I confessed my crush to my manager, carpenter treating colleague poorly, and more

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

1. I confessed my crush to my manager

I’m asking for advice about my manager. He’s a tier above me, and it’s frowned upon to hangout with different tiers outside of work hours, though it still happens. My manager told me he takes the rules very seriously, although I recently learned that isn’t true because he does hangout with lower tiers outside of work, and has flirted with women in his department, which feels hypocritical.

He was transferred over to my department a couple of months back, and while he was going through the training process leading up to it, I confessed my feelings for him. I explained that I want to honor a professional relationship, but that I owed it to myself to tell him that it was more than just a crush for me. He accepted the compliment and said we can’t date because we work together, I said that I would have been willing to change shifts or departments, and he gave a memorized summary of the rules and said we would’ve had to get the whole thing approved by HR, etc. Even though it was a soft rejection, it didn’t feel like an outright lack of interest.

My confusion is this: one of his closest work friends said that he was known at his last facility for following women he liked around like a puppy, and that he brought that same energy to this site by pursuing another woman who was flirty and also married. I also found out from someone else that he is now in a relationship, since before I gave my confession. I don’t understand why he didn’t use my moment of confiding as a way to be open as well about seeing someone, instead of giving a recitation of the rule book.

He also became way more friendly and quirky/playful with me after my confession — more familiar with how he chatted, seeking out more eye contact, more jokes, more lingering. I took that as a reason to hope, but now I feel like I was just an ego boost for him and that I was vulnerable and honest for nothing. Now I don’t think I can trust anything he says as a friend or manager.

Noooo, this is all a problem. You have a manager who’s known for following women around “like a puppy” (which is creepy and could easily be harassment at work), is pursuing a married colleague (while in a position of authority, no less), and is now being friendlier than before to an employee who confessed to having a crush on him. All of that is gross and at odds with being an effective manager (and a decent coworker, for that matter).

Your end of this pales in comparison to his, but you don’t “owe it to yourself” to confess an attraction to a coworker, particularly one in your chain of command. Where attraction is involved, you owe it to your coworkers to prioritize their comfort at work over your romantic interest in them. (That doesn’t mean coworkers can never date. It means that you need to see real signals of reciprocated interest first, and still not make dramatic confessions that will put someone on the spot, and it does mean that people in your chain of command — in either direction — are off-limits.)

But you’re right that you can’t trust your manager as a friend or as a manager. You can’t trust him as a friend because he’s not your friend; he’s your boss (more on that here). And you can’t trust him as a manager because he’s shown himself to have terrible judgment.

Truly, this man is bad news on all fronts. You want professional distance, nothing more.

2. Carpenter treating colleague poorly

My workplace was having some new cupboards installed, so we were encouraged to work from home unless we needed to be on site. The day after, the two colleagues who had been in shared that the main carpenter had been very unpleasant to his much younger coworker, calling him stupid, making unkind comments, and being rude to him.

I keep thinking about what I would do in that situation and I can’t decide. What would you advise? Report him to his company? Ask him to keep his tone respectful when in our office? Tell the young coworker he is being treated poorly and it isn’t right? Do nothing?

We are renting our offices within a building owned by a larger organization that occupies the rest of the space, so the contractors were bought in by our landlord (after much back and forth about who was responsible), so we don’t have a direct relationship with the carpentry company.

You have every right to say to someone who’s bringing that sort of hostility and disrespect into your workplace, “Could you please talk to your colleague more respectfully? It’s very disruptive to hear this.” Or even just, “Whoa, that’s not okay here.” You’d also have standing to call his company and share what happened (even without a direct relationship with them.)

3. Leaving when you’re a director and your departure will result in disaster

I’m writing with a follow-up question to your March 31 post, “How do I train my team to do my job without making it obvious I’m planning to leave?”

In your response, you say, “The more senior your job gets, the more it’s your responsibility to ensure things like that are taken care of. If you’re a department director saying “no one will be able to cover even the basics if I’m buried in an avalanche tomorrow, oh well, too bad,” that’s a problem. That kind of planning is part of that job.”

What do you do when you’re a department director, and no one will be able to cover even the basics because you’re so overworked and understaffed? I’m the director of a very small department that has outsized impact on both internal and external partners. My supervisor and my grandboss (the head of our organization) acknowledge that my job description is at least two full-time positions and that I’m doing even more work than that. I’ve told them that the situation is unsustainable and that without additional staffing and support, I will leave. My manager knows I’m looking, and knows that the staffing situation is why. As part of these conversations with him, I’ve documented what will happen if any of my responsibilities aren’t done, and made suggestions about how to ameliorate those consequences, so he’s very aware of the impact that my departure would have.

I’ve read your site long enough and been burned here enough to realize finally that this situation will never change There’s also literally nobody who can do the majority of my job. When I do leave, what is the best way for me to approach succession planning? I have full documentation of everything that I do, but nobody in my department would even be considered by higher-ups and HR for coverage of my responsibilities, due to how their positions are categorized. I haven’t left yet because I feel so guilty about leaving my staff and the communities we serve, but my burnout and anger are finally strong enough to outweigh the guilt.

You can’t do succession planning in the situation you’ve described. You’ve done the other part of my advice from that post, which is to make the situation very clear to someone above you. They are aware. You aren’t simply seeing the situation and neglecting it. You’ve escalated your concerns and been clear to the organization’s leadership about the risks they’re taking and the fact that you don’t have the ability to resolve that on your own. They know. They are choosing not to deal with it.

You can leave with a clear conscience and no guilt.

4. Company isn’t paying my employee for a lunch break she’s not taking

I just started a new role, and I wanted to check on something that’s happening for one of my direct reports. I think this is a “legal, but your boss sucks” kind of situation. My hourly direct report travels for work. She charges her time from when she leaves her hotel room in the morning until when she returns at night. The days can sometimes be very long.

When she gets paid overtime, the finance team doesn’t pay her until she hits 45 hours, because technically she “had a lunch break” even though she worked through that lunch most of the days. Also … she’s on a work trip. She woke up early to get on a plane. She’s not at home. She has much less control of her day because she’s on someone else’s schedule. They’re really going to take out these five hours?

Do I advise her to take the lunch break, or how do I best advocate with our finance team to just pay her for the full-time worked?

Actually, it’s not legal! If she’s working through lunch, they’re required by law to pay her for that time (or they need to explicitly tell her that she is required to take a real lunch break where she is not working and then enforce that).

However, if they’re currently paying her from her travel time from her hotel to her worksite and then back later, that’s more than they’re required to do by law (typically that would be considered akin to a commute if it falls outside her work hours), so on a practical level it might be a wash.

If you want to address it, the framing you want is: “I’m concerned that we’re out of sync with federal law on this, since if she’s working rather than taking a lunch break, we can’t legally dock her for a break.” You could add, “I also don’t want her to feel we’re nickel and diming her, given what long days she’s working and how disruptive this much travel can be to someone’s life.”

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