future manager is a bigoted jerk, boss hasn't paid me back, and more

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

1. Is my future manager a bigoted jerk?

I currently work in a team of about 20 people. We have a director who oversees three managers, each of whom oversees a group of employees.

My old manager, Buffy, resigned a few months ago, so while we looked to backfill her position, Buffy’s team was temporarily split between the other two managers, Willow and Anya. I’ve been reporting to Willow since Buffy left and things have been going well.

Our director Giles announced in an email earlier this week that they’d finally found Buffy’s replacement. The new hire, Xander, will be starting in a few weeks and Giles’ email stated that everyone who’d reported to Buffy before her departure would report to Xander.

Out of curiosity, I googled Xander, and instantly found his Twitter account. And I’m not happy with what I saw. He rarely tweets on his own but consistently retweets men’s rights activists, anti-BLM accounts, and other accounts that run the gamut of oppression and marginalization (and I’m 100% sure that it’s the same Xander because his last name and profile pic are the same as his LinkedIn).

I don’t want to work under this person. Would it be overstepping to ask for a meeting with Giles to request that I stick with Willow as a manager? I have a good relationship and some strong social capital with Giles and am willing to be 100% honest about my reservations. Also, is it appropriate to go to HR over this? In addition to the fact that I’m a woman who doesn’t want to work for a misogynist, any of our clients could google Xander and see what I saw, and I believe it would reflect poorly on our company as a whole.

Especially since you have a good relationship with Giles and strong capital to spend, it would not be overstepping to share your concerns with him and and ask to stick with Willow as your manager. Even if you didn’t have such good capital, it would be okay to do that — your concerns aren’t akin to “Xander seems annoying”; they’re “I’m wary of working for someone with these deeply concerning views on women and people of color.”

And yes to HR as well. Frame it as “I’m concerned about his open embrace of viewpoints that harm women and people of color, and what that means for the biases he’ll bring as a manager, as well as about clients googling him and finding this.” If you have coworkers who share your concerns, encourage them to speak up too.

2. Boss hasn’t paid for his share of our group collection

My small team works from home, but we all stay in contact with each other via Teams messages/calls and weekly meetings. A team member, Julie, went out for surgery, so we decided to all chip in to send her flowers. Our boss, Tristan, was out of office during this group email discussion, so I texted him to keep him in the loop and not assume he wanted to contribute. He said he did and asked for my Venmo, which I provided.

All members on my team have paid me through Venmo at this point, with the exception of Tristan. In both email and our recent team meeting, I said, “Julie will be getting her arrangement today! Thanks again for contributing. If you still need to, my Venmo is @(myname).” Tristan even thanked me and another person on the team for arranging it in our meeting.

At this point, I don’t feel like I will be getting anything from him. Part of me feels like I should just eat his portion to safe face and embarrassment (just the thought of having to ask him directly mortifies me). The other part wants to get paid! It isn’t a tremendous amount by any means, so chasing him feels a bit silly. I also don’t want to learn that he may have sent it to the wrong person (and yes, I’ve quadruple checked my texts/emails to ensure my info is correct, since that also crossed my mind). The coworkers I trusted to speak about this with are split decision. Do I let it slide, or find a way to bring it up again? And if the latter, how do I make the asking as “unweird” as possible? He’s an awkward person to speak to by nature anyway, which doesn’t make just going to him jokingly about it an option. I’m still holding on to hope and waiting, but have little confidence on receiving anything.

You absolutely need to raise it with him. Imagine if you were in his shoes, thought you’d paid, and had no idea that you were causing this kind of consternation in a team member who felt they couldn’t raise it with you and instead was just preparing to eat the cost of your share. You’d presumably be mortified by that, right? Give him the benefit of the doubt that he’d feel the same way and assume the most likely scenario is not that he’s trying to rip you off but that signals just got crossed somewhere.

Message him this: “I’m trying to close out the accounting for Julie’s flowers and I don’t have your portion yet. Could you Venmo it to me today so I can close this out?” Just be matter-of-fact and assume good intent on his part.

3. Should I have told my manager I’ll be out for surgery, even when I didn’t know the dates?

I have had a minor health problem for a while. I first got a referral for surgery to fix it as I was starting at my current company and I declined as my provider couldn’t offer a definite answer on how much sick leave I would need.

The problem got progressively worse and just before Christmas I asked to be scheduled for the operation. They asked me if I would accept a short-notice cancellation time and I accepted. On a Thursday, I was offered an opening to have the operation on the following Tuesday. I then called my supervisor to let them know and to make arrangements for me to be absent Tuesday – Friday and work from home for the week after.

My supervisor’s comment is bothering me. She said she didn’t know I was waiting to have this operation. My partner also thinks I should have let them know about it earlier. I did not because it is private health-related issue. What is your take? (Also, it is a very slow time at work. My absence will not burden my coworkers.)

Ideally you would have alerted them to the general situation earlier (“at some point in the next few months I’m going to need X amount of time off for surgery, but I might not know the dates until a few days before”) but it’s not necessarily a big deal that you didn’t.

In a lot of jobs, that kind of notice would help people plan and so it would be courteous to offer … although in other jobs, it wouldn’t be terribly actionable without knowing the specific dates.

But you felt like this was your private medical info and you didn’t dates nailed down yet, so it’s not outrageous that you chose to wait until you had something concrete to share.

Was your manager registering an objection to not knowing about it, or just observing that she didn’t? Her comment about not realizing you were waiting on for surgery doesn’t necessarily carry any implied criticism. But if she clearly was criticizing you … well, lots of medical situations require someone to be out for four days (which is not an enormously long time) without any notice at all. She’s going to have to get used to that as a manager. But if her point was that she could have done helpful planning if she’d known this was coming, even without knowing exactly when, that’s a fair point and you can incorporate that into your thinking going forward.

4. My boss won’t let us ever finish a project

I’m starting to feel I’m just inflexible, and maybe that is your assessment as well.

To cut a long list of stories short: My CEO involves himself in every area of the company — HR, recruiting, art, engineering, and project management — and won’t let tasks be completed. Each time a task is finished, he brings forth improvement ideas he picked up online or from partner companies. We spend months writing and finishing job descriptions, he wants them redone. Company meetings finally have a format, he “has a few good ideas” and they get reworked almost monthly now. I feel like nothing I do matters, and like my position and experience do not matter.

When I brought this problem up and told him I want to have the win of a task being done and finished, he replied, “But you do finish! And then we innovate and make it better!” He sees no problem at all with continuous reworking … but I want to move on and do the next thing, not work on something and then spend months “improving” each time I finish. Is it really me?

It’s not you. This way of working would drive most people mad — it’s very reasonable to want the satisfaction of finishing a project and not feeling it will go on forever and ever, and it’s very reasonable that his style makes you feel like your time and energy aren’t being used well.

But this is the way he operates and he’s the CEO, so you’ve got to assume this is how things are going to remain and decide whether you’re willing to work there knowing it’s unlikely to change.

5. How can I screen for candidates who are willing to push back on me?

I’m conducting interviews for a new position, and one thing I want is someone who’s willing to push back on me when they think I’m wrong (within reason, of course). However, I’m not sure how to determine this in a job interview. Obviously, very few applicants are going to want to argue with their interviewer, and if I just ask them then everyone’s going to say yes, so that question tells me nothing. Do you have any ideas?

Start with this: “Can you tell me about a time when you had to push back on a coworker or manager when you thought they were mistaken about a decision? What happened and how did you approach it?” And then ask follow-up questions about their answer to try to probe beneath the surface and get a better sense for how the person really operates. The right follow-up questions to ask will depend on what their initial answer is, but you could consider things like: “I would think X would have been challenging — how did you approach that?” … “What happened after that?” … “What things have you found are key to making sure you’re heard in a situation like that?” It might also be interesting to ask about a time when they thought something was a mistake but didn’t push back, and why and what their considerations were.

And at either the start or end of this discussion, you should explain that you’re seeking someone who’s comfortable pushing back on you when they think you’re wrong, so it’s clear why you’re digging into it.