update: I won money on a work trip to Vegas – do I have to donate it to my employer?

It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past.

Remember the coworker who won money at blackjack during an off-evening on a business trip to Las Vegas — and then her manager said she should donate the money to her employer, since she was in Vegas on their dime? Here’s the update.

I was glad that my hunch that I was under no obligation to donate my winnings was right, and I was appreciate of the support and suggestions about how to handle the situation. And don’t worry, my husband is a tax attorney so all the necessary tax-related matters were handled correctly!

As for the original situation – a few days later on a conference call, I was asked to give a summary of the conference, which I did. At the end my boss chimed in – kinda snidely – and said “you forgot to mention you found time to gamble. Did you know she won several hundred dollars?” to which her boss immediately responded “woo hoo! I hope you treated yourself to a nice dinner!” and other folks on the call responded similarly. In the cacophony of enthusiastic responses, my boss managed to work in something about “making a donation back to the organization” but everyone either didn’t hear her or ignored her. She never brought it up again.

I am happy to say that I am no longer at that organization and therefore no longer reporting to the manager in question! The whole “donate your winnings back to the company” was one of many really strange, annoying, and awkward things about working for her. Ex: a few weeks later, she requested a “conversation” with me to discuss my footwear in the office. Turns out she was upset that I was “wearing rain boots around the office” – in actuality, I hadn’t changed out of my rain boots and into my office footwear immediately upon arrival, but had instead worn them while walking to the kitchen to put my lunch in the fridge at stopping at the bathroom, a totally of maybe 5 minutes (and we worked in an office that is casual, and does not have frequent clients or other outside visitors.)

Across the board her expectations for her team were really out of step with the rest of the organization – she wanted us to adhere to a stricter dress code (and we are not externally-facing and don’t have clients we interact with regularly), she chastised us for emailing senior leadership directly (despite their requests that we do so, and the fact that the organization prides itself on being relatively flat)…I could go on and on, but everything came down to the fact that she was an intense micromanager who seemed really out of sync with the culture of the rest of the organization. However, she is also the type of person who treated those “below” her in rank completely differently than those “above” her, and senior leadership loved her. She ended up getting a major promotion a few months ago, which made her even more challenging to work with. I tried to switch to a new role on another team, but it would have been 6 months before that move could be made. I was lucky to find a new role at a different organization with a great culture and a manager who supports and encourages me rather than nitpicking and micromanaging. And I got a significant pay raise and better title!

Interestingly, on my last day I had an exit interview with two members of senior leadership. One was on the phone because she was traveling, and the other – Sarah – in person. At the conclusion, Sarah asked if I had a minute to chat one on one. She asked me bluntly if my manager’s “style” contributed to my decision to leave. I ended up being much more candid than I had planned about how difficult it had been to work with my manager. Sarah told me point blank that senior leadership was very divided about her “approach” to managing her team. I was shocked by this – if there was such a divide, and one that a member of senior leadership was willing to share with me, then how on earth did my manager get promoted to actually being a member of senior leadership? This confirmed that moving on from the organization was definitely the right thing – I had been feeling torn because I was at that job for less than 18 months and the organization had a mission I was really passionate about, but sometimes its better to cut your losses.

I’ve been in my field and in nonprofits for almost 15 years – she is by far the most challenging person I’ve worked for or with. A lot of readers chimed in about this being indicative of non-profits, and I have to say, that has not been my professional experience at all. The vast majority of people I’ve worked for and with have been smart, capable, committed individuals doing thankless work in hopes of moving the needle just a bit. I’m proud of the people and organizations I’ve worked with and for (with one glaring exception!).

Thanks to everyone who contributed to the conversation – your counsel and support was helpful in navigating this situation!

{ 43 comments… read them below }

  1. Radio Girl*

    Sounds like the micromanager has higher-than-necessary expectations for her team. That can be a plus in some situations and a minus in others. Nonetheless, it sounds like you made the right choice!

    1. Artemesia*

      To me ‘high expectations’ is about quality of production — not about nitpicking footwear or the ridiculous idea that a business trip to Vegas should not ‘have time’ for any gambling and if someone neglected their work to gamble, they owed the money to the organization. This was the subtext of her obsession about that. I didn’t see any examples of a focus on excellence, just on being annoying.

    2. Observer*

      I don’t think that she has “high expectations” in the sense of expectations of performance or accomplishment. She has “high demands” or “high expectations of submission”.

      1. Lance*

        Yeah, that’s really the thing: nothing we’ve seen here is in any way performance-related. Everything is nitpicky, or her own personal ideals. That doesn’t make for a very good manager.

    3. I Wrote This in the Bathroom*

      Yeah, I would not classify these expectations as high – most of them were not work-related, and those that were, were in fact counterproductive (e.g telling her staff not to email the senior management directly after the senior management asked them to do so). So, unless by high we mean “she must’ve been high when she came up with these rules”, nope, not high.

    4. Talbot*

      I think after the “woo-hoo” conference call, I would have fired off an email to the grandboss, using the gambling incident to lead off. I feel by them openly having such a different reaction than she did opens the door to bring up her issues. Something along the lines of “I wouldn’t normally see it as my place to evaluate a boss’s management style, but there have been a few incident’s lately that make question whether she is in sync with the rest of the company. [Explains gambling incident]. It wasn’t until hearing everybody else’s reaction that I realized how different her position was than the rest of the senior management team. [Goes into other incidents].”

  2. Woodswoman*

    OP, thanks for this update. I’m glad you were able to find another position where you’re doing well, and to give feedback to management about the issues of your former supervisor when you departed.

    I also want to thank you for standing up for the people who work at nonprofits. I’ve worked in nonprofits for most of my adult life and in my experience, like your perspective, the dynamic you’ve described has been the exception.

  3. I work for a non profit*

    I’m so glad you’ve had a great outcome from this, OP!

    I have to say that I *do* think that this is typical of non profits, sadly. I agree that there are tons of people who are dedicated, hard working, and really well qualified who work in non profits making a real difference.

    I also think that because of the tendency towards an attitude of ‘we are a family’ that lots of non profits have, there’s dysfunction there – which leads to strange sayings like:
    “You are expected to work without pay for a charity above your contracted hours.” *my boss actually said that to our team.
    And ”those winnings are ours, not yours!”

    1. StellaBella*

      I had a boss like this too in a non-profit. She was making 6 figures and all of the small team were on 50% salaries of very low pay but expected to work 60-100% total. It is illegal where I live and all of us after 3 years left the org and she continues to hire and abuse others with this nonsense sadly.

      1. Artemesia*

        I have worked with a lot of non-profits in cooperative ventures or have consulted with them and one pattern I have often seen is that the ED is a good old boy someone on the board knew from his country club or previous employment or church or whatever who turns out to be a poor manager or leader but is untouchable. The job is often a well paid sinecure for someone who views it as akin to retirement. It is a shame that the pay is so low for the people working their tails off to get the job done and often so high for ineffectual leadership.

    2. Victoria Nonprofit (USA)*

      Generalizations like this are so silly. There are a wide variety of nonprofits, just like there are a wide variety of small businesses and corporations and government agencies and etc.

      I’ve spent my career in nonprofits, with budgets ranging from $500k to $150 million (and staff sizes from 4 to 400+). Some were well-run machines. Some were held together by an effective staff that smoothed out the vagaries of a crazy founder. They’re each their own entity.

    3. CoveredInBees*

      Are you familiar with the blog ‘Nonprofit AF’ (formerly Nonprofit with Balls)? They cover a lot of this with humor. At my last job, it was the only good thing about Mondays.

  4. Quake Johnson*

    I don’t know why but I’m just picturing Lilith from Cheers/Frasier as this manager…

    I also love that everyone else was happy for OP’s good fortune and Manager’s suggestion of giving back to the company flopped. Although it would’ve been so much sweeter if someone had said “What? No, of course not!”

  5. StellaBella*

    I am glad you got out of the organisation and glad her weird comments were ignored. I am also very glad to hear your experiences in non-profits have been overall very positive. I admit this has not been my experience, but am glad for you!

  6. only acting normal*

    Senior management is divided, and she got promoted anyway, because some people really like being sucked up to. So much so they are willing to ignore or explain away the suck up treating others badly.
    If the senior person with final say over the promotion likes being flattered then the senior people who see through it will get railroaded. Sounds like Sarah and person on the phone are in the latter category, hence their candour. Maybe they’re hoping to gather exit evidence to bolster their point.

    1. AdAgencyChick*

      There’s probably some of that going on (liking being sucked up to), and perhaps ex-boss is also very good at one aspect of her job, especially if it’s fundraising. Lots of organizations, nonprofit or for-profit, will put up with all kinds of bad behavior from a rainmaker because they’re more afraid of having to replace that person’s moneymaking abilities than they are of having to replace a bunch of junior people who quit because that person is an a-hole.

    2. Beaded Librarian*

      Part of me wonders if her ‘management style’ wasn’t quite as obvious to some people until she was promoted to their level?

  7. Jemima Bond*

    I loved this letter because it had the enjoyable WTFery without any real worry for the employee or their job/emotional well-being; a true “don’t even worry about this your boss is a divvy” one. Plus I loved the mental image I got from the parallels Alison drew:
    LW attends county agricultural show whilst on a day off during a work trip. LW arrives back at the office leading an adorable piglet on a length of rope.
    LW: Hey Boss, I won this prize while I was away on that conference, so as you suggest I am donating him back to the organisation as our office pet. His name is Percival and he likes apples and belly-scratches.
    Boss: … *looks nonplussed as Percival gazes up at her, blinking pale-lashes eyes, and places a small pink trotter trustingly upon her lap*
    Percival: Oink.

  8. Indie*

    I always like to try and puzzle out whether these types of bizarre, petty orders come out of a sheer love of power (“Stand and deliver: your money or your job”) or whether, having no earthly idea what managers are supposed to actually do, they just conclude that it’s a about ‘being in charge…something something’ and getting whatever subserviance they can wrangle in the form of an extra dresscode and removed on the doorstep rainboots.

    Bringing up something in front of others without anticipating their reaction would suggest ignorance. However going after an employee’s own money sounds like deliberate malice and a power trip; surely no one can be that ignorant!

    I will never figure out this type.

    1. snowglobe*

      I think you are on to something there, with (some) bosses that think if they are “in charge” they need to prove it by ordering their staff around, in everything from dress code to margin size in their reports. They really don’t know what else managers are supposed to do to prove they are managing.

    2. gecko*

      I think those petty orders are often about inappropriately acting on feelings and anxieties. Like, people can and will self justify the most petty stuff.

      I think, this boss has an image of herself that she wants to represent, and when her employees don’t stick perfectly within that image she 1) isn’t applying empathy to understand why and 2) sees it as harmful to her own image. This gives her bad feelings and anxiety, and she has the power to tell her employees to change their behavior, and when she “reminds” them of the rules…they stop doing the thing that feels harmful to her ego and she feels better. What’s not to love about being the boss eh??

      I guess I should say, I don’t know that that’s her emotional life but it’s a flow of logic I can understand. No one wants to feel bad; some people resolve their bad feelings inappropriately and get trained that that’s a method that works. Almost everyone feels like their own actions are justified. I think remembering that is pretty helpful both in dealing with people and in understanding how my own actions are perceived.

      1. EPLawyer*

        I think you are on to something here. She has this image of the best run, most professional, most dedicated team of all. Because if its the bestest, then she deserves to be promoted. Strict dress code shows how professional they are. Donating winnings back show hows dedicated the team is to the mission.

        LW messed with that image by not doing these things. Because reasonable people would not. This got manager all het up and she doubled down.

      2. LQ*

        I really like this comment. I think that it is incredibly important to remember that people are never the villians in their own stories and so thinking through the logic that people are using to get to the justifications can help address them. (And to think through what of my own behaviors might appear villainous.)

        I have a boss who some people think is wildly unpredictable, but as soon as you set your perspective in line with his. it all falls into place and makes a lot of sense. I can tell you how he’s going to respond to just about everything I do with a very high level of accuracy, and when I’m off it’s fairly trivial. I’m sure there are people who think the same about me or anyone.

      3. Jaybeetee*

        I was about to comment similarly! IME, most of the “bad managers” I’ve had or seen have been “insecure” managers in some way or another (or it’s been a systemic issue with the workplace where the manager was being crapped on inappropriately as well and it was continuing the downhill roll). Managers who didn’t feel respected or secure in their sense of authority, and responded with pettiness, micromanaging, “bossiness” (obviously they’re bosses, but I mean that barking-order “do what I say when I say it, because I say it” attitude), or other poor behaviour. Such behaviour actually tends to make whatever their issue is worse, because, well, they’re just going to be less respected by their reports, even if they do have compliance from them. Managers that only flex their muscles when necessary tend to be more widely respected and get better performances from their reports than thes who constantly squeeze in order to constantly remind themselves that they still can.

      4. Not So NewReader*

        What I saw was the mentality of “what is mine is mine and what is yours is ALSO mine”. The kind of thing we see in some marriages where one partner is always thinking “me first”.
        I hope they don’t put her near the company’s finances. Her lines are blurred and her potential to cross over is in place.
        I heard a story of an individual being given a company credit card. Since their name was on the card, they figured it was theirs. So, surprise!, they put the own purchases on the card, because after all, the card had their name on it. Things got interesting as the person kept repeating, “But the card has my name on it, I can use it for my own stuff too. It’s got my name on it.” All you can really do with a person who keeps repeating themselves like that is let them go. They either do not understand or are faking it pretending that they do not understand. The net result is the same no matter, they can’t do the job because they do not follow the rules.
        And this woman here reminds me of the person in my story.

    3. GiantPanda*

      At least in some cases it’s superficiality. People sticking to a stricter dresscode = everything looks nice and tidy = everything under control = everything runs smoothly = good management.
      It’s the same kind of thinking that makes managers require precises start times and clean desks and following procedures for procedures’ sake when the job doesn’t actually need it and more flexibility would improve everyone’s life.

      Real good management does not work that way, of course.

    4. That girl from Quinn's house*

      I had a nasty boss who was like that on dress code. She’d get mad if people wore weather appropriate clothes to work (jeans and snowboots for wading through slush, etc), and then changed into business clothes when they got in.

      We all took mass transit because the building had no parking: she, of course, had a dedicated parking space next to the front door.

  9. Phoenix Programmer*

    Ugh this brought flashbacks to my awful manager. Especially the passive aggressive attempts to shame you in front of senior leadership.

  10. Commanderbanana*

    Your (former! Yay!) boss is an ass, and it’s really unfortunate that your (former! yay!) organization is failing so spectacularly at managing this. I also had a very micromanaging boss who reliably had 100% turnover every year under her, but she kept getting promoted because she was buddies with our department director. I’ve been gone for almost two years and I still routinely get emails from former coworkers who are trying to help current employees of this organization get the hell out of there. And their Glassdoor reviews are really something to see.

  11. Dessi*

    This is a satisfying update. I do wonder how Alison feels about being very candid in edit interviews, specifically a situation like this. I’ve done this before. I’d think it’s fine so long as it’s done diplomatically and only share what’s truly necessary?

    1. CoveredInBees*

      Yes. I think the elements you mentioned are essential. Also, in this case, the OP was asked about this topic very directly. As long as you maintain a professional tone (no namecalling, venting, tangents, etc), I think being very candid would be called for.

      In the one exit interview I did that involved being very candid, my interviewer also wasn’t the least bit surprised by what I’d said. Those were her actual words. People in previous exit interviews had said the same and she’d witnessed it firsthand.

  12. Bowserkitty*

    Alison, I missed the first post but I am highly amused you mentioned Des Moines in your anecdote originally!!

    OP, this sounds like a fantastic move for you jobwise and I am happy all of the other senior leadership reacted the way they did.

Comments are closed.