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

1. We have to demote a really dedicated manager

I’m involved in a small, local nonprofit animal shelter. I started as a volunteer and am now an officer of the board. Two years ago, our very competent office manager quit. After two crash-and-burn failed hires, one of our part-time kennel help wanted to try to step up into the position. On a trial basis. Over a year ago. And while she was never officially given the job, things just … limped along. Kasie is awesome in many ways, great with people and incredible with the animals. But she lacks the initiative and judgement to successfully fill this role. I will add she is open about having ADHD, which (from what I’ve read) is probably the source of her shortcomings.

For the last year or more, we have been operating with the board president fulfilling way too many of the manager responsibilities for Kasie, which is not sustainable. One of our long-time board members, Jane, is willing to step into the job and has been hired with a tentative start date soon.

Kasie is a very dedicated employee, and being manager of our animal shelter is way more than just a paycheck to her. I’m comfortable stating this is her dream job. She knows Changes Are Coming and has voiced she has no plans to leave, but I want to make this change as smooth as possible.

I guess I’m looking for advice on moving someone who is dedicated to a cause to step down to a lower position and accept a new manager. I’m also wondering if ADHD is (or should be) a factor in dealing with any of this.

Has someone been giving Kasie feedback all along and is she aware that the board didn’t think she was performing the role successfully? If so, this is a lot easier because it will be a logical extension of that conversation, which you can frame as, “As you know, we’ve been concerned about X and Y and need someone in this role who can do Z. The work has been suffering in ABC ways and we’re now at the point where we need to bring in someone to run things differently. We’d like you to move to focusing on DEF while Jane takes over the manager role.”

But if no one has been giving Kasie clear feedback, this is messier! You’d still use the basic framing above (without the “as you know”) and be candid about the ways in which things haven’t been working … but in that case, the board should recognize its own role in making this harder, and use this as impetus to commit to being more forthright about concerns in the future.

Also — make sure you’re not hiring Jane just because she stepped up, or you risk the same situation you had with Kasie. The board needs to be really clear with Jane (and with itself) about what doing the job well looks like and needs to be more hands-on about ensuring the new staffing decision is working out.

2. Our training about hostile work environments feels like a hostile work environment

I work at a small but thriving business with a small group of employees at headquarters (myself among them) and a larger contingent of contract workers at other locations.

Our city and state require all employers to adopt a sexual harassment prevention policy and to provide employees with sexual harassment prevention training. While most places I’ve worked complete this requirement using an online curriculum consisting of pre-recorded videos and multiple choice questions, this business teaches it live via video call with a member of the C-suite who is not in charge of HR. (In fact, as far as I can tell, we don’t have a dedicated HR team; HR-related duties are instead spread across a number of directors and execs along with their other duties). This class happens in a video call with the executive (“Kyle”) and about 20 other participants at a time, cameras are required to be on, and he will call on anyone and everyone at some point during the class to answer questions.

I’m sure this format works fine for some people, but I find it deeply uncomfortable. His blunt delivery on some of these topics leaves a really bad taste in my mouth (“Pop quiz, if nobody else is in the office and two coworkers at an equal level decide to have sex on their desk, is it technically harassment? Jane, you’ve been quiet, I bet you have an opinion on this”). There are also scenarios in this training that are sadly relevant to my personal history in a way that other people in the office are definitely aware of (and to a certain extent Kyle is also aware of), so I feel really exposed having my face on camera for that — or worse, being called on to answer pop quizzes that hit too close to home. I’m sure other people aren’t thinking about me as much as I am in those moments, but after the last session I wound up in the bathroom crying and I really don’t want to repeat that experience.

I reached out to Kyle and my manager and asked if this year I could fulfill the requirement with a pre-recorded version of the training instead (the city provides one on their website free of charge). I used the word “accommodation” and directly referenced why this training is difficult for me without getting into sordid details. I immediately received a phone call from Kyle stating that he does not believe the training provided by the city government and authorized by the state are legally compliant with city and state regulations (both city and state websites say it is), but further that he doesn’t want to accommodate requests for alternate training because “holding these trainings in-house is a huge source of revenue for the business.” (Your guess is as good as mine about what that means. If I had to guess, I bet we pass the cost of training the contractors on to their companies as part of the services they contract us for.)

This is bonkers, right? Is it legal? I did ask him if he was saying that the revenue stream was more important than the risk of creating a hostile work environment during a training about hostile work environments, and he did then say I could take the state-and-city authorized version instead, so my immediate problem is solved. But he emphasized that I shouldn’t tell anyone else because he doesn’t want people thinking they have other options, and I’m wondering if that’s as legally shady as it feels.

It’s weird, but as long as they offer accommodations as required under the Americans with Disabilities Act, they’re not breaking any law. It’s odd that they want to create their own (apparently badly done) training rather than using the ready-made one offered by the city (and even odder that they’re trying to claim the city’s training wouldn’t comply with city regulations), but given Kyle’s remark about it being a source of revenue, I’d bet you’re right that they charge the contractors’ companies for it. (Even that doesn’t fully make sense, but what else could it be? Is unqualified Kyle out there selling this to completely separate companies too?!)

The part about him telling you not to tell your colleagues that you’re getting this accommodation is sketchy — you have a legally protected right to talk with coworkers about working conditions (unless you’re a supervisor, in which case you don’t) — but the rest of it is legal.

3. If I’m graduating this spring, when should I apply for jobs?

I have a question about applying for jobs as a college senior. I can imagine that higher level jobs will have long hiring processes, but for entry-level office jobs is it okay to apply now, even though graduation is four months away? Or is it better to wait until closer to when a person will actually be available to start working?

Yes, start applying now. You might be too early for some jobs, but for a lot of them, the hiring process could easily take four months (if not longer).

4. Are there really so many nonprofit jobs?

You reference not-for-profit vs for-profit sectors a lot. I used to think I understood what nonprofit work was … like the Cancer Society or Doctors Without Borders or something. But you reference it so often, I’m beginning to wonder …. can there really be that many nonprofit jobs the U.S., or am I misunderstanding what it is?

Your international audience thanks you.

Nonprofits accounted for 12.8 million jobs in the U.S. — nearly 10% of private-sector employment — in 2022, the latest year with data available from the U.S. Bureau of Labor Statistics, and there are 1.9 million registered nonprofits in the U.S.

But nonprofits aren’t just the type of advocacy or service-based charities you’re thinking of; they also include arts organizations, museums, trade associations, religious institutions, private foundations, fraternal organizations, chambers of commerce, civic leagues, and lots more.

5. How to ask for more vacation time instead of a raise

I’ve been with my employer for the better part of a decade. I’m a senior-level employee and have a lot of capital, get great reviews, etc. The work is challenging and rewarding and we help a lot of people. We aren’t expected to put in crazy hours, but I often feel like I’m close to my limit in terms of what I can reasonably do without sacrificing quality, and the work can be very draining. My employer is a small-ish but growing local business.

I’m in the U.S. and employees who have been there a few years get just over four weeks’ PTO annually, only some of which can roll over. We don’t have separate sick leave, so PTO covers illness and vacation.

What I want more than anything is more time off. I’d happily forgo a salary increase for a few years if I could get more PTO. I’m wondering how I can try to negotiate for this, what arguments I could use, and how much to ask for. I’m sure they won’t love the idea but I don’t think there’s any downside to asking, and if I was successful, it would be incredible. I’m even open to periodic unpaid leave. I just want more time to rest.

The next time it would be appropriate to ask for a raise, ask for this instead. You can be pretty straightforward about it: “The thing that I really want right now more than a raise is additional PTO. Would you be open to giving me two additional weeks of PTO per year in lieu of a raise?”

I picked two weeks because it’s a good solid chunk while still being reasonable, and also gives them room to come back with one week if they balk at two. You could also run the math on how many weeks of pay a typical raise there would be equivalent to, and factor that into your thinking too.

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

1. Is stubble unprofessional?

Is having a few days of facial stubble unprofessional? What about showering every other day? How do I know when I’m well-enough groomed?

I’m a cis man who is reasonably adept at social interactions generally but struggles to pick up on unwritten norms/rules (like how often to shave). I got rid of a goatee in college and have generally shaved all my facial hair for every in-person workday since then. I also currently shower every day I go into the office, though I sometimes skip it for WFH days.

I’m considering a change for three reasons: (1) I was reminded of how much of a literally bloody hassle it is when I got to stop shaving for a couple months during parental leave. (2) I’m no longer at a job that has on-site showers for production reasons and safety reasons to shave. (3) I just learned that a lot of men shave every other day rather than daily, and it wasn’t that long ago I heard the argument that daily showers are bad for skin and hair, so I’m beginning to question my previous understanding of grooming rules.

I’d be happy to shave like once or twice a week, as waiting longer between shaves seems to reduce my rate of nicks and irritation. Is it a bad idea to go into the office having showered 2 nights before and shaved 2-4 nights before? My wife knows little about male grooming expectations, so I don’t know who to ask.

Showering: it varies by person. Some people need to shower daily to meet our culture’s expectations around looking and smelling clean enough for work. Some people don’t. Is there a noticeable difference to a bystander between how you look and smell when you showered in the last 24 hours versus when you didn’t? If not, you are someone who can go longer in between showers. If there is, you are not.

Stubble: as long as it looks like an intentional style choice (and not patchy or unkempt), stubble is fine in many, and probably now most, offices. There are still some conservative fields where it’s frowned upon, but they’ve quickly become the exception to the rule. (That said, avoid stubble for an interview, where you’re generally expected to turn up looking more polished.)

2. Should I try to keep an employee who’s leaving because of my predecessor?

I have just joined a small startup as head of engineering. Upon joining, I found out that one of the more experienced engineers has handed in his notice after accepting an offer elsewhere. As this is a team of four, his leaving would be quite impactful.

The reason he gave for leaving is that he wants to be promoted to senior engineer but his old boss wouldn’t do that. In private, he has told me that the previous head was not respecting him and would say things like, “I don’t need to listen to your opinions, you’re not a backend engineer.”

Less than two weeks after I’ve arrived, said employee has come to me and said that he feels my management style is so vastly different from the previous manager’s that he wants to stay; I have given him autonomy and trust which I believe he was previously lacking.

So far, I have said to him that if he proved to me over the next month or two (during his notice period) that he could show the maturity and drive expected of a senior engineer, and show a significant improvement in his soft skills, we could have a conversation about him staying. My concern is that I am encouraging him to leave it quite late to possibly renege on his accepted offer, and that he may end up leaving the company anyway if I don’t immediately promote him.

Should I keep him on this path, giving him the option that we revisit his notice? Or am I lining myself up for trouble down the line? Is there anything else I can or should do?

This is tough because you just joined the team and are still getting the lay of the land.

Normally I’d say that if someone was leaving for a reason that is now moot, and they’re someone who you were sad to see go, you should absolutely be open to letting them stay (assuming you haven’t already hired their replacement). There’s no reason to just oppose that on principle.

But this is messier, since you don’t necessarily have enough info to know how much you should want to keep him — and it sounds like there are some soft skill issues, at a minimum. I would not be leaping to keep someone with soft skill issues.

I’m also not sure it made sense to tell him that if he was able to do XYZ during his notice period, then you could talk about him staying. That’s leaving it very up in the air when you both need to be able to make solid plans (you so you know whether you need to hire a replacement and transition his projects, and him so he knows whether he’s actually taking that other job or not). Plus, is he really going to be able to demonstrate those things in a month or two? Particularly when you’re still new and learning the team?

In your shoes, I’d be seeking insight from others who work with him to try to make a decision now, rather than a month or two from now.

3. Was I wrong to settle with my company rather than continuing on to court?

In my previous role, I was subject to harassment, discrimination, and retaliation for over half a year prior to being terminated. I knew that I had a strong case, had been collecting evidence throughout, and connected with an attorney right away. In the end, I took a settlement. I decided that it would be better for my mental health to stop reliving those experiences. I also worried that a jury trial might be risky in my libertarian state, not to mention the expensive court fees.

I am proud that I stood up for myself while I worked there and after. But since I opted for the settlement, I have also entered into a confidentiality agreement. So while my former coworkers can probably make educated guesses about what happened, the wider world doesn’t know. New hires and new external partners won’t know what kind of company this is. And the bad actors can continue to skirt the laws.

I wonder what can be done, if anything, to help future victims of this company and their discriminatory practices. Was my choice of a settlement too selfish and short-sighted?

No, settling wasn’t selfish or short-sighted. It’s not your responsibility to make this company change, no matter what the personal cost to you might be; it’s the responsibility of the people running the company.

Moreover, even if you hadn’t signed a confidentiality agreement, your ability to hold them accountable would be limited. Yes, you could tell people in your network about how they operate and leave online reviews. But the impact of those things generally won’t outweigh the impact of making them pay financially — which has at least some potential to motivate them to clean up their act so they don’t get hit with future legal bills too. (That doesn’t mean they will! It just has a shot at it.)

4. How to make a conference travel request at a brand new job

I’m in the final stages interviewing for a role that uses a niche tool, and which I’ve been an active member of this tool’s user community for a few years. In recognition of my contributions to this community (knowledge sharing, answering questions on forums, etc.), the company that owns the tool recently sent me a voucher for free admission to their annual conference. The conference is scheduled for three months after the estimated start date of the role I’m interviewing for, and flight/hotel costs are not covered by the voucher.

I would love to attend the conference if possible, but am unsure how and when to approach the subject with my new employer if I end up with the job. The hiring manager had mentioned that some team members have attended in the previous years and I think it could be a great way to get to know the team if others attend as well this year, but I don’t want to press the issue so new in the role. What do you think?

Once you start the job, say this to your new manager fairly early on: “ToolCompany actually sent me a voucher for free admission to the conference since I’ve been an active member of its user community, but it doesn’t include travel. If NewCompany wants to send me, I’d be happy to go if so and could do ___ there.” (Fill in with things beneficial to NewCompany.)

5. Resigning right before or after a stock vest

I have a stock vest scheduled for February 15. I’ve accepted a new job that starts March 2, and I was originally planning to give notice on February 2, with my last day being February 17. That would allow me to give two weeks’ notice and still have a short break before the new role.

However, I’ve seen multiple colleagues in the past give notice and then be walked out or have their resignation accepted immediately, which would have caused them to forfeit unvested equity. I’ve also seen other teams allow their staff to work through the notice period. My specific team hasn’t had any good data either way, though I think I’m on good terms with my manager and team.

Because of that, I’m now considering resigning only after the vest occurs, possibly even the same day or shortly after.

My concern is that this could make my employer upset or feel blindsided, but I also don’t want to put myself at financial risk by giving notice too early. I’m not trying to be deceptive, just careful.

From a professionalism and workplace norms standpoint, is it reasonable to wait until after the vest to resign, even if that means giving little or no notice?

Yes, it is reasonable to wait until after the stock vest; people do that all the time, for this exact reason, and it’s additionally a good idea because you’ve seen that you might not be allowed to work out your notice period. However, ideally you’d find out if the new employer has any flexibility on your start date so that you can still offer two weeks notice; if you explain that leaving earlier will affect you financially, they might be very willing to give you an extra week or two. (People request this all the time, too. They may or may not be able to agree, but it’s not unreasonable to ask.)