Ask a Manager

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

1. Should people be fired for big, public mistakes?

I’m curious about your thoughts on Major League Baseball’s recent blunder. They released a new series of hats that have the logo imposed on top of the team location. For the Texas Rangers, they did not think through the word they would create.

Tetas is a slang word for breasts in Spanish. If you were managing a team that let this slip through, how would you handle it? Would people be fired for something like this?

I’m not a fan of firing people for single mistakes in their work (conduct is in a different category), unless there’s something about the mistake that goes to their fundamental fitness for the job. If someone was already struggling, sure, this could easily be the final straw — but if the person responsible was otherwise doing a good job and you were happy with their work previously, there’s no point in firing someone for one blunder (even a big one). In fact, if the person is generally conscientious, there’s a good chance that they’re now more valuable to you than they were a month ago because they just learned a massive lesson that’s likely to stick with them and be incorporated into their work going forward.

Also, with this kind of mistake, there were presumably many people who signed off on the design and should have caught it before it was finalized. It points to a need to change their processes so it can’t happen again, not to firing a dozen people for missing it.

2. Managing a former friend

I am struggling in my current toxic workplace and I’m keen to get a new job, but opportunities in my niche technical field and local area are rare. One such job has come up this week and whilst it’s not directly what I do now, I think I would be a viable candidate and would be happy working at this new organization. However, I met with the hiring manager who outlined the current team, which includes a friend who I have not spoken to in a year due to her professional behavior (breaking confidentiality and getting former colleagues into trouble, basically acting like she is in Mean Girls). It’s so awkward! I can’t imagine being her manager and supporting her when I feel like she is lacking in values that are core to professional conduct.

Should I still apply for the job and hope I can skate past the awkwardness? Or save myself the trouble? The hiring manager mentioned that line management could be discussed; I have wondered if confiding in him would make me look dramatic. This may all be moot if I don’t even get an interview but I’d rather make an informed decision.

Can you get yourself to a place where you can manage her fairly and objectively? If not, you should pass up the job; it’s not fair to anyone (definitely the ex-friend, but also the rest of the team and the organization hiring you to manage her) to come in already knowing that you’d be hindered by the history in a pretty significant way. But I don’t think it’s impossible to walk into a situation like that and manage fairly! You’d need to keep in mind that people can change and she may have learned some lessons in the last year and be willing to give her a fair shot at showing that she has. If you see that she hasn’t, you’d need to address that the way any good manager would (and you would benefit from knowing what to be looking out for, just like with the letter about the chaos employee earlier this week), but you’d need to come in with an open mind. You’d also likely need to have an air-clearing conversation with her when you start, along the lines of “I know we have history but as far as I’m concerned, we’re starting fresh.”

If that feels impossible, pass this one by.

If you do apply, I think you’d need to disclose to the hiring manager that you know the team member but have fallen out of touch. I wouldn’t share much more than that because of the risk of it just seeming like capital-d Drama, but if you don’t disclose it at all, it’s likely to come out at some point anyway and will seem very weird that you didn’t. (Be aware that if you do that, they’re likely to ask the employee about you … but from a minimizing-drama standpoint, if there’s anything to be aired out there, it’s better for it to be now rather than after you’re on the job.)

3. Executives winning company raffles

I work for a company with about 500 employees. Every year the company hosts a large professional conference and all employees are required to attend. On the final day of the conference, door prizes are awarded.

This year, the organizers had each attendee put their name tag in a box, and names were drawn at random to determine the recipients of the prizes. The prizes ranged from books by presenters to gift cards to one large prize that was worth close to $1,000. When the prizes were announced, four of them, including the large final prize, went to people who work in senior management. This rubbed me the wrong way and I want to know if I’m off-base to think that the most senior staff members shouldn’t be entering raffles like this. I was able to see the drawing from my seat and there didn’t appear to be any cheating. I just don’t feel like their names belonged in the drawing to begin with. I’d much rather see an administrative assistant or the entry-level recent college grad walking out with a prize than someone whose salary is ten times as large. What are your thoughts?

You are not off-base. Senior level managers should not enter raffles where they’ll be competing for desirable prizes with lower-paid employees, and the optics if they win a big-ticket item are really bad. The gracious move would have been for them either not to enter or, when they won, to decline and ask for a new pick to be drawn.

4. Is it weird to suddenly start going by a nickname a year into my job?

I’ve been working in a remote job, my first full-time job in my industry, for a little over a year now. The entire time I’ve worked there, I’ve gone by my legal name, Anne. I use it in my email signature, and pretty much everyone I am in contact with addresses me as such.

However, in my personal life, I go by Annie pretty much all the time. I put Anne in my email signature when I first started because I’m pretty new to the professional world and it seemed like the savvy thing to do, but now seeing how many people I am in contact with use their nicknames in the professional world, I’m more inclined to use my nickname.

Since I’ve worked at this job for over a year and have gone by Anne the whole time, would it be weird to suddenly switch my email signature to Annie? I’m mainly concerned with it seeming weird to my boss, who is the primary person I’m in contact with at my job. Especially since it’s remote, it feels so much more awkward to slyly switch my name in my email signature and hope everyone catches on.

It will not be weird! Switch your email signature to Annie. You can either leave at that, or you can say to your boss, “By the way, I should have said this when I started but I actually prefer Annie so I’ve changed it in my email signature and didn’t want you to be confused.”

And yes, it’s totally fine to go by nicknames at work. Not, like, Keg Master or Big Balls, but a normal name that’s just a diminutive? Yes.

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

1. Employee can’t figure out what accommodations would help her do her job

I work at a small organization where I wear many hats, including HR-related items. We have an employee, Nicole, who shared with us about a year ago that she was diagnosed with some conditions that make executive functioning difficult. We immediately approved her requests for an ADHD coach, project management software, and additional weekly meetings with her manager. In this last year, Nicole continues to not meet expectations in areas such as meeting deadlines, communicating effectively, and decision-making/prioritizing. When her manager discussed this with her, she frames the issue as “my work isn’t organized for me, therefore I find it difficult” and when asked to identify additional accommodations, she says she doesn’t know what she needs because it’s still a new diagnosis for her — and has implied that because of her disability, we need to accept that she may not meet expectations in these areas.

My concern is that this is not an entry-level position, so it is not feasible for Nicole’s manager to organize every task on her behalf or to identify what other accommodations or resources may be helpful. I think we are at the point where Nicole may need a more formal PIP or PIP-like intervention and a discussion about her responsibilities with identifying tools, resources, and accommodations needed for her to organize and execute her duties. Am I off-base? If not, do you have any suggestions of how we can talk with her to help her re-frame her accountability?

You are not off-base. You’ve provided the accommodations she asked for, you’re willing to provide more if she can identify something that would help, and she’s still not meeting the requirements of the job. The Americans with Disabilities Act does not exempt employees from meeting core job requirements; it requires employers to work with the employee to attempt to find accommodations if they exist, but doesn’t protect the person’s job if they can’t perform its essential functions with accommodations.

It does sound like it’s time to move to something more formal like a PIP. But before you do that, have a conversation with Nicole where you explain that the problems are significant enough that that will be the next step unless she can suggest additional, specific accommodations to try, and ask her to work with the coach to figure out what might help.

2. My boss wants my employee to report to him

I’ve been employed for 12 years at the same company in product development. I have been a manager of product developers for seven of those years, with four people under me. Over time, people have left and we’ve not rehired, so I only have one direct report remaining, Sarah, who I’ve supervised officially for seven years.

My boss is proposing that we change Sarah’s supervisory structure — I would handle the “day to day” of her work but my boss would be her supervisor of record and meet with her periodically, and we would jointly handle performance reviews. The reason to make this change would be that we’re a small team, and I’m the only person who reports to my boss who supervises someone.

I’m feeling angered by this as things are going very well with Sarah. She is sensitive to hierarchy and I feel like she may look at this as a promotion and that I’m no longer her boss. The other thing is that my supervisor doesn’t know anything about product development, and Sarah is a product developer. My supervisor is an operations specialist. That’s why he would still need me to do the day-to-day. This bothers me especially because in the beginning of my employment, there was a lack of structure and direction for newcomers, with official supervisors not providing direction. I often would end up mentoring and even serving as a direct supervisor to new people, including Sarah, even though I did not have a place in the official management structure nor any compensation and I was doing it on top of my own job. I was young and eager to prove myself, and I didn’t realize I was letting the manager slide by and walk all over me. Seven years ago, the manager left and I was given the formal manager role. This worked well for me because everything finally aligned — my role, my title, and my compensation. I feel this change would be a step backward functionally instead of forward. What advice would you give me?

You have a lot of good reasons to push back on the change. Talk to your manager and share them, as calmly and objectively as you can. In particular, emphasize that you’re concerned that you’ll still be responsible for a significant portion of Sarah’s management but without the title, and that the change feels like a demotion even though you’ll still be doing much of the same work.

It would be one thing if your actual function were changing, but it sounds like your responsibilities aren’t significantly changing, and it’s fair to ask that your title continue to reflect the work you’re doing.

3. Men are gross in our non-gendered bathrooms

My organization has slowly been moving towards non-gendered toilets. When building or upgrading facilities, toilets are now individual rooms and marked as all-gender. This is great! It’s progressive, inclusive, and by and large we’re all here for it.

Except … the men are gross! The biggest change my female colleagues and I have noticed is that non-gendered toilets are far more likely to be dirty, broken, and seats are constantly left up. We want the toilets to be welcoming to everyone, not just yet another place where we have to put up with how feral men can be.

One of our admin staff tried to combat this in a recently refurbished block of half a dozen toilets by attempting to label two of them as “women only.” This was swiftly shut down since it comes across as exclusionary and not what we’re about, although her intent was just for women to not have to visit somewhere a dude has just liberally shaken himself around like a sprinkler.

I don’t know who raised these grommets, but do you have any advice for combatting this? I don’t like the idea of attempting to remind everyone of what amounts to basic bathroom etiquette (and embedding mothering stereotypes in the process).

Consider a mix of single-sex and non-gendered bathrooms. That’s all I’ve got, given this particular set of facts, although it still leaves the non-gross men stuck with gross bathrooms.

If only it were practical to have full-time bathroom attendants like at a fancy restaurant.

4. How do I tell interviewers I was fired from my last job but it was because my dad was sick?

I was at a job I truly loved for about 18 months and was ultimately fired for “performance issues: not meeting job standards.” This was because six months prior to my termination, I had found out my father was dying and only had a few months to live. I thought I could handle working full-time and handling my dad three hours away, but ultimately, he died and my job performance did suffer and 30 days after he died, I was fired. (Hindsight being 20/20 here, I wish I had just taken FMLA but let’s not debate that now. I also really don’t want to get into whether my company should have fired someone 30 days after their dad died. I think what they did was total crap, but I also admit I wasn’t performing at 100% either. I’ve accepted the termination and have moved on.)

I am now searching for a job. I actually got an amazing offer, but when I filled out the initial application, I selected “no” for the “Have you ever been terminated from a job before?” question. Once the company found out that wasn’t true, the offer was rescinded. So now I am being honest and telling people the truth. But here is the issue — I’ll be in the middle of a phone interview and will be asked if I’ve ever been terminated from a job. I’ll say yes and explain it was performance-related (because I don’t want them to think I did something illegal) and it was because I had a dying parent I was struggling to take care of, who ultimately passed away. Inevitably, there is an awkward silence, an apology for the loss of my dad, and then a few days later I’ll get a “thanks but we’re moving in another direction” email.

How do I stay honest about my job history without making it awkward but also ensuring hiring managers understand that had there not been this horrible life event happening, I probably wouldn’t have lost my job?

I think where you’re going wrong is saying that the firing was performance-related. It was performance-related, but it’s not that you couldn’t do the job — it’s that you were juggling a horrible situation outside of work. The performance framing is making it sound like you couldn’t cut it, when that’s not really what happened. You said you’re worried that they’d otherwise think you did something illegal — but that wouldn’t be a typical leap for them to make!

Instead, you should say, “In my last job, I was doing well until there was a very serious health situation in my family. It was very difficult to juggle that at the same time as my job, and ultimately I couldn’t do both and they let me go. That situation has since been resolved, and I don’t expect it to come up as an issue again.” (I want to be clear that I’m not referring to your dad’s death as a “situation being resolved” but rather to your focus at work being so divided.) If your old manager would be willing to attest that you were doing well until your dad got sick, you could add, “My manager at that job would confirm I was performing well until that happened.”

I’m sorry about your dad.

5. Cold-calling for internships

Someone cold-called me today and asked if we do internships. I said yes, but you have to be a student of a particular college that we have a relationship with. They then asked, “So what do I do to apply?” Um … be a student at the college I mentioned? I am not management so can’t interview potential interns, so I told them to please email my boss. They proceeded to push for his email and I calmly said, “It’s on our website.”

When I was looking for jobs in my field (media), I was told Absolutely Do Not Cold Call. “No phone calls” was included in every job listing. You sent your application in and crossed your fingers. Have things changed or are the rules for internships different? In 2025, it seems weird and pushy that a young person would call rather than emailing. I’d love to read your thoughts on this.

Things haven’t changed. Some people have always called even when they shouldn’t — because they see it as attractive gumption, or they think it’s the only way to stand out, or they figure the rules don’t apply to them, or they just got bad advice somewhere along the line. It has always been so, and so it shall remain.

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

1. I get bad vibes from my new boss

A new director recently joined my department, and I’ve had an immediate bad feeling about her. I’m not typically quick to judge, and I recognize that she reminds me — at least in some ways — of a family member who is a bit of a narcissist. I want to stay professional and give her a fair chance, but I also don’t want to ignore my instincts if they’re picking up on real red flags.

I’ve just been having a gut feeling and maybe, unfairly to her, I am reacting to speech patterns and mannerisms that remind me of my relative. I don’t think I’m imagining all of it though. For example, despite us having met several times in person, she has made no effort to introduce herself to me or ask any questions about me or my role. I suppose I could have taken more initiative myself to engage, but since she is the leader of our team, it feels like initial outreach is her responsibility. I have a fair amount of influence and seniority at my company, but that is not obvious to new people, and to me it feels like she is ignoring or snubbing people who she perceives as having less power. There is probably a more generous way for me to look at this complaint (e.g., bosses can be introverts too) but something just feels off.

How can I balance professionalism with due diligence in assessing this situation? And how do I determine whether my concerns are valid or just baggage from my past experience? I don’t want to accidentally start a whisper campaign over something as subjective as bad vibes.

Keep your eyes open, but until you have actual signs that there are real problems, treat her exactly the way you would if she weren’t setting off your alarm bells.

It’s very possible that you’re reacting to baggage from a family member. It’s also possible that you’re not, and instead your gut is picking up on something real. But until you know for sure, there’s no action to take! After all, if you decided to just blindly trust your gut, what would that look like? You definitely shouldn’t go around sharing your concerns with other people (which I’m assuming is what “accidentally start a whisper campaign” refers to) when she hasn’t done anything! And if you let your gut affect the way you interacting with her, there’s a very high chance of making the relationship worse than it otherwise would be — like not taking any initiative to engage with her even though taking that initiative could help you professionally. (We can argue over whether that should be her responsibility, but the fact is she hasn’t done it herself — so the more relevant question is whether it’s in your best interests to initiate some contact yourself, and in many cases it would be.)

You asked about how to balance professionalism with due diligence in assessing the situation, and the answer to that is easy: professionalism wins out, because it’s in your own interests to remain professional. As for due diligence, that just means being willing to give the situation time. At some point, once enough time has gone by, you’ll have learned more about who she is and how she operates, and you’ll know whether your concerns are valid or not. But you won’t know that from day one, just like you wouldn’t know it about someone who wasn’t setting off alarms for you either.

2. I got in trouble for sending mail with upside down flag stamps

I’m an admin who processes our outgoing mail. We buy rolls of stamps that over the last couple of years have had a three-flag design. For whatever reason, my brain has trouble with orienting them — I often place them on the mail upside down. (You can see here that they have even been posed for purchase upside down.) It’s not intentional, it’s not a political statement on my part, it just happens when I’m peeling them off and working in a hurry. My supervisor, however, has gotten very upset about it several times. I’ve tried to do better, but he wrote me up today for “making political statements in the company’s name with company materials” when he saw one I accidentally placed upside down.

I want to speak to his boss about this to explain and ask if this can be removed from my file. Do you have any suggestions? My coworker suggested I go to the optometrist and get some kind of note but that seems like overkill.

Yes, a note from the optometrist would be overkill.

Your boss isn’t wrong to tell you that you need to place the stamps right-side up. I know it seems like a small thing that might not matter, but because the upside down flag is a symbol of distress, there is a movement around placing flag stamps upside down to make a political statement. It’s reasonable that your boss doesn’t want company mail going out with what could look like a political statement on it, whether or not you intended that way. Or just looking sloppy, for that matter — it might not be something you personally would notice or care about, but other people do and some will read it as less polished.

You can certainly try explaining that this was a mistake, not an intentional act, and asking that the write-up be removed or at least if you can add a response to the write-up explaining it was a mistake. But your boss isn’t wrong to be concerned that it’s continued to happen after he’s told you to stop — whether you intended it or not, you’re still sending out mail with what looks like a political statement on it, and you say it’s happening often — and so you do need to figure out a system for making sure it doesn’t keep happening. (Can you lay them out correctly oriented before you start applying them?)

3. Using inappropriate passwords when someone else might see them

I work for a large organization as the LMS manager. Someone recently reached out to me because they forgot their password. When I looked it up, I was surprised with the word they chose. I’m not offended but I felt that it was inappropriate for a workplace (mild swear but not offensive — “asshat”). I let them know they need to change it to a more workplace-appropriate word, reset the password back to the default, and they changed their password right back to the inappropriate one. (Makes me wonder how they could forget that!)

I know passwords are to be private but if you forget it and have to ask for it, I do see them. Is using swear words in password okay for work? Should I not have said anything and just laughed it off?

Well, first, in a secure password system, no one should be seeing anyone else’s passwords, even IT.

But in a system where someone else can see the passwords and might need to retrieve one for someone, it’s pretty bad professional judgment to use a swear word (mild and ridiculous as “asshat” is; it’s really on the far fringes of what qualifies as a swear word, but we don’t have a good name for the work-inappropriate category it is in). It’s even worse judgment to refuse to change it after being directly told to.

It’s not something I’d bother pursuing any further (unless you’re the person’s manager and there’s a pattern of bad judgment, in which case it’s the pattern that would matter more anyway), but I’d certainly think of them as someone with questionable judgment after this.

4. How to say thanks to a senior leader doing a great job in a terrible time

I’m in an industry that’s been very hard hit by the insanity around the executive orders. The actual policy changes and funding cuts, combined with the sheer chaos, volume of new directives, and inconsistency around what’s going on have been brutal. Everyone at my organization has been working around the clock for weeks to try to figure out how to navigate the next meteor that has come crashing through from the government.

With a few exceptions, people inside the organization have been amazing about this. We’re exhausted and confused, but people are pulling together and trying to problem solve as much as we can. We have a couple of senior leaders that I don’t work with regularly, but I’ve spent a ton of time with recently. One in particular has been nothing short of heroic. He’s been kind, patient, always available, expert, and fundamentally decent in every single interaction I’ve seen. He manages to combine a strong leadership steer with an ethical grounding and a recognition for the humans he’s working with that is not easy to figure out in the current nightmare. I cannot imagine how he’s doing it, and I shudder to think where we would be if he weren’t here. Is there any way that it would be appropriate to thank him for this? I know gifts are supposed to flow downward in the workplace, but this is so far above and beyond that I’d love to give some token of thanks for what he is doing. Any recommendations? A bottle of his favorite drink? A gift card to a meal out? Something else?

I’m a broken record about this but: a personal note telling them everything you said above. That will have more far more meaning, and probably be kept and cherished far longer, than any physical gift you could give him.

5. My company is violating the state law on paid sick time

Our office is in California and has three full-time employees. We’re paid by the hour, at the end of the month. In 2024, we were only allowed 24 sick hours and now this year as well. If we’ll need more than 24 hours, we must use vacation time or log zero hours. I’ve told the owner in mid-2023 and again in December 2023 that when we received the employment law posters employers are required to display, they clearly showed that as of January 2024, California employers must provide 40 hours of paid sick leave per year. I’ve also called our payroll company and asked them about this, and they stated our employer is not in compliance. They called and spoke to the owner’s daughter, who reports our monthly hours, yet nothing changed. What do we do about this? My two coworkers will not deal with this and are afraid to rock the boat.

File a report with the California department of labor. California happens to be a state that is very assertive about enforcing compliance with its employment laws, and they’ll handle it from there.