Posted by Ask a Manager

https://www.askamanager.org/2025/08/my-boss-says-i-should-work-more-since-my-health-insurance-costs-so-much-coworker-delays-our-meetings-and-more.html

https://www.askamanager.org/?p=32648

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

1. My boss says I should do more because my family’s health insurance costs so much

I have a fairly senior position at a small nonprofit, and I was the first woman on staff to have a baby. I could tell it was hard for my boss, who is used to people being on call constantly, to adjust to my new work-life division.

Currently, our organization is facing a fundraising shortfall, and my boss has called me in for several meetings where he told me that since I have my wife and baby on the company’s health insurance plan, I’m actually the second-most expensive employee after him, and that I really ought to fundraise or “deliver value” twice as much as other employees he named, because I cost so much. (Fundraising has never been a part of my job before, but I get that we’re a small org that needs to pull together. I understand that everyone else on staff either has just one dependent partner, or has the family on the partner’s plan — my wife doesn’t get health insurance through her job, though, so this is our only option.)

I am curious about how to manage this with my boss (and I’m also really stressed out and doubt I can successfully add fundraising onto my responsibilities). Should I tell my boss to change the policy to raise my employee contributions? Is there some kind of discrimination happening here?

Wow, that’s wildly inappropriate. If your organization wants to move more or all of the cost of insurance premiums for family members on to the employee rather than shouldering it themselves, they have the option to do that. But telling you that you need to contribute more value than everyone else on staff because your family is on their health insurance? Noooo.

Discrimination based on family status isn’t illegal at the federal level, but it is in some states and Washington, D.C. If you happen to be in one of them, this would indeed be illegal. If you’re not, you don’t have legal options, but you still shouldn’t tell your boss to increase your health insurance payments. This is a benefit you were offered as part of your compensation, and you are entitled to use it.

You should, however, consider how stable this organization is as an employment option long-term.

Related:
my company wants me to investigate what expensive medical treatments employees are having and why

2. How do I explain I’m staying remote when everyone else has to return to the office?

My company is enforcing return-to-office (RTO), beginning in September. I have managed to squeeze out of it, so to speak, as I got medical accommodations. When I first got it, the planned RTO was for June, and I was told by HR and my manager I didn’t have to disclose anything I was uncomfortable with, and since it was far away at the time, I didn’t bring it up. RTO was delayed, then delayed again, and about a month ago we were told RTO would be in September.

One team mate had also already planned a move before RTO was announced, so thankfully I won’t be the lone worker on Zoom meetings, but I hadn’t gotten the accommodations at the time, so I didn’t tell the team at the same time she did.

Recently I asked for someone to cover my vacation, and forgetting the specific dates of RTO, I asked a work group chat if anyone could cover. My coworker, Jay, said he could, I said thanks, and then he reminded me that three of those days were the first three days of RTO. I finally said that due to medical accommodations I would not be returning, and he said cool.

Now I am wondering what to do. I know not saying anything would be weird and wrong, and people will be confused as I do not look like someone who requires medical accommodations and I have driven to the rare in-person meetings before. Do I just make a big announcement to the full team group chat? I don’t want to make a big announcement while we’re in a meeting, as I have to be honest, I’m not great at thinking on my feet on what to appropriately say when asked questions verbally.

It depends on how much you’re comfortable sharing.

If you’re comfortable sharing that it’s a medical accommodation, you could just say at some point before the RTO date, “By the way, I want to let people know I’ll be remaining remote because of a medical accommodation.”

If you don’t want to share that, you could say, “I want to let people know I’ll be remaining remote” (or “Jane has signed off on me remaining remote” if you think you’ll need to spell that out). This one risks causing more drama, since people may wonder why you’re getting to stay remote when they’re not. You could potentially lower that risk by adding something like, “It’s a long story” or “Personal reasons I’d rather not go into.”

But if you’re willing to just state plainly that it’s a medical accommodation, that’s likely to be the lowest-drama way to do it.

3. My coworker has delayed our meetings for months

I first joined my company when I was still in college, when I took a year off from school due to the pandemic and worked as an intern for a large corporation. I really loved the team I was on, which included my manager “Gina” and her good friend “Hannah,” who I collaborated with on a few projects. I got along great with Gina (and she’s now one of my mentors), but never really felt like Hannah was vibing with me. But she was friendly enough.

After I finished school, I returned to the company full-time and kept in touch with a lot of teammates from my old team. Two years in, I realized I didn’t love my current role and wanted to explore other teams, including one that Hannah had moved to since we worked together. On Gina’s recommendation, I reached out to Hannah and set up a 30-minute coffee to catch up and learn more about her team. My company’s culture encourages coffee chats with anyone and everyone, and to put time on people’s calendars to do so. If people are busy during that time or need to push it for whatever reason, it’s totally normal for them to ask to move it to a different time or to suggest a new time in the calendar software.

For whatever reason, this coffee with Hannah kept getting moved. Sometimes last minute, sometimes a few days out, sometimes by her, sometimes by me. This happened for all of last fall, and once we were at the holidays, I said it made sense to just reschedule for sometime in the new year. I had kind of given up hope of meeting with Hannah, but I had made other connections with people on her new team in the meantime.

Fast forward to spring of this year, and Hannah is hiring for a position at my level. I reach out to her again to set up time to chat about the role (again, as is expected at the company — for internal moves, you meet with the hiring manager casually first to learn about the role, and then officially apply). Instead of getting a “sure, send me an invite” response from her, however, she kind of brushed me off, saying that she was busy prepping for an upcoming business trip, there were already a few people in the pipeline for this role, and instead I should make more connections with other people on her team (which I had been doing for the past six months!) and then she’d be happy to answer any remaining questions if I had any. With encouragement from Gina and Hannah’s boss (who I also worked with on a different team), I took this to mean that Hannah didn’t have the time to meet with me, but to go ahead and apply.

Big mistake. Hannah sent me a terse email saying I was ineligible for the role and my lack of communication (I hadn’t responded to her message declining to meet with me) further demonstrated that I would not be a good fit for her opening. This came as a complete shock to me, but I took the feedback in good faith and resolved to improve my communication skills.

My current manager (aware of everything going on) recommended I set up time with Hannah a few months after this incident to check in on how I was progressing toward becoming a better candidate for Hannah’s team (perhaps for a future opening elsewhere on the team). I communicated this and she seemed receptive, so I put time on her calendar for a 30-minute coffee chat in June … only for the same thing to happen as last fall. It’s August, and we still haven’t met — the meeting keeps getting pushed, sometimes last minute, sometimes a few days out, occasionally by me, but mostly by her. It’s probably been moved at least 5-8 times by now, and each time there hasn’t been a single word from Hannah acknowledging it.

I’m finally supposed to meet with her this week, and I just saw she’s moved the meeting to over a month from now! I’m getting the feeling she doesn’t want to meet with me at all, at which point she should just say something to me about it instead of kicking the can down the road. And would it really be so hard for her to take 30 minutes to meet with me? I’ve never had this happen to me at this company — the culture is very much that if someone wants to have a coffee chat with you, you make time, even if just out of politeness.

How do I approach this? Are there any scripts you’d recommend to confront her about it? Do I go ahead and cancel it altogether again? Or should I just let the meeting keep being postponed? For what it’s worth, her role is still unfilled, not that I would want to work under her anyway after this entire ordeal.

For whatever reason, Hannah doesn’t want to meet with you or hire you, I’m sorry. Who knows why — it could be something from when you last worked together, it could be that you remind her of a hated cousin, it could be irrational, it could be a pet peeve, it could be based on something legitimate. But at this point, it’s very unlikely that continuing to pursue either a coffee chat or a role on her team will lead to anything more than frustration. I don’t see much point in talking to her about it; you’re better off just dropping it and looking at other teams.

4. I wasn’t informed of a decision, and I’m feeling undervalued

I’m currently working part-time as a contractor with an organization where I’ve felt fairly integrated into the core team, despite my contractor status. Have been working there for a couple of years.

For the past few months, my primary responsibility has been managing/leading a hiring process for a C-suite role. After many months of interviews and deliberation, we narrowed it down to two finalists. I had a clear preference between the two (which I shared), but the final decision-makers (which included my boss) ultimately selected the other candidate.

What really stung was how I found out. No one from the team told me a decision had been made — I only learned about it when the finalist who wasn’t selected emailed me to thank me for my time after they found out they didn’t get the role. That was the first I’d heard that my boss (and others) had made a decision.

I’m not upset about the outcome — I understand that leaders sometimes make decisions that don’t align with your preferences or advice. But I was hurt that my boss didn’t think to update me on the final decision before they executed it, especially since I’ve spent far more time and effort on this hiring process than any other member of the team. Hearing the news from a third party felt like a real lack of acknowledgment of my efforts, and it left me feeling pretty demoralized. Having been a middle manager myself, I can’t imagine making an offer without updating the hiring team (and hiring manager) involved first.

A bunch of this is amplified by my own insecurities — I often struggle with whether I’m truly seen as a strategic contributor, or just as someone doing behind-the-scenes admin work, on this team. This experience reinforced those doubts. I’m actively working through these feelings (with the help of a therapist!), but it’s definitely a slow and ongoing process.

So here’s what I’m grappling with: am I right to feel upset about how this was handled, or am I being dramatic? If so, how can I express to my boss that this genuinely hurt without coming across as overly sensitive? Does it matter that I’m technically a contractor? I’m not looking to create conflict — I just want to name what I’m feeling and how it’s impacting my motivation. But honestly, it’s made me question whether I want to keep working here.

It depends on exactly what your role in the hiring was. For example, if you were doing the initial recruitment and screening and then passing strong candidates off to decision-makers for later interviews, it’s not weird that they made a decision and made the offer without informing you. That’s very normal for that role! Your work could be extremely valued and appreciated and it still wouldn’t be weird that once you handed off your part, they just ran with their part. On the other hand, if you were part of the final interviews and decision-making, then it’s a little more surprising — although even then, it’s not necessarily that weird; if you’re not the final decision-maker, these things happen and generally people are expected to roll with it if they’re not the primary decision-maker.

In either of those situations, questioning whether you want to keep working there because of it does seem like a very disproportionate reaction, so I wonder if there’s something more going on, aside from this situation.

5. Am I being ghosted?

I have had three interviews: hiring recruiter, peer, potential manager. I was told after interviewing with the hiring manager that I would be contacted to schedule a fourth in-office with the CVP. It’s been over 24 hours and I haven’t heard anything yet. I’m concerned about being ghosted, since they got back to me quickly to schedule these previous interviews.

24 hours is nothing — in all cases, but especially when there’s now a new person’s schedule in the mix. If you haven’t heard anything after a week, check in then.

Of course, it’s also possible that you are being ghosted — that happens all the time in hiring — but it would be wildly premature to conclude it at this point.

Related:
why haven’t I heard back after my interview?

The post my boss says I should work more since my health insurance costs so much, coworker delays our meetings, and more appeared first on Ask a Manager.

https://www.askamanager.org/2025/08/my-boss-says-i-should-work-more-since-my-health-insurance-costs-so-much-coworker-delays-our-meetings-and-more.html

https://www.askamanager.org/?p=32648