It’s five answers to five questions. Here we go…
1. Boss is pushing me to out my boyfriend to promote our bar
I work as a manager for a bar. I’ve been doing my job for about five years, and for the most part, I love it. My staff are great, I like the customers, and I even liked the owner (until recently). I thought I had the perfect job until I started dating John. John is a semi-famous entertainer who came into the bar and struck up a conversation with me. We bonded over our working-class childhoods and coming from immigrant families, and before you know it, he was giving me his number and we were hanging out outside of the bar. We’ve been dating for six weeks and it’s the happiest I’ve ever been.
The problem is with my boss, “Luisa.” Luisa is convinced that John is a gold mine in PR for the bar and will not stop trying to get me to pressure him to post about and frequent the bar. This is complicated by the fact that the bar is a gay bar and John is not publicly “out.” When I got sick of her pushing for John to appear on our Instagram story and told her to stop asking, she told me to take some time and think about how committed I am to the bar, which I considered a veiled but probably empty threat (she is otherwise a very hands-off owner).
The most recent thing she did that really crossed the line was taking a picture of John and I kissing in the parking lot when he came to pick me up after closing. She showed it to me the next day, talking to me about how romantic of a story it was and how the bar brought us together. I freaked out and made her delete it, but I’m starting to feel like it’s either quit the job I love or risk my boyfriend being outed. We’re too small to have HR.
Luisa is wildly out of line.
Would you be willing to leave your job over it, if it came to that? You obviously shouldn’t have to, but knowing if you are can influence the way you approach this. Ideally you’d say to Lisa, “I like working here and would like to stay a long time, but I want to be clear that this is a hard line for me. I will not pressure John to promote the bar or publicize our relationship, and I need to know that you understand and accept that. If you don’t, I’d need to move on, but I don’t want that to be the case.” In fact, you might even lead into this by saying, “You asked me to think about how committed I am to the bar and here’s where I’ve landed.”
2. Can I ask my boss’s boss to get her more training?
I am managed by a really kind person who is a first-time manager. She prides herself on having learned project management through “trial by fire” at other jobs, but this is her first time managing a team of people and not her own deliverables.
At a recent staff retreat, everyone she manages requested more clarity, more communication, and better systems. I can see her trying, but it seems like she is doubling down on the approaches she developed as a direct contributor and expecting that to work.
She is really kind and I don’t want to be mean, but I think the skills she developed on her own aren’t serving her effectively as a people or project manager, and I can see my peers losing confidence in her ability. I don’t think she realizes that this is an area for growth for her, but I can see it hurting the team and eroding some of the trust that her kindness has built up.
I’ve been trying to find free project management trainings to share with our team generally in the hopes that she takes advantage, but I don’t think she sees the problem. Am I totally out of line? Is this something I can go to her boss with or is that disloyal?
You aren’t out of line, but sharing project management trainings with the team probably isn’t going to solve the problem. She needs to know that this is an area she actively needs to work on. And project management training on its own isn’t likely to be enough; she needs manager training.
Her boss is the one best equipped to deliver that message, and to ensure she works on it. It’s not disloyal to have a discreet conversation with her boss — who I’m going to call Jane — about it; your loyalty is presumably to the team as a whole and when there’s a problem it’s not wrong to point that out (if anything, I’d argue it’s the opposite). That said, whether to actually talk to Jane or not depends on things like what Jane is like, how much rapport you have with her and how frequently you talk, how skilled Jane is as a manager (and how well you think she’d handle this — would she consider it useful input that can inform her own coaching of your boss, or would see treat it as a five-alarm fire and make things worse), and whether you trust Jane to keep your name out of it.
Alternately, do you have the kind of relationship with your boss where could talk to her about it directly? One way to frame it would be, “I don’t think the systems we’re currently using are serving us well, like we were talking about at the staff retreat, and I wanted to talk with you because I’m concerned it’s eroding some trust on the team.” You don’t need to solve it for her, but pointing out that there’s a problem she needs to solve might be useful if she can hear that sort of thing without being defensive (although not all managers can).
3. Can I post this flowchart at work?
I work in a government office. The team I’m on does technical work, but many jobs (including mine) also involve some writing.
We’re located in a highly religious area. Several of my coworkers are members of this religion, which prohibits profane/obscene language. I practice a similar faith, and I choose to avoid this type of language as well (for example, I do not say “oh my god”).
That said … I kinda want to post this flowchart at my desk (original source). I’m confident it would come across as, “Wow, Jane still has strong feelings about this topic” and not as, “Oh, that’s just swear-happy Jane again.” But this is still a bad idea in a work context, right?
Yeah, don’t post it. It would be pushing the limits for a lot of offices that weren’t populated by people who avoid profanity, and yours is. Plus, government. It’s a bad idea.
4. I don’t know which job to pick
I internally moved onto my current team a year ago, leaving a job in executive talent management/succession planning to executive compensation. Pivoting has been really exciting, and I’ve enjoyed the opportunity to learn something new.
Recently, my grandboss approached me and asked me if I would be interested in switching from the executive compensation role and into a compensation role supporting my company’s new brick/mortar businesses. These businesses are a new, high-growth area for my org and would give me more things to learn.
This sounds exciting! There are some great parts of the role and team I’d be supporting, but my bread-and-butter is supporting the executive team and I really enjoy the specifics of what I do now. My boss/grand-boss have been clear that it’s my choice — they’ll backfill whichever role I don’t do. Problem is: I really don’t have a preference. There are clear pros/cons to each but the core factors that would drive me to one over the other (pay, hours worked/location, etc.) are identical. How do I make this choice? Is it okay to tell them to just put me where they want me?
You’ve factored in the work itself, pay, hours, location, and the teams. Have you factored in stability too — like is your current role potentially more secure than one in a new, not-yet-entirely-tested area of the business? And what about who you’d be working for? If you like your current boss and the other is an unknown, I’d put some weight on that (or at least try to find out more about them).
If you’re genuinely torn, it’s fine to tell them you’re really enjoying what you’re doing now and the new role also sounds great so you’ll go where they think you’ll be most useful. But before you do that, try choosing one for a while and sitting with it for a couple of days to see if any more decisive feelings emerge (and then if you have time, do that with the other one too).
5. How to explain looking for another job so soon
I’ve been in my current role for just over six months, and it’s become very clear to me that it’s not a long-term fit. I’m performing well and my boss likes me, but there genuinely isn’t enough to keep me busy at the pace I work at (I think they were expecting someone slower) and there’s a management style mismatch (she’s a micromanager who won’t release control over anything) with my boss that will become unbearable if I stay there much longer.
I took this role after an eight-month period of unemployment. Given that, I’m guessing that looking for a role so soon will look concerning to recruiters. How do I approach that?
You can be straightforward about the workload mismatch! “I really like to keep busy and there isn’t enough work for that in this role, so I’m looking for something faster-paced.” Leave out the micromanager part; the workload itself is a perfectly good reason (and wanting more work doesn’t carry the same risks that wanting less work can.)
Just make sure to really do your due diligence on any new job before accepting it so that you have the best chances of a long stay at the next job (rather than ending up with two short-term roles one after another).
