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

1. My intern asked if my pregnancy was planned

I’m pregnant with my first child. I’m just finishing my first trimester and have been sharing the news with my manager, reports, and coworkers. It’s gone really well — even my sometimes stodgy boss was delighted!

I’m wondering what, if anything, I should do in response to my intern’s reaction, though. Like everyone else I manage, I told her one-on-one behind closed doors. Her response was really odd — she asked if the pregnancy was planned. (For the record, I am in my late 30s.) I was so taken aback in the moment that I didn’t even know how to respond. I think I may have just laughed it off. The more I think about it, though, I’m wondering if I should talk to her about her response and explain how inappropriate that question (or really any question related to a pregnancy!) is. She comes from a pretty sheltered background — religious home schooling followed by a small conservative college experience — so this might just be her genuinely not understanding that this isn’t an appropriate response. Do you think I should say something, or just let it go?

Oh my! I could argue it either way. One one hand, it might have been an awkward remark that she kicked herself for later and it would be a kindness to let it go. On the other hand, maybe she thinks it was fine and doesn’t realize there was anything wrong with what she said and will happily ask it again. But since she’s an intern and part of the reason she’s there is to learn professional norms, I’m coming down on the side of saying something.

It’s always more awkward to bring up something like this after the fact, but you could say, “I want to follow up on something you said the other day. When I told you I was pregnant, you asked if it was planned. I want to make sure you know you should never ask that of a colleague — or really, anyone unless you’re extremely close to them (and maybe not even then!). It’s a very personal question, and it’s information someone will share if they want to, but not something you should ask.” If she seems mortified, you could add, “Please don’t be mortified. I realize you probably don’t have a lot of peers getting pregnant and so may not have much experience with pregnancy announcements. I just wanted you to know going forward.”

2. Should I cold-email companies a second time?

I am a recent college graduate who’s been out of school for three months and is actively looking for a job in my field. My last internship recommended me a few places I can reach out to, and inquire about job openings. Of course, I heeded their advice and sent all of them cold emails. After all of them said they had no openings (or just didn’t respond), I turned to Indeed and other job posting sites instead.

I would still like to work at one of the places that were recommended to me, and I’ve had no contact with them for two and a half months. I’m tempted to try another round of cold emails to re-inquire about openings, but I don’t want to come off as an irritating stalker man and/or hurt my chances of working with them in the future. So in your experience, how often is too often for sending a second cold email? Or, would it be better to not do so at all?

Don’t go back for a second try. The truth is, cold emails rarely work. Sometimes they do! But most of the time they don’t. Most places advertise the openings they have. If they don’t, it’s usually because they plan to hire from their existing network, and the chances of you being the perfect fit for an opening that you haven’t even heard described are slim. Again, this doesn’t mean it never works — occasionally it does. (Although it does, it’s usually with small businesses that don’t have great hiring processes … which are often rife with problems and not an ideal place to start your career.)

It was fine to send the emails originally because, who knows, it could have led to something. But re-inquiring a second time risks being annoying, and there’s little chance of a pay-off. You’re better off putting most of your energy into applying for jobs that you know for sure exist and are hiring (along with things like building your network). I wouldn’t prioritize Indeed though — try to find niche sites for the field you want to work in.

3. Should I write my boss’s performance goals?

My boss, Kenny, is not great. He hides in his office, doesn’t mentor junior team members (I’m senior on my team, junior only to Kenny), is dismissive of groups we work closely with (to the point of emailing us during other teams’ presentations and meetings), and is slow to adopt and quick to reject new methods that would really help our work. I’m frustrated and applying elsewhere. This role would be perfect for me if Kenny wasn’t my boss. I feel like he could be threatened by me, but his role is very secure here. He’s been at my company for 11 years, managing for 6. I’ve been here for 3.5 years but have 6 years of experience in my field.

I brought my frustrations to his boss, Sara, six months ago and again today. I had a list of concerns from my team and had examples for each. (They come to me, not Kenny, because they feel like he doesn’t listen. He doesn’t.) Sara and I discussed the list, and ultimately, I told her today that I will be exploring other opportunities to grow in our company. She was sympathetic and understanding. (She’s an incredibly reasonable and capable supervisor, except for not managing Kenny well.) She tried to say that Kenny just doesn’t have soft skills and is still learning, but he’s been a manager for 6 years.

Anyway, at the end of the meeting, Sara said the annual goal setting is coming up and she would consider my concerns. All employees at my company write performance goals, and generally, I like the process. Sara asked me to look at my list of “Kenny doesn’t…” items and rewrite them as goals for him to use in 2020. This sounds crazy, right?! I would love you to provide some context or maybe language to push back. Sara could easily rewrite my list as “I will…” goals for Kenny. I don’t want to do any more of his work than I’m already doing (managing temps, mentoring interns, writing role descriptions, etc.) and writing his goals feels crazy.

Sara said Kenny’s job is secure until he screws up. I (politely) pointed out that Kenny lacks management skills, but Sara’s hands are probably tied. I’m ready to move up and use my skills in a better department or company regardless.

Yeah, Sara shouldn’t have asked you to do that. Kenny should be writing his own goals, and he’s not capable of doing that, Sara should be the one working on it with him, not you.

That said, it’s possible that this is an opportunity to get some pressure put on Kenny to operate differently. It’s not right that Sara is putting this on you, but if she’s basically saying “write down what you think Kenny should be achieving in the next year,” I’d take her up on that.

4. Can ask my coworker to recycle?

My company has been going through massive growth in the past year and a half (growing from 25ish to almost 50 employees!) and the precious space we had is being filled. A month ago, another new coworker started and now sits at the (previously empty) desk next to me, and I’ve been trying to make her feel welcome.

She’s also now sharing my very small trash can. I’m not sure if the company just didn’t realize they forgot to give her one, or if one is on back-order, but even though it still lives under my desk, she’s started using it as well. I don’t care about that; there’s usually enough room for both of us.

However, she’s taken to throwing away a LOT of recyclables even though we have very clearly marked recycling in the kitchen, and it makes me feel awful! We go through a lot of 11″x17″ paper in the nature of our work, so it’s very obvious when 25 sheets of large paper are sticking out of the small trash can. I’ve been waiting until she’s not around and then taking the large/obvious recyclables to the kitchen to recycle on my own (large papers, plastic water bottles, etc).

I really don’t mean to be passive aggressive in my behaviors, and I hope she’s never noticed (it’s usually after she leaves for the day). I just feel awkward telling her to recycle something when it’s not my business to tell her what to do. But she’s new — what if she didn’t see the recycling in the kitchen? Should I mind my own business and keep acting as recycling police after she leaves, or should I speak up, potentially making her feel ashamed, or coming across as overly nosy?

Say something! It’s not about giving her orders, it’s about explaining there’s a better way to handle that trash. Because she’s new, it’s reasonable to assume she simply might not realize it. And you even have a bit of extra standing to say something because she’s filling up your trash can (now apparently your co-owned trash can, but still one you have an interest in).

You can just say, “I noticed you’re putting a lot of paper in the trash can. It should actually go in the recycling bin in the kitchen.”

Obviously, don’t turn it into a war like this one, but a simple comment like this is fine.

5. What does “entrepreneurial” mean in a job posting?

What does “entrepreneurial” mean in a job description? I think it means proactive, innovative in developing solutions, and passionate but I’m not quite sure. Does it literally mean you have to have started your own business or nonprofit or side project? Do I have to work outside of work (in my spare time) to be a viable candidate? I prefer not to. FYI, I am a product manager though I have seen “entrepreneurial” in descriptions for other roles.

No, it doesn’t mean you need to have started your own business. “Entrepreneurial” in a job posting is referring to character traits — it means that you’re able to take a project and run with it on your own, without being told what to do every step of the way, and that you’ll have a drive to build or grow something. It’s about being proactive and innovative, as you mentioned. Someone who likes a lot of structure and existing systems and policies to guide what they do might not thrive in that job. Someone who’s willing to figure things out on their own and take some risks might.