rude or a non-team player? Doing it over Teams feels dicey. I’m good at my job, I just want to do it during my actual work hours.

The next time she asks you to work late, address the pattern: “You’ve asked me that a few times lately so I want to make sure you know that I generally need to leave at 5 ET (3 your time). If you’re likely to need something from me same-day, please let me know earlier in the day if you can.” If you’re willing to stay late in very rare emergencies, you can add “except in very rare emergencies.”

One caveat: are other people on your team remote or are you the only one? When you’re the only remote person and especially if you’re in a different time zone, sometimes you do need to be more aware of the impact that has on their work. In many situations it won’t matter, particularly if you’re good at your job. But there are some circumstances where, for your own job security, you’d want to get ahead of any grumbling about it. I don’t have any reason to believe that’s happening here, especially since your boss shut your coworker down, but if you’re the only remote person it’s smart to stay alert for signs of it.

4. Contact doesn’t use reply-all when she should

I am running into a problem with someone I have to email regularly, Kaitlyn, who should reply-all so that everyone cc’d on emails can see her reply, but consistently forgets to do it. One other person, Mike, and I are Kaitlyn’s clients. For a variety of reasons I am usually the person who contacts Kaitlyn, but I always cc Mike since he also needs to see Kaitlyn’s response. Kaitlyn almost always replies only to me, meaning I have to add Mike back in my replies to keep him current on what is going on. We asked her once before a while back to “please reply-all so Mike can see,” but it doesn’t seem to have stuck.

My impression of Kaitlyn is that she is young and relatively new to the workplace. We have other frustrations with her (usually we are contacting her because something has gone wrong). Mike and I have not said anything else to her about the cc problem after the first time because we’re more focused on getting our problems fixed and we’re both worried about piling a complaint on a complaint and on getting snippy with our tone. But this is genuinely frustrating and annoying. What’s a polite way to ask/remind Kaitlyn to remember she has to keep us both in the thread?

You’re getting excessively worried about piling on or sounding snippy — probably because you’re feeling snippy because you’re frustrated. But letting that deter you from being direct about it just means that by whatever point you finally do say something, you’ll be even more likely to sound irritated because your frustration will have built up. It’s much kinder — and easier — to just be direct about this kind of thing as soon as you realize it’s a pattern.

So: “Kaitlyn, we’ve mentioned it before but it hasn’t stuck: we really need you to reply-all when you respond so we both see your responses.”

And then if it still keeps happening, it’s fine to get more terse: “Please include Mike on this response and others in the future.”

You’re her clients. It’s completely normal to let her know what your work needs are!

5. What’s the definition of “three business days”?

Last week, I was directed by a company’s customer service representative to contact their case manager. I sent the case manager an email early Tuesday afternoon and received a response later that afternoon saying that she had received the information, was in the process of reviewing it, and would respond back with a decision within three business days. Which in my opinion would be Friday at the latest.

After going most of the day on Friday without any response, I called the number provided with the email and asked to speak to the case manager, explaining that I was supposed to receive a decision within three business days and today was the third day. The receptionist told me that the case manager takes Fridays off so her third business day wouldn’t be until the following Monday. Is this normal? Isn’t “business days” based on a five-day work week excluding holidays? If the roles were reversed and they needed a response in three business days, could I claim I was on an extended vacation so it could be two weeks before I worked three “business days”?

It wasn’t a life-or-death situation but who gets to decide what is deemed a business day? Several business I deal with are now closed on Friday so this may happen in the future with bill paying/payments, filing/returning paperwork, etc.

Business days are understood to mean Monday through Friday, excluding holidays, unless something else is clear from the context. If someone means “three of my own workdays, which are different than the typical schedule,” then the onus is on them to spell that out — ideally by just saying something like “by Monday” rather than expecting you to do any contorted calculations.

What you encountered was just one weird practice, not something you’re likely to run into repeatedly.

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{ 35 comments }

{ 35 comments… read them below or add one }

  1. NurseThis*

    Re: #1, Pre-pandemic there was a pattern of colleagues requesting to WFH because of child care issues. The manager thought it meant “yes you can work from home in this specific instance”. The coworkers thought it meant they could WFH whenever they wanted, blank check. It blew up when a coworker without kids noticed how often she was the only one in the office for emergencies and asked about WFH. She was told no and then she pointed out her coworkers were WFH 4-5 days a week.

    The manager had no idea that the reasonable occasional WFH had morphed into a staff working 80-100% at home. Then this snowballed to people taking time off without charging it to PTO. It all needed to be spelled out and consistently applied. Clarify clarify clarify what’s allowed and what’s not.

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    1. Cmdrshprd*

      I think it also depends on if Sally is salary exempt or hourly non exempt.

      In a previous job, SME were salary exempt, and while they got the same amount of PTO as hourly staff, the rule for them was PTO had to be taken in full day increments (8 hrs) so if they did any work in a day they did not have to take PTO. So for appointments that they needed a half day or a few hours off they did not have to use PTO so in practice they had unlimited PTO to a certain extent. But they often worked over 40 hrs, when needed and on nights/weekends.

      In the same company, some managers would allow hourly non-exempt employees to flex their hours, as long they stayed at or under 40 hrs a week. So an hourly staff could take a half day and make it up the rest of the week, or start early/late and still work their 8 hrs. In that regard they also kinda had unlimited PTO.

      By unlimited PTO I mean that you could take more time off than we technically had and/or without having it deducted from you PTO bank.

      All of the above was within reason. If a salary person wanted to take a week off and not use any PTO by sending one email per day that wouldn’t fly. Or if an hourly staff wanted to take 3 days off and work 40 hrs in 2 days that would not be okay.

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    2. r..*

      To be frank I am quite baffled with how the manager would have had no idea of this occuring.

      We’re obviously talking about a company culture with an expectation for onpremise work. Where is the manager? Are they not checking occasionally on the work environment?

      Do they not talk to their employees on a regular fashion? (I have a 1:1 with all my direct reports once a month and a skip-level with indirect reports at least once a year) If they do, and if they don’t notice most of their staff aren’t in the office most of the time, what exactly are they doing in this meeting?

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  2. Oaktree*

    Controversial opinion: I know lots of people hate reply all, but more problems are created by not using it than the annoyance of extra messages.

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    1. Nodramalama*

      I don’t think people hate reply all when there’s a business need for all those people to be on it. They hate reply all when someone does it for like, an organisation wide email

      Reply ↓
  3. Caroline*

    #1 – is this collaborator of Sally’s part of your team or subject to the same PTO flexibility your team has? Is it possible that Sally described your team’s unofficial flexibility and their work buddy is interpreting it more generously out of jealousy?

    I think I have similar flexibility — I’m exempt and work plenty of overtime, so I don’t use PTO for small things like taking a long lunch or popping out for a dentist appointment – my team is the same. We also work with groups that are paid hourly and coverage-based and short-staffed, with very little schedule flexibility. I can see someone misinterpreting my team’s flexibility from the hourly group’s point of view as extremely generous, if they’re not understanding the stress/late hours with no extra pay/travel expectations that go with it. When I hire new people, I give them a little spiel about how to make decisions about whether to burn PTO or not, and give them extra guidance the first few times they need some flexibility. I also coach them not to rub it in with the hourly teams, but I can’t always control that (it’s a small town so some of my people have personal relationships with the hourly group, and talking happens.)

    I would consider just sitting Sally down (or your whole team if there’s a chance of confusion elsewhere) and giving a talk about PTO usage. You could do it close to the end of the year and frame it up as a 2025 expectations conversation.

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    1. Cmdrshprd*

      OP4 I think you just unfortunately happened to email the case manager on the 1 day out of 5 that interferes with their Fridays off, and you got a boilerplate response or maybe an auto response.

      if you had emailed on any other day it would have been fine, Monday email response would have been due on Thursday EOD, Wed. email response would have been due Monday etc…

      I would say customer service response deadlines are more guidelines are like job hiring process take the time you are given and double/add a day or two to it. So if they said Friday, I wouldn’t expect/worry until at least Monday or Tuesday.

      I get it’s frustrating as a customer, but often things take time, and if they spent time sending updates at every deadline things would take longer. would you rather they take 2 mins each to update the 40 requests that it is taking loner aka 80 mins, or spend that time actually working through the requests?

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      1. KateM*

        I’m not sure about your math. Wouldn’t Wednesday mean due Tuesday instead of Monday, Thursday mean Wednesday instead of Tuesday, and only Monday be Thursday as expected?

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      2. Emmy Noether*

        Mh, if they are really interpreting “workdays” as ” days I work” at this place, then everything except mon-thu would be affected. For Wednesday it would be a response Tuesday, etc. And if this is because it will genuinely take three days of work to do, then that sort of makes sense (except it should be communicated as “by Tuesday”, not expressed in working days.)

        Reply ↓
  4. Rev Sev*

    #3 – One option would be to offer to connect with her first thing in the morning, 9am your time and 7am her time.

    Reply ↓
    1. Sleve*

      Or you could split the difference. You’ll reciprocate with a 7pm finish for every time she does a 7am start. Oh and it looks like it’s her turn, since you’ve already done yours.

      Reply ↓
      1. Isben Takes Tea*

        I might go for this if somehow this were a work requirement, but why would OP need to adjust their schedule just because a coworker asks them to?

        OP, I would consider it in the same way as if you worked at a retail store; it may be more convenient for your coworker if you stayed past your scheduled shift and helped vacuum and close up the shop, but you were assigned to be there early to open. It is not your responsibility to stay late just because they want you to; in fact, you could get in trouble for triggering unscheduled overtime. The ask itself is unreasonable. You should have NO qualms about giving a flat no or routing it back to their manager in the future.

        I work remotely with people across multiple time zones. I cannot fathom asking a colleague to work late last-minute to accommodate my schedule/workload, let alone regularly!

        Reply ↓
    2. EllenD*

      It depends what the colleague 2 hours behind wants. I had a team member who worked very different hours to me. He 6.30am to 3pm and me 9.30 to 6pm. Initially we had teething problems, but then we built up a rhythm. If he wanted my comments, he’d send before 3pm and I’d respond before I left so it was waiting for him when he arrived. Equally, I could delegate stuff to him at 6pm and by the time I arrived the following morning it would be done. It cut down waiting time. Meetings had to be arranged between 10am and 2pm. Once we got this rhythm going it was very efficient, as it cut down waiting time.

      Reply ↓
  5. Thepuppiesareok*

    OP3 is it normal in your industry for coworkers to ask each other to stay late? Because it’s not in mine. It’s actually considered rude and unprofessional. The few times it’s happened I’ve just ignored it because it’s so far outside of the norms for my industry. I work on mountain time and would never dream of asking my east coast coworkers to stay late. If I happen to be speaking to a client of theirs and it’s a question I can see they’ve been working on I’ll check if they’re still online and if so send a quick message, but that’s it. If I need something from them and they’re done for the day I send an email for them to get to when they’re back at work. Just like they don’t ask me to come in early I don’t ask them to stay late.

    Reply ↓
    1. Cmdrshprd*

      I would say the more relevant question is “is it the norm at this company.” It may not be the norm for the industry but could be the norm for the company.

      With that being said, it does not seem like the norm since the boss officially denied the request for OP to shift her hours.

      I do think it could be a valid question if most of the work/company was done on mountain time, but OP was remote on Eastern time.

      I have seen some remote positions that explicitly say the job is based on 9-5 EST, so a person in PST could apply but they would have to work 6 am to 2 pm PST. I could understand the frustration if OP and coworker had to frequently collaborate and they work off hours. OP might be a unicorn candidate that the company/boss has decided the trade off is worth having OP on board and coworker needs to realize the decision has been made.

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      1. Nodramalama*

        Yeah I think company norms really matter here. At my work people aren’t usually asked to work late but it would also be pretty uncommon to have a regular hard out by 5.05 and theyre not planning on logging back on after (i.e if they have to do a a school run)

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    2. Educator*

      Another perspective on #3: I work across several time zones, and occasionally coming in early or staying late is a really normal business expectation. If we all stuck to just 9-5, we would have trouble moving essential projects forward. Everyone understands that, and tries to share the burden of working outside of typical hours equally. Someone who was overly rigid about logging off at exactly 5:05 would really be out of sync with that culture of mutual compromise. You’ve got to know your company’s vibe on this stuff..

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      1. Myrin*

        That doesn’t seem to be the case at OP’s company, though – after all, the manager her coworker went to (which I think is in itself pretty outrageous, honestly – you don’t just go to supervisors and tell them you want another person’s hours changed!) said bluntly that it’s not necessary.

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  6. The Nanny*

    100% this is just my personal bias but I am so curious if Kaitlyn from #4 is their nanny. Simply because this is a thing that comes up a lot in nannying situations where the nanny feels more comfortable contacting one parent (or one parent unfairly has all of the Child Knowledge so it would be useless to ask the other) and the other parent ends up sidelined in the communication.

    IDK! Something about Kaitlyn being “new to the workforce” and OP4 mentioning they have other frustrations with her as a unit is pinging Nanny Bells for me.

    I agree with Allison in any case.

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    1. Not A Manager*

      I just re-read that, and I think you’re right. If it’s true that this is a domestic employee, I’d try to articulate clearly the reasons why it’s important for all the adults in the family to be included in every discussion. I’d also take a look at why one of those adults is primarily the one contacting the employee.

      Reply ↓
    2. len*

      If this happens to be correct and the LW was intentionally vague in order to anonymise the situation then this comment seems unhelpful. If it’s not correct then I suppose it’s also unhelpful.

      Reply ↓
    3. Emmy Noether*

      Mh, it didn’t read like a nanny to me. The use of the word “contact”, then having to email frequently about problems (wouldn’t there be more talking and less emailing with a nanny?), and having the “impression” she’s new to the workforce (would have seen a CV and been sure for a nanny).

      It does sound a bit like maybe Mike and LW are a couple. Maybe a daycare situation? Happens all the time to my husband and me that one of us will email someone about our children (daycare, extracurriculars, various administrative offices,…), putting the other in cc, and they will reply to just one of us. Since it’s usually one-off emails, we just forward it between us. It is kind of low-level annoying, though.

      Reply ↓
  7. Captain dddd-cccc-ddWdd*

    OP3 (work hours in different time zones) – So she’s continuing to make these requests even after officially asking for your hours to be permanently changed and being told no? I would be inclined to go back to whoever she made that request of and let them know it’s still happening – they probably think this is solved. I expect she disagrees with their decision so is now trying to take it into her own hands.

    It is tempting but ultimately unproductive to start sending meeting requests for 6am her time etc.

    Reply ↓
  8. Emily*

    I do think #5 was a tad impatient. If I was told 3 business days on a Tuesday, I would allow through all day Friday to receive a response and would then follow up on Monday if I had not heard. The case manager should have been better at communicating what her business days were though, since they weren’t the typical Monday through Friday.

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    1. KateM*

      I was thinking the same as it was on Tuesday afternoon so even in the best case, three days would be pretty much Friday EOD.

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    2. Nodramalama*

      Yeah I agree in my line of work cob Friday is basically anytime before beginning of business Monday. I certainly wouldn’t expect anything during Friday day.

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    3. Joron Twiner*

      Normally I agree, but if the issue was really urgent, I understand following up as Friday draws late. Especially since in this case OP was instructed by someone else at the company to contact this person–this isn’t an initial inquiry, it sounds like a follow up/escalation to me.

      Reply ↓
      1. Nodramalama*

        I think the issue here is that LW interpreted it as getting a response on Friday by the LATEST. And that three business days is sometime not at the end of the day on Friday. But in reality a response at 5pm on Friday would have been within 3 business days so to follow up before then is unrealistic.

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  9. Nodramalama*

    For LW1 I seriously doubt sally meant she literally thinks you are sending her some kind of secret coded message that would suggest she has a mental illness. At MOST I think she means that she’s been intepreting your responses as wink wink nudge nudge take PTO whenever.

    For LW3 I wonder if any of this could be mitigated by contacting your coworker earlier in your day? I wonder if possibly she just runs out of time to factor in the two hour difference.

    Reply ↓
    1. londonedit*

      Thanks for this, because I really didn’t grasp what was meant by ‘sending secret messages’. So Sally thinks the OP has been doing a ‘nudge nudge, wink wink, technically you should stick to 200 hours a year but really you can do whatever you want’ thing? But why has she been telling people that? Is it a situation where the colleague has mentioned something about taking a day off and Sally has said ‘Oh, technically I don’t have enough holiday for my time off next week either, but Jane says I can take as much time as I want’ or something? The whole thing seems quite odd to me. I’m also not sure why the OP jumped to the idea of a ‘mental health issue’ (?) but I think they definitely need to clarify with Sally – is it a misunderstanding on Sally’s part about how the PTO works? Or was it a misunderstanding on the colleague’s part, and Sally didn’t say anything about unlimited PTO? Whatever it is, it definitely needs clarifying.

      Reply ↓
  10. Collaterlie Sisters*

    I completely understand why OP1 thinks of mental health issues as if you spend a lot of time with someone in a crisis with schizophrenia or bipolar the secret messages can come up so much. It could just be an overreaction to the phrase but I wouldn’t dismiss it out of hand

    Reply ↓
  11. Artemesia*

    If the employee continually doesn’t CC, then don’t do it for her. Instead contact her and ask her to resend the message reply all. If SHE has to actually do the extra step she may remember and get in the habit.

    Reply ↓
  12. RLC*

    LW2, you are so polite and considerate to be asking about water flossing etiquette in the workplace!
    Years ago I had a colleague (adult braces wearer) who would brush and floss whilst carrying on a conversation with me. We worked outdoors so no office washroom; I asked him to turn away or at least let ME wander off until he finished the process.

    Reply ↓
  13. r..*

    LW3,

    considering she already went ahead and talked to your higher-ups — and if she did that without first advising you, this is quite rude — and got told off, I’d say you should talk to your manager.

    If you were my report I’d like to know about this situation, because it tells me that I have one of two situations at hand:
    1) There’s a genuine problem with timezone differences where your coworker is facing impediments to her work she can reasonably expect to see solved and not have to put up with in a permanent fashion.
    2) Your coworker is disrespecting the fact that your working hours are agreed between you and your manager, despite that she’s already been effectively told she needs to accept your working hours as what they are.

    Both situations would be my job to sort out, either on my own or in conjunction with whatever others I’d have to loop in.

    Reply ↓

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