my boss keeps warning me she’ll get in trouble if I commit fraud (I’m not)

by Alison Green on October 23, 2024

A reader writes:

I started a part-time voluntary position a couple of months ago. There are reporting lines, annual appraisals, etc. just the same as a regular job and it’s in a very niche area which closely matches my field, a rare opportunity! In a lot of ways my new manager is excellent — she’s experienced, committed to career growth of her team, etc. I am excited to work with her! However, I’ve had a few interesting conversations and would like your advice.

First, on three separate occasions, she has said that if I commit fraud one day, she’ll be penalized in her career, go to jail, etc. but that “she’s willing to take that risk to help me achieve my dreams.” These are long conversations so it is not misplaced humor. I went through an extensive background checking process before being accepted for the position and I’ve previously worked in highly sensitive areas that require integrity and reliability. I don’t want to get drawn into justifying my background or intentions, but I do want to resolve what seems to be a concern on her part so that we can move forward.

Secondly, I am excited about what I can bring to this position and have asked how I can support her career or objectives. She had to go through a lot of admin to bring me on board, and I want to return something back to her too. She’s insistent that all she wants is for me to have a good experience and there is nothing I can provide for her in return. (I accept that we are in different life situations and that this may be correct, so my plan is to create opportunities for more junior staff who do not have the same opportunities as the managers.) We’ve had this same conversation several times too and I find her statements awkward because it feels like it is creating an obligation that I can never repay, and that I am being asked to repeatedly express my gratitude.

I respect my manager as a leader and want to work well with her, so I would value some advice. What could be the thought processes and motivations behind a manager making these types of statements? How can I respect and acknowledge her viewpoints and concerns while closing out these types of conversations, especially the ones that question my integrity and reliability?

Well, don’t commit fraud, obviously!

I’m sure you don’t need to be told that, and it’s really odd that she’s brought it up three times. It likely has nothing to do with you — maybe she’s an anxious person, or she heard about that happening to someone else, or who knows what. I doubt it’s that you’re coming across suspiciously!

If she had just said it once, I’d write it off as just a random awkward moment. But bringing it up three separate times is sufficiently weird that you should ask her about it. For example, you could say, “You’ve mentioned several times that if I commit fraud one day, you’d be penalized. Is there something I’ve done that’s worried you about my ethics? It’s so far from anything I’d ever do and I’m concerned I’ve somehow given you the impression you need to worry about that.”

On the second point, about wanting to repay your manager in some way: I think your framing is wrong here. She presumably went through a lot of administrative work to bring you on board because she judged that it would be useful to her and/or the organization to do that, not because she was doing you a favor. That’s how hiring works, even for volunteer positions: both sides benefit, and there’s no debt incurred. (Actually, with volunteer positions, if anything it’s in the other direction; they should be grateful to you.) The only thing you owe her is conscientious work while you’re there. There’s nothing to repay.

I do want to know what’s making you feel that you’re being asked to repeatedly express gratitude. Is that because your manager keeps referring to how much work she had to do to bring you on? Or do you feel like that’s all you can offer if she won’t let you repay her in some other way? If it’s the first option — she keeps seeking out your gratitude — that’s inappropriate and you should internally roll your eyes and ignore it. But if it’s something being internally generated by you, I refer you back to the previous paragraph! You don’t need to repeatedly express gratitude for being hired (and most managers would find it uncomfortable if you did; if yours seems to want it, that’s a problem).

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{ 111 comments }

{ 111 comments… read them below or add one }

  1. Mornington Crescent*

    I can’t be the only person wondering if the boss is projecting because she’s actually the one committing fraud, right?

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    1. Bossy*

      Ha ha popped into my mind for sure! This is very weird- LW is gracious about it. I think I’d be like Are you calling me a criminal or what?

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      1. Bossy*

        We could go even further and wonder if boss worked so hard to get LW working there so that when the fraud hits the fan? Musta been volunteer! But that would be fanfic territory… lol

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      1. Dawn*

        That was actually the thought that popped into my head. She literally said, “I’m willing to deal with you committing fraud if I have to!” like a kind of nudge-nudge wink-wink, which is a really weird thing to do if you’re not actually implying that it’s ok to commit fraud.

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        2. Strive to Excel*

          I read it more as “taking on any employee puts me at risk because they might commit fraud, but you seem really eager so I’m taking that risk”.

          It’s still a REALLY WEIRD take, because that’s NOT how it works. Unless there’s an industry with really weird and penalizing industry norms out there? I work in accounting which is pretty dang strict and superiors get in trouble is if they’re negligently signing off or collaborating on bad/fraudulent work. But they have to be shown to have been negligent/not exercised a reasonable duty of care, it’s not just “oh your employee committed fraud, to jail with you!”

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      2. Tinkerbell*

        Maybe the nature of the job means you have to focus hard NOT to commit fraud? Like, I’m sure there are some regulatory-type jobs where doing things the lazy way would be illegal and you have to have enough integrity to do it the tedious way to ensure all your Is are dotted and your Ts crossed…

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    3. Hapless Bureaucrat*

      It crossed my mind.

      The “willing to take that risk to help you achieve your dreams” part is SO WEIRD. Hiring someone, even in a volunteer role, should never be risky for fraud in itself? What the heck is the manager even saying here? Is she suggesting OP commit fraud and just do it well?

      I can’t read this in any way that doesn’t raise red flags about either the manager’s ethics and judgement, or the organization’s internal controls.

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      1. RIP Pillowfort*

        Thank you. I am struggling to understand what kind of job this even is if your manager is saying they’d risk you committing fraud to achieve your dreams.

        Like what are ya’ll even doing? Should this even be an unpaid volunteer position? Is volunteering for this work even legal?

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    5. Heart&Vine*

      Yeah – it’s like when cheaters suddenly become really suspicious that their partner is cheating with zero evidence. Because if they can do it…

      Either that or the boss heard a rumor or mixed up some background check and think OP has a history of fraud (but then why hire them)?

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    6. Workaholic*

      That’s the first thing I thought of. like the cheater always accuses the other (innocent) party of cheating. is she working on somehow framing OP to take the fall if fraud is found?

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    7. Prefer my pets*

      That was EXACTLY where my mind went! Only less about “projecting” and more about “laying groundwork for a fall-person”

      I sadly have actually seen this happen twice in my career so no doubt I’m jaded. (Though both times failed, & in the end the correct person went to prison, but it was a LOT of stress on the person they set up in both cases and their reputations still took a hit)

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    8. juliebulie*

      Oh, yes. Or else she might be sort of encouraging OP to commit fraud for some reason. I’ve never had anyone say to me “I’ll get in trouble if you break the law, but I don’t want to stand in the way of your future.” That’s really bizarre. To me it almost sounds like “you’re gonna have to commit fraud in order to get ahead, but do it sneaky so I don’t get in trouble.

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      1. Olive*

        This is how I read it too.

        Once could be a misspeak or a joke that landed wrong, but three times is *weird*. I feel like the answer to the letter kind of downplayed just how weird it was. I’d feel very unsettled working with her, but I don’t know the right answer except to be err on the side of professionalism rather than getting overly friendly.

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      2. Irish Teacher.*

        I interpreted it more as the boss is so invested in having people eternally grateful to her that she has to make out she’s doing them this huge favour and taking a huge risk by taking them on. “I could go to prison if you do anything wrong, but I’m willing to risk that, not because your work benefits me but because I’m such a good person that I want to see you succeed, regardless of the risk to myself and all I ask in return is your eternal gratitude and for you to continually remember how you owe everything to me.”

        But yeah, I can see your interpretation too.

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        1. Missa Brevis*

          That’s also how I read it and it’s better, I guess, than actually encouraging someone to commit fraud, but that’s still a really weird and toxic set of expectations to throw at an employee!

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          1. MigraineMonth*

            Especially a volunteer! Everywhere I’ve volunteered has thanked *me* for the whole doing unpaid labor thing, not told me they were “helping me achieve my dreams” (??!?).

            I’m sure there are super-competitive volunteer/unpaid internship opportunities out there that can help launch your (hopefully paid!) career. Even at those, though, you don’t “pay back” the trouble your manger went through hiring you.

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        2. LW*

          Yes, this resonates with the interactions I’ve had with her and links with the second point about conversations where it comes across that I’m being expected to express gratitude (again).

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      3. Antilles*

        That was my read on it. Sounds like a wink-wink hint about OP ignoring regulations in the name of just getting the job done. Of course you should follow all the accounting guidelines and I would never suggest otherwise, but hypothetically if you “forgot” a form and just forged ahead, there’d be no way of knowing and it would help us meet our deadlines *cough*.
        Terrible idea for OP of course because you know if it goes sideways, the boss is going to act shocked shocked that there was violations going on in this establishment and scapegoat OP.

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    9. I'm just here for the cats!!*

      I actually wondered if the OP was a BIPOC and that the manager has some weird racist hang up that people of X ethnicity are more likely to commit fraud.

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    10. Smithy*

      While I don’t think that’s impossible – I do wonder if this is a type of work where these reminders are done hyper frequently because of how relevant it is to their work.

      I’m thinking of places that have lots of “wash your hands” reminders. Obviously there are staff who wash their hands every time and don’t need this level of reminder – but because of how important it is to that industry (i.e. food service, healthcare) – they need to make sure that percentage of people who don’t hit that every time metric are given as many prompts as possible to do that.

      My job includes a lot of “if you ever want to contact this external contact, you MUST include me.” There are coworkers who hit 100% compliance and it has never crossed their mind once about not doing it. But there’s enough people who regularly don’t, who do it based on their judgement (and not our team’s), etc. So, those reminders regularly go out a bit more sternly than would be necessary for those 100% colleagues.

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    11. MotherofaPickle*

      In my experience, it was because the employees under the manager had egregiously broke the law…to the extent that the entire department was completely cleaned out and all of it happened under Supervisor’s watch (dunno why he was kept on…but that’s another story).

      He came into my office twice a week to “check up on me” and would repeat the same horrible stories AT LENGTH WITH DETAILS the entire time.

      I was young and dumb at the time, but I was about three days away from circumventing my actual boss and going straight to HR with a Formal Complaint when he was removed as my direct supervisor. My Actual Boss said it was a result of his former team being completely cleaned out due to felonious happenings and he was trying to warn me against it. I know better know.

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    12. Richard Hershberger*

      Definitely a possibility, but it is also possible that someone working for her in the past committed fraud, or she heard about this happening to someone else, and this has occupied real estate in her head ever since.

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      1. lyonite*

        This is where I’m going with it. She’s sitting there thinking “what would I do in that situation” (or “what should I have done better”) and it’s coming out at the OP.

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      2. pally*

        Yeah, my thought too- someone in her past did commit fraud. And it’s something she will never forget. And she doesn’t think that by the continued mentioning of it, causes the OP to wonder.

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      3. LW*

        It is weird! I’ve worked in this industry for 9 years and never had conversations like this before. I’m only a few weeks in and I can give the readers complete assurance that I have not done or said anything that would cause concern. It is so completely outside what would is expected that it occurred to me that maybe there’s a medical reason like an undiagnosed condition? She’s also covering for her manager who is on extended medical leave so my other thought was that it’s the result of her stress levels being maxed out which is making her anxious and less… proportionate… in her responses. You know like when you are super tired and you don’t think as clearly? But three lengthy conversations is a lot!

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      4. LW*

        Could be this. There are some other issues going on that are quite serious – none is fraud, but maybe they’ve had that too and I just don’t know about it yet!

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      5. yvve*

        it also sounds like this is a super small, church (?) related volunteer position– exactly the kind of situation where I would expect “professionalism” to take a backseat to bosses personal anxiety about something she heard about or experienced in other context. I think there’s a pretty good chance nothing more complex is going on here than “she had heard about this and doesn’t realize she’s bringing it up weirdly”

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    13. Lisa*

      My first thought as well. People often project their bad behavior onto other people. Partners who are cheating will often accuse their partner of cheating, for example. I’d be taking a closer look at her work, to be honest.

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    16. steve*

      Or if she’s low-key encouraging fraud (which she thinks would benefit the org in some way) by repeatedly mentioning that she’d be willing to take the fall for it.

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    18. Ms. Eleanous*

      Oh! right. Crescent — my brain’s suspicion section must be asleep today.

      My thought was that a past intern had gone horribly bad with no way to see it coming.

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    19. Generic Name*

      My very first thought.

      And my second thought is that this volunteer position sounds more like it should be a paid position. The person who is overseeing your volunteer tasks is usually called a “volunteer coordinator” and not your manager. They have you work on stuff for the benefit of the nonprofit organization (this organization IS not-for-profit, right???) and not to the benefit of one individual’s career. Honestly, this whole situation is very strange, and I can’t help but think that something not completely above board is happening.

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    20. Little Bobby Tables*

      The first thing that came to mind was a story I heard about a business owner who would tell new hires “There are two rules here: You don’t steal and you don’t lie.” The owner turned out to be a thief and a liar.

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  2. supeisedcanuk*

    The best way to repay your manager is obviously don’t commit fraud. No just do a good job. You don’t really owe your boss anything. You don’t need to bring shovel and meet her at 2am or offer to be an alibi.

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  3. Ellis Bell*

    In addition to the “how can I alleviate your concerns/where is this coming from?” conversation, I’d try to find out if you really are “being asked to repeatedly express my gratitude.” If you’re right, that’s a very concerning view of the power balance and it will show in other ways. Possibly it’s just very awkward conversational style where there’s no thought about how things land. I think I might approach this by doing my best not to make any particular shows of gratitude? She says you don’t owe her anything; take her at her word and see how that goes down. If she goes on about the admin involved in hiring you, or the risk of going to jail, pucker your brow very slightly like you’re seriously considering the issue as a work idea and as though you’re not sure what present day and practical solution to the work issue she is in need of. “You’ve mentioned that before, do you want to change how you hire, or do you have all the admin help you need now though?” or for the fraud fear: “Is there anything in our process we can make more transparent, like checks and balances to keep things as visible as possible?”

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    1. MigraineMonth*

      LW, you mentioned wanting to repay her for the work she did hiring you. Did she also bring up how much of a hassle the hiring process was for her? Because that’s not a great sign, either; she’s expecting gratitude from those she holds institutional power over for *doing the basics of her job*. Gratitude, like gifts, should flow downwards.

      The only manager I’ve had who even mentioned the hiring paperwork was… overall a pretty bad manager. He said I qualified for the senior developer position, but that was extra paperwork for him, so would I settle for the junior developer position and starting pay? (No, no I would not. Fortunately he retired a few months later.)

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  4. CowWhisperer*

    My first education job ended when the principal was arrested for fraud against the state.

    He never said anything like that – but I’d personally be more cautious in an organization where my manager’s main concern if I perpetuated a fraud was her career taking a hit rather than the outcomes to her cause or the workers.

    That level of self-centeredness does remind me of my first principal.

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  5. Panhandlerann*

    OP isn’t even getting paid. So it seems doubly unnecessary for OP to need (or to feel the need) to express repeated gratitude. Perhaps the manager should feel grateful that OP is volunteering.

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    1. Great Frogs of Literature*

      This struck me, too. I get that it’s a great opportunity, but OP is LITERALLY WORKING FOR FREE. By all means pay it forward by putting other people in the way of opportunities, but the payment for this particular opportunity is the free labor.

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  6. Pomegranates*

    “she has said that if I commit fraud one day, she’ll be penalized in her career, go to jail, etc. but that “she’s willing to take that risk to help me achieve my dreams.””

    What tone is she using when she says this? Because if it isn’t a bad joke then it does sound like she’s telling you *wink wink nudge nudge* that she will help you commit fraud if that is something you want to do. Which, obviously, is mind-bogglingly bananapants.

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    1. H.Regalis*

      As written, it totally sounds like a fish, which is just so goddamn weird. I can only speculate on why she keeps saying this, but it’s fucking odd. If she continues on this conversational line, is there anyone else there you can talk to about it, OP? Another volunteer, your grandboss, someone else on staff, anyone like that? Someone trustworthy who knows your boss better than you do and could maybe shed some light on what the heck she is on about.

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    3. KOALA*

      Right, and that along with OP feeling like they have to express gratitude for the job is giving sketchy vibes. Like at some point the manager is going to press OP to either do or overlook the manager doing something unethical or illegal under the guise of “You should be so grateful I hired you that you don’t question this and just trust me”.

      I’m just not understanding in what world “willing to take that risk to help me achieve my dreams” makes sense at all. If the manager believes it would lead to reputational harm or jail, that would mean that OP’s dreams would also be derailed because they along with the manager would suffer in their career or go to jail.

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  7. Caramel & Cheddar*

    The boss sounds wildly paranoid, but pretending for a second she’s not: if this is a job where a) the danger of someone committing fraud is this high, and b) that the manager would be the one taking the fall for it, this really shouldn’t be a volunteer position no matter how many background checks you passed. You simply do not have the same accountability as a volunteer as you would as a staff person, nor should you.

    I wondered if there was someone in your role or a similar role before you who did commit fraud that led to these questions, and she was warned that if it happened again she’d get fired, but that feels like something she would have told you alongside her fear of fraud being committed. I think there was a letter a couple of months ago where the admin person embezzled a bunch of money from the company and then the company went way overboard with the next admin assuming she was going to engage in criminal behaviour from the get go, when obviously that’s a ridiculous assumption to make.

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    1. Venus*

      I think it’s fine to be a volunteer position. The more unusual part is that if this involves financial accountability with opportunities for fraud then there should be checks to address this. I might suggest this to the manager.

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    2. Lisa*

      Eh, I don’t know that it should be paid, really. “Don’t commit fraud or you’ll lose your paycheck” has certainly not stopped any other fraudster in the past. I think there may be an element of feeling like the organization “owes you” if you’re a volunteer, but again, that’s an attitude others who were paid took because they felt they weren’t getting paid enough, or were being passed over, etc, though really that was just them coming up with excuses to justify their criminality, not actual reasons.

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    3. Madame Desmortes*

      I’m treasurer for my union local, a voluntary elected position; all elected positions in the local are on a volunteer basis. (The state-level union has paid employees, including the organizer who works regularly with us.) It’s every bit as responsible a position as any treasurer position would be. We’re not a giant local, but to give you the idea: more money than I make in a year (gross salary, not even net of taxes) passes through my hands as treasurer every single month. (Most of it goes straight to the state and national organizations as per-capita dues.)

      So volunteers can indeed have weighty responsibilities, in some organizations.

      That said, I’m starting to have questions about the financial controls in evidence in this organization. My local has plenty of them, not because I’m an embezzler (I assure you I’m not!) but because someone in this position might be, and do a lot of damage thereby.

      OP, in your shoes I would absolutely ask your boss about the organization’s fraud-prevention measures and to whom you should report any irregularities you notice. On the off-chance the boss is looking to fob off her fraud on you, this would at least put her on notice that you’re no pushover.

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    4. MCL*

      I have been a treasurer for a few different small organizations (a local political campaign and a local neighborhood association). This was entirely volunteer but the potential for fraud was definitely there. Yeah, you’re reporting and accounting for revenue and expenses, but at the end of the day it’s the honesty of the volunteer (me, in those cases) that keeps things on the up-and-up.

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    1. Spooz*

      This was absolutely my first thought, but then why is the boss being all “nudge nudge wink wink” about helping the LW achieve her dreams even if it means committing fraud?

      I’m glad Alison suggested having a clearer conversation, and I understand why the framing is “Is there something about me you’re worried about?” but I wish the LW would just ask “Is there a reason you keep bringing up the possibility of committing fraud?” Because I am very sure that it has nothing to do with the LW and everything to do with the boss and I want to know without giving the boss an “out” to deflect or not fully explain!

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  9. MK*

    Do I understand correctly that she is saying that if you commit fraud, not just in this particular position, but at any point in the future, she will be penalized in her career and possibly go to jail? Because this makes no sense to me.

    Admittedly we don’t know OP’s country/culture, but someone being punished for a crime a person they managed in a volunteer position committed is not possible in any modern criminal law system. Even supervisors who were grossly negligent in overlooking their subordinate’s crimes aren’t punished (exceptions allowing if their negligence is an offense in itself). Her being penalized in her career is less bizarre, certainly her being known to be your mentor and advocate may affect her standing if you end up becoming a criminal, but it’s still an overblown concern; most people wouldn’t rush to condemn someone because they hired someone who turned out to be dishonest.

    Is there some context here I am missing?

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    1. Strive to Excel*

      There are industries/countries where supervisors can be found to be exercising insufficient Duty of Care responsibilities; ie, if the manager is supposed to be reviewing and signing all audited financials, and they’re not actually reviewing well enough to catch employee errors/fraud, they can get into trouble for not doing their review job well enough. But you have to be a) pretty high up in an organization to have that sort of duty of care and b) be extremely negligent. Heck, take a look at Theranos and how long those trials have been going. People remember Elizabeth Holmes and some of the investors, and basically nothing else – and that’s a huge public fraud case with a lot of ongoing publicity.

      I have no idea what industry and country OP is in but this manager sounds mildly bananpants. Also maybe like she’s trying to make OP grateful to her, which…ew.

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  11. Yikes*

    Someone soon: ARE YOU SURE YOU’RE NOT COMMITTING FRAUD?

    All kidding aside, this is weird. It smells like she’s frauding and is feeling you out for your level of okayness with it. Or, less illegal but still not great, she had a subordinate do crimes and is now fighting the last war. But I am leaning hard to the former.

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  12. Czech Mate*

    I’m so intrigued by the “she’s willing to take that risk to help me achieve my dreams.”

    If that wasn’t part of it, I would guess that your boss has had employees in the past who have committed fraud. I could even see where a former employee said, “Well, you never TOLD ME not to commit fraud. Obviously I didn’t think it would affect YOU” etc. and so she’s trying to cover her bases.

    The fact that she said SHE’S WILLING TO TAKE THAT RISK makes me feel like she WANTS you to say something like, “Oh yeah, insider trading has always been an ambition of mine” or something. Please give us an update if you ever have one!

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    1. English Teacher*

      It’s weird how it’s phrased, but I think the meaning is this: Manager is saying she could get in a lot of trouble if Volunteer commits fraud, but Manager is willing to take the risk OF MENTORING Volunteer because she believes in Volunteer. Not the risk of committing fraud. That explains why Volunteer feels like the line is fishing for gratitude. It is.

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      1. Irish Teacher.*

        That’s my interpretation too. My feeling is that the manager wants the LW to feel like the manager is doing her a favour by permitting her to volunteer when really volunteering is sort of doing a favour and that the point is “look how good I am to you. I even let you volunteer here despite the fact that, for all I know, you could commit fraud and claim I put you up to it and get me arrested. You really owe me one for being willing to take such a huge risk in order to help you achieve your dreams so you should work really hard for free and never be unavailable or ask for anything from me.”

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          1. What name did I use last time?*

            It’s also really unclear to me how generously doing volunteer work is somehow “achieving your dreams!”

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  13. tabloidtained*

    Putting everything you’ve said in this letter together, I expect your manager is (clumsily) expressing her commitment to you. She fought to have you on board, she’s willing to take whatever risks come with a new employee because she wants to support you and your career, and she wants nothing from you in return.

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  14. Jane Bingley*

    All the other ridiculousness aside, she really shouldn’t just… trust you not to commit fraud! There should be systems in place to ensure that your work is regularly checked and verified by someone else, whether that’s her or a board member or an external accountant. You don’t prevent fraud with wishful thinking and guilt-inducing conversations.

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  15. Olive*

    I feel like the best case scenario is that the boss is extremely awkward and unaware of social and professional norms and thinks she’s making a repeated joke that’s bonding them. But even that isn’t great behavior from a boss, and the LW should be cautious although not paranoid to keep a very high level of transparency and professionalism.

    Given this is a volunteer job, I hope this is going to end up being a great stepping-stone for the LW.

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  16. Pay no attention...*

    Is the OP’s volunteer job on the up-and-up? Like maybe this position shouldn’t be unpaid and that’s the fraud that the boss is sticking her neck out over. It certainly wouldn’t end up with jail time but she sure is laying it on thick.

    Another thought… I hope I’m wrong… is the OP part of a group of people stereotyped as being dishonest or thieves? Is the manager racist?

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  18. CommanderBanana*

    OP, you’re a volunteer. Your boss should be falling over themselves thanking you because you are literally working for free. Her telling you that she’s willing to risk jail (wut) for you to “achieve your dreams” (lol wut) because you might commit fraud (double wut) and that would mean…she goes to jail?

    I have been a volunteer at many nonprofits and currently volunteer for 3 regularly, and I would not tolerate someone trying to make me feel like I should be grateful to them because me working for free is somehow them helping me achieve my dreams (seriously wut) and I definitely would not be ok with them constantly reminding me that I should not commit fraud.

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  19. MaryWinchester1967*

    Maybe fraud had happened, although hopefully not under that manager’s nose. I once worked at a company where I had very strange interactions with the accounts payable group in Canada every time I had a question. I’d been told that they had been with the company for a while and knew a lot, so it would be ok to ask them questions if my co-worker didn’t know the answer.
    He too was relatively knew, so sometimes he’d just say “ask Canada”. They always acted very suspicious of me. When I asked him what I’d done, he shrugged and said “they’ve always been like that”. We were in the Dallas office.

    After a while my co-worker told me he pestered someone in Canada until they told him what happened and why the US payables team was so new. There had actually been fraud. An IT guy started it and got away with enough that the company pressed charges. The former accounts payable person figured out what he was doing but, instead of reporting him, demanded a piece of the action. I think she also was arrested. The former accounting manager somehow didn’t get fired. He got a position he wanted. I have no idea why he was rewarded, especially since a third person figured out what was going on, and he ignored her when she reported it.

    I’d point blank ask if fraud had happened and, if not, what’s up with all the warnings.

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    1. CommanderBanana*

      ^^ This. I started work at a nonprofit right after a previous employee was sentenced to jail for embezzling over $100,000 over two years (doctored travel expenses, mostly, if I remember right).

      The org responded by going completely bonkers over travel expense reimbursement. Bonkers as in, I got called at home while recovering from surgery by the head of accounting to be told that I wouldn’t be reimbursed the $2.10 for buying a pack of gum while on travel because “gum wasn’t food.” Bonkers as in, the head of accounting scrutinizing what people were eating while on travel and refusing to reimburse if you’d ordered something she didn’t deem “appropriate” like having a smoothie for lunch because that somehow made it a “snack” and not “lunch” and therefore not reimbursable.

      She retired while I was there, and I also was verrrrrrrry curious about why Ms. Gum-Is-Not-Food was allowed to keep her role after the embezzlement happened on her watch. There were enough complaints about her scrutiny that I think her retirement was sooner than she would have wanted it to be.

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      1. Silver Robin*

        Sounds like she convinced them she could (and would) go really hard line about reimbursements to avoid future issues and then, true to her word, turned into Guacamole Bob and eventually the org realized that was doing more harm than good.

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  20. The Ultimatee*

    Part of what drove my ex-friend to abruptly quit his job at our then-mutual employer was his manager’s repeated reminders to not be cavalier with the passwords he (the manager) was sharing with him (my ex-friend) on post-it notes.

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  21. remix mealtime*

    The combination of:
    –it’s happened 3 times now
    –“she’s willing to take that risk to help me achieve my dreams” (WTF)
    –it’s a volunteer role to boot
    –the OP has this really over-the-top, misguided sense of gratitude and “I’m sorry I exist” vibe for the fact that the boss had to do background checks during on-boarding when that is all a very standard part of most (if not all) volunteer roles nowadays. (especially at an org this obsessed with “fraud prevention”).

    has me thinking that the boss is a whackjob, she’s not going to change, this is waaaaaaay too much drama for a *volunteer* role (LW doesn’t even get paid!), there are plenty of other ways to get that service credit, LW!!!!!! Run away immediately before 5-0 shows up at your door.

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  22. I should really pick a name*

    We’ve had this same conversation several times too and I find her statements awkward because it feels like it is creating an obligation that I can never repay, and that I am being asked to repeatedly express my gratitude.

    I don’t really understand this because it sounds like the LW is initiating these conversations.

    Reply ↓
    1. Silver Robin*

      I read it as part of other conversations. Like, they start out talking about Project X and LW says something about being excited to work on it or whatever and Boss launches into “just make sure you do not commit fraud! I took a risk on you!” etc.

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      1. I should really pick a name*

        It read to me like a continuation of:

        I am excited about what I can bring to this position and have asked how I can support her career or objectives

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  23. Allegra*

    There’s a combination of things here that make me think not that the boss is actively committing fraud or trying to incite the LW to do so, but *is* actively cultivating a weird power dynamic to make LW feel very dependent on the boss for any future success. “There would be huge repercussions for my life if you do something bad, but *I* am willing to take that risk for *you*.” “I did SO much work to bring you on board, but you don’t need to do anything for ME, it’s just enough to know that I’m giving you such a HUGE opportunity.” And LW says they’re constantly being made to feel like they’re proving that they’re grateful.

    OP, *you* are the one giving of your time for free! This feels like a “protests too much” situation where the boss is trying to reverse the situation on you, trying to make *you* feel indebted to *them* for “exposure” or “the opportunity”. Also, and I mean this gently because you seem extremely kind and conscientious–I don’t personally think it’s normal to be asking one’s boss how you can support *their* career development? It feels like that’s something that should flow one way. I have a great relationship with my boss, but that’s not something I’ve ever felt expected to do–I just do the best job I can for her and then we succeed together. So I’d just want to unpack why you feel like there’s an expectation that you, the unpaid volunteer, need to be doing something to help your boss’s career.

    It’s just weird flags for me that add up to an unsettling picture of expecting some kind of quid pro quo in the future, “because I did SO much for you, and took on SO much risk for you!” If your manager is constantly reinforcing “I’m taking a HUGE risk by giving you this chance to achieve your dreams,” then if they ask for something that gently pushes a boundary, it’s easy for you to rationalize it, because, hey, they’re taking a risk with you, apparently. And then they just keep nudging that boundary out. And that’s not a normal or healthy work dynamic, and I would trust your instincts if you feel like you’re being made to perform gratitude excessively. You’re working for free, and while you can be grateful for the opportunity, all you owe them is your honest work at the task set before you.

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    2. duinath*

      I agree with this read of the situation. I don’t necessarily think the boss will “call in” that debt she seems to have very successfully convinced LW is owed, I think it sounds like she just enjoys that dynamic. Not because she *will* hold it over LW’s head, just because they both know (or, more accurately, think) that she *can*.

      If anything, I think she might ask for small favors, nothing that will chip away at that “debt” but things that you maybe wouldn’t take the time or effort to do, otherwise.

      The fact she keeps bringing up how much work it was to get LW onboard, and what a risk she’s taking, while seemingly stonewalling any attempt to “repay” her really have me thinking this is the most likely.

      LW, you don’t owe her anything. You’re volunteering your time and effort, which is a very kind thing to do and not something you should be making up for in any way.

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    3. Cordelia*

      I have direct (paid) reports and would find it very odd if they asked me how they could support my career goals – that’s not what they are there for! I’d find it even more inappropriate from a volunteer. I’m there to support their career development, my own manager is supporting mine. The purpose of volunteering is – presumably – to gain valuable experience for yourself, and to help the mission of the organisation you are volunteering for, it’s not to help your manager progress in her career.
      I’m also a bit confused what you mean about creating opportunities for junior staff who don’t have the same opportunities as managers – are you trying to help them with their “career goals” too? Is that really your role in this organisation?

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  26. LW*

    It is weird! I’ve worked in this industry for 9 years and never had conversations like this before. I’m only a few weeks in and I can give the readers complete assurance that I have not done or said anything that would cause concern. It is so completely outside what would is expected that it occurred to me that maybe there’s a medical reason like an undiagnosed condition? She’s also covering for her manager who is on extended medical leave so my other thought was that it’s the result of her stress levels being maxed out which is making her anxious and less… proportionate… in her responses. You know like when you are super tired and you don’t think as clearly? But three lengthy conversations is a lot!

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  27. Pete*

    I am assuming this is a political campaign and the boss is the politician. The weird power broker behavior of the boss is common in that career path and the competitors of the politician are always looking to nab them on campaign finance fraud.

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  28. LW*

    On the second question about gratitude: I’ve volunteered for the same organization in overseas locations and I’m at the same level as my manager. We were peers while she was bringing me on board and were going to have different responsibilities, but now she is indefinitely covering for her manager then she is kinda my reporting line too. We are both volunteers.

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    1. What name did I use last time?*

      Oh, the fact that she’s a volunteer too puts it in a little different light. Is it that she’s an amateur at some aspects of the job and is thrashing around at random?

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    2. Grits McGee*

      LW, is this organization government- or government-adjacent? I ask because I am a government employee in a field that often relies on volunteers, and there are rules governing what kinds of work volunteers can do versus what must be done by an employee. In our org, the cool, professional development-type work would be off limits to volunteers. If any of this sounds relevant to you, then maybe that’s why fraud keeps coming up? If not, then just ignore this comment!

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  29. LW*

    Responding to Alison, I don’t initiate the conversations about wanting to deliver value to the enterprise and to make the relationship with my peer/manager reciprocal. I have read this column for a while and approach work (of all types) with the mindset that I am being engaged because I am seen as bringing value to that enterprise. The dynamic is more like a friend who keeps reminding you of how much they’ve done for you and needing reassurance of what a good friend they are. Same dynamic here, just the work version!

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  30. Purple Turtle*

    Maybe the boss is the one who wants to commit fraud at some point and is now testing the waters, i.e. looking at OP’s reaction to see if they’d be willing to cooperate?

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    1. LW*

      I really don’t think this is it. But it’s a valid point to raise and I am going to consider what action I need to take to ensure I’m not caught up in anything.

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  31. BigLawEx*

    My new theory is that if someone is writing to an advice column, something is going on beyond the question. This one feels like LWs ‘spidey’ senses are pinging and she’s not sure why, but pinning it on these odd conversations.
    There are a boat load of books from The Gift of Fear onwards that tell us to trust the unexplained unease. I ask the LW to do that here.

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  32. LW*

    I really appreciate all the comments and advice. It has given me a lot to think about!

    On the fraud point, next time it is raised I am going to ask directly if there is anything that I’ve done to give her concern, given that this point has been mentioned several times?

    The background that there are other (non-fraud) misconduct issues is potentially contributing to her heightened alertness towards anything conduct-related. I’m going to directly ask if there has been fraud previously. If there is, I want to know about it and make decisions accordingly. I do not think there is any possibility of me being set up, but I would probably not stay working there if there had already been fraud by someone else – it’s too much risk to my career.

    I am also going to flag the “fraud” discussion to the enterprise coordinator and national coordinator. I may frame this as “I wanted to see if these concerns were shared at your levels or if this is a specific concern of [manager]?” This is partly to protect my back, but also they may well be astonished that this is even being discussed.

    On the second point, about gratitude, my plan is just to close those discussions with something like, “I’m pleased to be able to bring value to [enterprise]” and move the discussion on.

    Reply ↓

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