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

1. Our new work stations will be outside our building’s security screening

I work in a government office, in a building that does full security screening of every person who comes in, with metal detectors and an x-ray machine for their bags. My department does some cashiering.

As part of renovations to the building, they are adding cashier stations to our office that will be pre-security, meaning people can come directly to us off the street with no screening. We’re assured these stations will operate as check-only, no cash, but I’m still nervous about doing this. I’ve expressed my concerns but have been told our department doesn’t have a choice, and we’ll just have to try it.

Do you think it’s reasonable to refuse to man these stations? And if I do so, what is the most professional language I can use?

Can you band together with coworkers and push back as a group? One person refusing to staff those stations is more likely to hear, “Well, it’s a requirement of the job so you’ve got to decide if you want to stay in it or not,” whereas a group of you all pushing back will have more power.

In doing so, you might point out that the fact that the building has that level of security indicates there’s reason to think there’s a need for it, and you and other cashiers shouldn’t be randomly excluded from those safety measures.

2. My boss surveyed the entire staff on my work after 90 days

After 10 years with my organization, I was thrilled to accept a big job as a division director. Among the department’s directors, I was relatively junior; however, leadership insisted that all they wanted was for me to be successful. I was new to the department and had not worked with anyone in it previously.

About 90 days in, my boss informed me that he’d circulated a survey to the entire staff (including the 20 employees who reported to me and 20 others who were not in my chain of command) to gain insights on “areas warranting additional focus” on my part. I thought that kind of feedback would be useful and said so.

The results of the survey were all over the place. More concerning, a couple respondents consistently left really vicious and in some cases wholly untrue comments about my conduct, professionalism, and qualifications for the work, to the majority of questions.

Before presenting me with the results, division leadership fed all the comments through ChatGPT to create a summary. When I requested the original responses, I could tell by their writing styles that three who reported to me made negative comments or false statements about me or my performance. A few others used the survey as an opportunity to air grievances about the division in general, including problems that had long pre-dated me and couldn’t possibly be resolved in under 90 days. So, the summary skewed heavily negative. Unfortunately, this was all leadership was able to focus on.

I won’t bore you with all the details, but ultimately, given the lack of support offered to me both before and after the survey, I chose to resign, and haven’t looked back.

How typical is it for team members to be asked to do a formal evaluation of their new director within 90 days of their start? I’ve worked professionally for over 15 years and was never asked to offer feedback about any of my supervisors. Is this an unusual practice?

It’s very normal to ask around about how things are going with a new manager; the new manager’s manager should be doing that, so that they hear about how things are playing out on the ground that they otherwise might not see. It’s much less usual to do it via an anonymous survey that apparently made it easy for people with an axe to grind against the organization to grind it against you simply because it was a chance to air broader grievances.

But what’s more problematic is that your leadership then just accepted that feedback unquestioningly and passed it on to you without getting more info or applying their own judgment to it. Part of the reason for managers to have actual conversations when gathering feedback about this kind of thing is so they can bring their own judgment to bear on what they’re hearing, as well as being able to probe when something seems surprising or off.

3. Two of us left and only one person is getting a leaving gift

Last week I left my job for one in another department within the same organization, and left on really good terms with my current team: leaving tea, cake, card, and promises to stay in touch.

As I’ve not yet been taken off the department mailing list, today I got copied into a message laying out details for another colleague’s (Tessa’s) departure: saying that there would again be a leaving tea, there was a card in the office to sign … and a link to an optional collection pot for a gift for the entire department to contribute to.

Logically I know I shouldn’t expect a leaving gift. I didn’t expect a gift! I was perfectly happy without a gift! And now I’ve seen my colleague is getting a leaving gift when I didn’t and, if I’m completely honest, I’m pretty stung by it. Adding insult to injury, I was in the department a lot longer than her, have been described as having turned around the area I was working in, and had periods where I felt very under-appreciated by my boss. It genuinely feels like a snub after I put in a hell of a lot of work into my role.

I suspect the main reason why this might have unfolded in such a way is because Tessa is part of a sub-team that has worked together for a long time, with a manager who is very on it with this sort of thing. I, on the other hand, recently got reorganized into a team that hasn’t worked together all that long, with a boss is pretty useless with “pastoral” stuff, so in some ways it doesn’t surprise me that this happened. Nonetheless, I still do feel decidedly under-appreciated by how this unfolded. (It doesn’t help that I’ve had a look on the collection pot website and seen that people throughout the department – including people within my chain of command who could have organized any hypothetical gift for me — have donated. If this was just amongst Tessa’s sub-team, I wouldn’t care quite as much.)

I’ll be going to Tessa’s leaving tea next week and am feeling uncomfortable about what a sour taste this has left in my mouth (and I obviously don’t feel that way about Tessa or most of my teammates!). I want to stay on good terms with my department, and my former boss has already expressed a hope that I’ll provide useful insight for him into the team I’ve relocated to, so I know I’ll be hearing from him again. I feel embarrassed about how much this has struck me, but I feel so tempted to say something to my former boss. Is there any way I address how bad this looked from my perspective – short of going, “Oh, I didn’t know this department did leaving gifts’ rather pointedly when Tessa gets her present, which I rather suspect would be slightly inappropriate(!)?

It’s absolutely because you’re on different sub-teams, and Tessa’s team has a manager who’s on top of this kind of thing and your team doesn’t. That’s all it is!

I hear you about people throughout the department having donated to Tessa’s gift, and so why didn’t they realize no one was organizing one for you … but most people don’t think that much about this stuff. Someone tells them a gift is being organized, they donate, and they don’t put much more thought into it. Yes, ideally someone would have thought, “Wait, Jane just left too and I didn’t see a gift for her” — but it’s not personal that they didn’t! It’s just people being consumed with their own stuff.

I do think there’s room to say to your old boss, “I don’t know if you realized this, but it didn’t feel great that Tessa is having such a fuss made over her departure when that didn’t happen for me, and I just wanted to flag it in case it’s something you can watch for when other people leave.” In other words, frame it as feedback for the future, not as “give me a gift now.” But it’ll be way more helpful for your peace of mind to just see that as reflective of things you already knew about your boss and not read more into it than that.

4. Should I tell my interviewer I like that the city is LGBTQ-friendly?

I have an interview coming up with a university in a famously queer-friendly area, and part of the reason I’m interested in this job and others like it is because I live in a less friendly area. Normally, I wouldn’t bring up anything identity-focused in an interview, but being a visible trans woman interviewing in one of the trans capitals of the world, I wonder if it makes sense to say something when they inevitably ask, “Why are you interested in this role?”

More generally, I’m just curious about how you’d advise any marginalized person to handle this, especially in the current moment where a lot of folks are considering these types of moves. One friend recommended saying something like, “This area is a really good fit for me culturally” and leaving the rest to them to figure out. What do you think?

They want to know why you’re interested in the job — meaning the specific role and its work, and so a strong answer will speak directly to that. You can definitely mention that the area is a good fit culturally (and that can be helpful when they know you’d need to move to take the job), but it should be more of an aside, not the focus of your answer.

5. How should my resume list many projects under one company?

I’ve worked at the same company for the past 10 years, but due to *gestures broadly*, I’m looking for a new position. The company I work for is basically a contractor, and I have worked on probably over 20 projects at this company, some for 3 months and some for 3+ years, and I’m usually simultaneously working on at least 2 projects.

The problem is, I don’t know the most useful way to put this experience on a resume! For any job posting I’m looking at, I probably have at least 2 projects that are the most relevant that I assume I should put first, but I still have room on my resume, so then what? Should I list the current projects I’m working on, or the longest running projects I was on? The most impactful? And what is the clearest way to show these aren’t the only projects that I’ve worked on, just like a relevant/recent subset?

Secondly, I’ve been promoted multiple times at this company and was also an intern before starting full-time. Putting just my current role makes it look like I’ve been that role the entire 10 years, so I assume I should put all of the roles I’ve been, but do I need to also put the dates? Can I just list them?

Yes, list the most relevant projects first. After that, choose the projects to list that (a) most closely demonstrate the skills that will be relevant to the job posting or (b) speak to a track record of achievement in general (so if you did something really impressive — built something, saved a failing project, overcame a challenge that had stumped others, etc. — include those things because they demonstrate that you are a competent person who gets things done).

You should list all your titles, and while you don’t have to include the dates for each role as long as you have the overall dates for your employment at that company, it’s often info that hiring managers want and that will strengthen your resume. So for example, it might look like this:

Oatmeal Association, June 2016 – present
Tasting Director, August 2025-present
Tasting Manager, December 2024 – August 2025
Oatmeal Taster, May 2020 – November 2024
Oatmeal Stirrer, January 2017 – May 2020
Groats Intern, June 2016 – December 2016
* accomplishment
* accomplishment
* accomplishment
* accomplishment

Or you can list the accomplishments for each role under the title they go with, depending on the specifics of what you’re listing.

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.