It’s five answers to five questions. Here we go…
1. Should I ask out my former boss?
From 2015-2017, I reported to a wonderful boss who I really clicked with personally and professionally. After I left the organization for other reasons (and he left the industry) we remained good friends. He and his wife are now divorcing, and I’m wondering … once everything is more settled, would it be terrible to ask him out? Assuming he were to say yes, could it hurt my career if people knew I was dating someone who used to be my boss? If it matters, I’m in my late 20s and he’s in his mid 30s, and we work in tech in the Bay Area.
He no longer manages you and you’re adults, so you’re both free to pursue something if you’d like. If you end up dating and people hear about it, they’ll probably talk — it’s interesting gossip, and people may wonder if something was going on while you worked together. If you’re both known to be professional, it probably won’t be a big deal — but do know you’ll probably have people speculating about it.
The other thing I’d think about is what it means for any future reference from him. If you become seriously involved, he can’t be a reference anymore. You might be willing to sacrifice that, but be aware of it.
And then of course, there are the caveats you always need when you’re thinking of asking out someone you know professionally: make sure you’ve paid attention to his cues, don’t come on weirdly fast, assume a soft no is a firm no, etc. (Really these are caveats for all situations, but no one lets me issue rules for the rest of life.)
2. My employee cc’s me on all his emails
I’m a director of engineering for a fortune 50 company. I receive upward of 1,000 emails a day, with 75% of them for awareness only but necessary nonetheless.
I have a direct report who manages a team of nine, all remotely. Said direct report copies me on everything — from meeting response notifications to emails to his employees to emails to IT about an employee’s PC issue. I’ve asked him in the past why he does it and he says he wants to make sure I know what he is doing at all times. I told him that I trust him, he does a great job and it is not necessary. Problem is, he still does it.
I need to have a conversation with him, knowing he can be sensitive and already feels like he has to defend his every move, I am afraid it will have the opposite effect on our work relationship. However, I need that volume of email to stop and for me to not be so consumed with it.
You’ve told him it’s not necessary, but have you directly told him to stop? Those are two different things, and that might be the disconnect.
But this is so straightforward that you really shouldn’t need to tiptoe around it. You should be able to say, “You’ve said you want me to know what you’re doing all the time — but I don’t want to know what you’re doing all the time! I don’t have the bandwidth for it; I need to focus on other things and this is flooding my inbox. What I want to stay in the loop on is your progress toward the big goals we’ve set, and we do that in our twice-a-month check-ins (or whatever). So effective immediately, I need you to stop cc’ing me on everything else.”
If you can’t say that directly, there are other problems here and I’d worry about what else he’s made you feel you can’t say! But I’d bet you can say this and it will be fine.
If he continues with the cc’ing after that, then you need to have a more serious conversation about how you assess his work and why he’s ignoring directly instructions to try to prove himself to you in ways that you’ve explicitly told him are making you less effective.
3. Do people care about my high school activities?
I’m a 21 year-old sophomore in college. I read your answer to the question about college extracurriculars, and have been adding on my leadership positions and honor societies (to be taken off when I get some actual job experiences under my belt). In a meeting with my school’s career counselor, she recommended I leave on even my high school activities. I graduated nearly three years ago and had a full-time job for over a year between high school and college. (If it matters, this was my first paid position.) It feels silly to leave it on.
Does anyone actually care that I was in marching band or youth group or worked with the local animal shelter? I know I need to have something on my resume, but I don’t want to come across as naive or frivolous when applying for positions.
Nah. If you were a freshman, it could make sense to leave on some stuff from high school, but you’ve been out of high school nearly three years. Focus on what you’ve done since then. (Do leave on that full-time job after graduation though.)
4. My bad coworker listed me as a reference
One of my coworkers was laid off two weeks ago due to coronavirus. She was an easy choice because her work and attitude weren’t great.
She and I were at the same level and I needed a few things from her every month, but other than that we weren’t in the same management chain and didn’t work together. Her office was next to mine so we’d have friendly conversations every day and I got along with her, but she yelled at her team constantly and wasn’t available to help them, so most of the office hated her. The reports I needed from her were always late and full of errors and her manager would have to fix it.
Because we were on friendly terms and her manager doesn’t want to be a reference for her, she’s now listed me as a reference and says two places where she interviewed might call me. I know it’s tough to find a job now, but I really don’t want to risk my reputation by lying and giving her a good reference, and I barely worked with her so there’s not much I could say anyway.
I got back to her and said, “I wish you luck finding a job, but I didn’t manage you or work with you much so I’m not a good reference.” But she said it’s too late, she listed me, and can I please tell them she was great to work with. Do you suggest I just don’t respond if a potential employer calls?
Aggh. I’d contact her again and say, “I’m really not able to provide a good reference, and you’d be better off giving them another name.” You’re not obligated to spell out why, but if you wanted to, you could say, “You’ve put me in an awkward situation. If I talked to a reference checker, I’d have to be honest and say that the work I got from you was usually late and had a lot of errors, and I used to hear you yelling at your team. I don’t want to harm your chances and I can try to ignore their calls if they contact me, but if they reach me, I can’t lie. So it would be better for both of us if you found a reference who’s not me.”
From there, it’s up to you. You can ignore the calls (which sends a message in itself), or you can give an honest reference. Personally I think the constant yelling at her team is worth sharing so she doesn’t inflict that on other people, but people come down in different places on this.
5. I might get furloughed — and may be pregnant
The nonprofit where I work recently sent out an email to update us all on the financial situation for the organization. It included mention that there may need to be furloughs if certain funding doesn’t come through, though it was not made clear who might be vulnerable for being furloughed. This is not unexpected, and I appreciate them being transparent about this possibility.
Normally I would not be too concerned by the situation since my husband is the main earner in our household and he and I have quite a bit of money saved at the moment. What makes the situation tricky is that we’ve been trying to get pregnant for the last few months (I don’t know at this moment if I am pregnant, but it’s possible I am). My insurance comes through my employer, and while I would hope any furlough would not last nine months, I know there are medical costs we’d need to keep in mind during any pregnancy (not to mention there’s a possibility the furlough could turn into a layoff if funding gets bad). If I am pregnant and do get furloughed, what would be my options for continuing insurance coverage? Should I try to swap over to my husband’s (his open enrollment isn’t until later in the year so I’m not sure if it’s even possible)?
Often with furloughs, the employer will continue your health insurance. But if that doesn’t happen or if you’re laid off, you’d have three options: (1) You could continue your same policy though COBRA but would need to pay the full costs yourself (which are often higher than people expect), (2) you could be added to your husband’s plan; losing your own insurance is a qualifying event that would allow you enroll outside of open enrollment, or (3) you could buy a plan on the Marketplace. #2 would probably be your best bet, but it’s worth comparing all three options.
should I ask out my former boss, employee cc’s me on everything, and more was originally published by Alison Green on Ask a Manager.
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