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

1. Coworker is poisoning a new hire with his bad attitude

A guy who works in our IT department, Steve, is just genuinely a negative human being, and pretty overt about it. He complains constantly about anything and everything, and really appears to hate his job despite remaining at the company for over 20 years. All managers are stupid, all decisions about his job/responsibility area are bad … you get the idea. Examples:
* Telling a visibly pregnant coworker that he “didn’t think bringing a child in the world right now was a great idea considering the state of things.”
* Wearing a truly enormous sombrero after complaining it was too bright in the open seating and informing everyone why he was wearing said sombrero.
* If anyone asks how he’s doing as a polite greeting, he informs them that this place is awful and he’s counting down the days until he can leave.
* He not regarded highly by management, but talks a big game about how he’s smarter than everyone, etc. He is no longer allowed to ask questions in department meetings due to his asking of very specific questions about his responsibility areas and perceived injustices.

He now has a college new hire working along side him to learn the area and is turning this new hire into a tiny version of himself. I am not Steve’s manager but have noticed the attitude shift in the college hire.

Would it be terrible to mention to management the attitude shift? Would a polite word to the newbie be out of line? I just feel like the new hire is learning “professional norms” from someone without any awareness of what those actually are and is a recipe for disaster for their career.

Yes, if you have decent managers, this is something you can discreetly mention to them — although really, whoever assigned Steve to train the new hire should have foreseen this!

It also would be a kindness to have a quiet word with the new hire — something along the lines of, “Steve is pretty unhappy here, as he’s probably told you, but the rest of us often don’t see things the way he does. I know you’re still getting acclimated and it can be really helpful to build relationships with multiple people so you get more than one perspective. Please feel free to come to me if you have questions or I can help with anything.”

But better yet, are you up for taking the new hire to coffee or lunch and just building a relationship with them? That itself, without even needing to say anything about Steve, might help them see the work through a non-Steve lens.

Related:
my new employee is getting bad advice from my older employee

2. If my friend announces I’m working with him, I’m worried my company will let me go

I recently reached out to a friend who’s building a new company, asking if I could invest small potatoes money in him. It’s only to a tune of a few hundred dollars a month, just to cover some basic services to keep the product running smoothly. He asked me instead to be his co-founder and CTO. The company is bootstrapped so I can’t afford to leave my day job (yet). I believe in this project and I’ll get to do good in the world.

Meanwhile my day job is capital T toxic, but I need the insurance (solo wage earner for my family) and a paycheck. I can’t leave and my industry is a trashcan fire for hiring right now due to AI. My company already knows I’m doing something similar, and its okay for me to have a second job as long as its doesn’t impact my first job.

The issue is this: the position with the new company is significantly more senior to my regular job. I’m a senior level individual contributor and I don’t see progressing here, nor would I want to given the toxicity. The new company wants to announce me and use it as a marketing tool to get more users. I worry such a visible marketing campaign might give my day job an excuse to just get rid of me (my boss regularly threatens everyone on her team with job loss, among other things). Even though I’ve successfully been doing the same amount of work as I will be doing for a year with their permission and it’s not impacting my work, I fear the increased title will give them an excuse to just oust me preemptively.

Can I block my work from my LinkedIn profile so I can (1) update it, and (2) contain the reach of the marketing campaign? It’s minimally likely that they would see it otherwise, as this will be the primary direction of the marketing campaign. Or will the blocking cause some kind of backlash on its own? The HR and head of my division are looking at my LinkedIn regularly.

There’s no way to reliably block your company from seeing the announcement. You could block specific people from your profile, but if an announcement is going out that mentions you by name, there’s no way to block them from seeing that (or from hearing about it from someone else who sees it). You’ve got to decide if the potential benefit of allowing the announcement outweighs the danger you think it would put you in — but absent some information to the contrary, I would assume it doesn’t warrant the risk (in any situation, but especially one where your friend needs a few hundred dollars a month to cover basic services — which says the company isn’t in a strong place currently).

3. Am I gaining an unfair advantage over my coworkers by occasionally working at the office in-person?

I work remotely for a company in a town about three hours away. Everyone has the option to work remotely, but only about a quarter of people with my position also have the need to work remotely because of distance.

I have family in the same city as the company office. I miss being in an office sometime and about 2-3 times a year I combine a trip to see my family with spending a day in the office. I think my bosses really like this effort and I like to think them seeing me in person and not just on a Zoom screen is helpful for my career generally speaking, although I don’t think there is any favoritism being shown by my bosses.

I always feel guilty though because the other distant remote workers don’t have this family connection to the city so it feels like I am taking an unfair advantage over them. Am I?

No. They are presumably happy with the benefits they get by working remotely. If they felt seeing their bosses in person a few times a year was important to them, they have the option to do that (hell, some companies would even foot the travel bill if they made a business case for it). Your circumstances are different and your preferences are different; that’s not an unfair advantage (although it may be an advantage).

4. Negotiating for paid parental leave when accepting a job

I recently interviewed for a great job at a great organization (in my neighborhood!). Sadly, they’ve gone with another candidate, but I asked them to keep me in mind for future opportunities. They responded very quickly to say that the role immediately below it may soon be available and asked if I’d be interested in it, giving the salary range.

The job I’d interviewed for would’ve been a $20-$30k pay increase for me, but this lower job would be a bit of a cut. However, I’d still be interested due to the proximity to my home, as long as the health care benefits are better than my current org. My only hesitation is that I want to have a child within the next year and it would be hard to take a pay cut if I don’t have paid parental leave.

I saw your advice about negotiating parental leave by saying you want to plan for the long-term, but my state will implement paid family leave within 6-12 months of when I’m hoping to give birth (and I have reasons for not wanting to delay pregnancy further). Is there a way to negotiate paid parental leave 6-12 months in advance of when the organization will be required to provide it?

The good news here is that it sounds like your willingness to take this job would hinge on their willingness to agree to give you paid parental leave … which makes this pretty simple since  you can just ask about it straightforwardly if you get an offer. Plus, you’re asking for something they’re about to be offering everyone as soon as the law goes into effect, so they don’t need to worry as much about setting a precedent as they would otherwise.

If they offer you the job, you could say, “I’d love to accept but there’s a chance I may need paid parental leave in the next year. I know (state) is implementing that in (month) but would you be willing to offer it to me before then? If we could agree to the same X months the law will offer when it goes into effect, just starting sooner, I would be thrilled to accept.” You could also add, “I should say that I’m not pregnant so don’t have clear timing on when or even whether I’d need to use it; I just want to make sure it’s there if I do need it before the law takes effect.”

5. What is a dotted-line report?

What is the purpose of a dotted-line report? What does it typically entail and what are good use-cases for it to exist? I see them sometimes in my org, but I don’t know what they mean.

If you have a dotted-line relationship to someone above you, it means they oversee parts of your work but not your job as a whole. For example, maybe you’re a fundraising assistant who reports to the fundraising manager but you also have a dotted line reporting relationship with the grants manager because you analyze data for her and report to her on grant-related deliverables. The fundraising manager is your manager for all the general manager stuff (overseeing your daily work, monitoring your progress against goals, doing your performance reviews, giving you most feedback, thinking about your professional development, approving time off, etc.), but the grants manager has the ability to assign you work and give you feedback on the work you do for her (and may contribute input to the performance review that your manager writes).

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

1. Should I say something about our intern’s bright blue pimple patch?

We have a paid intern on a four-month term with government. He has some social anxiety things and general workplace norms we have been working with him on.

Last week, he showed up at a virtual internal team meeting with a blue star sticker on his forehead. It took a while to figure out it was a pimple patch.

Do we say something? I know there is a move among young people to wear bright and patterned pimple patches in public, but at work I expect them to be hidden.

Pimple patches at work are increasingly getting normalized and seen as no different than a band-aid — but at work you’d generally want to choose a neutral one, not a bright blue star, just like in many/most offices it would feel out of sync to wear a bright novelty bandage with a Pixar character on it on your face.

But this is what internships are for: to learn professional norms. So I’d approach it from that angle: “Bandages are obviously fine at work, but if it’s on your face, it’ll look more professional if you choose a neutral one rather than a bright color. This is one of those things that people generally don’t come in knowing, and exactly why internships can be so useful.”

There are some offices where a bright blue pimple patch would be fine too, but I’m guessing yours isn’t one of them and it’s to his advantage to know that.

2. Have the rules around mentioning kids when networking changed since the pandemic?

I ran into a former boss at a professional meeting recently, and when we were catching up she mentioned a job that she thought would be a good fit for me. We talked briefly, but I told her it wasn’t right for me right now because I have young children and need more flexibility. Was this unprofessional?

My friends and I were discussing this later and we’re pretty split: half of them thought I shouldn’t have mentioned my kids at all because it risks “mommy-categorizing” me and will curtail future recruitment, and half thought mentioning kids/families/life at work has become more socially acceptable in the last five years and employers respect people who know their worth and have boundaries around work and family life. (Interestingly my mom-friends were mostly in the first group while the dads in the group thought employers respect work/life balance.)

We’re in a conservative industry (think finance, but it’s not that) but it’s 2026, and the realities of being a working parent are much more openly discussed now. What do you think?

I don’t think it’s any surprise that the men had a more optimistic view than the women, since the women are the ones who actually need to deal with how this still works. But I think there’s a difference between talking about your kids in an interview (where I’d still avoid it, because you don’t want to give them a reason not to hire you) and saying it when you’re catching up with a former boss and are explaining why you don’t want to pursue a particular job.

In either situation, mentioning your kids wouldn’t be unprofessional — just possibly unwise in the interview scenario. Even in 2026, there’s absolutely still bias against female candidates who interviewers think might less available or less dedicated due to their kids. (The men you talked to have probably had different experiences themselves, but it’s well-documented that there’s a mom penalty far more there’s a dad penalty.)

3. Do I have to give four weeks notice when I quit?

Our employee manual requests two-week notice periods for non-management and then increases in increments for roles in management and higher. In my position (department lead), the “suggestion” is four weeks for a notice period. We’re in an at-will state in the U.S.

Last year, the company went through a RIF where many staff were furloughed without severance or a notice period. I became the only leader in my department overnight. No one has been asked back, and the folks who were able to find other work were considered resignations (again, no severance or payout for PTO accrued). As the months have passed and the chaos from this RIF has worsened, I’ve begun interviewing for other roles. Recruiters are asking how long I’d need for a notice period, and I’m worried that four weeks is hurting my chances.

Ideally, I would love to give two weeks of notice, take a week off to just breath and reset, and then start fresh(ish) in a new role. My burnout is real and I know hopping into the next role immediately will not be good for my mental or physical health. But this approach seems like it will burn bridges with a company that I’ve built almost 10 years of good will with. Alternatively, a four-week window with no break at all seems abysmal for a number of reasons, and that’s assuming a new company can hire on that timeline.

My most recent datapoint for comparison was a manager (in name only, as their entire team was furloughed or quit) who gave two weeks notice. I heard from them that their boss (a company owner) reacted terribly to the resignation and made their anger clear. I also heard from colleagues that other executives were complaining about the short notice period. During the notice period, I discovered there was absolutely zero redundancy or support for this person in their role and leadership had no idea how to cover the work. Of course, this isn’t the resignee’s fault and they worked their butt off to support a transition. But their reputation with company leadership has been unfairly tarnished.

Do I have options here? Frankly, I struggle to move past the fact that this company released employees with no notice or support last year and yet has the gall to be upset with resigning employees this year. But I also need to factor in my professional reputation and the realities of a competitive job market.

They can “request” four weeks notice all they want; it doesn’t obligate you to give it. Two weeks notice is what’s standard, and it’s reasonable for you to give that. That would be true regardless, but it’s exponentially true with an employer that doesn’t offer severance in lieu of notice. If their finances made doing that impossible, then so be it — but they’ve forfeited any standing to take issue with you giving two weeks notice (which is still two weeks better than what they did on their side!).

If they want a certain amount of notice from people, they need to have policies and practices on their side that offer the equivalent in return (and even then, they won’t always get it, because that’s not how this works). But they don’t. They have the opposite.

That doesn’t mean they won’t be upset when you resign; you can’t control that. But you can act reasonably on your side — meaning that you give two weeks notice — and say, “Unfortunately I’m not able to give more than a standard two-week notice period; I tried to make longer work but couldn’t.” And including the word “standard” in there is intentional.

Related:
can my employer make me give four weeks notice when I quit?
can I give 2 weeks notice when my employer says they “expect” 4 weeks?

4. Could I ever have a manager and an employee swap positions?

I manage a department in a public sector organization. The work is very technical/specialized, and good people are hard to find. Everyone involved is on a pretty generous payscale, in my opinion.

I have two specialists who are relatively young, ambitious, flexible, and eager to learn. I also manage two managers who have long experience and a lot of knowledge, but who are pretty taciturn and set in their ways and keep a lot of knowledge in their heads without documenting. The department was without any leader for some time before I joined, and while the managers filled the gap to some extent, neither of them was interested in vying for a further promotion. In practice I supervise all four.

I have high hopes for both specialists but they are both somewhat frustrated at being stuck where they are until one of the manager positions opens up. Previously I had explored adding more grades to the specialist position so they had more promotions ahead of them, and I had successfully raised their salary scales, but our organization is currently having economic headwinds and more adjustments like that will be very difficult for a while.

One of the specialists, Alexa, is very good at advocating for herself and inquires from time to time what options are available for her advancement. She definitely has options if she doesn’t advance here. She does great work, possibly the best in the department, and is always working on improving her already high skills.

It gets to the point that it feels like she is more suitable as a manager than her actual manager. Often I direct a question at her manager, Jody, that I see as a higher-level question she should answer, but then often (and to my declining surprise) she defers to Alexa. Alexa is far more proactive and big-picture-mindful than Jody, who sort of plods along and seems to take the easy/reactive route whenever possible.

Is there a framework in which I could make Jody and Alexa swap positions? Or is this broadly out of the question in most cases? What might be the groundwork to make it feasible, if ever? I honestly think Jody has a perspective and habits more suitable to the specialist position, and Alexa to the managerial position. But that doesn’t mean Jody wouldn’t react negatively to the idea, which would be a salary downgrade. (I could move around reporting lines so that Jody doesn’t literally report to Alexa, though — Alexa could manage the other specialist.)

Have you given Jody feedback on the weaknesses in her work or would this come as a total surprise to her? Before you think about having them swap positions, this is the first piece to tackle; if Jody isn’t meeting your expectations for her work, she deserves to know that. Totally aside from the Alexa complication, you should be coaching Jody and giving her feedback about how to improve.

As for a swap: possible but unlikely. If your sense was that Jody dislikes managing and wishes she could take a step down to a specialist role, then you could feel her out on whether she’d ever like to seriously explore doing that (although the fact that it would involve a pay cut makes it fairly unlikely). Otherwise, though, you’re better off managing Jody more forthrightly (including considering letting her go if she’s not performing at the level you need after coaching, although I can’t tell whether or not that’s the case). You could also consider just promoting Alexa to manage the other specialist, although if this is a team of four with no employees beneath the other two managers, that’s a lot of management below you for what doesn’t sound like good reason.

Really, I think you have a Jody problem that’s impacting everything else.