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

1. Interview questions meant to identify covert North Korean workers

As you may already know, with the rise of remote work, some sectors in the U.S. have had an issue with North Korean workers applying for work while pretending to be a U.S. citizen, with an American liaison hosting their work laptop in the U.S. and providing aid with documents and such. Since this has been discovered, some interviewers have of course tried to find ways to weed out these fraudulent applicants, and I was wondering what you think of the matter.

I heard today of an interviewer who would ask candidates to repeat a phrase like “Kim Jong Un is a fucking asshole” to prove they aren’t from the DPRK. It seems effective, but I feel like this could be sketchy on the legal front. My kneejerk reaction was that this could be seen as discriminatory based on political beliefs, but I realize that even if it were covered by states with those protections, it would be difficult to pursue. I also think the inability of any current DPRK citizen to legally work in the U.S. would negate claims of discrimination based on national origin. I do think it could be an issue if this wasn’t requested of all candidates interviewed, and wonder if it could seem stereotypical to the level of racial discrimination. Do you think this is as messy of a solution as it seems? Do you know of or have any ideas for what other solutions interviewers could implement here?

It’s an absurd solution. First, it assumes a North Korean citizen would be incapable of repeating those words insincerely and in the pursuit of what they saw as a greater good, which is likely a flawed assumption. Second, it makes them look incredibly weird to everyone else (both because of the request itself and because if this is what they consider a strong security practice, that’s a problem).

I don’t know what the right security solution is — that’s way outside my expertise — but there are entire fields specializing in it, so step one would be to consult with someone whose job it is to know!

2. I promised an employee a promotion before I should have

I manage a 25-person department in a large, bureaucratic organization. The department is organized into three groups, and I was an outside hire a couple of years ago. Generally speaking, my staff is great — we punch above our weight in a lot of our work.

Last summer, the organization started going through a process improvement push. As part of that, my boss (who is in the C-suite) told me that he would support me in doing a small reorg in my department to create a fourth group on my team focusing on more strategic projects. I am excited by this idea, because if anything is holding my team back, it is the difficulty of focusing on longer-term projects when we have so many immediate deadlines. This reorg would allow me to promote Paula, who is developing into a rock star. We’ve already informally moved Paula into a position that focuses on process improvement, but being able to give her a small team and turn her loose to focus on strategic work could be huge for us. Also, I worry that without these changes I will eventually lose her to someone else, either an internal team with a promotion opportunity or another company.

I know you’re going to tell me this next part was a mistake, but I told Paula about the reorg/promotion idea shortly after my boss and I agreed to put it into motion. And then, I ran into a bureaucratic nightmare of trying to get HR approval to make the changes required. I need to reclassify a position to promote Paula and create a team for her, and I keep getting told “not right now.” The broader organization is going through budget tightening and it’s hard to get approval for spending more on salaries (which the promotion would require). We have support to make these changes from the C-suite, but everything is going really slowly.

It’s been eight months since I floated this idea with Paula, and I’m still working on actually getting approval to do it! My boss is supportive. His boss is supportive. It’s just going really, really slowly. I’ve been up-front with Paula on what’s going on but I worry that she is going to lose confidence. What should I do, since I can’t go back in time and stop myself from discussing this with her?

Does your C-suite boss have any pull to expedite this? Ideally the next step is a conversation with him to express your concerns about losing Paula and ask him what a realistic timeline is so that both you and she can plan. Emphasize that you want a realistic timeline, not an optimistic one, and also ask if there’s anything you should prepare for that might derail that.

Right now, the most important thing you can give Paula is very, very realistic info about what’s going on and what the timeline will likely look like, so that she doesn’t feel like she’s being strung along or being fed overly optimistic projections. “I’m so sorry about this but it’s going to be at least eight months because of X” is more confidence-enhancing in her shoes than hearing “it’s really slow going but we’re working on it” every so often — because the former is specific and you won’t sound as much like you’re stringing her along. You can also ask if there are things that she wants during the waiting period that you can offer — maybe that’s a title change or authority to do X or help removing obstacle Y. Or maybe there’s nothing, but you should talk with her and find out.

Ultimately, you might lose Paula if this drags out, but that’s just the reality of how these things go.

3. My boss didn’t include a major accomplishment in my review

I work for a nonprofit that underwent a major systems overhaul last year, replacing outdated internal tools with a new CRM. The transition was rocky and in the months following launch, many of us worked significant overtime to stabilize workflows and prevent service disruptions. During that period, I consistently worked 60-hour weeks identifying and documenting system issues critical to our department’s function. One project in particular required substantial independent effort and had a surprisingly helpful impact on improving operations.

Because of the organization’s financial strain from the rollout, staff received only modest cost-of-living increases this past review cycle, with no merit raises. I’m genuinely okay with that, as I value the mission and benefits, and I understand the constraints.

My concern is recognition, not compensation. In my 2025 performance review, my supervisor did not mention my largest post-launch contribution. I added context in my written response, but it wasn’t reflected in their evaluation. In a recent one-on-one, I asked whether the extra work done during the transition period could be considered in next year’s review cycle.

My supervisor seemed to interpret my question as a complaint about compensation and responded by explaining the organization’s budget deficit. I clarified that I appreciated the context but didn’t push back or mention that I wasn’t asking for more money.

Now I’m concerned about two things: first, that my contributions during a uniquely demanding period won’t be formally recognized, and second, that my supervisor may have misinterpreted my intent as dissatisfaction with pay.

Is it reasonable to expect that work done in a particularly intense period (like a major system rollout) would carry over into the next performance review cycle if it wasn’t fully captured in the previous one? Should I proactively clarify with my manager that my concern is about accurate recognition of my contributions and not compensation? If so, how direct should I be?

I want to advocate for my work without coming across as transactional or tone-deaf to the organization’s financial realities. At the same time, I don’t want a significant effort to effectively disappear from the record.

I can see why your manager interpreted it that way — usually when someone is concerned about considering a particular piece of work in a particular review cycle, it’s linked to money. In part that’s because in a lot of organizations, the content of a particular evaluation doesn’t matter that much year to year; rather, the content’s main impact is on (a) your pay and (b) your overall rating. If your overall rating was already very high and you’re not advocating for it to be increased, I can see why your manager assumed what you were advocating for was money. It sounds like you really just want the work itself it be recognized within the narrative of the review — which isn’t unreasonable, but that’s probably why she missed it.

You could go back to her and say something like, “I think I miscommunicated my interest in having the X work included in my review. I’m not asking for a different raise or even a different rating; rather, it was such a significant part of my work this year, and I believe had strong enough results, that ideally I’d like it be included in the written record of my work for this period.”

4. My job might want me to take on new work — how do I ask for more details?

I currently work in accounts receiving but the bulk of my experience is in accounts payable. At my current job, the accounts payable Major Dames might be retiring by the end of the year. I have been approached to take over their duties (along with some automation).

I asked how much time I had to think and was told Q3 at the earliest (because The Major Dames might push back their retirement). I’ve taken the time to think and I want to move forward with this. How do I approach the conversation in which I want to say, “Yes, I want this. What does it look like? Like title *ahem* pay … etc.” Should I ask what concerns they might have with me now so I can address them? The more I think, the better it seems but instead of getting wrapped up in the fantasy of better money and more pay, how do I instigate the conversation: tell me more?

Be straightforward! “I’ve given it some thought and I’m very interested. Can you tell me more about what that would look like logistically, as well as what it would mean for my title and pay?”

Be prepared for the possibility that they might not have been planning to change those things! If that turns out to the case, you could say, “Based on the increase in responsibility, I was hoping we could consider X or similar for a title, with a salary change to reflect the increased work.”

You don’t need to ask what concerns they might have with you; from what they’ve said so far, they might not have any. If they do start to seem less solid about moving forward with this, at that point you could ask whether they have specific concerns about your ability to take on the work, but based on what’s been said so far it doesn’t sound like you need to ask that right now.

5. I need business referrals but I also need friends

I am a professional fine artist. I’m building my business around custom commissions for clients. My paintings are at a price point where they’d be considered luxury goods by a lot of people and as a result, my business relies heavily on referrals. I am lucky and grateful to have a lot of friends who are very supportive, very impressed with what I do, and tell their friends about it. However, I don’t want to fall into the tupperware party trap of turning all my friends into business leads.

I’d love to hear from other readers in similar situations about strategies they use to grow their business without wrecking their social lives.

I’m happy to throw this out to readers, but as a general rule I think it’s fine to say once, “If you’re ever interested in a commission or know someone who is, I’d love to talk about it!” Saying it once is completely fine — you’re letting them know of your availability. After that, though, assume they’ll tell you if they’re interested in doing that; they may be friends who are very supportive but not likely to pay luxury-good prices for art, and that’s okay!

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).