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

1. My coworker keeps crying in meetings

A few years back, I was early in my career and one of the more junior members on a small team. One of my coworkers, “Mary,” would regularly cry during internal meetings about really routine stuff. Mary was senior to me, but wasn’t management and worked in a support role.

This would happen a couple times a month and wasn’t related to work stress or projects she was working on, but more just that she was a Very Emotional Person and didn’t do a good job keeping it in check. As an example, if the group was discussing a document we were writing about, say, sailing, she might jump in to share her opinion. She would start in a matter-of-fact way and then get teary eyed, start to cry, and interject something like, “I’m sorry, you know how emotional I get. My dad was a sailor and this issue is just really close to my heart!” It was always sort of sweet (she clearly was passionate about our work!), but felt inappropriate and out of place in a team meeting, especially given it was so often and about such routine stuff. Everyone would get visibly uncomfortable when it happened (shifting in their chairs, looking down at their hands, etc.) and a couple of coworkers mentioned it to me over the years. No one ever addressed it directly in the moment; there’d be some awkward silence until someone jumped in to get the conversation back on track. This continued regularly for the several years I was at this job, and I never got any indication that anyone talked to her about it directly.

I never brought this up with my supervisor because it just felt … silly? It did take the meetings off track, but didn’t really present any major problems. I was so junior, I think I felt like this was out of my lane or it would be “tattling” or maybe even insulting to my manager that I might be insinuating she wasn’t managing her staff well. It also just didn’t feel worth expending political capital on at the time. For what it’s worth, Mary was okay but not great at her job and was very nice but also a little quirky, and could be kind of difficult to work with (though more in the “bumbling/doesn’t always know what they’re doing” than “unpleasant and incompetent” camp). How would you advise handling something like this? Should I have brought this up with my supervisor? Or was my “I have a quirky coworker I have to deal with and it’s not a big deal” instinct right?

If Mary were doing this in one-on-one meetings with you and your meetings were regularly getting off-track because of it, you could have brought it up with your manager in a “this is happening / what’s the best way for me to handle it?” way. But in group meetings where you were one of the most junior people, it made sense to leave it to others to decide whether or not to flag it. That’s not because you would have been insinuating your boss wasn’t doing her job well if you raised it, but just because a junior person without much capital isn’t responsible for addressing this stuff. (Or — was your boss in the meetings where this was happening? If so, she wasn’t doing her job well, but if you were more senior you could still have raised it in a “do you think you could talk to Mary? this keeps happening and derailing our discussions” way.)

For the record, in general: Getting teary in a meeting once, it happens. But regularly crying in meetings can be disruptive and is something that person’s manager should check in with them on.

2. My boss only wants to hire from my coworker’s friends

I’ve worked in this small (only five people) company for over three years. Last fall, one coworker was let go and my boss (who owns the company) decided to hire a new employee who would partially take over my position, allowing me to spend more time on other projects.

He decided to hire Lisa, who was friends with my other coworker, Jane. She was culled from Jane’s Facebook friends list and hired almost immediately after completing the required background check.

Lisa was hired to work a specific part-time schedule: five days a week, give hours a day. She is consistently late, does her makeup at the front desk, spends a majority of her time having social hour with Jane, and has yet to learn anything of substance to help her do her job. She’s been here five months.

Recently, she put in her notice. On the surface, I’m fine with this; it means I am no longer holding her hand through basic tasks or listening to her chit chat for hours at a time while neglecting actual work. However, the issue now is that Boss 1 and Jane are again culling through Jane’s Facebook friends list to find another new employee to take over. This makes me livid. I do not want a Lisa 2.0 situation where the new employee is buddy-buddy with Jane and does not get any work done. I don’t want our office to turn into a social hour; I just want to get my work done in a timely manner with few distractions.

How can I express to Boss 1 that I think he needs to go through traditional channels to post a job listing, and not rely on Jane’s friends to apply and fill the position? Is it even worth it?

Yeah, this is a terrible practice, and it would be a bad idea even if Lisa had ended up being an excellent employee. Hiring only from one person’s network is far too limiting; it means the bar for the role will only be as high as her most qualified (and interested/available) friend even if there are more qualified candidates out there, you’ll only be assessing applicants against a small pool, and you’re likely to end up with pretty homogenous candidates. That’s before even getting into the fact that Jane is apparently happy to spend a large portion of her work time socializing with any friend who’s hired, and your boss is apparently willing to allow it.

I don’t know how much influence you have with your boss, but ideally you’d say something like, “Could we advertise the position this time so that we have a deeper pool of people to select from? I think there are some really talented people with the qualifications we need, and we’d likely get a stronger and more diverse pool if we advertise.” You could add, “Since I’m relying on this person to take over ABC so I can do more XYZ, I want us to be able to make the strongest hire we can.” (Any chance your boss is doing it this way because he doesn’t want to sort through a ton of applicants? If so, does it make sense for you to offer to do that part of it?)

If you have pretty good rapport with your boss, you could also point out privately that hiring Jane’s friend didn’t go well last time. You could say, “Of course anyone from Jane’s network could throw their hat in the ring if they’re interested, but I feel really strongly that we should consider other candidates too.”

3. My boss doesn’t believe I’m not going to leave

I have a good relationship with my boss. A few months ago, I was dealing with a serious issue at work involving someone who reports to me. While my boss was supportive and tried to help, they had to defer to HR. The HR person managed this very poorly and made the situation much worse. After several weeks of inappropriate comments and actions by the HR and ongoing issues with the employee, I was exhausted and demoralized. So I resigned.

My boss talked me out of resigning and helped to correct the issues with HR. I don’t know exactly what happened, but the HR person was terminated.

Now my boss seems to feel as though I’m still a flight risk. They have made several comments about “when you leave.” It’s to the point that they are hesitant to let me start new projects because “who will lead this when you go?”

I’ve reassured them that I’m not leaving. It might be true that I hadn’t given them enough of a chance to address the problem before I resigned, but I also feel it probably was finally taken seriously because I did resign. But now it feels like they are just waiting for me to resign again. They know that I have opportunities elsewhere (my position is in high demand). However, I really don’t want to leave.

Do I talk to them again when I can’t promise anything? I plan to stay, but who can promise that they won’t ever leave a job? I suspect that my telling them again that I intend to stay won’t have any greater impact.

What your boss is doing is odd! If they’re concerned you have one foot out the door, they should sit down and talk with you about it. Since they’re not, you should initiate that conversation. Say something like, “You’ve made several comments implying you think I’m likely to leave in the near future. I wouldn’t have agreed to stay on if that were the case. Obviously nothing is written in stone, but I have no plans to leave and don’t see that changing any time soon. Can we move forward with the understanding that I’m just as committed to staying as I was before all this happened?”

After that, if your boss continues to say things like “who will lead this when you go?” you should address it right in the moment by saying something like, “Whoa, what’s making you worried about that?” or “I think we’re on very different pages about my plans. I don’t plan to go anywhere and would like to take on projects like this! How can we figure this out?”

It sounds like your boss is worried you’ll leave the next time something happens that you don’t like. That’s not entirely unreasonable, but refusing to give you any new projects because of it is. If direct conversation (along with the passage of some time) doesn’t resolve it, you’ll have to start assessing whether the situation feels salvageable.

4. When should I tell job candidates I’ll be on maternity leave soon after they start?

I am currently hiring for my first-ever direct report. We have just about finished the first round of interviews and it has me wondering when I should inform potential new hires that I’m pregnant and will be taking maternity leave. Because all interviews are phone/Zoom currently, it’s not obvious I’m pregnant and I’m carrying very small so even in person it would be hard to tell for certain. Depending on start date (and obviously the will of the baby), I’ll have three to four months with them to get them onboarded and comfortable. But it still seems like something I should disclose before they’re hired so it’s not like, “Happy first day! By the way, I’ll be out for three months after your first three months.” Am I overthinking? Or when/how should I bring it up?

You can probably find a natural opening for it in interviews — like if you’re describing what the person’s training would be like or what you’d expect them to accomplish in their first year, that’s a good place to mention it, along with how it will affect their job (for example, who they’d report to in the interim or whether there’s anything of yours that they’d be covering). But if it doesn’t come up before you’re making an offer, definitely mention it as part of the initial offer conversation. You could just say, “By the way, I want to mention that I’m pregnant and expect to be on maternity leave from X-Y. We have plans in place for coverage, but I didn’t want you to be surprised by it when you start.”

5. Applying to a company when I turned down their offer a few years ago

Three years ago during a job search, I was offered positions from two different organizations. There were many things I liked about Company A, but the pay was too much lower than I was making at the time. The pay wasn’t listed in the ad, so we were a bit into the interview process before I learned the salary. I let the hiring manager know the salary was the main reason for not accepting the offer.

Instead I accepted the position with Company B, which had higher starting pay and an opportunity for advancement. This job has been okay – I’ve learned a lot and the work is interesting. But there are cultural and leadership issues that are less than pleasant, though not quite toxic.

Company A now has a position advertised that is several steps higher than the one I turned down several years ago. It’s a bit of a stretch position. I have many of the qualifications, though not all. This time, the pay rate is listed in the ad so I know it’s a salary I would accept.

Should I address in the cover letter that I’d previously turned down a job offer in this same department? It wasn’t the work or the people that deterred me, it was solely the pay. How do I word that without sounding like it’s all about money? I evaluate job offers based on multiple factors, but sometimes the economics needs to be the deciding factor. Or has this bridge been burnt?

Turning down an offer doesn’t burn a bridge! Go ahead and apply and say something in your cover letter like, “Several years ago you offered me a role on your team. I wasn’t able to accept at the time, but remained interested in your work and I’d be thrilled to connect with you about the X role now.”

That it — you don’t need to get into your reasons for turning down the previous offer. If they want to know, they can ask about it but this is enough to get the ball rolling and also remind them that they got to know you a bit previously. Also, if the hiring manager from last time still seems to work there, after you apply email her a note reminding her of your past conversations (you can use similar language to what’s above) and let her know you’ve applied for this new role. (Attach your application materials so she has them with your email too.) Since they liked you enough to offer you a job last time, she might be excited to hear from you.

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