It’s five answers to five questions. Here we go…
1. I feel horrible about reporting my boss’s tax fraud
I recently left a job I loved dearly because my boss stopped paying me. We had a great relationship leading up to that, so when she said she couldn’t pay me and then flipped out because I told her I was leaving, I was pretty surprised. She said some ugly things that really hurt, then tried to act like we were best friends and asked me not to tell anyone else in our profession about what happened. Just a few days later, I realized that even though she’d classified me as a 1099 worker for a year and a half, I really should have been a W-2. My tax bill was astronomical and my tax preparer told me I’d been misclassified. I reached out to my old boss and asked if she could fix this. She refused and said that even if she did, I would have to pay her back for “overpayment.” I already talked to a lawyer who told me that’s insane.
I know I need to report her for tax fraud and request reclassification from the IRS. I also know that the consequences could be very bad for her. I still feel some weird need to protect her or fix her mistakes. We’d been fairly close and I know she’s going through a very difficult time in her personal life right now, but so am I, and it’s her fault. How do I get over the guilt of feeling like I am betraying a boss who already betrayed me?
You’re not betraying her by expecting her to act ethically and legally. And you’re not betraying her by filling the appropriate paperwork to correct your own tax obligations. She is betraying you by expecting you to eat thousands of dollars to cover for her violation of the law … as well as by attacking you when you declined to work for free (!) and by threatening you with (fake) repayment consequences.
You’re not requesting reclassification from the IRS to get revenge on your boss; you’re doing it because it’s a necessary step to straightening out your taxes — a situation that she created.
Frankly, you’d need to do that even if she were being lovely to you. But she’s not being lovely; she’s being a complete jerk. That sucks — this is a job you loved and someone you were close to — but that’s on her, not on you, and you can’t let it deter you from protecting your own finances.
2. Are there any limits on employee computer monitoring?
I have reason to believe my employer is planning to install desktop monitoring software on at least some computers within our organization. The particular program is one that’s, as I understand it, incredibly invasive (to the point of being a keylogger), and the management responsible for this project is being very tight-lipped. Even most of IT hasn’t been told this is being done, which has definitely raised eyebrows since they’d have to support whatever it runs on; from talking with them, I can’t imagine they’d be deploying this particular program if it were their choice. All in all, it sounds incredibly shady if we aren’t being told what will be monitored, and why.
While I’m sure employers have the legal right to monitor the computers they own, are you aware of any limitations on what they’re allowed to monitor, or how they’re allowed to use the information they gather? I’m prepared to accept that I won’t like the answer, and I suspect that even though I’m opposed to these programs on principle, there isn’t much I can do since nobody who’s worked on this project is aware that I know about it. If I have to find another job, I will, but I’d rather it not come to that.
Legally, employers can monitor anything done on their devices or their networks. Assuming these are work computers being operated on their networks, they can monitor literally every action you take down to every key you press. Some programs let them watch your screen while you work or see randomly taken screenshots of what you’re doing at any given time. (To be clear, most employers don’t do this! But some do, and legally they can.)
Restrictions on what they can do with the info they gather: They can’t use it to discriminate against you for your health, religion, or other protected class (for example, if they saw an email to your doctor about a medical issue or saw you browsing a web page from your religious institution, they can’t use that to discriminate against you). If their keylogger logs the password to your personal email account, they can’t take that password and use it to log in to your personal email and go rooting around in it later. And they can’t use their surveillance to interfere with unionizing or other organizing.
But they can monitor it all if it’s on their devices or networks. A small number of states require that employers provide notice to workers that they’re doing this kind of monitoring, but most don’t.
3. My boss asked if I regret accepting my job
I’m in my early thirties and spent most of my professional career at the same job. The work was engaging and I loved my colleagues, but it took a serious toll on my mental and physical health. My former manager left a year ago for a job in a more conventional office environment. When there was an opening in her office early this year, she encouraged me to apply. I did and got the job. Naturally, I was thrilled—not only was I leaving a job I’d grown to dread, I’d also be working under a manager I really connected with.
It’s been two months now and I fear I’ve made a huge mistake. I had a sense going in that my new colleagues wouldn’t be as warm and expected the work to feel less meaningful, but I didn’t realize how adversarial some people were or how unfulfilling the work would be.
My manager’s style is still friendly and encouraging, but many of the people at her level or above are shockingly petty and spiteful, the kind of people who’ll ice you if they think you have a nicer office than them or who misstate your title in a way that makes you appear inferior (think “assistant” instead of “administrator”). One person in particular has been driving me up the wall – for example, whenever they decide I’ve made a mistake, they’ll send me a critical email and copy leadership, including the big boss. Oftentimes, these “mistakes” are actions someone else took or they lack critical information to understand why I took a particular action and why their solutions wouldn’t have worked.
My responsibilities also aren’t what was suggested in the job description. I’m ostensibly implementing systems and processes to improve office efficiency — turns out that mostly means calendar management and making sure the fridge is stocked with the bosses’ favorite snacks.
In my last check-in with my manager, she asked me whether I regretted taking the job. As I hadn’t expressed my dissatisfaction to her, I was surprised and wasn’t sure how to respond. While I mentioned that I’d appreciate having more substantive duties, I didn’t feel like I could share negative feedback about people who outrank my manager, especially when she can’t do much to change their behavior.
I also can’t see an upside to admitting you regret taking a job. Her asking me that felt like she was admitting to pulling a bait-and-switch on me with this position in an effort to fill a vacancy with someone she knows she works well with. I’m not sure what to do and I’m also feeling a little betrayed. Is there any point in sharing some version of these feelings with my manager or am I better off adopting a head down, mouth shut approach until more time passes and I can start job hunting in earnest?
I don’t think her question is necessarily an acknowledgement that she pulled a bait-and-switch. It’s possible, but it’s also possible that she didn’t intend this but things changed from the way she expected them to play out, she’s aware of that, and she’s checking in on how you’re feeling.
I do think there’s value in having a more candid conversation since you knew her before taking the job and she recruited you for it. Don’t just tell her you’d “appreciate having more substantive duties” (as it sounds like you did); tell her that the job is fundamentally different from what you came on board to do and ask if, realistically, that will change. Focus there rather than on feeling betrayed, since this is the actionable piece.
Also, you mentioned needing to wait until more time passes before you can job search. You don’t need to do that. There’s no reason you need to stay at a job that isn’t what you signed up for, and if you leave quickly enough, you can keep this off your resume entirely. Job search now.
4. Can I contact a CEO who offered me a job previously to ask about job openings now?
I am starting my job search after two years at Company A. Last time I was on the market, I had great interviews with Company B and got an offer from them that was initially my top choice, in part because of how much I liked Company B but also because the role at Company A was a lateral move on a team that wasn’t that interesting to me. Ultimately Company A gave me an offer for a much more exciting team and for a higher level, so I accepted. After the dust settled, the CEO of Company B (who had interviewed me) sent me a very kind email saying essentially, “I’m sorry to hear we won’t be working together in the short-term. But careers are long, keep in touch.”
Now that I’m in the job market, I’d love to revisit Company B. I’ve been watching their jobs page and they are hiring, but they haven’t posted any good matches for me. I can just keep an eye on the jobs page and apply if they post a good fit. But would it be out of line to email the CEO letting her know I’m in the market and would love to explore any opportunities they may have? Would it be better to email asking to catch up with her? Option 1 feels more honest, but I don’t want to come off like I’m saying “give me a job.” Option 2 may be more tactful, but I also have no idea how to network with a CEO! I worry about taking up her time without really having anything to talk about.
Email the CEO and don’t beat around the bush — say right up-front what you’re hoping to connect about. That’s more respectful of her time, and it’s a normal thing to do. If you just ask to “catch up,” you could be waiting weeks for there to be room on her schedule, whereas if you just tell her why you’re writing, she’ll be able to take action on that immediately.
You can simply say, “You interviewed me a couple of years ago and offered me the X role on your Y team. I ultimately took another offer, but you encouraged me to keep in touch. I’m now looking for my next step and, given how much I liked what I learned about Company last time, I’d love to talk about any opportunities you have that might be a good fit.” You could add, “I’ve been watching your jobs page and haven’t seen the right opening there, but wanted to connect with you as well.”
5. As a manager, how much credit should my resume take for team accomplishments?
I’m a program director at a nonprofit and have started thinking about my next step and working on my resume. In the program that I manage, a team of people all work closely together to deliver results. I’m never sure how to reflect this in a resume — I don’t want to take credit for work that was delivered by 10 people, but if I manage those 10 people, is that what I ought to be doing?
For example, say my team successfully advocated for an increase in the state’s education budget, from $10b to $20b. In that case, which approach is better: (a) “Successfully advocated for a budget increase from $20 to $40 billion in 2024,” which I think best emphasizes the outcome, or (b) “Worked with a team of five to develop a campaign strategy that secured a budget increase to $20b” — in other words, giving others credit and being more specific about what my contribution was. I’m always conscious about not wanting to take credit where it isn’t do, but also don’t want to do myself a disservice when I know I played an important role.
To some extent, it depends on exactly what your role was. If you were taking a lead on, say, the lobbying, it makes sense to write, “Led successful lobbying campaign that resulted in a budget increase from $20 to $40 billion in 2024.” On the other hand, if you were managing the people doing the lobbying, I’d do it this way: “Managed a team of five to successfully lobby for a budget increase from $20 to $40 billion…”
In general, though, “managed a team that achieved X” is nearly always a reasonable formulation.