my boss is my boyfriend and won’t give me a day off, coworker asked my employee to hide info from me, and more — Ask a Manager


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

1. My boss is my boyfriend and won’t give me a day off

The owner of the restaurant where I work is my boyfriend and the general manager. I asked for a day off a month ahead of when I needed it off. It’s on Mother’s Day and, yes, it is one of the busiest days of the year. But I have worked there for three years and never took a day off, unless he wanted us to go on a vacation. He recently hired someone two weeks ago and promised her Mother’s Day off because it’s her birthday. I have missed out on so so many things in the past three years because he needed me to work

I am loyal and I want to help him out, and I generally don’t complain. This one time I do and he acts like I’m the worst person ever and how dare I. I’ll lose hours and maybe even my place where we live together if I do take it off. I feel like I live one life and I feel like he is just treating me like a body there, like I’m replaceable, and he keeps on working me to the bone but refuses to see it in my way at all. It’s just unfair and I don’t know if I should quit or just firmly say I’m taking the day off.

Consider leaving both the job and the relationship.

It’s true that in the restaurant business, it’s hard to get days like Mother’s Day off; that’s part of the job. But if he’s offered that day off to a brand new hire, while not giving you any days of your choosing for three years, there’s a problem here, with both the job and the boyfriend. And it sounds like you think that if you take the day off anyway, that itself could jeopardize your relationship (“I’ll maybe lose the place where we live”)? Start thinking seriously about what’s keeping you in both these entanglements (the job and the man), and at a minimum start trying to separate them out from each other. It might get a lot easier to clearly see the state of the relationship if you’re no longer working together.

2. Our boss is MIA

I work at a small nonprofit. I have one supervisor above me, Jill, who is managed by our executive director, Sara. Sara is a great person and has been very open about having some family and health challenges in the past couple years. Since I joined the org a few years ago, she has gone from an engaged and effective leader to a totally absentee boss.

We don’t have anyone on staff to handle HR issues or approve payments for needed supplies, which means we often end up spinning our wheels while we wait for her. Emails go unacknowledged. I’ve learned to contact her exclusively by personal cell, and those messages are often ignored until it becomes a crisis. She does not attend staff meetings or communicate with the staff broadly.

Jill doesn’t have the tools and skills to run the org. We have talked about contacting the board directly but are concerned about a blow-up. Sara is close with the board president and we are worried about being seen an insubordinate or untrustworthy,

I feel demoralized. I care about the mission but I am worried about our reputation in the community and our ability to maintain funding if our leader continues to be unresponsive. I feel that if a lower-ranking staff person was this inaccessible or unreliable, they would have been fired a long time ago.

Not to make this break-up day, but you should consider getting out. In a small organization, having an absentee leader when no one can step in and run things in their absence is unworkable. It means the organization won’t accomplish nearly what it should be (hugely problematic if you’re a mission-driven nonprofit) and your job will be a constant exercise in frustration.

That said, if you want to try to determine if this is solvable first, the right move is for someone (probably Jill more than you, or someone else senior or who has good rapport with Sara) to have a heart-to-heart with Sara where they lay out the impact her absence is having and the need for someone to handle the things that she’s not. If that’s already been attempted and you haven’t seen meaningful changes, that’s your answer. But if no one has tried that yet, it’s time; Sara may not realize how bad things are, and it’s a service to her and to the organization for someone to spell it out. That’s especially true if someone might eventually go to the board; you want to be able to say you’ve tried talking to Sara directly first.

For what it’s worth, this is the sort of thing the board should hear about — and it’s not insubordinate or untrustworthy to bring them issues this serious, especially after you’ve tried to resolve the problems with Sara directly first. The bar for staff contacting the board should be pretty high, but what you’ve described meets it.

3. My colleague asked my employee to hide information from me

A colleague just asked my employees to keep secrets from their supervisors, and I’m not sure how to address it. This colleague and I are both at the director level and are still fairly new in our positions (within the last year), but as he is an attorney (and much older man), he is paid nearly as much as our CEO and is generally deferred to by people throughout the organization.

Last week, while I was out of town, he approached one of the entry-level staff members on my team, Jane, and asked her for some information on behalf of one of our board members. None of the information was confidential by any means, but for some reason he specifically directed Jane not to tell her division head or me, the department director. She did as she was told. The requested information was related to a situation that blew up yesterday, and both the division head and I were caught off guard. When the division head and I were trying to address the situation, Jane told her direct supervisor what had happened with the attorney and how uncomfortable that made her. (My team is well-known throughout the organization as being very tight-knit and supportive of one another.) The supervisor then reported the attorney’s actions to the division head, who told me.

This is obviously unacceptable, but I’m not sure the best way to handle this. How do I protect my staff, prevent this from happening again, and restore my team’s trust?

There are times when a higher-up might need someone junior to pull specific information without talking about the request with others, when the situation is sensitive and they’re trying to avoid gossip (for example, during an investigation into potential wrongdoing, or financial info that could lead to job cuts). So this hinges on whether there were legitimate reasons for asking Jane to keep the request confidential or not. If there weren’t, then this is a conversation with the other director about not putting your staff in that position unless there’s a clear need for confidentiality, and it’s a conversation with your team about what to do if they’re asked to keep something confidential (which should include who is in a position to make those requests of them, and what steps they should take if they’re uncomfortable with something they’ve been asked for).

4. We’re supposed to have a team meeting to discuss feedback for our boss

I’m on a team of about half a dozen people supervised by Barnaby. We all have regular but infrequent skip-level meetings with Barnaby’s boss, Calvin.

It sounds like people have mentioned to Calvin in the skip-level meetings that Barnaby is not approachable. He passed that feedback on to Barnaby, and Barnaby asked one of my peers, Alfred, to organize a team discussion to gather more details on where that’s coming from and what he can do to be more approachable. Barnaby will not be at the meeting. Alfred will moderate and provide an anonymized summary of the takeaways back to Barnaby afterwards.

I’m not clear whether this meeting was Calvin’s suggestion or Barnaby’s idea or whether Calvin knows it’s happening. I trust Alfred’s judgment and believe he will do his best to get good feedback and actually anonymize it, and I have no reason to believe that anyone else on the team would feel differently.

But … this is kind of weird, right? I guess I empathize with Barnaby that it’s tough to get nebulous negative feedback and I understand why he’d want to involve the team in figuring out what specific actions he should take to improve communication. And I’m willing to give him benefit of the doubt that he’s doing this in addition to self-reflection/talking to peers for advice/asking Calvin for details or suggestions. But it still feels like it puts the team (and especially Alfred) in an awkward position, and it almost feels like it could be a prelude to discounting the feedback, like if people can’t provide (or don’t want to share with the whole team) enough specific examples of times he was unapproachable then he can write the whole thing off as unfounded? Is this a smart way to approach an inherently awkward situation, or is somebody falling down on the job here?

It’s a little weird, but it’s not necessarily a terrible idea if people generally trust Barnaby and Alfred. If either of them isn’t trusted, the whole thing falls apart — people won’t give candid feedback, and there’s no point. But if people trust them both to act with integrity, and also trust Barnaby not to react poorly to honest feedback even if it’s uncomfortable to hear, I can see where this came from: since if the issue is that people don’t find Barnaby approachable, he’s not well-positioned to get candid info from people himself. That said, my first choice would be to have Calvin lead these conversations, not put it on Alfred … but I can also imagine someone thinking people will be more candid when speaking in a group of peers without their boss’s boss there.

So much of this depends on really specific group dynamics that it’s hard to give a general ruling — but I don’t think it’s inherently bananas.

5. As a manager, when do I need to announce my pregnancy to my team?

I am a very newly promoted (two months) manager leading a team that I used to be a high performer on for several years. I think my team is awesome, I’m trying to build credibility as a leader, and the transition is going about as well as it can.

I am also three months pregnant with my first child (I found out literally three days after accepting the promotion), and I’m wondering what my obligation to my team is regarding when to notify them of my upcoming maternity leave. I should also point out that I’m in a male-dominated workplace and I am the only woman on my team.

I know your previous advice states to let your coworkers know whenever you are comfortable sharing, but waiting to tell my team after the 20-week scan feels too late. I handle some of the workload of the team as well, and there will likely be issues with coverage while I’m out, and that’s probably where I’m feeling this sense of obligation from. I am going to manage this as best I can through cross-training in advance, but this will largely be unavoidable. What do you think? As a manager, do I have an obligation to disclose my pregnancy to my team earlier when my absence will impact them?

Waiting for the 20-week scan is not unreasonably long. That still leaves you four or more months for your team to prepare for your leave, which is significantly longer than people get with many other types of medical leave. If this is the disclosure timeline you’re comfortable with, use it; it’s not an uncommon one to see.



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