Ask a Manager

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

1. My coworker doesn’t listen and then pretends she was never told

I’m having an issue with my coworker, Christine. I am in no way her supervisor so I’m not sure there’s anything I can do, but here goes!

Basically, she complains that our boss, Lars, doesn’t tell her things and then Lars gets upset with her afterwards for not knowing. I can see why that would be incredibly frustrating. Except the last couple of times she has told me that’s happened, I was in the room with them and I know Lars told her the correct info.

For example, Lars told me and Christine that we were going to use Form X instead of Y. The next day, Christine used the wrong form and Lars asked her why. Christine tells me Lars never told her, so I said that he did in fact the day before. First she says she wasn’t in the room, I remind her she was. Then she says he must have been talking to me and not her, but it was just the three of us in a small room and I talked about it with her afterwards so I know she heard him. Then she says she just “wasn’t listening” but again, we talked about it so I know she knew.

From other experiences with her, I don’t think she has a great memory, but instead of admitting or realizing that, she just says Lars never told her things. She’s done the same to me even though I can send her screenshots of our chat or forward emails that she’s replied to. It’s mostly complaints about Lars, which doesn’t directly impede my work, but when she does it to me, it’s frustrating that I have to ask her to do something three times and then she takes zero responsibility for dropping the ball.

She is job searching, so is there really anything I can or should do or should I just hope she moves on soon? That might be part of it too — she’s just checked out mentally since she’s planning to leave. But honestly I’d rather have her just say “Yeah, I know we’re supposed to use X instead of Y but I don’t care” instead of lying to me about it!

There’s a decent chance she’s not deliberating lying but is simply a scattered mess and not keeping track of stuff. She could be genuinely surprised when she’s confronted with evidence that she was previously told things. There’s also a decent chance that she is lying — that she sees it as a way to save face and doesn’t understand how bad it makes her look.

It doesn’t really matter; it’s frustrating either way. I don’t think you need to do anything about it — as you say, you’re not her manager — but you also don’t need to pretend you don’t see it happening. If you want, the next time it occurs, you could say, “I don’t know if you realize this happens a lot — you’re sure Lars or I never told you something when we actually did. Sometimes I was there during the conversation with him, or I have emails that you replied to confirming you knew. Is everything okay?” If she thinks she’s getting away with it, this might drive home that she’s not and maybe nudge her to do it less in the future. Or it might have no effect at all! But you’re not required to pretend you don’t see it. (Similarly, the next time she complains to you about Lars not telling her something, feel free to say, “I don’t know, a lot of times when you’ve thought that in the past, it’s turned out that he did tell you.”)

2. Should I correct a candidate who assumed I was a man?

I’m a woman with a name that reflects that: let’s say Anne Smith. I don’t work in a male-dominated industry.

We’re adding new people to our team for work that we’ve got a contract to cover, and I’m pre-screening the candidates by having short phone interviews. The role is research on a very specific topic (let’s say metallic red teapots with brown spouts produced in the south in 1853), but we’re just looking for people with a MS in pottery and 2+ years of teapot experience. I’ve compiled a solid short list quickly and I think we’ll have the jobs filled in record time.

Yesterday we got an application from Fergus, a candidate finishing a PhD on exactly the topic we’re working on. And of course that PhD came with many years of experience doing research. On paper, Fergus seems perfectly (over) qualified. So I reached out to schedule a phone screen, addressing him by him by his first name and signing the email with my first name, which is the norm in our industry (but perhaps not in the region of the U.S. that he is in). He promptly wrote back with, “Mr. Smith, here are dates/times that work for me, thanks, Fergus Jones.” I ignored the “Mr.” and wrote back a quick, “Thanks, I’ll call you at date/time — Anne.” Fergus responded with, “Sir, I look forward to speaking with you then.”

It’s not bothering me that he doesn’t seem to know the gender of the person he’s talking to, but I would be mortified if I realized at the start of an interview that I had misgendered the interviewer multiple times (and I sound like a woman on the phone). So I debated responding with a clarifying email (“Just a heads-up that I’m actually Ms. Smith”) but asked my partner for his two cents. He said, “Hey, if Fergus can’t see that the signature on your emails is a big and bold line that says ‘Anne Smith (she/her),’ is he really going to be that great of a researcher? Ignore it and see how he handles it at the interview.” Good point, but I miss things sometimes too, so I also ran it by a friend who hires in a more male-dominated industry. She responded, “Do you have your pronouns in your signature? He’s doing it on purpose.”

So … uh … is this really a thing? Do I try to clarify over email in advance or see what happens in the interview? Most of us in the company have our pronouns in our signatures and many people in the agencies we work for do as well. And it’s great that his experience so closely aligns with what we’re looking for, but we do have several other strong candidates: I’m not worried about filling the positions.

I doubt he’s doing it on purpose. There are people who are hostile to the idea of pronouns in email signatures — or to respecting people’s pronouns generally — but they don’t normally take an openly hostile stand while they’re trying to get a job with you.

It’s more likely he’s (a) defaulting to the sexist assumption that anyone with hiring authority would of course be a man and (b) not paying enough attention to see the big glaring sign in front of his face that you are not. Both of these are problems if you’re hiring someone who needs to have attention to detail and an ability to work respectfully with women.

You do not need to try to save him from embarrassment over his own actions by clarifying pre-interview. Let him learn the lesson on his own (if he will, which he probably won’t).

Note: it’s possible Fergus is from a culture where Anne isn’t a common name and he doesn’t recognize it as typically feminine. His use of “sir” also might point in that direction since that’s not how we typically write emails in the U.S. But it doesn’t really matter because both the points above still hold, given that your pronouns were right there.

3. I told a networker the truth about my awful old boss but they didn’t believe me

Last year I left a role on Team A where I routinely got screamed at. As you might imagine, it was a really bad place to work: favoritism, no empathy from leadership, inconsistent expectations, high workload with high expectations and zero resources. And of course, the screaming.

Thankfully I moved onto a new team B where I’m treated very well. There is an opening on my current team and on my old team — both are essentially the same job I have now and had then. Someone on LinkedIn reached out to me and asked if I was the hiring manager (obviously I am not) and if not, could I tell them about the role(s) and/or introduce them to the hiring manager or someone else to ask questions. No problem! I am happy to help out and answer questions. It turns out they have applied only to my old department, so my response was something like, “Sure, I can introduce you to someone, but to be completely transparent, part of the reason I left that team is because I do not enjoy being screamed at.”

I know the job market is rough right now — a lot of my friends are struggling. But I believe in being honest about this kind of thing and I don’t want to encourage someone to walk into that situation. But the person who reached out to me about this clearly didn’t believe me. I think I’ve done what I can and I know I don’t have any obligation to do anything else, though I did give her the name of the hiring manager (the screamer). What I’m curious about is if there is a better way to be up-front about this kind of thing or if there’s anything you would have recommended doing differently?

Kudos to you for being straightforward about it. You’ve given them important information that’s often very hard for outside candidates to get (until they start working there and discover it too late). You can’t do more than that; if they don’t believe you, it’s not your job to convince them.

Sometimes people refuse to accept this kind of info because they want the job so they they tell themselves it couldn’t really be as bad as you said, or that you fed into the problem yourself (you deserved to be screamed at — the office version of “your skirt was too short”), or that they’ll just somehow have a different experience. It’s short-sighted, but it happens. To be fair, sometimes people do have a different experience! Some people have a higher tolerance for yellers, or vibe with the boss in a different way, or just don’t care as much as others would. But not believing you is weird.

I don’t think you need to change anything about how you approached it. Your response was pretty perfect, in fact. You gave the relevant info matter-of-factly and concisely. What someone does with it is up to them.

Related:
should I warn job candidates about how bad my company is?

4. Former employee keeps hassling me to come back after I was fired

Last winter, I was let go from a company where I had worked for seven years. Now that they’re in their busy season, a former direct report has been contacting me constantly, begging me to come back.

He was always a bit erratic when I was his manager, going through periods where he’d make bizarre claims like being independently wealthy and not needing the job, only to later demand a $10,000 raise because he was struggling financially. His work was good and he filled a niche we needed, so I tolerated his emotional outbursts, even when they involved him venting to me for 45 minutes at a time. Odd people deserve jobs too, right? However, now that I’m no longer being paid to manage this kind of behavior, I’m not thrilled about being dragged into work drama again.

I’ve offered to help out during the busy season because I’d like to repair my reputation at the company, where I was once a valued employee before burnout led to my departure. My former boss informed me that the higher-ups rejected the idea of me returning, but they didn’t tell my former employee this. Instead, it seems they’ve told him that I burned bridges, and now he’s pressuring me to “mend fences,” saying the team can’t manage without me.

I’m currently searching for my next role and am hesitant to alienate anyone who could potentially help me find work. What should I do?

Realistically, how likely is this guy to help you find work? He seems to have terrible judgment (on display when you worked there, plus now in hassling you to return after being fired; even if he doesn’t know you were fired, his belief that it’s appropriate to badger someone into returning to a job doesn’t speak well of him) and I’m skeptical that he’s a valuable contact who you need to preserve a relationship with at all costs. You could simply ignore his messages.

But if you don’t want to do that, there’s nothing wrong with saying the next time he contacts you, “I’ve offered. They’ve declined. I’m not going to pursue it further, so please stop asking me to.” Or skip the details and just say, “It’s not on the table, so please stop asking about it.”

5. Rejected by text

After a phone interview, an in-person interview, and a work sample (unpaid), I’ve just been rejected for a job over text. The rejection itself doesn’t sting as I had decided the job isn’t right for me, but I can’t get over them doing it by text!

Should I say something? Is there a way to without sounding catty? Ordinarily I think I’d just leave it, but the person who sent the message had told me they’ve only worked there seven weeks. Part of me feels like maybe someone should tell them how unprofessional it is, especially at this stage of the process.

Is a quick “Thanks for letting me know, this is news I would have rather received over email or a phone call, but all the best in your search” even worth it or should I just forget it ever happened?

Ugh, why do people do this?! This is not a casual “I’m running 10 minutes late, meet you inside” message. It’s professional news of some weight and it should be treated that way.

As for whether or not to say anything, I’m torn. On one hand, it’s good for hiring managers to get feedback about this sort of thing, and you might be telling her something she genuinely had never thought about and she might rethink it for the future. On the other hand, when you give feedback about how a rejection was delivered, there’s always a risk that it’ll bite you in some way in the future. For example, if a job opening comes up there next month that you’d be perfect for, will she not contact you about it because she’s embarrassed or feels chilly toward you now (whereas she would have contacted you otherwise)? Or if you apply there in the future, same concerns.

I really hate telling people not to deliver well-warranted feedback because it plays right into the problematic power dynamics already present in an interview situation, and also because employers will never learn if they don’t get feedback from candidates … but you’ve got to balance all that and decide how much you care about each piece of it.

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

1. Is it weird to bring my toddler’s sippy cup to work with me?

Is it weird to bring my toddler’s sippy cup into the office? I drop her off at daycare in the morning, and she brings her milk in the car. I don’t want it to get gross in the hot sun all day, so I bring her cup inside to rinse it out. When I get into the office, I drop my stuff off at my desk, then go rinse the cup in the kitchen and stick it back in my purse. Quick, no big deal. However, every time a coworker sees me with the cup, they (understandably) ask a confused “Why do you have a sippy cup?” On a few occasions, I’ve been stopped in the hall or pulled into a meeting on my way back to put the cup away, so then I’m left holding it while discussing an important work topic. And it’s hard to be taken seriously while holding a Tommee Tippee.

This seems like such a non-issue, but now I’ve started to feel a bit weird about it. Like by bringing the cup into the office, my mom-life is bleeding over into my work-life and I’m announcing to everyone that I’m *A Mom* (even though all of my coworkers know that I’m a mom). I think my question is not whether or not it’s appropriate, but from a professional standpoint, is there any reason I should stop bringing the cup into the office, or should I do something differently?

I’d love to say that you don’t need to give it another thought. In reality … you might. It depends on your office and, to some extent, your industry. If you work in an office or a field with a lot of sexism and/or you have to struggle to be taken seriously, the sippy cup might not be doing you any favors. It shouldn’t be that way — the fact that you care for a child should have nothing to do with how you’re seen at work — but in reality sometimes it does.

If you wanted to play it absolutely safe, I’d be more discreet with the cup. Dump the milk out outside and then leave the cup in your car, or at least put it in your purse when you’re going to and from the kitchen. Is this silly? Yes. Are there still real biases against women of young children in some offices/fields? Yes. Are those potentially intensified when you are visibly performing a child-related task in your office during a work day? Also yes.

On the other hand, if you don’t struggle to be taken seriously, change nothing. Especially if you’re senior-level and widely respected, it can be a social good to let your own behavior be a counterweight to problematic norms.

2. I don’t have time to answer a new employee’s questions

I’m an employee on a team that, due to a series of unexpected departures, is currently very understaffed. Our office is in a constant state of panic with everyone rushing around to get projects done by deadline. Our manager, Diane, oversees several teams across multiple offices and is always in meetings, so she doesn’t have much time to help us and is very hard to reach. But she and other higher-ups have been desperate to get more people onto our team ASAP, and so a few months ago they hired a brand new graduate, Todd, with no experience in our field other than summer internships. (The rest of us have been on the job a decade-plus.)

Diane initially assigned one of our team members, Vincent, to train Todd and answer his questions. However, Vincent ended up leaving a few weeks later due to an unexpected life event. Diane has not yet assigned someone else to train Todd, and now that we are scrambling to cover Vincent’s projects, the rest of us REALLY do not have the bandwidth to take on training duties. But I happen to sit across from Todd, so he is now directing all of his questions to me. And so now, in addition to the huge amount of my own work, I am dealing with a steady stream of questions from Todd. These are not procedural or factual questions that I can just ask him to look up — they tend to be specific to whatever project he is working on, such as “Do you know why the numbers in this column don’t add up?” or “Does this sentence I wrote make sense?” I often have to go over to his computer and examine his work in order to give a confident answer, and it starts to take up a decent amount of time.

I tried to help as much as I could in the beginning, because I can tell that Todd is a hard worker who is trying hard to learn. I also don’t want him to be fired, because we do need the help! But the questions are not abating as time goes on, and I feel like they are starting to add an unsustainable amount of stress to my workload, particularly when we are in crunch time on deadlines.

Is this something I should address with Diane — and if so, what would be the best way to do that? Or is it Todd I should be talking to?

Talk to Diane. Estimate how much time you’re spending per week helping Todd and the impact it’s having on your workload, and tell Diane that you’re not able to be Todd’s main trainer unless other projects are taken off your plate to give you time for it.

Since Diane is hard to reach, you could put this in an email.

If her answer is that there’s no on else to help and you’ll have to make do, let her know that you can either help Todd or do XYZ in the coming weeks, and ask her which to prioritize. If she sticks to “just get it all done,” then say, “I’ll do what I can, but if we’re not moving any deadlines I’m going to need to prioritize those, which means I won’t have time to give Todd as much help as he’s asking for.” (In other words, treat this like you should any unrealistic workload problem.) Then explain the situation to Todd and suggest he speak with Diane himself about getting what he needs.

Related:
I’ve been overworked for months and my manager won’t help

3. Is wet hair unprofessional?

I saw a discussion today about whether it’s unprofessional to have wet hair at work, with the consensus being that it is and reflects badly on employees. But some were arguing that this is racist and/or sexist because curly and long hair takes longer to dry and generally that hair will belong to women and/or people of color. (There was also a discussion about whether it’s reasonable to provide gym and showering facilities for use before work or over lunch but then expect people to dry their hair before coming back to work.) What are your thoughts?

It depends on what your particular hair looks like when it’s wet. For example, I have long, straight hair that when wet requires three hours to stop looking like I just got out of the pool. But not every hair type does that (especially not curly hair). If you don’t look like a drowned rat when your hair is wet, it’s typically going to be fine. If it’s a borderline case, it’ll help to put it up or tie it back.

I can’t see how it’s unreasonable to provide gym and shower facilities but still expect people to return to work looking professional. Yes, for some people that will mean blowing their hair dry or tying it back, but for many people it won’t. (And for many of the people who need to, the convenience of having those facilities on-site makes it worth it.)

4. My coworker doesn’t want our boss to know about his mistakes

I am on a small team in a medium-sized, fast-growing company. There have been discussions around promoting me into a leadership role and reorganizing our team to have one or more junior colleagues report to me directly. This is great and I am excited for the opportunity if or when it happens.

Currently my role is similar to quality review over the work that the others on the team produce. The issues I identify are not generally performance-related; they are typically mistakes made due to limitations in the process and/or tools. Notification to the individual and manager, when appropriate, is factual and not personal (example: “found issue X, recommend Y to resolve”). This will continue in the new team structure.

My.question involves a concerning behavior of one person on the team who will likely report to me in the future. He gets defensive if our current manager is copied or notified for any negative issue. Most issues are dealt with individually, but some require guidance from our manager. When this happens, my colleague gets upset and says “(manager) doesn’t need to know.” This pushback makes me wary of trusting them on my team if the restructure happens as planned. And regardless of any restructure, I want to shut this behavior down.

I have already tried explaining to him that these reports are not personal and do not reflect on his performance, but I don’t think the message is being received.

The next time he says that your manager doesn’t need to know about something, reply with, “Jane expects me to loop her in on this type of thing because of X.” If it’s true you could add, “If you’re worried about it reflecting on you, I can tell you this isn’t a big deal — everyone on the team has corrections like this, it’s routine and expected, and you don’t have more than anyone else.” (Again, only say that if that’s true.)

If you do become his manager, it’ll be useful to know that he approaches mistakes this way. It means you may have to do more digging about what’s really going on in his area, won’t necessarily be able to take his word for things, and can’t assume he’ll alert you if something goes wrong. That’s super useful to start off knowing, rather than finding it out down the road. It could also be something you address with him once you’re his boss, possibly framed as, “I know you worried in the past about Jane hearing about X or Y. I want to talk to you about how I approach mistakes and how I’d like you to think of them and communicate about them.”

5. People are annoyed with my backlog, but I have a medical accommodation

I’ve been working at a fully remote job for six months. I’m an individual contributor who gets assigned X number of a certain type of project every month. While clients do need these delivered promptly, this isn’t a vital business function, nor does it save lives. About three months ago, a chronic pain condition I have started getting worse. About three weeks ago, when it became clear that I was really behind with no improvement in sight, I told my boss Tony. I was surprised at how quickly and easily my company agreed to an ADA accommodation of a reduced workload for several months while I adjust treatments with my doctor. It really made me feel positively about my company.

Well, we’re now into the first month of my reduced workload, but I’m still digging out from last month. I’ve been upfront with Tony about how far I’m behind and gave him a realistic timeline for getting it done. He didn’t ask any follow-up questions. My grandboss Laila told me to get my work done as soon as I could, but also seemed understanding that I’m working at a much reduced pace.

When I send a project out to the client, another department at my company is notified. There have been a few annoyed emails from this department, including one with many manager cced. They have every right to be testy — these clients paid for services and they should get them on time. But there’s only so much I can do right now. I’m getting a bit frustrated that Tony or Laila didn’t say anything to this department. I understand they can’t talk about my accommodation, but I would have thought they’d let them know that things will be coming out late and they’re aware of the situation. Am I being too extra if I ask Tony to say something? I really don’t want my reputation tanked with this department and I don’t want to wreck client relationships.

No, ask Tony to say something! Ideally he’d explain to the other department that there are extenuating circumstances slowing things down and X type of work will be delayed for roughly Y months. What to say to clients is trickier and depends on details I don’t have, but Tony should be working with you on messaging about that too.

Since that’s not happening, explain to Tony that you’ve noticed people seem annoyed and you think it would help to offer context, and ask him to help you let people know what’s going on so it’s clear to them that he’s in the loop and you’re not just dropping the ball.

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

1. My neighbor, her nephew, my kid, and her dogs

My question has to do with kid work. I recently found myself in an uncomfortable situation with my middle-schooler, Falcon, and I’m wondering if I handled it badly. My neighbor, Jane, asked Falcon to check on her dogs and take them for a walk while she attended an event. She offered $15/hour, and since Falcon loves dogs, he agreed. The request was for him to spend two to three hours walking and playing with the dogs, starting between 5 and 6 pm.

On the afternoon of the event, Jane texted, asking if Falcon could instead stay at her house until she returned around 11 pm. She also mentioned that her adult nephew, Hank, would be at the house with Falcon. This change was … unexpected. We only saw the text after returning home from Falcon’s soccer game, by which time Jane had already left for the event. Neither of us had ever met Hank before, and all we knew about him was that he had learning disabilities.

Falcon was uncomfortable with the idea of spending several hours in a house with an adult stranger. But, since Jane had already left, we felt obligated to fulfill her request. I accompanied Falcon to the house at 6 pm. We walked the dogs, played with them in the yard, and greeted Hank, who was sitting in the dark and ignored us. Falcon was afraid of him. We played outside with the dogs for a couple of hours until it became too dark and mosquito-y to reasonably remain outdoors. We then brought the dogs inside and waited together in the front room with them until Jane returned, as neither of us was comfortable leaving Falcon alone with Hank.

When Jane got home, she noticed dog poop in the kitchen, which we hadn’t seen because Falcon was too scared to go in there (it was attached to the room where Hank was hanging out in the dark). It appeared that Hank and/or the dogs had stepped in the poop and gotten it all over the place. Our best guess is that the pooping happened before we arrived, as we were with the dogs fairly consistently from 6 pm until Jane’s return. Jane handed Falcon $75 as payment, but I texted her the next morning, offering to return the money since we hadn’t prevented the dogs from soiling the house. Jane asked us to return $50, which we did.

I feel terrible about the whole situation. I don’t think Jane should have put my son in the position of being alone for hours with a man he didn’t know. Falcon feels guilty for not doing a better job with the dogs. I’m wondering how could I have handled this better. Beyond letting the dogs out earlier, of course. I feel like I’ve both traumatized my child and let down my neighbor.

This is 100% on Jane. Falcon agreed to a specific job: playing with the dogs for a couple of hours, on his own, ending no later than 9 pm. Jane unilaterally changed that to “stay at my house for six hours with an adult man you don’t know.” Even if Hank had been friendlier/less intimidating, this wasn’t an okay thing to ask of a middle-schooler, particularly without checking to see if he’d be comfortable with it and possibly talking with you as well. (Frankly, even if Falcon were comfortable, I don’t think it would have been an appropriate ask. If Hank isn’t capable of taking care of the dog himself, and is someone who might smear dog poop all over the house without cleaning it up, an unprepared middle-schooler isn’t the right person to be alone with him.)

If we could go back in time, ideally you would have coached Falcon to tell Jane that he couldn’t stay later than the time he agreed to (or even told her that yourself). You say you felt obligated to fulfill Jane’s request, but you weren’t obligated; the request wasn’t the one Falcon had agreed to. I don’t think you needed to offer to return the money although I can understand the impulse, given the poop situation. But Jane should have refused that offer and should have apologized for how things unfolded.

2. I submitted a time off request 3 months ago … and am still waiting

I work at a small company, about 50 employees. Last year, the owner turned over day-to-day operations to a VP who has been with the company for the past 10 years. I report to the VP and am one of four people with the company in a managerial position.

Over three months ago, I submitted a leave request for the week of Christmas. I have been in this industry for over 20 years and that week is historically the slowest week of the year. I usually do not take off that week so that my staff is able to travel to see family (my family is small and local). Last year, my brother-in-law died on Christmas and my husband does not want to be home due to the bad memories from last year. Because it is Christmas, I submitted my request early to make sure it was timely and before any other requests were submitted.

The VP has not made a decision on my leave request and advised me he is still “thinking about it.” I’m very frustrated. I feel disrespected and unappreciated. I only earn two weeks of leave per year, which isn’t much and often causes issues as my husband has considerably more leave and we are unable to travel due to my lack of leave. It is also use or lose, so if I do not use my time by the end of the year, I will lose it. I feel like my vacation time is being held hostage. Never mind that I have to pay for the AirBNB and flight and my husband has to request leave as well for that week. Everything is in limbo over this and the costs are rising each day. The difference in the cost of the flights between early June and September is nearly $1000. I’m so angry and disappointed.

I’m willing to quit over this. My issue is that I don’t think the owner is aware of the issues with the VP, and I’m not sure how to bring it up as he has stated multiple times that he has complete faith in the VP and trusts him 100%. I do not think it is appropriate to withhold PTO approval (or denial) for over three months, all while the cost of my vacation plans are now increasing and I will not be able to use the leave before the end of the year if this vacation request is not approved. Any guidance would be greatly appreciated in how to address with both the owner and VP.

Talk to the VP first! Say what you’ve said here — the costs are rising with each day that you wait, the time off is use-or-or-lose it, and you need to be able to plan. Ask what he needs to give you a definite answer by next week.

If he doesn’t do that (or if he denies the request), talk to the owner. “Having complete faith in” the VP and “trusting him 100%” doesn’t generally mean “I believe he will never miss anything / could never benefit from help changing his perspective.” And you’re a high-level employee who’s been there for a decade; the owner probably would want to know that you’re on the verge of quitting over something so easily solvable.

All that said … two weeks of vacation time is very stingy for a management level position, and even more so after 10 years. I’d also find it grating to be in a high-level management role but still be required to get approval for a meager amount of time off during a slow period. No one should need to wait this long to have PTO approved, but typically PTO approval for managers at your level is much closer to a rubber-stamp; making you wait months for no discernible reason is ridiculous. Is this the only thing where your company is stingy and overly rigid? I’d be inclined to reassess how well this place treats you (in money, in benefits, and in respect) and compare it to other options that might be out there.

3. What do I do when my company firewall blocks a website?

On occasion I will open a safe-for-work link but it will be blocked for various reasons. Sometimes it’s because it’s a “advocacy website” (which, my job is in advocacy, so I don’t totally get) but sometimes it’s for pornography. This is absolutely mortifying! (And I must stress, there’s no reason to believe these links are actually NSFW!) What should I do when this happens? I usually do nothing, but I am very embarrassed at the idea of our IT team getting an alert that I tried to access porn at work. Do I need to email them about it and clear the air?

Nah. They’re probably well aware that the software misfires, and you’re undoubtedly not the only person it’s happening to. However, it would be fine to message them, “FYI, OatmealAlliance.com is being blocked as ‘pornography,’ which it obviously isn’t.” That way you’re informing them about a problem (their blocking tool needs refinement) and if it happens to bring you peace of mind in the process, so much the better.

If these are sites you need to do your job, you should add, “Can you please unblock it? I need it for a project I’m working on” (or similar).

4. Greeting people you’re not sure you’ve met before or not

Low stakes question, but do you have a favorite way to acknowledge people who you’re introduced to and aren’t sure if you’ve met before? Or you know you have, but they don’t remember and you don’t want to put them on the spot?

I’m usually in the latter category, but may be moving into the former. The default seems to be “nice to see you,” to cover all bases, but honestly I hate it. Curious if you have anything better?

“Nice to see you” is a classic among politicians and others who do lots of glad-handing for a reason: it covers you in case you’re forgetting that you’ve met the person previously. You could go with “hello, how are you?” but there aren’t many other options for this specific context.