my employee bothers her coworker with constant questions

by Alison Green on March 29, 2022

A reader writes:

I manage two employees who share an office. Jane is a long-term employee and stellar worker. Katie is a new employee in an entry-level assistant role. Jane has been venting that Katie peppers her with many intrusive questions. For example: “Who was that on the phone?” … “What did you just print?” … “Where are you going?” … “Where were you?” … “What was that person talking about?”

I’ve seen it myself because Katie asks me similar but much less frequent questions and I notice the awkwardness when I go into their office to discuss projects with Jane and can feel Katie staring at me, or making audible acknowledgments, as if she’s part of the conversation. I’m afraid this could lead to Jane quitting in the long run. Is this just a case of social ignorance or should I step in and address it? If so, how do I tell her to, professionally speaking, mind her own business?

I answer this question — and three others — over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

Other questions I’m answering there today include:

  • How do I ask my assistant to return the change when she picks up lunch for me?
  • How can I support a whistleblower?
  • Customer asked me to send a recommendation to her boss
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{ 181 comments }

{ 181 comments… read them below }

  1. Me (I think)*

    The whistleblower letter is kind of scary. I get why the media would be interested, but why the family of the deceased harassing her?

    1. Jessica Ganschen*

      I’d imagine that they’re lashing out because they’re grieving and have convinced themselves that despite being a whistleblower, she didn’t do enough to prevent it.

      1. Elizabeth West*

        If so, they need help, and I hope they get it/got it. Harassment is not acceptable, but the family and reporters should be targeting the company, not the whistleblower. The company’s negligence is the reason the person died.

      2. Goldfeesh*

        I wonder if the family has displaced anger that the whistleblower refused to do the job which resulted in their loved one doing the job which resulted in the person’s death.

        1. Emi*

          This would be my guess, especially if the worker who died was junior and less skilled, more vulnerable to coercion, something like that.

      3. Magenta Sky*

        Or they’re trying to get her as involved as possible as a witness in their lawsuit against the employer.

        Either way, there are proper ways to handle it, and what’s described isn’t it.

        1. Clisby*

          That was the first thing I thought of – not that they blamed her, but they’re asking her for more information on the dangerous situation.

          1. Clisby*

            However, that’s why you hire lawyers. People who are emotionally involved in a case should not be talking to potential witnesses.

        3. Observer*

          If I recall the original letter correctly, the employee had already given their testimony etc.

      4. Not Tom, Just Petty*

        Or even that she agreed to do everything required, but they still are calling, “you are going to testify, right?” “you are going to tell the truth, right?” “you are going to do the right thing, right?”
        Like a nightmare version of a job applicant confirming a company received his application.

      5. exlibrarianator*

        I’m assuming there is a lawsuit, and the family is trying to determine if the company had previous knowledge of unsafe conditions, and what they did to fix (or cover it up). If they know someone had already reported or spoken to the company and the company failed to make corrections then it would be evidence of the company being at fault.

    2. Batgirl*

      Thank you for filling in the blanks there! You can’t always read the whole story on that website. I was mystified why any employees at a new company would be harassing her.

    3. Bagpuss*

      It may be that they are involved in lots of campaigning or publicity over the issue and are trying to push her into being part of that, or tat they want her give them endless details – it may not be harassment in the sense of threatening her.
      (it’s also possible that her getting forced out because of her whistleblowing meant that their family member ended up doing the dangerous part of the job instead of her, or that they feel she should have specifically warned their family member, or that the employer spread misinformation about why she left and they belive that she was responsible for the accident)

    4. Aphrodite*

      I would suspect the family wants to enlist her in an upcoming lawsuit against the company. If their lawyer can show that a previous employee thought or knew the job was risky then their suit is much stronger.

      1. pancakes*

        I wouldn’t suspect that because they’d have to be getting terrible advice to be trying to DIY communication about such an important part of their case in such an off-putting and ineffectual way, or simply refusing to follow decent instructions. It doesn’t really matter, though — however they justify it to themselves, their behavior is inappropriate harassment.

      2. Team WFH Forever*

        While this is definitely a possiblity, assuming this is in the US, the lawyer for the family would be the appropriate conduit for this, the person to reach out to and potentially issue a subpoena for testimony. The family calling is inappropriate in a legal sense to make the call, and could in theory jeopardize a case depending on what was said and how.

        1. nonegiven*

          ‘Made redundant’ is the way they say ‘laid off’ in the UK and maybe other places. So it probably isn’t the US.

          1. Forrest*

            Yeah, although it would still be inappropriate and potentially damaging to a case here (since she could legtimately decide not to testify, and it would be very undesirable to compel her.) But of course, people do not always behave in sensible or rational ways, especially if they are grieving.

          2. Ace in the Hole*

            I’ve heard “made redundant” used in the US. It’s less common than “laid off,” but not terribly unusual.

    5. All the words*

      What sprang to my mind is that the family of the deceased may be trying to file a lawsuit and are “harassing” the new employee to try to obtain information that would help their case. Problematic, for sure, but not necessarily malicious.

      1. Richard Hershberger*

        That was my thought, but it should be the lawyers doing the investigating, not the family. One reason to have a lawyer is as an advocate who has a bit of distance from the occurrence.

        1. Ally McBeal*

          Exactly this. The new employee is known to the family of the deceased, and therefore would naturally come up in the discovery process. The employee can then decide if she wants to participate voluntarily or wait to see if a subpoena comes. I’m not sure I’d be able to rise above the harassment and voluntarily participate, if I were in her shoes, so it was in the family’s best interest to stop directly harassing the poor woman and let the lawyers handle everything.

    6. Covered in Bees*

      It could be misplaced blame. If employee had done the dangerous thing when asked, their relative wouldn’t have had to. This is not fair in the least at all but grief can make people seek out a source of blame and they might have been stopped from harassing the ex company.

      1. Mannheim Steamroller*

        In other words, “our relative died because OP refused to.”

        In that case, they should just sue OP for wrongful death.

      2. Green great dragon*

        This is the only thing that makes sense to me. Maybe they feel the employee didn’t do enough to warn the relative or something like that. Totally unfair of course, but sometimes grieving people aren’t fair.

    8. Nanani*

      They may be being fed wrong information by the company or have gotten an incorrect impression of who is responsible because whistleblower is in the media coverage, but the company is a faceless corp or something like that?

      And sometimes people lash out when they’re greiving.

    9. lost academic*

      It’s common for there to be some rewritten history or at least a narrative that’s pushed when someone leaves no matter the reason – and in this case doubly so, since the employee left and then there was a fatality. Maybe the story they’re trying to tell is that it was improper training that was the result and that was her fault – I can definitely see that.

      1. RagingADHD*

        For all we know, the employer could have accused the whistleblower of sabotage.

        “That machine was working just fine until WB left. We fired them for incompetence and now…look what happened.”

        It’s not that hard to make people believe the worst.

    10. ResuMAYDAY*

      They probably want her to testify on their behalf, and give them any more information that will help their case. They could also be setting up fundraisers and memorials, and want her to take part in them.

      1. Mannheim Steamroller*

        Or they want to sue her for “causing” their relative’s death (by refusing to risk her own life).

          1. Marzipan Shepherdess*

            Well, it wouldn’t be rational, but when we’re reeling from a beloved family member’s preventable, utterly unnecessary death then we often aren’t fair or reasonable. In fact, if that company HAD listened to the LW’s warning about working conditions, LW’s late successor wouldn’t have been killed on the job – another reason for the family NOT to blame LW for that terrible accident! But the stark truth is that LW is alive, their colleague is not and the latter’s family would naturally prefer that it was the other way around.

            But as for the innocent and brave LW; isn’t this where the LW’s current employer’s HR department and legal department should become involved? With all due respect to the grieving family, should they really be allowed to go on harassing the LW at their workplace? Does an employee have a legal right to be free from harassment while on the job, or does that only apply to the behavior of their colleagues – not outsiders? Alison, what’s your take on this?

  2. Wisteria*

    Normally I’d suggest that you first coach Jane to address this herself, but it sounds like Katie needs significant enough coaching that it makes sense for you to take it on.

    You can do both concurrently. With Jane, start by letting her know that you will be coaching Katie, and ask her whether she responds in the moment and how. Let her know that she has your imprimatur to respond to Katie in the moment and coach her on the how.

    Expect that you will need multiple conversations with both to achieve harmony. Coaching is never a one-and-done talk.

    1. Sara without an H*

      Good suggestion. I noticed that the OP reported that Jane had been venting to her about Katie’s behavior, so really, there are two employees in need of coaching.

      Coach both employees, then follow up as needed.

    2. Ama*

      Yeah I think Jane needs some reassurance from OP that it is okay for her to tell Katie bland non-committal answers like “oh, it’s nothing you need to worry about” or “just some work stuff.” She may be having an issue figuring out where she can draw the line between providing info Katie might need to know for training and what she doesn’t have to answer — for that matter it sounds a lot like Katie doesn’t know where that line is either.

      1. Momma Bear*

        I agree. I think this is two-fold. Jane can say, “That was not work-related” and leave it at that and Katie can also learn not to be so nosey. I wonder if some of it is also Katie feeling anxious about a new job and just wanting to know what’s going on. Sometimes intrusive behavior is really about someone else’s anxiety vs what you are doing/not doing.

    3. Chili pepper Attitude*

      I’d tell Katie that you have directed Jane to say, x script, for questions that really should wait or not be asked. And tell Jane to say x script or similar.

      Give them some wording so they have a direction to get them started. Katie knows it is you giving this direction and both know this is the process you want, it’s not really them (even if it is).

      1. Wisteria*

        I’m a little tickled at the thought of an unwanted questions process.

        “Katie, per my instruction, Jane shall henceforth answer prying questions with lyrics from The Mikado. Please do not take it personally, that is the process. I recommend you acquaint yourself with I’ve Got A Little List so you can recognize when this happens.”

  3. TimeTravlR*

    In some cases, you don’t need to set up with a food delivery app. You can just order and pay online and have your assistant go pick it up.

    1. Nanani*

      This is a thing food delivery apps general handle, and depending what restaurants are nearby, a food delivery app may be the only practical way to do so.

      Wasn’t long ago that unless you were in a handful of major metros, all food delivery was either pizza chains or full-blown catering for 100s of people. Delivery apps cover both arranging drivers and coordinating pickups for a lot of places.

      1. ArtK*

        Delivery apps can also be horribly unreliable. I’ve had orders mysteriously cancelled or stolen several times. We do use online ordering sometimes, but always go and get the food. We try to order directly from the restaurant as well; the delivery companies can take up to 30% of the purchase price. That’s above and beyond any “delivery fee.”

      2. Artemesia*

        I order food on line or by calling all the time and then someone picks it up. You don’t have to use one of those rip off services to do this. Just prepay on line. And this situation is a good example of give an inch. The first time change didn’t come back, the OP should have mentioned it. Now the employee feels entitled to her money.

        1. Nanani*

          That’s great if you live somewhere where restaurants do that, but my point is that outside very select areas, only a few pizza chains offer this kind of thing off-app. Most restaurants don’t have their own delivery infrastructure even now. Can’t prepay online when the restaurant website doesn’t have that option, or redirects to DeliveryMunchies anyway.

        2. somanyquestions*

          Now the employee feels entitled to her money

          And isn’t that a disturbing turn? Who does that?

      3. 1-800BrownCow*

        “Wasn’t long ago…”. Actually that is still true for some people today. Try visiting some very rural areas. Although on the flip side, having an assistant go pick up food in those locations isn’t ideal either. Where I grew up, the closest place to get food is 30+ minutes away and many businesses still only take cash. Using delivery apps is not an option, you either bring your lunch or eat from the vending machine.

        1. Nanani*

          Indeed!
          The “you should order direct from the restaurant!” crowd either don’t know or don’t care that a lot of places just -don’t have restaurants- that offer this. Even if you rang them up, a cash only restaurant will still require your pickup person to bring cash, which is LW’s whole problem.

          1. Wisteria*

            The “you should order direct from the restaurant!” crowd either don’t know or don’t care
            [snip]

            What an odd response. The recommendations were qualified in a way that I find makes it obvious that the responders do both know and care that the option might not be universally available. Furthermore, if the letter writer is ordering lunch frequently enough to lose close to $60 in change over three weeks, then it’s highly likely that they live in a place with high restaurant saturation, which makes ordering direct a reasonable thing to try. An answer doesn’t have to solve the problem for every person everywhere to be a viable one for the LW.

        2. Rolly*

          “Where I grew up, the closest place to get food is 30+ minutes away ”

          I don’t see how this relevant to the OP’s situation.

          I mean, I guess I should look forward to someone working on a submarine to chime in with how we’re all taking getting pick-up food at work for granted.

      1. Ace in the Hole*

        Assuming the restaurant accepts direct online payment, which most in my area don’t. Heck, we still have a lot of businesses that are cash only… you can’t even pay with a card in person. Many of them accept phone orders for take-out, you just have to pay when you get there.

      2. Zombeyonce*

        Yes, this is likely to almost double the amount OP is spending on lunch with the service fees and the tips. Plenty of restaurants don’t have direct ordering online, but OP would likely end up spending less by just letting the assistant keep the change rather than using a delivery app. (Not that I recommend that, just that Alison’s suggestion overlooks this.)

    3. Iroqdemic*

      In the Before Times when I was still in the office, we would Paypal or Venmo each other for stuff like this. Made it way easier.

  4. Aspiring Chicken Lady*

    I would want to offer the whistleblower a sort of communications firewall. Even if normally people can come to the office and ask for an employee by name, I’d have the reception staff ask for the purpose of the visit and then automatically set an appointment rather than providing immediate access. And expressly encourage the whistleblower to screen any calls from unknown numbers by having them go to voicemail. Using filters on email messages to pull out things related to the case might help too. (And if listening to the messages or reading the emails is upsetting, have someone else review them first)

    It’s the kind of protections that could be put in place for someone who was being stalked.

    You could even have “internal” and private communications, like an alternate email or phone number so that the whistleblower could “safely” interact with team members etc.

    Obviously, it depends on what the person wants or needs, but offering specific examples may help to shape their “ask.”

    1. Avril Ludgateau*

      On that note, I feel like “employee safety” should be a reason to practice discretion with an “all employees are listed publicly on the website” policy. On one hand I understand the employer’s desire for transparency, but it should always be opt-in. Many people have completely legitimate safety concerns; the whistleblower in letter 3 is just one example.

      1. Pomegranate*

        That’s a good point in general. However, in this case the requirement for the public listing is from the whistleblower’s professional organization, such as maybe professional engineering society. Basic employment information and accreditation status are typical to be public information for such professions. I wonder if the professional body can temporarily restrict access to employment information, but it wouldn’t be something the employer can do.

        1. Littorally*

          This. My profession requires that my name, record number, current employer, past employers in the industry, and elements of my disciplinary record (if any – happily, I’m clean) be publicly available on a website operated by our regulator. My company has no power over this.

          The ability to minimize opportunities for stalking is a really important discussion, but there’s a solid chance it’s not something that’s actionable for this OP or their hierarchy.

          2. Yup, another Jennifer*

            But OP says “and per the regulations of her profession she is listed on our website” – not a professional org’s website. I actually wonder how much that is actually the case, and how much it’s a norm but not a requirement.

            2. Observer*

              It’s still something that is required by the regulating body, not the the OP being obnoxious. I think we can trust the OP when they say that it’s actually required.

    2. ferrina*

      I love this solution. If it’s possible that the whistleblower can have their communications screened so they only work with vetted clients, that would be a relief. If that’s not possible, setting aside part of their day for special projects where they don’t have to work with folks that might harass them might be a relief.

      I’d add that you should make sure that the whistleblower is very aware of the EAP and is allowed as much flexibility as possible for both legal issues and taking care of their mental health. Be explicit about what benefits they have available and what they should do to trigger these benefits (don’t just hand them the brochure, but walk through it with them).

  5. KittyKate*

    The whistleblower one is shocking! I feel badly for the employee, but grateful she works with a great manager.

  6. WomEngineer*

    LW 1 might also clarify how much overlap there I should be between Jane’s and Katie’s roles and/or if they’re supposed to have a mentor/mentee relationship. Are there aspects of Jane’s role that Katie should be privy to? Also I’d Katie interested in a similar role to Jane’s in the future?

    I may be biased as someone in an entry-level role, but Katie’s questions didn’t strike me as intrusive. I’d ask similar things to my mentors at work to understand how everyone’s roles are supposed to work together.

    1. Dust Bunny*

      They struck me as intrusive. If your coworker gets a phone call do you ask who it was, or do you assume that if you needed to know about it, they would tell you?

      The questions the LW provided don’t sound like things Katie needs to know. They sound like mindless compulsive questioning about things that Katie doesn’t need to know unless, well, she needs to know (for work), and there is no basis here to think that Jane is hiding needed information from her. Katie’s curiosity doesn’t entitle her to pester Jane about every little thing.

        1. Clisby*

          I don’t, either. Possibly because 9 times out of 10 the answer is “another telemarker.” If I overheard him make some comment like, “What do you mean, he’s dead?” I’m sure I’d ask, but so far that hasn’t happened.

      2. Hey Pal*

        This. It sounds so exhausting! Like sharing an office with a toddler. Katie may be genuinely trying to learn, but she is going about it in a way that’s inappropriate, disruptive, and alienating. All the more reason for coaching from the LW!

    2. Zan Shin*

      As one who has been mentor and mentee – if I were doing routine copying and it was important for my mentee to know what, why, and how, we would have already been working on this project jointly. None of this was implied in the OP letter. Just questions out of left field about another’s own tasks.

    3. Wisteria*

      It’s fair to want to understand how peoples’ roles fit together, but asking “Who was that on the phone?” … “What did you just print?” … “Where are you going?” … “Where were you?” … “What was that person talking about?” is not the way to go about it. The answers to those questions are just as likely to be personal as work related, and you don’t need to know that Jane was on the phone with her spouse, printing out her summary for her performance review, going to/in the restroom, or that Joaquin was talking about their prize-winning petunias.

    4. CatPrance*

      “Who was that on the phone?”
      “What did you just print?”
      “Where are you going?”

      That’s not intrusive? Someone listening to my phone calls and wanting to know who was on the other end? Someone wanting to know what I just sent to the printer? I stand up and the person wants to know where I’m going?

      That’s really intrusive. That’s downright nosy. Understanding roles is important, yes, but “Where are you going? What did you just print?” is waaaay beyond “understanding roles.”

      1. Antilles*

        Agreed. At absolute most, you might be able to occasionally comment/ask about the phone calls if it sounds like something particularly notable.
        Like, if you hear someone screaming loud enough through my phone that you hear it sitting across the room, you can get away with asking “oof, that sounded rough, everything okay?”. Or maybe if I sound super-thrilled and talk about we’re looking forward to working together, you could say that it sounds like there’s “good news”.
        But this is very much a pick-your-spot / read-the-room kind of thing that you do on super-rare occasions, not a standard practice.

        1. Arts Akimbo*

          Ouch, this reminded me of an employee I was training! We were on the sales floor, in front of customers, when I said a quick “I’ll be right back” to her. She said, LOUDLY, “Do you need to tee-tee?” I was shocked into silence for a second, then I just repeated, “I’ll be right back.” smh

    5. yikez*

      “Where are you going” and “where were you” aren’t things that a mentee really needs to be privy to, and if you’re asking coworkers that you should probably cut it out.

      1. KRM*

        And if this is Katie’s really inelegant way of saying “people stop by and ask for you all the time if you’re gone for longer than 5′, what do I tell them?”, then you coach Katie to say “Hey Jane, people often come by looking for you, what would you like me to tell them when you’re not here?”. That way Jane can say “tell them to come back at 2” or “I’m stepping out for lunch, if anyone is looking for me tell them I’ll return in 45′”, or what have you. Otherwise it’s just inane questioning on Katie’s part that would drive me insane.

        1. yikez*

          I would be tempted to overshare, but that would probably just lead to more questions.

          “I was changing my tampon.”

          “Yeah!? What kind do you wear?? How’s your flow?? Is it regular!??”

          1. The Rafters*

            I did something similar to a now former boss who was – not nice would be an understatement, and it wasn’t just me. He was so taken aback by my comment that he shut his trap, turned and walked away. The BS slowed down a little bit after that until I was able to make my escape.

    6. Antilles*

      A bunch of the questions listed by OP aren’t mentorship type questions though.
      Where’s the learning opportunity in knowing that I just printed a copy of a report or that I was grabbing lunch? Or that I was on the phone with a client discussing a generic project?

    7. Nanani*

      It sounds intrusive in the sense that it’s over-familiar, like something a nosy neighbour who thinks you’re closer than you do would ask about every visitor to your door.
      Not to mention the tedious nature of being interrogated on every minor thing you do in the course of one day will grate over time. If it was part of Kate’s job to shadow Jane, Jane would be proactively explaining it wouldnt she?

    8. JSPA*

      You might also be pushing the boundaries of legitimate questioning, then. If the only reason you’re in on a conversation is because of the location of your desk, it’s generally not legit to ask follow up questions.

      Here’s a thought exercise that you can carry out in real time. Before you ask a question based on something you happen to overhear, imagine starting it with, “I’m sorry, I couldn’t help but overhear, and if it’s not personal, would it be OK to ask…”

      And then decide whether that’s really a question you ought to be asking. 3 times out of 4, it probably isn’t. The 4th time–even if it’s a judgement call–will be far more acceptable, if you didn’t ask the other three.

      (Sure, keep your eyes and ears open! But asking for more information, consistently? Unless you’re the owner’s kid, and given all kinds of slack because people assume you may be inheriting the business some day, that’s too much. Nobody has an absolute right to be read into every interaction, in every place that they work. Or, for that matter, in other social situations. Defaulting to, “What’s their deal” is maybe fine in high school; this isn’t that.)

    9. Observer*

      may be biased as someone in an entry-level role, but Katie’s questions didn’t strike me as intrusive. I’d ask similar things to my mentors at work to understand how everyone’s roles are supposed to work together.

      So, and important piece of advice. Do NOT do this. There are many other ways to find out how people’s roles operate, how different roles interact etc. On the other hand, this is actually NOT a good way to get the information you legitimately want.

      When you ask people where they are going, who they are speaking to, what someone said, etc. you are asking for information that is likely to be personal, not appropriate for you to know and / or simply not relevant or intelligible without a lot of context that you don’t yet have. At best it wastes people’s time and annoys them. And yes, asking people for information that you don’t need and have no right to is definitely intrusive.

    10. Medusa*

      You ask your mentors what they just printed? I don’t understand how that’s not intrusive. If it’s for you then they’ll tell you.

  7. Essentially Cheesy*

    As an assistant – I would never just “keep the change” if I were sent/volunteered to go on a lunch errand by a manager. Ever. Order details or fuel usage or whatever other details are out the window.

    However, in this day and age, we do utilize at least one food delivery app and cash money usage is not an issue. I can see how it would quickly add up though!

    2. irene adler*

      And here I’m thinking: The least I could do for someone who did me this kind favor is to let them keep the change.

      But then, no one’s ever brought me my lunch.

      1. Cricket*

        I had the same thought. When I had an entry level job at an office, one of the execs had a “I’ll buy if you fly” policy where she would cover both of our coffees or lunches, if I would be willing to go pick them up. Where is the LW located where $20 would result in significant change from lunch, anyway? Around here, $20 would barely cover a sandwich, a soda, and a bag of chips. I would also consider that the assistant might be dropping a dollar or two in the tip jar when picking up takeout. But I do understand that prices are regional.

        1. Yorick*

          Where I am, you CAN buy a lunch that’s in the teens. Even then, the more expensive lunch place my husband and I sometimes go to during the week (we both work from home) is $28 for both. And you can also go places that are like $8 for a lunch combo. So either way I’d be pretty mad not to get my change back.

        2. Underrated Pear*

          I don’t think it matters how significant the change is, unless it’s like $0.14 or something. I would never dream of just pocketing a few bucks of my boss’s without being explicitly told I was free to keep the change!

          And I guess it depends on what and how much you eat, but I live in one of the most expensive areas of the US, and when I occasionally grab lunch, it’s about $10-12 (poke bowl, burrito, salad, 1-2 basic sushi rolls). Sure, you *can* easily spend $20, but assuming that few regions have lunch options that are significantly less than $20 does not line up with my experience. The LW said it’s been about $60 over 3 weeks, which equals *at least* four dollars per lunch if she got lunch every single day (and much more than that if it’s just 2-3x a week). But again, moot point!

        3. BritChickaaa*

          Do you not have Meal Deals in the USA? Over here, a sandwich, bag of crisps and a drink costs £3.50.

        4. Ace in the Hole*

          In my area, you can easily find lunch for $10-15. Less if you don’t mind fast food. Some examples of what’s available for about $10 here: bagel sandwich and coffee, large burrito with chips and guacamole, cheeseburger with small fries and a drink, two slices of pizza with a drink and cookie, large salad with lots of toppings from the local deli…

          I think the key is to look at how much LW was expecting to get back in change. If she were only short a couple dollars, it would be reasonable to think the employee might be putting it in the tip jar. But LW says she’s missing $60 over just a few weeks…. that’s a lot!

      2. CatPrance*

        People in my office will occasionally run out and get something — hamburgers, taco salad, or whatever that they have a taste for, and they’ll offer to pick up something from McTacos or La Burger Vita for coworkers.

        If I hand someone a $20 for a burger and fries, I damned well expect to get my change back, and I’d expect my change for a $10 as well. (McTacos and La Burger aren’t all that pricey.) We all end up picking up lunch for each other, and there would be some definite side-eye and Questions Asked if the bag o’ food wasn’t accompanied by the change.

        1. urguncle*

          I think it’s probably best to keep in mind both a power and salary differential in the letter that doesn’t exist from round-robin picking up your coworkers occasional lunch and if the same person always picked up the lunch, they might feel differently.

          1. Yorick*

            That really doesn’t matter. It’s not ok to keep someone else’s money even if they make more than you. And in some jobs, this is part of an assistant’s role (not all jobs, so OP should think whether they should stop relying on the assistant for this even without the change issue).

          2. somanyquestions*

            No, that is completely not OK. Keeping someone’s change is not ever a thing, unless they told you to do so.

      3. KateM*

        From original letter, the change was sometimes more than the lunch – OP giving $20 for a $9 meal etc.

      4. Littorally*

        I guess it depends on how much the change is. If the OP hands her assistant a $20, is the assistant picking up $10.50 worth of food or $18.50 worth?

        2. Dust Bunny*

          Irrelevant. It’s still not the assistant’s money. If the assistant doesn’t like the extra driving on her own car she needs to take up mileage reimbursement or whatever with management.

      5. Essentially Cheesy*

        I think it would have to take the manager saying explicitly “and keep the change for doing me a favor” or “get yourself a sandwich too”. But it would have to be said, out loud, and directly.

        But in this day and age of expense reports – where every dollar (nickels and dimes and pennies) are counted – even claiming $20 on lunch probably would not work when the receipt doesn’t match.

      6. ferrina*

        Depends on how much the change is. If the change is an inconsequential amount to me, I’d let her keep it (assistants tend to be underpaid). I’d let $1-2 slide (based on my personal budget and comfort level). I’d also let it slide if they didn’t realize that I wanted change back, but that would be a 1 time thing and need to be a pretty small amount.

        The weird thing to me is that the assistant has been getting lunches for a while and only recently started keeping the change. Why the change in behavior? Has she been going through financially tough times and thought her boss wouldn’t notice? Is she resentful and feeling entitled to the money? Is she distracted and hasn’t even noticed that she hasn’t been giving the change?

        1. Medusa*

          My guess would be that she is distracted, although that’s based on nothing besides my own experience

        2. Kelly L.*

          That’s why I think the theory that the menu items have gone up in price is very possible.

    3. Orora*

      If an assistant is sent to get lunch, they should be reimbursed for their mileage or transit, because it’s required for their job. If the assistant volunteers, reimbursement is not necessary, but throwing them a few dollars once in awhile for gas is a thoughtful gesture.

      However, in neither case should the employee deduct these amounts from the change unless specifically authorized to do so.

      1. Yorick*

        In some cases, the assistant may be able to walk over and pick up the lunch. Reimbursement wouldn’t be necessary, but if she’s hourly she should still be paid for that time.

        1. Dust Bunny*

          If she’s doing it on the clock then she’s already being paid for her time. If she’s off the clock she has standing to refuse.

      2. Khatul Madame*

        The letter did not mention that that assistant needs to drive to get food. They may be in the city where cafes are within a short walking distance, or there may be a deli/coffee shop in the building.

      3. Kippy*

        If they’re in a downtown metro area they probably aren’t driving anywhere so no gas reimbursement needed. If I run to pick up lunch for my boss, I’m probably getting it from one of the six places in my office building.

    4. Antilles*

      For me it depends on what we’re actually talking about when we use the word “change”.
      If we’re talking about a buck or some coins, then it’s whatever; if you want to make a big deal over 43 cents, you can go ahead and buy your own lunch from now on.
      If we’re talking a more significant amount, then of course you return it.

    5. The Rafters*

      If OP doesn’t want to use a cash app for whatever reason, she can also give her admin smaller bills.

  8. Richard Hershberger*

    Katie sounds exhausting. Were I in Jane’s position I would be asking that seating be rearranged. And yes, if nothing else changed, I would be looking elsewhere. Life is too short for this nonsense.

    1. Heffalump*

      Rearranging the seating strikes me as a Band-Aid. Katie would probably start bugging whomever she sat next to. I’m a believer in shutting down unprofessional behavior, full stop.

      1. someone*

        Rearranging isn’t a good solution from LW’s perspective but can be from Jane’s perspective. Katie will likely annoy her new neighbor and still be LW’s problem to solve, but it won’t be Jane’s problem anymore.

      2. anne of mean gables*

        Honestly – it would be doing Katie a kindness. I don’t know why or how she is operating under the assumption that this is normal workplace conversation, but she deserves to have the opportunity to align herself with office norms.

    2. LittleMarshmallow*

      In my office we have someone that does this (she’s 6 years into the working world and still hasn’t figured out that people hate this) Her motives seem to be around feeling important because she knows what everyone is doing. Moving her doesn’t help. She just wanders if she’s not sitting by someone interesting enough or moves focus to her new area people. It’s very annoying and I wish our managers would do something about it. They know about it because everyone vents to them about it too, but they won’t address it so here we are 6 years later and people just try to avoid her as much as possible and hope she quits eventually.

      I hope LW can address this early so that their employee will learn what is and isn’t grating to others so that she will be less likely to end up like ours.

  9. blackcat lady*

    Re: whistleblower – first off I am NOT a lawyer. I realize the family is not threatening her so a restraining order is not an option. But they are hounding her at work and this is where my legal knowledge is zero. Can you help her get legal advice for any kind of a “keep away from me” letter? Can you document the frequency of visits and phone calls to show that it is a disruption to your company?

    Since this is a revisit of old letters was there ever an update?

    3. Velawciraptor*

      If the family doesn’t have a legitimate need to come to the office, the company could issue a trespass notice (essentially written notice that they are not welcome on the property and that, if they return, police will be called and trespass charges will be pursued).

      I don’t know that that’s an option that LW wants to pursue. Putting in writing that you’re going to call the cops on a grieving family isn’t a great look and LW says that the press remains interested. But it’s there.

    4. RagingADHD*

      In some places, a charge of harassment doesn’t need to be threatening in order to qualify as a crime.

  10. Shoney Honey*

    Sometimes your lunch is more expensive than you think. When I would give my (then) boss his meager change from a $20 my boss would say “It was just a $12 sandwich!” but actually, no, it was a $12.99 sandwich AND you upgraded to truffle fries AND you got a drink AND I tipped the hostess that prepared and brought your lunch to me. Not saying that’s what is happening here, but it’s worth a thought.
    I was so glad when my former company put a rule in place about assistants no longer picking up lunch. They were concerned about liability (someone getting in an accident), not concerned about assistants, but it was a lovely change. I always brought my own meals from home (on a special diet due to health issues), so I couldn’t pick anything up for myself. I wasn’t getting mileage or any sort of reimbursement for the driving, and I would often have to rearrange my lunch timing to pick up his food. It was very pleasant to be able to say, “Sorry, I can’t do that anymore, remember?” when he would ask me to pick up his lunch for him. That was a hard change for him, though. His assistant prior to me was with him for 20 years and not only picked up his lunch for him but once she got it back to the office would plate his food and even cut up his meat.

    1. A Simple Narwhal*

      Goodness, did she pat him on the head and tell him he was a good boy for eating all of his veggies too?

    2. Dust Bunny*

      “not only picked up his lunch for him but once she got it back to the office would plate his food and even cut up his meat.”

      Dear gods did she feed it to him, too? Yikes.

    3. Tipstipstips*

      Omg! That’s hilarious!!

      The only thing that gave me some pause in your description is tipping the counter staff when picking up an order. This is far from a typical practice to my knowledge (I tip waiters, delivery drivers, but I don’t tip when I pick food up). I would say you shouldn’t tip on behalf of someone in a situation where it isn’t necessarily expected without clearing it with them first. Like, *you* might contribute to a tip jar every time you grab coffee but you shouldn’t do that with someone else’s money.

      1. Shoney Honey*

        Absolutely a fair point to not do this with someone else’s money, but I have always tipped for takeout. I used to work as a hostess, and when a takeout order would come through, I had to do all the things a waitress did for that order – prepare salads, box food, hand-blend milkshakes and prepare drinks. So I had to prepare orders while also doing all my other hostess duties, and that was challenging. That may not be the case at all restaurants, but it was enough to instill in me to tip for takeout. In fairness, I did tell my boss this as well – I would always remind him I was going to tip a buck or two and he was fine with it.

        1. The Rafters*

          Since COVID, I normally tip even for pickup; I figured the staff may not be getting the hours they used to pre-COVID and I figure every little bit helps.

          1. CupcakeCounter*

            Same – I would usually throw a buck or two on takeout orders from a traditionally sit-down restaurant but nothing like what I would tip on a delivery or if I was eating in-house. Started giving a more traditional tip during Covid because I knew how hard that industry and those workers were hit and now that everything has opened back up in my area, simply kept doing it because I started paying attention to the amount of work that still had to be done.

        2. Gumby*

          I tip for takeout too but not as much as eat in. Because with take out no one is washing my dishes for me or bringing me refills on my drinks. So I might tip closer to 10% than 20-22%.

    4. Cricket*

      Yeah, maybe LW knows to the penny how much lunch should cost, but if not, s/he could start asking for receipts to confirm that the assistant is in fact pocketing $20/week. Maybe prices at the usual restaurants went up. I just wonder if the LW is really giving the assistant a $20 bill every time, how much does the meal cost, because for the assistant to pocket $4/day, it would have to cap off at $16, and that seems tight.

      1. Rolly*

        “s/he could start asking for receipts”

        No.

        This is not that complicated. Just ask for change. The OP should just ask for the change, or that it be left on their desk.

        1. Cricket*

          You’re right, there’s no need for the LW to not be straightforward. I wonder actually if the assistant is already providing receipts and that’s how LW knows how much the change should be. Come to think of it, whenever I have picked up anything with someone else’s money, I have given them the receipt. As the LW, though, I would still want the receipt regardless of the change situation, to be sure I know how much my order cost, that it was charged correctly, and that I gave enough money to cover my order. Otherwise it would cross my mind that perhaps I *wasn’t* giving the assistant enough and that it was coming out of her pocket, and maybe she feels awkward to bring it up. I feel like that’s been an AAM question, come to think of it—how do I tell my coworker/boss I can’t pay for their coffee/lunch anymore?

      2. Goldenrod*

        I used to get my boss’ lunch. I would never dream of keeping her money! I would keep the change in a purse in my desk which would then go towards the NEXT time I bought her lunch.

        She was horrid. But that’s neither here nor there. If this is a regular thing, the assistant should not be pocketing the change, that is extremely weird.

        But also: due to the power deferential, I would strongly advice OP to just use a delivery service, as Alison suggested. The assistant may not be happy to be doing this, but may be afraid to speak up. I certainly was.

    5. Nanani*

      This is especially likely if the boss hasn’t been going out to buy their own meal in many years and just hasn’t noticed the price increases.
      Still, it’s a use your words and find out situation.

    6. Artemesia*

      The phrase ‘fix a plate for him’ just always fills me with rage which seems silly. I think it comes from my background in. a religious culture where women were expected to ‘fix plates’ for grown men and wait on them. It symbolizes sexist culture that demeans women to me. The only time except serving dinner from the kitchen that I ‘fix’ my husband’s plate is if was helping the kids get their meals and so I made his with mine.

      1. Shoney Honey*

        I understand exactly what you mean. I grew up in this culture and married into a similar one. My (now former) mother-in-law still insists on fixing a plate for my 14-year old son (something she did not do for my daughter at that age, fwiw). It makes her happy to do it, she swears. I tell him all the time that is something special his grandmother does for him because she loves him very much, but he should not expect it from anyone else. We once brought dinner over to their house after she had a shoulder injury and she kept trying to insist that I make his plate for him. I politely declined. She went into the kitchen and took his plate and started trying to shovel more food onto it and then arrange it for him, all one-handed. Such a weird, infantilizing thing.

      2. Dust Bunny*

        I definitely did not grow up with this and it fills me with silly rage, too, because it’s something we’d only do for a very small child or someone who was unable to come to the table (ill, injured, frantically finishing our Hallowe’en costume for us, etc.). Everyone else who was able-bodied and able to carry a plate served themselves.

    7. Kelly L.*

      Ayup. I’ve definitely had the boss who was like “It’s a $5 sandwich, so here’s my $5!” and then blithely skip away, never mind that tax and tip exist, and that would end up coming out of my pocket because she’d be MIA until it was time to eat.

      1. Cricket*

        That’s why I refuse to coordinate group food orders at work, or use my food delivery account. Most people want to calculate the cost of their food exactly, then maybe round up to the nearest dollar, forgetting to factor in the $1.99 delivery fee, tip, and tax. Calculating everyone’s actual total and making sure everyone pays their share is too exhausting. I rarely partake when someone else is ordering, but when I do, I am overly generous to make up for that inevitable coworker who screws over the orderer.

      2. jtr*

        You know, my mind went kinda here – what if some of the food has gone up in price, so the assistant has been covering those, and just figures it all evens out?

        I think she should use her big kid words and say that prices have gone up, and NOT pocket any change, if that’s the case, though.

        1. Kelly L.*

          There may not be any change anymore. Let’s say the bill used to come to $19, now it’s $21, boss still sends $20, assistant is paying with boss’s $20 and covering the other $1 herself. And doesn’t feel comfortable telling boss they’ve been underpaying.

  11. Been_There_Done_That*

    Regarding the change keeper, first, I wonder about the OP’s workflow that literally keeps him/her from obtaining and eating lunch? I’m all for hard work, but it the situation is as described, perhaps there is a larger issue that needs to be addressed? I mean no time to eat? What happens when a potty break is needed? Are phone calls taken in the john? Beyond that, is the assistant getting in a personal vehicle to go get lunch for the OP? Is the assistant going anywhere that assistant would not be going anyway? I think I would try to avoid having an employee consistently and informally be tasked with running out to grab me lunch. I think the better approach, if the OP is literally that busy, is to build food delivery into the budget. Alternatively, make that type of errand running part of a job description and make a company vehicle available to do so, with the associated insurance. The company lawyer will lose some relaxing lunch time over the issue of what insurance applies if there is an automobile accident and whether there is workers comp available if the assistant is out running errands that may or may not be considered work related. I don’t think keeping the change is appropriate, but I think OP has some larger issues to resolve beyond the change.

    1. Xaraja*

      I thought the same thing about why the boss is not able to eat. I guess technically my bosses sometimes seem to run all day though.

    2. CatPrance*

      Maybe there isn’t a food source stand within easy walking distance, food delivery isn’t a possibility, meetings and paperwork and administrivia keep OP from going out for lunch, and a similarly tight personal life keep OP from bringing something.

      I have no trouble understanding that. Me, I usually bring my lunch, but I have coworkers who have entirely too much to do in their lives for that to be an easy possibility. Someone with a 45-minute commute, two kids to get out to the bus and a third to drop off at daycare does not have a lot of extra time in the morning — or in the evening.

      1. Been_There_Done_That**

        Well my larger point was that if there is *consistantly* no time to shovel food down your mouth the issue is not keeping the change; the issue is some combination of poor time management, poor delegation and understaffing/insufficient operating capital. If I’m not misreading the OP, the impression I got from the OP is that this is happening on a regular basis, not just every once in a while. No matter what your job, you need to eat sleep, bathe, go to the bathroom, dress, etc. I don’t accept that there is no time to acquire food in some manner other than getting someone to voluntarily run out for you, in a manner that is informal and uncompensated to the person running out. Either OP needs to figure out how to acquire food, or, create a business process that results in food showing up on the desk that doesn’t rely on the uncompensated kindness of co-workers.

        1. Anonym*

          In that case keeping the change is still a major issue, though, and not what the OP asked about. It’s a very different conversation about workloads, etc. And the situation is super duper common where I work (although people typically grab a granola bar or something from a nearby vending machine rather than have someone get them lunch… then again most of them don’t have assistants).

          Pocketing someone’s money without their permission is theft, and super not okay. If the assistant has concerns about any aspect of the situation, she should bring them up, not steal.

    3. someone*

      I’ve seen this occasionally in more senior folks around me. It’s usually lots of meetings back-to-back. You may have 5-10 mins between meetings but that’s not enough time to go out and buy food.

    4. Joielle*

      Eh, idk, I’m not even that important of a person and sometimes my work day plays out such that I don’t get a break until like 3 pm. Sometimes it’s just a weird day and you end up having to put out several fires in a row on top of whatever else you needed to get done. I don’t have an assistant though so when that happens to me, I just eat a handful of nuts or whatever from my desk drawer snack stash. I don’t think it’s that unusual.

    5. Essentially Cheesy*

      Or manager could just pack a lunch for themselves. Crazy talk, I know. *rolls eyes*

      1. pancakes*

        They weren’t asking for advice on whether it’s ok to buy lunch rather than bring it. It’s a little crazy that multiple commenters are offering it anyhow.

    6. ferrina*

      If I had an assistant (and I wasn’t remote) and it was feasible, I would 100% ask them to pick me up lunch on a semi-regular basis. I frequently have really busy mornings (back-to-back meetings, things that need my review asap, etc.) and everything is a domino affect, so if I can’t get it done, I’m making other people late or adding to their stress. By the time it’s calm enough to get or make food, it’s 2:30 or 3. That’s just the nature of my role and my industry. I don’t mind, but if I had an option to eat lunch at a more reasonable time, I would appreciate it (and let my assistant keep the change)

    7. The OG Sleepless*

      Bwah ha ha I see most of you have never worked in health care. It’s extremely common in animal hospitals, and I assume human medical type places, to have absolutely no time to eat. Like, you can’t even physically get to your food and shove it in your mouth. I’ve waited until 3 PM to eat lunch many times, gone more time than I would have though possible without peeing, forgotten to drink water for hours. I’m lucky that I work with relatively sane management and I’m efficient, so I get lunch more often than not, but lots of places will tell pet owners “come on in and we’ll squeeze you in” far beyond the point where there is no more squeezing to be done, so you just manage. But anyway, I have occasionally been stuck with no lunch packed and no way to get any, and a staff member will grab me something while they’re out. I always send my debit card with me, but if I sent cash I would expect them to at least make the gesture of giving me my change back.

  12. Redhead*

    I’ve done a recommendation for a customer before. Not as awkward as you think! I was a graphic designer and I never had to fix her work, so I said that and she got her new position. Bonus — we gained a new customer when she changed employers!

    1. MM*

      Ah, thank you for this, I was really struggling to understand what a recommendation for a customer could even mean!

  13. TootsNYC*

    I think the manager for our buttinski coworker should, after that conversation, also be ready to say, when in the office to talk to Jane, “Katie, this conversation doesn’t need you to participate; we’ll keep the volume down so you can focus on your own work.”
    And maybe focus is part of the problem, so that should be a “tactic coaching” approach as well. Encourage Katie to wear noise-canceling headphones, or if the convo is going to be very long, have it in the manager’s office instead of the shared office. But also point out that sometimes we get mildly disrupted and the correct path is to ignore it and get back to focusing despite that anyway (it’s a useful skill–to be able to focus on the book we’re reading even if the person next to us on the bus or in the airport waiting area is having a conversation).

    But redirection right in the moment is a good thing for a manager to do.

    Also, perhaps after having that convo with Katie, the manager can give Jane some scripts to use.

    It can be tough, because when I’ve been a rookie, I’ve learned a lot by observing other people at work. Asking intelligent questions can help me learn a lot. “Joe said the project might be late; what do you think is making that happen? How will that change our process?” or “Why did you ask Wakeen to handle that instead of Pedro?” might get me info that makes me better at my job. But I also always did my own thinking well before I opened my mouth, and I paid attention to whether my senior colleague seemed receptive, both in terms of timing and in terms of content.

    But Katie’s questions don’t sound like she’s a serious and self-directed learner here.

    1. I went to school with only one Jennifer*

      I strongly suspect that Jane would not have been annoyed by questions like those.

  14. TechWorker*

    LW1 – you also need to be aware of the difference between a report ‘venting’ and a report ‘telling you about a problem that needs fixing’. By default – you should usually assume the latter! It might be something you can coach your report to fix, it might be something you can fix yourself, it might be something that isn’t possible (or high enough priority) to fix – but then you should talk about that. Or yes, they might be venting about something they have no expectation of changing, but you should ask that rather than assume it. (And sometimes people assume things can’t be fixed, when actually they can.)

  15. Camellia*

    Regarding the disappearing change – OP said this was a recent development, that up until a short while ago the change had been left on her desk. I would wonder if the change HAD been left on the desk as usual, and perhaps someone else was helping themselves to it. For example, any new coworkers around, or something like that?

    So first I would simply ask, “Have you been leaving my change on my desk as usual? Because I noticed it’s been missing the last couple of weeks.” Then see what the lunch-bringer says. They may explain that prices have gone up (I know that eateries in my area have increased prices, sometimes as much as 40%), that they started tipping (as others have mentioned), or whatever. Or they may mumble an answer because they’ve started keeping it to pay for gas, since gas prices have gone up, or because they decided to start tipping themselves for the service of bringing you your lunch. At any rate, just ask.

    1. eggberrt*

      On lunches….why not just talk to your assistant? If keeping the change is a new thing after a non trivial history of not keeping the change….clearly something is different. And it seems unlikely that its just a spontaneous decision to start stealing your money.

    2. jtr*

      Oh, I didn’t even think of that! But, yeah, talking to her would be the first cut at a solution.

    3. Me*

      Yeah this was my first thought! If OP isn’t there when the coworker returns and it sits for a while…is someone else taking it? It may be a combo of things also.

  16. NyaChan*

    My coworker is a Katie and I’m convinced it is all rooted in insecurity and FOMO. When she joined our team she was largely overlooked for leadership roles because it was a temporary position. This offended her and even now that the role is extended and we have given her projects commensurate with her experience, she can’t seem to shake the sense that she is being left out or should have more influence. This results in daily requests to be added to ongoing chats, email lists, and meetings. Even if we point out that it doesn’t require her presence (with a team our size, a meeting can quickly morph from actionable discussion into a useless conference call), she’ll insist that she’ll just be an “observer” who won’t interfere. If you pass a question along to her, she’s convinced that you must be leaving out history or context. Unfortunately, she hasn’t seem to realize that behaving that way actually makes her coworkers want to share less, not more.

    Our solution so far has been to write out word for word where her role starts and ends. It improved a little because she couldn’t continue to claim that random projects were somehow part of her responsibilities. But anything adjacent still produces intrusive questions and frantic communications if anyone genuinely does forget to tell her something before it is announced to the rest of the team (she doesn’t actually need to know before everyone else. she just sees it as a slight to her status to find out alongside others).

    1. Dust Bunny*

      OMG y’all’s manager needs to shut this down. You shouldn’t have to hand-hold her insecurity through all your projects. “You will be included on the projects on which you need to be included,” should be all she needs.

      1. Wisteria*

        Given that the insecurity is rooted in how the team treated her, they should have to build her trust in them, or as you say, hand-hold her insecurity through all their projects.

        1. Hey Pal*

          I don’t see anywhere that she was mistreated, just that she wasn’t eligible for leadership positions while in a temp position. To me it actually sounds like the team is doing *too much* to accommodate her disruptive behavior. Why should people have to share team-wide announcements with her before everyone else, just to soothe her FOMO? Her insecurity is hers to manage; not her coworkers’.

  17. eggberrt*

    On lunches….why not just talk to your assistant? If keeping the change is a new thing after a non trivial history of not keeping the change….clearly something is different. And it seems unlikely that its just a spontaneous decision to start stealing your money.

  18. raida7*

    god yes you need to address it.
    It’s not just a social thing – talk with the newbie about what their current role is, what they want to do longer term, what they are interested in, where they hope to go in the business, etc.
    To me it sounds like she’s either a) trying to get a broader understanding of the business and her team’s work so she can pick up work, be included in more important tasks, etc. or b) she’s lonely as hell and is going with ‘ask lots of questions’ so she’s having conversations.

    the latter is social stuff, but also of value to you as her manager because it tells you something about her work environment, how she as a staff member needs social interaction, is anxious if she’s left out, etc – all good for a Manager to know.

    the former – what does the role lead to? Anything? has she done more advanced work previously elsewhere? did someone suggest to her that learning on the job will be good for getting non-admin roles? is she bored with her work and if so is it due to a misalignment of expectations?

  19. Despachito*

    What struck me in the OP2’s case is that OP is perhaps not so keen in the assistant bringing her coffee/lunches. My impression was that the assistant very actively offers herself, and OP just goes with the flow but without being particularly enthusiastic about it (see her comment that she would be perfectly OK with the coffee from their kitchenette but feels obliged to reciprocate).

    I’d think about reconsidering the whole situation. Do I really want the assistant to bring me coffee/lunches, or does it create more hassle for me than if I just drink the coffee from the kitchenette? If I do not care too much for the bought coffee and feel an urge to reciprocate, I’d probably say “no, thanks” the next time the assistant offers herself to bring me one.

    Also for the lunches – if OP decides that she does want her assistant to bring them, I’d probably address it with her in terms of whether what I give her is sufficient (because who knows? the prices may have gone up, and I’ve read letters here how an assistant had to cover a part of the boss’s lunch from their own meagre purse) – if this is the case, it will not make her feel wronged, and if not, OP will be able to elaborate and ask about the change be given back to her without feeling she is doing injustice to the assistant.

    But personally, in a situation as described, I would probably want the assistant to stop bringing me food and drinks altogether – she is too zealous and it would be too much of an emotional burden on me to keep track of all these little favors.

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