tl;dr: Upper management urges me to warn my team against participating in a fundraiser for a former boss, who owns our direct competition.

Locale: US. Bob is my former mentor and CEO of a very small (<20 people) IT company. Work for Bob was my second gig after coming to the US and I loved every aspect of it. Bob was a great manager and a superb mentor. in general, he has a reputation of not only an expert but also a cool boss.

I can't stress how much I enjoyed work for Bob. Still, I've had outgrown his shop and become a team leader in much larger (>2000 people) company. In principle, we are his competition, but due to the sheer size difference, it shouldn't matter.

Recently I have heard that Bob has very serious health problems. Right now, he is unable to work and experiences financial stress. His spouse established a fundraiser for him. One of my teammates, also a former employee of Bob had told us about this during the lunch break. Recently, my supervisor informed me that she knows about this conversation and feels it is not acceptable. According to her, Bob is our competition and we shouldn't help him. I should neither allow my team to talk about the fundraiser nor support it myself. She also asked me to talk about the situation with my subordinate who mentioned the fundraiser. She wants me to warn him that such behavior may lead to more serious consequences.

I found this request quite shocking as the help is not related to Bob’s company, but to Bob himself. I do not want to talk to my team about this situation, but going against the will of my manager is unreasonable. On the other hand, I do like Bob and want to help him as much I can.

What would be the most professional way to proceed in this situation?

EDIT 1: The fundraiser allows anonymous donations.

EDIT 2: I work in California.

  • What state are you in? It turns out that most of the pertinent anti-retaliation laws are state-based.
    – Ben Barden
    Commented Mar 13, 2019 at 19:27
  • @JoeStrazzere I added information that one can help anonymously. Nevertheless, it does not address the situation when I donate anonymously and my supervisor asks me later directly if I had helped Bob. I know it sounds unreasonable, but the situation is unreasonable from the beginning.
    – user101274
    Commented Mar 13, 2019 at 19:28
  • 1
    @BenBarden California.
    – user101274
    Commented Mar 13, 2019 at 19:31
  • 3
    "What would be the most professional way to proceed in this situation?" In my opinion, you should find a new employer that recognizes you as a professional, and treats you as such. This kind of top-down, anti-community management is both odious and badly out of sync with modern employment practices that are proven to be better for the bottom line, and for customer and employee satisfaction. See e.g. consciouscapitalism.org or agilemanifesto.org. Commented Mar 13, 2019 at 19:42
  • 1
    ...or, alternately, if you do not wish to lie, say something like "Ma'am, I don't believe it's any of your business what I do on my own time with my own money." Of course, there are tradeoffs for everything, and sometimes standing on principles can cost you.
    – Ben Barden
    Commented Mar 13, 2019 at 20:18

2 Answers 2


Technically, it is reasonable for your workplace to set rules about what sorts of things may be discussed on work time and with work devices.

Your employer should not be trying to tell you what you may or may not donate to, or what you may or may not do in your free time. It is reasonable to tell you what you may or may not do as a representative of the company, and what you may or may not discuss during work hours. There are workplaces, for example, where discussing any sort of fundraiser would be considered unacceptable.

Now, in this particular case, I find her reasoning about why to not discuss this fundraiser both objectionable and short-sighted, and you may wish to bear it in mind when considering whether you wish to continue employment at this organization or under this supervisor. However, the general blanket ability of the workplace to constrain such things does offer you a way forward.

You go to your subordinate, and say something like "I have been informed that we are not to discuss this topic on work property, using work devices or during work hours. This policy itself is likewise not up for discussion using work resources." Optionally, you may add "If you'd like to talk about it with me after work hours, I am available." and provide some means of contacting you that does not use work resources.

She has absolutely no right to tell you what causes you may or may not contribute to with your own money. If you feel that her making that demand was sufficiently out of line, and you think you'd have support from your upper management in this, you can discuss it with them. If you it is generally your experience of her that she is a reasonable individual, you could alternately discuss it with her. Perhaps she has some reason beyond the most obvious for objecting to your old boss?

Worth noting that this may cost you with her. This has probably already cost you somewhat with her. Offering to continue the conversation with your subordinate, telling her that you're donating money anyway, pushing back with her and/or taking this to management are all reasonably likely to cost you with her to varying degrees. You will have to decide how much to censure yourself in the face of her unreasonable position. Regardless, she has no right to tell you what to do as a private citizen on your own time or with your own money.

The simplest answer, and the one that is the least costly for you while still not poisoning your relationship with your subordinates or leaving your old boss out to dry would be to donate anonymously, let your team know that word has come down from higher that it's no longer a topic of discussion for work hours, and leave be. Anything past that is you taking on a personal risk in order to attempt to challenge this particular bit of toxic workplace culture that your supervisor is attempting to put in place. If you're going to take on personal risks in order to challenge your supervisor in matters of workplace culture, you should understand that that may lead to your needing a new job in the near future.

  • "She's not allowed to tell you what you may or may not donate to, or what you may or may not do in your free time." This isn't accurate. Many employers do drug screens, which is likely a free time activity. And if an employer dislikes the things you say or the activities in which you participate (including the things on which you spend your money), they are well within their rights to terminate your employment. Commented Mar 13, 2019 at 19:19
  • @BillHorvath Good point. There are states where that is not so, but OP isn't living in one of them. Edited.
    – Ben Barden
    Commented Mar 13, 2019 at 19:43
  • @BenBarden sounds reasonable, I especially like the suggestion that I can add "If you'd like to talk about it with me after work hours, I am available.". It's simple but conveys the message that I care about Bob.
    – user101274
    Commented Mar 13, 2019 at 20:06
  • @Ramhound There are state-level laws prohibiting retaliation (ie, firing) for various activities. California's suite of same is pretty robust in the political sphere, but it doesn't appear to cover this case. (obIANAL)
    – Ben Barden
    Commented Mar 15, 2019 at 17:03

This is a fundraiser for an individual, who happens to be your previous boss, and who also happens to own a company that competes in the same space as your current employer.

Your current employer certainly can attempt to prohibit you from engaging in activities that are directly in competition with their business, but this doesn't fall into that category. They may be trying to strong arm you and you may very well be afraid or worried about losing your job if you were to support this fundraiser. But sometimes in life we have to take a stand for our own values and for the things we think are important, even when those things put our own selves at risk. Is this one of those times? If so, follow what your heart tells you is the right thing to do.

Your employer may hold sway over you to a certain extent and they may wield a certain amount of power over you, but they don't own you. They don't get to have the liberty of dictating to you how you choose to live your life and who you choose to surround yourself with. If supporting Bob is important to you on a personal level then that's what you should do. You may risk losing this particular job, but there will be many jobs in your life. You only have one Bob and you only have one opportunity to be his friend and to show him that he holds a place of importance in your life.

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