updates: the shady investor, the needy boss, and more

Here are three updates from past letter-writers.

1. Should I work with this investor or run for the hills?

My letter was actually published the same day I was leaving for a vacation. While I was away, I had some time to really reflect on your response and think through my next steps. What stood out to me the most in your response was when you said that this investor seemed cavalier about my protection; after reflecting on my interactions with him, I think this statement hits the nail on the head. I am also incredibly grateful to the commenters for sharing words of wisdom. Nearly everyone was urging me to not pursue this opportunity. Several people had even expressed that they were in similar situations that didn’t pan out the way they had hoped. I knew in my gut that something wasn’t right, and I think I just needed some validation.

I came back from vacation knowing I would not be taking part in this opportunity and interestingly enough, I never heard from the investor again. This pretty much confirmed exactly what I was thinking in the beginning, which was that he was perhaps viewing me as a means to an end. To be fair, I did not bother to reach back out either. We essentially both ended up ghosting each other. I am glad I did not spend any of my time giving him my ideas or knowledge; my husband recently started his own business, so instead, I’ve been pouring my free time into helping him grow it. It’s been extremely fulfilling, and I am able to get that “entrepreneur bug” out of my system!

I sincerely wish this investor the best in his business endeavors, but I’m happy I didn’t take him up on this offer.

2. My new boss needs constant reassurance

The good news is two-fold: Jim has had some wins in his area of work that seem to have calmed his anxiety at least to the point he’s not fretting at me constantly about his own work. He’s definitely an anxious person though — I hear from him at least once a week about how much he’s worried that generative AI is going to take over his job. That’s easier for me to ignore than a stream of anxieties in our one-on-ones though. The other part of the good(ish) news is that due to some big miscommunications with him, I implemented shared note-taking for our one-on-ones and that has turned out to also help give our meetings better structure. We have a shared running document where we add notes about the current meeting at the top and save all the previous ones below. We both add agenda items to this document. It’s definitely helping keep our weekly one-on-ones on track and gets me around the issue that I don’t want his advice on anything I’m working on because I can think more carefully ahead of time about what to discuss (oddly, he’s constantly suggesting I use generative AI on my work tasks, even though he’s super anxious about this technology — I ignore that advice too).

The bad news is that his anxiety is the least of his problems. He works incredibly fast on projects that really need thoughtful work, says yes to everything with no prioritization for our team which has resulted in us being signed up for work that is nowhere near what we should be doing, and makes a lot of mistakes. After more than a year in this job, he still doesn’t understand the fundamentals of our technical field. I spend a lot of time correcting his misconceptions, although I’ve realized it doesn’t really do much good so I’m trying to pull back on doing that too. My grandboss, Jim’s boss and my former manager, is highly uninvolved in our team’s work to the point I doubt he is seeing the majority of Jim’s mistakes. All this to say, I am pretty sure I’m not long for this job, which is disappointing because it used to be a great position. I have hired a summer intern so am planning to stay through the summer since there’s no one else to mentor them, but am thinking of giving notice at the end of the summer and working as a freelancer/contractor for a while. Very excited to be my own boss! Thank you again for your great advice.

3. I deliberately over-claimed a tuition reimbursement (#3 at the link)

Shortly after I emailed you, I actually got offered a much higher-paying job at a company in California and decided to take it, so I ended up just paying everything back in full and it feels like a weight off my shoulders. I’m much happier at my new job too and have a lot less stress. I wanted to say thank you again for your advice – it was very much appreciated.

how do I come to terms with giving up on my dream job?

It’s the Thursday “ask the readers” question. A reader writes:

I have a very specific training and “dream job,” which for the sake of this question let’s say is archaeology (although it’s not). I’ve been passionate about archaeology since I was a teenager and have both an undergraduate degree and master’s degree in it, as well as years of research assistant experience and a number of conference presentations. Unfortunately, the job market for archaeologists is very limited, and most positions either require a PhD or specific mechanical/technical training I don’t have. While I applied for the few number of positions available to me, I unfortunately didn’t get any (and the salary tends to be below the cost of living for the cities they’re located in).

As a result, I got a job in an entirely unrelated field. I enjoy the work, the pay is reasonable for the location, and I am genuinely interested in the org’s mission. It’s just not what I imagined myself doing. Of course, going and getting a PhD is always an option if I want to return to archaeology, but I’m not sure I want to dedicate four to six more years of training just to enter the unstable academic job market, especially when that four to six years in my current job/general field could see me getting multiple promotions/salary increases. I guess I’m just looking for advice from people who have been in similar situations in how to come to terms with this. How do you mentally pivot from seeing your future career in one specific way to an entirely different career/field/goal?

Readers, what’s your advice?

Read an update to this letter

should I leave my job with great benefits, coworker has a quote about weapons in their email signature, and more

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

1. Should I leave my job with great benefits but a problem boss?

I need some help figuring out if I should stay in my current accounting job, or if I should start job searching. I work for a pretty small business, about 80 people across four locations. The office I work in has eight people, including the two owners. The good things here are very good, and the bad things are pretty bad. I only started here five months ago (but I have a solid work history, so I’m not super concerned about leaving soon if I need to).

Here are the good things: I am essentially working part-time for full-time pay and benefits. The owners overstaffed this role so I’m working about 15 hours a week making a competitive market salary for a full-time role with my title. I get to completely set my own schedule, come to the office when I feel like it, and work remotely when I feel like it. I don’t deal with any clients, so I truly can just work whenever I want as long as all the work gets done in a timely manner. Some days I start work at 7 am, and some days I don’t start until 4 pm, depending on what I need to get done in my personal life. The owners are only in the office about 15-20 hours a week and don’t monitor us at all. I have unlimited PTO and the owners really let us take advantage of this benefit. People routinely take 6-8 weeks off a year, including the owners, and no one gets any flack for it so long as work is done. My husband and I are actively trying for our first baby, and I genuinely don’t think I could find this work/life balance and level of flexibility at any other company.

Now the bad: When I was hired, the owners were honest with me that they weren’t 100% sure why I was being hired. They explained that the person working in the finance department already was overwhelmed, and they didn’t know if it was due to business growth or because she couldn’t handle the workload. It became immediately apparent to me that she just couldn’t handle the workload, so this department is overstaffed (hence why I’m only working 15 hours a week, sometimes less). When I mentioned this to the owners, my manager explicitly told me he knew we were overstaffed, but he planned on making no changes. This colleague, “Marissa,” has more education and experience than me. But she’s making my life hell. She’s a very nice, friendly person, but doesn’t understand even the basic concepts of our type of work. She is routinely going through my work and changing it (even though she’s not my manager) and screwing it up so I’m constantly redoing work. When I explained what was going on to the CEO, he told me it was my responsibility to handle “personality conflicts in the workplace” and that he “doesn’t know enough about what I’m doing to determine who’s right.” Because our CEO has zero knowledge about my type of work, when I try to explain things to him, he gets angry if I don’t do things the way he wants. For example, he constantly wants me to change our financial statements in ways that are not legal. When I tell him the changes are not permitted under IRS rules, he calls me insubordinate and sends me home. My name is signed on those financial statements, and if we’re ever audited, I’d be the one at risk. Also, I feel like my skills are atrophying already, and my sense of norms are being warped. My manager yells at people and everyone here just acts like it’s normal. I’m doing so little work that it feels like I’m not growing or progressing at all.

Do the benefits outweigh the drawbacks, or is this a cut my losses and run scenario? If it makes a difference, while I do want flexibility in my career so that I can start my family, my husband is going to be a stay-at-home father, so long-term my career success is more important for us than my ability to be really flexible.

If it weren’t for your CEO pressuring you to break the law — and calling you insubordinate when you explain you won’t! — I’d tell you that this just comes down to what you personally value most: flexibility versus satisfying work and professional growth. There’s no right answer to that; it depends on what’s most important to you. Some people would love the situation you have (minus the legal issues), even with the Marissa situation, and others would be itching to get out. It’s a personal call.

But the legal issues and the CEO’s handling of it tilt the scale to “get out.” That’s a serious situation that could have legal and professional ramifications for you even after you’ve left this job and it’s not worth it, even for the very real benefits you’re getting in return.

Read an update to this letter

2. Coworker has a quote about weapons in their email signature

I received an email from someone who works for my company but in a different location, and they had a TV show quote in their email signature. Normally I wouldn’t have thought twice about it but the quote was from The Mandalorian: “I’m a Mandalorian. Weapons are part of my religion.”

I should add: we work adjacent to higher education. I feel like referencing weapons even in a quote from a show is probably in very poor taste!

I’ve obviously never met this person and I’m not sure about what, if anything, I should say to them about it. Thoughts or advice?

WTF? That’s wildly inappropriate in a work context. In an era of workplace violence, it’s outrageous that (a) someone would think this was a good thing to put in their work email signature and (b) it hasn’t already been swiftly dealt with.

Forward it to HR or whoever plays that role in your company with a note that you were alarmed to see it and hope they’ll ensure it’s removed. Don’t engage with the person directly about it; they might just say no, so you need someone with the authority to handle it to handle it. (Ideally that would be their boss, but I’m suggesting HR instead because I assume their boss has seen the email signature by this point and for some reason hasn’t found it worth addressing.)

3. I don’t want people to think my pronouns and time zone are part of my name

I’m a director at a fairly progressive company that’s predominantly remote. Recently, the powers that be dictated that everyone is “encouraged” (read: “you have to do this”) to add their pronouns and time zone to their name in Slack. I don’t want to do this! My name isn’t “John Doe (he/him) (PST),” it’s just “John Doe.” There’s no bigotry angle here, as I already have my pronouns and time zone in my Slack profile and did so willingly before I was asked to. I have a real problem with my name being presented as anything other than my name, but I’m worried that not doing this will be interpreted as some sort of political stance when it’s not. Is my only option to bite the bullet and do it even though it bothers me on a personal level?

Yes, it will definitely be interpreted as a transphobic stance even if you don’t intend it that way, because what you’re saying doesn’t make sense any other way. No one is going to think your name is “John Doe (he/him) (PST).” It’s going to be obvious that that’s your name, your pronouns, and your time zone. It’s no different than if your company wanted you to include your job title after your name in your email signature, as many do — no one is looking at “John Doe, engineer” and thinking “engineer” is part of your name.

So the good news is that you don’t need to worry about that at all! You can include your pronouns and time zone without any risk that they will appear to be part of your name.

(If “encouraged” truly does mean “required,” though, that’s a problem since it can force people to out themselves or declare pronouns they don’t identify with. Encouraging it is good; requiring it isn’t.)

4. Can I mention the work I do for my disabled spouse on my resume?

I’m a carer for my disabled spouse — not formally or legally recognized, but in practice I do an awful lot of administrative work, scheduling, advocacy, research, and communication on their behalf. This has definitely helped me develop and demonstrate significant experience in all these skills, but I’m not sure if it’s something I can or should include on my resume or job applications. I’m concerned that employers might worry that my role as a carer might impact my attendance or performance. And if I were to include this experience, I’m not sure where or how to do so! I’d really appreciate any advice you have on this.

Leave it off. In general, work that you perform for your household or family doesn’t belong on your resume — partly due to convention, but in larger part because there’s no way to assess how well you did it. If you frequently dropped the ball, were horribly disorganized, and regularly messed things up, a prospective employer would have no way of knowing that … and there’s no appropriate way for them to probe into it. Plus, your family members can’t be references for the work (and they’re also much less likely to fire you than an employer would be!).

5. Helping an intern with the transition from intern to employee

I work for a small nonprofit where I’m the only full-time staff member (my boss, our executive director, works part-time and on a volunteer basis, so I’m the one running things day-to-day.) We’ve had a paid internship program for about a year and a half now, and it’s been great. One of our interns (Greg), who has been with us since the internship program began, will be coming on as a full-time staff member in a few weeks. I’m thrilled, because Greg is fantastic and a perfect fit for our organization, and having him on full-time will really help take stuff off my plate and help our organization grow.

I’ve onboarded new hires before, but since Greg has been working here for over a year (and honestly operating much more like an employee than an intern, in terms of the level of ownership he’s been able to take on), I know that the onboarding process should be a little different than it would be for someone who’s totally new to the organization. Do you have any recommendations for how I should structure Greg’s onboarding into this new role and what that onboarding should include? Is it just the typical onboarding process minus the “here’s how our organization works” part? Are there any other things I should incorporate to help him transition smoothly from a part-time intern to a full-time staff member?

Do all of it, just like you would if he were brand-new to the organization — because there are probably holes in his knowledge about how your org works that you don’t know about (and that he may not even be able to identify). In fact, although it wouldn’t be practical, I sometimes think there would be benefits to re-doing new employee orientation once people are six months in, because everyone misses a lot in the beginning.

You can explicitly tell him your plan at the start — “I’m going to go over everything with you that I normally would with a new hire. Some of this will be familiar to you, but I want to make sure you don’t miss out on anything just because you’ve already been interning with us.”

In addition, think about what’s changing for Greg now that he’s moving from intern to staff. What expectations will be changing? Are there things he didn’t have the authority for previously that he will have now? Do you want him to manage his work any differently? Step up differently in certain areas? Whatever those things are, spell them out explicitly. (That said, generally you won’t be able to anticipate all of those little changes, so assume you’ll be naming some as you realize them, too.)

my job makes me feel like I’m the worst kid in gym class

A reader writes:

I work a job that is typically considered high-stress in a low-paying industry. My workplace and the satellite offices will get together on days the workplace is closed to clients and take us for a (paid) day of team-building fun. We go bowling, play paintball, go to arcades, that sort of thing, in teams that are randomized across offices so we mingle. These outings typically include free restaurant meals and sometimes free alcohol.

The problem is that I have terrible motor skills. This is not “just” clumsiness or a problem of fitness. The long story short is that I should have received more aggressive PT and OT after a years-long period being bedridden as a child. I just don’t have typical adult body coordination and, despite some later in life PT, I never will. My hand-eye coordination is zilch. I can’t drive or ride a bike or play most video games. I have difficulty tying shoes and my handwriting is only legible because I took years of calligraphy classes. This usually doesn’t affect my life too much — but I can’t bowl! Or aim a gun in paintball, or shoot pool, or throw darts, or successfully do any of the other barsports-adjacent activities that we do at these staff days. My body simply cannot do the thing.

Everyone else has fun at these things, but people definitely get exasperated when I end up on their team. I’ve watched the “ringers” of our workplace (we have a few former pro athletes) quietly — and not so quietly — switch over to a team when they see I’m on it to balance it out. I’ve been at this organization longer than most and having to humiliate myself and irritate a rotation of my full host of coworkers every six weeks is taking a toll.

I don’t know if I can ask that we switch to other activities especially given that everyone else, including coworkers who are living with more impactful physical disabilities, do fine. Being embarrassingly bad at foosball tournaments isn’t exactly a disability to be accommodated, but I feel like I’m not a part in the bonding rituals. I feel terrible dragging everyone else down and it’s really alienating to know I am the infamous bad luck charm of our entire organization. I don’t even know what I’d suggest as a replacement, given that the options we have already are very much inclusive of fitness level and it’s not anyone else’s fault I have weird muscles. I love my job otherwise but this is bizarrely disheartening. Any advice?

Please speak up! This sounds awful for you, and it’s not right that it’s happening so regularly. It would be one thing if they organized these sorts of activities once or twice a year, but every six weeks?! That’s incredibly frequent.

I’d also bet some cash that you’re not the only one who finds the “let’s showcase our physical coordination” days to to be too much. I know I’m a bit of a broken record on this topic, but employers have an obligation to be thoughtful about this sort of thing — especially when it’s happening every six weeks — and to make sure the mix of activities they’re selecting is truly inclusive. That doesn’t mean they can’t organize the occasional bowling or darts tournament; they can. But if they’re organizing team-building with this frequency, they need to do more to mix it up and account for a wider range of physical ability and interests on your staff. (And I know you said the activities are already inclusive of fitness level, but … they’re not. You being a case in point.)

So please do talk to whoever organizes these and ask if they can include more variety. Could they consider, I don’t know, a picnic? A movie outing? A cooking class? A tea and coffee tasting? A paint-your-own-pottery session? A non-physical volunteer project? Or even just … a free day off? You don’t actually need to team-build every six weeks and, particularly in a high-stress field, I guarantee people would appreciate a day off. (And really, if it’s high-stress, I’ve got to wonder if it might be slightly less stressful if you weren’t losing one full day every six weeks to go play darts and so forth … but I know that’s not the point of your letter.)

Alternately or in addition to that, can you give yourself a different role on the days where the activities involve motor skills? Can you volunteer to be the score-keeper, the referee, or the photographer? (You can do that even if those things aren’t really needed.) I bet there are a lot of different roles you could just announce you’ll be filling that would get you out of doing stuff you’d rather not be forced into. If you’re worried about pushback, you could explain ahead of time to your boss or whoever organizes these that that’s what you’re going to be doing and why.

But please do speak up. And if you feel awkward about it, remember that the professed point of all these activities is team-building. They’re not achieving their purpose if one person on the team is being systematically alienated by them. A decent employer would want to know.

Read an update to this letter

my former employee is badmouthing me to my staff

A reader writes:

I recently hired an employee in a pinch because we thought he could fill a gap quickly and efficiently, but it turns out he was terrible and either dishonest or in denial about his own skills. He did not listen or follow instructions, and his customer service skills were awful. Many times, even after after coaching, he was unable to complete tasks correctly.

After six months, he decided to resign. He wrote an email saying that he couldn’t work for me anymore because I am angry and hostile. He also wrote that after speaking with other employees, he has concluded that I am an unhappy person with anger issues, and that he feels that attempting to change the atmosphere would not be possible as this is just who I am at my core.

It’s one thing to raise the issue that our professional interactions were not positive (which is valid, I admittedly lost my patience with this guy), but it’s another for him to say that I’m an unhappy person at my core. He doesn’t know me.

If I’m honest, I just didn’t feel like I had a lot of recourse, and I was angry about it. He frustrated me several times a day and I admittedly stopped putting forth effort to handle his shortcomings in a better way because I was tired of it.

I really want to set the record straight with this guy, that he doesn’t know me personally and I’m not an unhappy, angry person. I failed as a manager, but he also failed as an employee. Is that worth it? More importantly, I want to set the record straight with my staff. How do I move forward with them?

I answer this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

my business partners won’t fire their problematic family members

A reader writes:

Our company has three partners: me, Lou (my husband), and Sarah (our best friend). Lou’s sister, Leah, and Sarah’s younger brother, Bobby, have worked here for over 10 years and basically feel untouchable and do as they please. Leah has made some effort to correct her actions and she primarily works with Lou so she’s less of an issue.

Bobby, on the other hand, has a history which has been documented and discussed with him numerous times. For example, it is now crunch time in our industry so while everyone else is working hard as a team, Bobby continues to make his own schedule, doesn’t follow the rules, and frustrates everyone around him. He knows that Sarah will always take care of him as she has been doing all her life. Sarah has always employed Bobby after he failed out of college. Bobby is now 49 and Sarah is 56 and the oldest sibling.

I’m the partner who other employees come to with numerous complaints about both Leah and Bobby, but especially Bobby.

We have documented issues, had numerous conversations with Bobby, given chances, but after a short time of improvement, he returns to the poor behavior.

There are grounds for firing both of them, although Leah is a couple years from retiring so I think we’re riding out that one. However, Bobby continues to take advantage of us and acts like he’s untouchable, because he has been. Even with numerous reprimands and changes (we’ve changed his job numerous times,) the end result is he’s lazy, unaccountable for his actions, and disappears while other employees notice.

Unfortunately there is a long family history with Sarah and Bobby, and she’s at her wit’s end on how to handle him.

We’ve hit a wall and I’m afraid we’re going to lose Bobby’s frustrated manager, Jackson. Jackson is doing a great job, but has no control over the situation. Jackson and as other team members have reached out in confidence to me about Bobby numerous times and we have weekly meetings with Jackson to discuss progress. But nothing happens in spite of me telling my partners that we need to do something firm and act responsibly.

We are a 10 million dollar company that the three of us have built from the ground up. 20 years into this, we’re all very close. Sarah and Lou are in a tough spot since it’s their siblings. I’ve put myself in their position and empathize greatly, but business is business.

I recognize this is a difficult situation, but think it’s greatly affecting our team right now and we all have to be on top of our game. I’ve been frank and honest with them both, but nothing I say sinks in.

Ultimately this comes down to whether the three of you, as partners, are willing to fire family members.

If Sarah absolutely will not budge on firing Bobby, no matter what he does, then you and Lou need to decide if you’re going to force the issue or not. Are you able to overrule her? Are you willing to overrule her? It sounds like that’s what it’s going to come down to.

Ideally, the three of you would sit down and hash out the reality of the situation. Is the business’s decision that siblings of partners are so protected that they’re not accountable and can’t be let go? Right now, that’s the way it’s working. Is the business — meaning you, Lou, and Sarah — willing to put real accountability measures in place for relatives, or are you going to keep them at all costs, no matter how they behave, no matter how much they demoralize the rest of your staff, and no matter who you lose as a result?

Those might be interesting questions to put to Sarah. (And you should put them this bluntly; don’t soften them.) But you and Lou need to answer those questions too, because right now you’re letting Sarah sacrifice your business needs to her desire to protect her brother. Are you willing to do what it will take to reverse that?

If Sarah’s top objective is to protect Bobby at all costs, does it make sense for you and Lou to remain in business with her?

If family members are untouchable, then you’re probably going to lose Jackson. You’ve asked him to manage someone without giving him any power to do that job — of course he’s frustrated! (If he wrote to me for advice, I’d tell him to get out because he can’t do the job he’s been hired to do.) You’ll probably lose other people over time too, because they’ll resent being held to standards that Bobby isn’t held to.

All this applies to Leah too. Even if she’s not as bad as Bobby, deciding to just let her go on being a problem for a few years until she retires will impact other people. And what if she doesn’t retire when you think she will? You could be signing on for five more years of this, or more, just to avoid dealing with the problem now.

Beyond the staffing issues, your business also is going to be less effective than it otherwise could be — because of the time and energy put into dealing with Bobby and Leah and the opportunity cost of not having someone better in their positions.

But ultimately you have a Sarah problem more than you have a Bobby problem. If Sarah is protecting Bobby and won’t let him be fired, none of you have any power to do anything about him … and Bobby sounds like he knows that.

When you say Sarah is at her wit’s end about how to handle Bobby, that’s because she’s not willing to use the most obvious option: removing him. When you ask someone to change over and over and they don’t do it, you need to accept they’re not going to do what you need, and proceed accordingly. In an employment relationship, that means you warn them that you will need to let them go if XYZ doesn’t happen, and then you follow through on that. You can’t just cajole and cajole forever.

The three of you have to decide — or maybe just you and Lou have to decide — which goal is more important: running an effective business or employing family members. Right now you’re functioning as if it’s the latter.

can I ask for proof that my employee tried to find coverage, boss interrupts me, and more

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

1. Can I ask my employees for proof that she asked other employees to take her shift?

I am a shift manager at a fast food restaurant. I have a question that my manager seems to be avoiding. Today an employee (Emily) texted me that she won’t be able to come in. I told her okay, but to ask Xio, Luis, Sam, or Carlos if they’re able to come in. She said yes, she would text them. I ended up being the only cashier the entire afternoon.

When I got off of work I was texting Sam, who is also my friend, just ranting about the shift. Well, it turns out Emily never even reached out to see if she was able to cover her. So I’m not sure if Emily texted the other three employees. It also had me wondering if she was faking being sick or just called out to hang out with Luis, who is also her boyfriend, because he didn’t go to school today either.

I was wondering if I’m allowed to, or legally able to, ask Emily for screenshots confirming that she texted the other employees? If not, do you have any advice on how to handle this situation? I’ve had issues with her in the past such as her work performance and inability to follow instructions.

There’s no legal reason you couldn’t ask Emily for screenshots, but it would be a pretty crappy way to manage — and awfully demoralizing for her if she was actually sick and if she did indeed contact some of them. If you really want to dig into it, you’d be better off just asking the others … but even that seems like focusing on the wrong piece of the situation. If you have issues with Emily’s work or her reliability, address those head-on and tell her what you need to see change. If it doesn’t change, then decide if it still makes sense to employ her under those circumstances.

But most of the time when a manager finds themselves wanting to demand this kind of proof from an employee they already don’t trust, it’s a sign that you need to deal with whatever the issues are that have made you not trust them in the first place.

I’d also suggest rethinking the system of requiring employees to find their own coverage when they’re sick. I know it’s incredibly common in retail and food service and I’m undoubtedly fighting a losing battle on this one, but when someone is legitimately sick, it’s not reasonable to expect them to call around for coverage.

2. My boss interrupts me while I’m presenting

Someone who used to be my coworker became my boss. She has some micromanaging and impulse control issues. While she was my coworker, I was asked to give two different presentations to various groups. The first time, she interrupted my presentation to say, “Oooh, tell them about this,” and “You should tell them that!” I hadn’t got to that part of my speech yet, and it was really distracting to have someone coach me in public this way. I received a scholarship for the college forensics team, so I am not a stranger to public speaking. I had prepared a perfectly complete speech, she just couldn’t help herself from trying to “fix” it while I was in the middle of presenting it.

To avoid this happening the second time, I “practiced” my half of our joint talk in front of her so she would know that I was doing a competent job. (She did not feel the need to run her half of the talk by me.)

I have been asked to make two presentations at meetings she will be attending this summer. How can I ensure that I am able to give my speech uninterrupted by unhelpful comments from my boss?

The simplest solution won’t work. I can’t approach her about this, because she has a habit of not remembering things, and will have no memory of her rudeness, so bringing it up will be a waste of time. I do not want to “practice” my speech for her. My options as I see them are: (1) ask a coworker to sit next to her and stab her in the thigh with a pencil if she interrupts me this way or (2) publicly shame her by handing her the slide clicker so she can finish the presentation to her satisfaction. Do you have a more diplomatic solution?

Years ago, some other activists and I disrupted a speech by a presidential candidate (yelling, unfurling a banner, showering the audience with flyers, and generally causing a disruption). Unlike many of our other targets, he handled it perfectly. Rather than getting flustered or seeming irate, he called out, “Let’s hear it for free speech!” and praised us for exercising our right to protest. He looked great — in control and unflappable — and our protest fell flatter than it would have otherwise.

I’m not suggesting you use that approach with your boss, but I do think it’s valuable to consider “handling interruptions with aplomb” to be a sort of 301-level public speaking skill, and looking at it that way could help. That would mean that assuming that you’re going to get interrupted and preparing for it. If you’re expecting her to interrupt, you can be prepared with responses like “yes, I’ll get to that, keep listening” and “I agree, that part is exciting, give me a moment to get there” or whatever else makes sense for your specific context, and you probably won’t be as thrown off by the interruptions because you’ll have planned from the start that they’d be coming.

Read an update to this letter

3. I hate my job — do I have to stick it out for a year?

I just joined a company in my field with an good reputation after being courted for the better part of a year. There were pink flags in the recruiting process, and some negative online reviews, but I chalked it all up to a few dissatisfied people. How could a company with a good overall reputation be that bad? Turns out, I am having the most negative experience. My burnout is such that I spend most days crying at some point or another, and I generally feel like I’m failing. I work on a team whose leader is unresponsive and provides no guidance or support, and that’s making my job so much worse. A lesson to everyone to do intense due diligence and not be swayed just by a big paycheck and a past good reputation.

Needless to say, I’m considering an exit strategy, but I’m concerned that I’m doing damage to my career. My last two job stays were 2.5 and 2 years, and before that 4.5 years. I left a job during the great resignation, and my most recent job I made the mistake of not bringing my concerns to my manager, which were ultimately fixable. I also made the mistake of announcing the new job on LinkedIn, because it seemed like the new norm to announce fast. Waiting to make sure a job was for me before putting on LinkedIn was a rule I held firm on in the past. I’m worried now that my reputation will be impacted by my leaving this job after such a short amount of time. It’s been only 6 weeks, but my concerns go beyond buyer’s remorse. I’m miserable every day. I’ve put feelers out at my old job, but otherwise, am I going to have to stay here for a year to make myself look okay reputationally?

What, no! You don’t need to stay at a job for a year to protect your reputation; you can leave whenever you want. Leaving quickly can be more of an issue when you have a pattern of short stays (because at some point you look like you’re always going to move on quickly) but that’s not your situation. Your last three jobs were perfectly solid stays, particularly with that 4.5-year stay in there.

It’s true that if you had, for example, only four jobs and you hadn’t stayed at any longer than two years, I’d assume you were likely to leave after two years again — and I’d take that into account if it were something that mattered for the job I was hiring for (it might or might not, depending). But that’s not your situation.

Plus, six weeks is so short that you can just remove the job from your resume and LinkedIn entirely. Go ahead and get out, so you can stop being miserable.

Read an update to this letter

4. What if an employee who gave notice won’t leave?

I work in a nonprofit on a team of six people. For various reasons, three of the six have left or are leaving: one left a few weeks ago, one left this week, and the third, Jane, has more flexible departure plans but originally said she’d leave next month. Now Jane has indicated her willingness to “stay for a while and help out during the transition.”

My manager asked me if I was interested in pursuing the third position. I have a long tenure and a unique skill set, but on paper it is a lateral move. After doing some research and speaking with others in my field, I went to my manager earlier this week with a proposal to upgrade that third position and reconfigure the others to better align with current best practices.

Today she told me she’s worried if she posts this upgraded position while Jane is still here, Jane will change her mind and decide to stay. Is that a thing? Surely if Jane gave notice and we’re moving forward with hiring a replacement, she can’t actually just decide to not leave … right? And I’d think she certainly can’t decide to stay and just automatically get the upgrade?

I can hold my own in an interview process for this role, so it’s not about thinking it should just be handed to me. But the idea that the outgoing person has the power to just … not leave has my head spinning. In theory, how would a manager handle this situation?

Jane can change her mind and offer to stay —but offer is the key word, because she would need your employer to be on board with that decision. It’s not up to her once they’ve already began planning for her departure, but she can ask. They have the option of saying, “Thanks for the offer to stay, but we’ve already made plans based on your resignation, so let’s keep your last day as June 1.”

As for what your manager should do: She should first decide if she agrees with upgrading the position. If she does, then she should decide whether she’d rather offer Jane the upgraded role, or move you into it, or consider a wider range of candidates through a broader hiring process. If she doesn’t want to put Jane in that job, then she’d need to be prepared to tell her that if Jane asks about it. That could mean telling her that the revised position was created with you in mind, or created for a different skill set, or that she doesn’t think Jane is the right fit for the revised job, or that they’re far enough along in their plans for her departure that they no longer have a spot available for her. The fact that your manager isn’t approaching it that way is worrisome — is she so inexperienced that she doesn’t know she can? Or so weak that she’s not willing to? Or is it possible she’s not being fully straight with you about her hesitations about revamping the role in the way you proposed? My guess is inexperience/weakness, but assess based on what you know about her.

Read an update to this letter. 

5. Do employers who say they welcome diverse applicants want me to declare my marginalized identities?

I have a question about that very common language that many employers have somewhere in the job description, something along the lines of: “We seek to hire, support, and promote people from all genders, ethnicities, and all levels of experience regardless of age. We particularly encourage applications from women, non-binary individuals, people of color, members of the LGBTQA+ community, and people with disabilities of any kind.”

I am a member of the LGBTQA+ community — I am a bisexual cis woman in a long-term committed relationship with another woman. Obviously, this is a pretty large part of my life and identity. But I struggle with interpreting what this statement means and what I should do about it. The issue as I see it is that some of these “preferred” qualities in the list above are obvious to the eye and likely to be noticed at some point in the application process just by meeting a candidate (i.e., someone’s skin color, if they use a mobility aid, or even if they list their pronouns as “they/them” on a resume or something like that). Others, of course, are not!

What is the appropriate way to disclose that you identify with one of these categories in an application, especially when your identity may not be directly relevant to the role? If I was applying to be a counselor at a queer youth center, I could talk about my personal experience as a queer person. But if I am applying to be a project manager at a consulting firm, then how or when would (or should) I say, “By the way, I am also a member of the LGBTQA+ community” if it’s not related to the work I would be doing?

I also feel like I have it way easier than some other folks – like, for example, the “A” in LGBTIA+ typically stands for “asexual” or “aromantic.” I can at least (sometimes) drop a comment about my partner and use her pronouns during small talk in an interview, but when is an asexual person supposed to drop THAT information in the application?! “Oh by the way, I’m single because I don’t experience sexual attraction towards other people” seems like a super weird thing to incorporate into an interview — but the company is SAYING that they especially want asexual people to apply! Do you have any advice on navigating this as an applicant?

You’re assuming that diversity statements like the one you quoted mean that the employer wants you to declare the marginalized groups you fall into — but that’s not typically the case. Generally, they’re trying to convey to prospective applicants that they’re committed to creating a workplace where a diverse group of employees can thrive. It’s information for you — not a signal that they want you to declare anything back (unless you feel it’s relevant to the work you’re applying to do, such as in your youth counselor example).

Also, a note: You also called these identities “preferred qualities” — but they’re not saying they will give preference to people who belong to those groups. In fact, it would be illegal for them to do that in the U.S., except with disabilities. They’re just trying to convey that they’re a welcoming workplace that strives toward equity and inclusion. (Whether or not they actually are more equitable than most is often a different question.)

can I give 2 weeks notice when my employer says they “expect” 4 weeks?

A reader writes:

I work at a large healthcare system and I am exploring new opportunities. We have a resignation policy that states that salaried employees (I fall into that category) are expected to give at least four weeks written notice of resignation. Additionally, it includes that personnel records will reflect if someone leaves before the “required” notice period.

In previous departures from organizations, I’ve given a two-weeks notice without too much issue. Any thoughts on giving only a two-week notice with my current employer even with the four-weeks notice expectation?

Yeah, some organizations are fond of announcing that they “expect” longer-than-standard notice periods from employees, without any real ability to require it.

Let’s talk about this in philosophical terms before we get to the practical ones.

Assuming that we’re talking about the U.S., where two weeks notice is the professional standard, and assuming that you don’t have an actual contract requiring longer notice (most U.S. employees don’t have contracts at all), most of the time this is B.S.:

1. First and foremost, two weeks is the professional convention. It’s what our employment system is built around, and generally employers make do with that just fine. (It’s worth noting that notice periods aren’t intended to give your employer time to hire and train your replacement — for most jobs, even four weeks wouldn’t be long enough for that. Rather, a notice period is just supposed to provide time for you to wrap up projects and transition them to whoever will be covering them in the interim.)

2. Expecting additional notice can put employees in difficult positions with their next jobs. It’s not generally too hard to set a start date for a new job four weeks off, but if you want to take any time off in between jobs, now you’re pushing the start date out further, and it can start to get harder to negotiate that.

3. When your employer has chosen not to give employees contracts (again, like most American employers) in order to preserve their ability to terminate your employment whenever they want, it’s pretty absurd to “expect” notice from you that they’re not willing to commit to themselves. (To be fair, if your employer always pays severance when they end someone’s employment — and when that severance always covers at least the same number of weeks of notice that they want from you — this argument holds less water.)

4. Moreover, most employers that ask for four weeks of notice or longer don’t bother to use that time well. A lot of people who give more than two weeks notice find that their employers don’t start on substantive transition work until close to the end of that period anyway.

So there’s the argument against it.

In practical terms, what happens if you give two weeks notice if your organization requires four? It depends on the organization. In some of them, absolutely nothing — sometimes that wording has been in the handbook forever but people give two weeks notice all the time and no one thinks anything of it … or they’d like more notice but are aware they won’t get it every time. In other cases, they’ll warn you that there’s a penalty for doing it — like that you won’t get your remaining accrued vacation time paid out (in states where they’re not legally required to pay it) or that you need to give the full four weeks in order to remain in good standing in their system, in case you apply again in the future. In theory it’s something that could come up in a future reference check too … but “we ask for four weeks of notice and she only gave two” isn’t especially damning.

And really, in every organization I’ve seen that asked for three or four weeks of notice, some people still resigned with less and just explained that their circumstances dictated that, and it goes fine. (It might not go fine if you’re dealing with a really problematic boss … but then the boss is more the problem than your notice period is.) In most cases, people are fine saying, “I know you prefer four weeks of notice, but unfortunately I couldn’t make the timing work out. But I’ll be here until (date two weeks away) and I’m committed to doing everything I can to help with a smooth transition.”

Now, there are some exceptions to this — jobs where longer notice isn’t just desired but is truly an industry norm beyond that one company, or where there’s obviously good reason for it (and healthcare, your field, is often one of those). If you’re in one of those and everyone you work with has always given the full four weeks — or someone didn’t and it caused great scandal — then you probably need to adhere to those norms.

But for most people, longer notice periods are more the employer’s hope than a true requirement* that has consequences for breaking it. The best thing you can do is to know your culture, know what people leaving before you have done, decide how much you care about what penalties (if any) your employer imposes on shorter notice periods, and then time your notice accordingly.

* To be clear, even two weeks notice isn’t a requirement, in the sense that there’s no legal way to enforce it. Leaving without notice can harm your reputation and affect future references — and I generally advise avoiding it except in unusual circumstances — but employers can’t make you stay if you decide to leave faster. 

Read an update to this letter

want a job? cool, there are 17 interviews…

Most people who are looking for a job welcome an invitation to interview and are pleased if they’re invited back for a second round. But what happens when the process extends to third, fourth, fifth, and even more interviews? Increasingly, that’s what job seekers are encountering, and it’s leaving them frustrated and exhausted.

In the past, companies typically held one, two, or maybe three interviews with a candidate before making a decision. But in recent years, many more rounds of interviews have become common, sometimes stretching into the truly absurd. I wrote about this trend at Slate today. You can read it here.

my coworker got drunk and punched another coworker in the parking lot

A reader writes:

I’ve been ruminating about a situation that happened at a previous workplace, and I’m wondering if I behaved appropriately or if there’s anything else I should have done.

This job started as an internship, but I was eventually offered a permanent role at a higher salary. This company was in the retail industry and I worked at their corporate office. Every summer, they would put on a large event that employees from across the country were welcomed to. It’s an after-hours event at a bar near the corporate headquarters. My team was tasked with setup for the event. The day of the event, a few colleagues and I bounced back and forth between this bar and corporate headquarters — dropping off stuff, putting decorations up, etc. Eventually, some of my team went to a different location for lunch since the bar’s kitchen was closed. The people at this lunch were me, an intern who on her last day of work (Sally), a contractor (Joe), and a full-time employee who was technically the same seniority as me (Bob), but had been at the company for three years so he was very trusted. All of us were similar ages, between 21 and 25.

We celebrated and wished Sally well, provided her with our contact info if she ever needed a reference, etc. Since it was a celebratory lunch, Bob decided to drink. Besides, he didn’t drive and wouldn’t have to be at his desk that day. With his first drink, we shrugged it off. Second drink, we’re questioning Bob if this is a good idea. Third drink, we are actively trying to get him to stop drinking. By this point, Bob is clearly drunk. He’s being excessively loud and can’t follow the conversation. He argues that since drinking is encouraged at this after hours event, it’s not a huge deal if he does it before. At this point, Joe suggests we get our check and leave.

However, instead of taking us back to the bar to work on event setup, Joe says he has to go to the corporate office to pick up something related to a medical condition. (Joe told me he actually didn’t need it as urgently as he made it seem, he just thought Bob wouldn’t be helpful with setup and wanted him to talk to our boss.) Joe drives us all together in one vehicle. While Joe is driving, Bob gets upset and wants to go back to set up. Bob and Joe argue for a few seconds. Then, Bob grabs the wheel and nearly causes us to hit a tree. In response, Joe backhands Bob and tells him to immediately stop or he will get us killed. Bob says that he was just trying to get us back on track and that he was joking.

At this point, Sally and I (in the backseat) are extremely on edge, but Joe is able to get us to the corporate parking lot. Bob asks if we can go to the corner of the parking lot near a designated smoking area so he can smoke a cigarette before going inside. Joe agrees and parks near there. It’s worth noting that the entrance near the smoking area does not have cameras on it. Immediately after we all got out of the car, Bob punches Joe in the face for “slapping the shit out of him for no reason.” Joe gets mad and starts to yell at Bob.

At this moment, my priority was making sure Sally and I got back into the corporate headquarters safely. I heard the two men yelling and cursing one another, but I did not see if they continued to get physical.

Immediately upon going inside, I found our boss, who was conveniently talking to a member of the HR team at her cubicle. I told my boss, “Bob and Joe are fighting outside. They’re yelling and Bob punched Joe. Bob was drinking at lunch and I think he may have drank too much.” I left out the detail about Joe slapping Bob in the car because honestly, I was so shaken up that I forgot, although I’ll admit it may have been unconscious favoritism.

Apparently, by the time HR and security got outside, Bob was smoking a cigarette like he said he would. Joe was gone. He was in a bathroom cleaning himself up.

I’m not sure of everything that happened behind the scenes, but here’s what I do know:

1. Bob paid for everyone’s lunch with a corporate card with permission from our boss. However, we are not allowed to put alcoholic drinks on the corporate card. Bob got a separate check for his alcohol and paid with his own money. I didn’t realize this at the time, but this rule was put in place to prevent employees from drinking on the clock.

2. Bob was our boss’s golden child. He had a rough upbringing and had a kid in his teens. As a result, my boss tended to give him more leniency in general, since “none of us knew what it was like to be a parent that young.”

3. Joe was not well-liked by our boss for being “weird.” However, I was much closer with Joe (not BFFs by any means, but we had similar personal interests like video games).

Although Bob got in trouble for drinking on the clock, his punishment was much lighter than Joe’s. Apparently, because there weren’t any cameras to show the fight, there wasn’t any way to confirm what happened. However, I was never asked for further details on what happened after my initial warning to my boss and HR. Sally wasn’t questioned either, since it was her last day.

Apparently, the company decided that because Joe slapped Bob (in response to Bob trying to take the wheel of the car), they would end Joe’s contract early. They argued he started it. Joe was permitted to stay the rest of the week to wrap some stuff up, which he did. When Joe told me about this, I apologized and asked if he wanted me to go to bat for him. He said no, that he didn’t want me to risk my job, and that he was happy to get out of the hellhole.

Bob talked to me at the after-hours event and asked why I told our boss and HR about the situation. I didn’t want to get on Bob’s bad side, but felt he was wrong in this situation. “I was worried it would escalate to be unsafe,” is all I said. Apparently, Bob took this as me apologizing to him (he was semi-afraid of Joe because of the “weirdness” and the fact Joe is much bigger than him).

I know I’m in the right for informing my boss and HR, since the punch and yelling occurred on the company’s parking lot. But I’m wondering if I should have stood up for Joe better, tried to stop the two, record what was going on, called the cops, or what. What do you do when your coworkers get into a physical altercation in your company’s parking lot?

It’s ridiculous that Joe got fired while Bob only got a light punishment. Bob got drunk on the clock, almost caused an accident with four employees in the car, and deliberately punched someone in the face. Those are all serious things! Joe shouldn’t have slapped Bob — but it sounds like it was a heat-of-the-moment reaction to keep all of you from getting killed, whereas Bob’s punch was just revenge.

If anyone was getting fired, it should have been Bob.

If your management felt what Joe did warranted firing, I can’t imagine why Bob’s actions didn’t too. How is deliberately punching someone in the face somehow less serious than Joe’s slap, even if we agree that Joe’s slap was unacceptable? Your company was basically saying “violent revenge is fine.”

As for what you should have done … it’s not your job to break up a fight, and you could have gotten hurt or escalated things further if you tried. Recording it might have been helpful after the fact but isn’t the kind of thing most people would think about in the few seconds when something shocking like this is going down (and really, you’d assume your company would believe eyewitness accounts rather than requiring video). You went inside and got help; that was appropriate.

If you could go back in time and do things differently, ideally I think you would volunteered your eyewitness account to your boss and HR after the immediate situation was over. They should have spoken with you about what happened as part of their investigation, especially if Bob and Joe’s accounts differed, but you didn’t need to wait to be invited to do that — it would have been fine to initiate that conversation yourself and say, “I want to share with you what I saw that day.” But it sounds like Joe discouraged you from doing that, so I can understand why you didn’t.

The other thing I’d change if we could is the impression Bob got from you — that you were apologizing to him! — because ideally he’d hear from someone other than Joe how out of line he was. I don’t know if you chose not to do that out of fear of Bob or from more of a general discomfort with conflict. If it’s the latter, that might be the strongest lesson to take away from all this — that you want to resolve in the future to speak up when you think someone is so much in the wrong. (Well, and also that your company sucked).

Really, though, a drunk coworker punching another is so outside the realm of what we expect when we go to work that it’s understandable if you didn’t react perfectly in the moment (how many people would?) and you shouldn’t second-guess yourself too much now.