Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Manage a Boss Who Steals Your Vacation Time
Transcript
- Lucas: So we have a listener question that I think is going to hit home for a lot of people. It came in through the Fexingo voicemail line, and it's from a woman named Priya who works at a mid-size tech firm in Austin. She says her boss, quote, 'expects me to be reachable on vacation. Not constantly, but she'll send a Slack message or an email and if I don't respond within a few hours, she follows up with a text to my personal phone.' Luna: Wow. The personal phone follow-up is a whole other level. Did Priya say what the boss's justification is? Lucas: Yeah. Her boss says it's just in case something urgent comes up — and that Priya is the only one who knows a particular client integration. So she feels like she can't really disconnect because she's the single point of failure. And I think that's the trap a lot of people find themselves in. Luna: Right — it's not just a bad boss problem. It's also a structural problem where the team hasn't documented the knowledge. But let's start with the boss. What do you actually do in that moment before you go on vacation? Lucas: Well, there's a 2025 study from the University of Massachusetts Amherst that looked at this exact dynamic. They tracked about 800 knowledge workers over three quarters and found that employees who checked email or Slack even once during a vacation reported 40% higher burnout scores in the following quarter, and they took an average of 2.3 more sick days compared to people who fully disconnected. Luna: Forty percent is enormous. And it's not like those people are getting more done — they're just making their recovery worse. Lucas: Exactly. So the first step is to reframe the conversation from 'I don't want to work on vacation' to 'Here's how we protect the business from my burnout.' That's a language shift that makes the boss hear it as a business case, not a personal preference. You say something like: 'I want to make sure I come back fully recharged so I can perform at my best for the team. For that to work, I need to truly disconnect. Can we plan coverage for the key items?' Luna: I like that. But what if the boss says, 'We don't have coverage, you're the only one who knows this'? Which is exactly Priya's situation. Lucas: Then you have to do the pre-work. At least two weeks before your vacation, you do what I call the 'out-of-office email audit.' You go through your sent emails from the last month and identify the five to ten recurring questions or requests that come to you. Then you write a one-page FAQ or a quick Loom video explaining those common processes. You share that with your boss and a couple of teammates before you go. Luna: So you're basically building a mini knowledge base for your absence. And then when the boss says 'but what if something new comes up?' you have an answer. Lucas: Right. And the answer is: 'If something truly urgent comes up that none of the documentation covers, I'm happy to be looped in — but let's set a clear threshold for what counts as urgent. A client asking for a status update is not urgent. A production outage might be. Let's define that together before I go.' That makes it collaborative rather than defensive. Luna: I had a friend who worked at a company where the CEO actually messaged someone on their honeymoon. Not about a crisis — just to ask a question about a presentation. And my friend felt so guilty that she answered. She said she couldn't enjoy the rest of the trip because she was worried about the next message. Lucas: That's the thing — once you break the seal, your brain never fully relaxes. There's a concept called 'attention residue' from a researcher named Sophie Leroy at the University of Washington. When you partially engage with work during a break, your brain keeps a thread of that task running in the background. So you're not really recovering even if you're at the beach. Luna: So what do you do if you've already accepted that you'll be reachable? Is it too late to set a boundary? Lucas: It's never too late, but you have to be more explicit. You can say, 'I've noticed that checking in during my last vacation actually made me come back more tired than when I left. I want to try something different this time. Can we agree that I'll be completely offline for five days, and if something truly urgent comes up, you can call me — but otherwise I won't check Slack or email?' Luna: I think that's reasonable. But I also think there's a cultural layer here. If the entire company treats PTO as a suggestion, then one person pushing back is swimming upstream. Priya's boss might genuinely believe she's being reasonable because everyone else does it. Lucas: That's a really good point. And there's data on that too. A 2024 survey from the Society for Human Resource Management found that 43% of U.S. employees said they felt pressure to work during their time off — and the top reason was that their manager set the expectation, either explicitly or implicitly. So the boss is often the bottleneck. Luna: So if you're a manager listening to this, what's the right thing to do? Because I think some managers don't even realize they're being the problem. Lucas: The simplest thing is to model the behavior yourself. If you send emails at 10 p.m. on a Sunday, your team will feel like they should be available too. But more concretely: before someone goes on vacation, have a five-minute conversation where you say, 'I want you to fully disconnect. Here's who to contact if something comes up. Let's review any critical handoffs now.' That single conversation reduces the ambiguity enormously. Luna: I want to circle back to Priya's specific situation. She said her boss texts her personal phone. That feels like a boundary violation beyond just work email. How do you handle that? Lucas: It is a violation. And the fix is to separate the channels. Before your vacation, you say: 'During my time off, I'll be muting work notifications on my phone. If there's a true emergency, you can reach me at this temporary number or via my partner's phone — but otherwise, I won't see messages until I'm back.' You're not saying don't contact me — you're saying contact me in a way that signals urgency. The personal text message is for friends and family, not for work. Luna: That's a clean way to renegotiate the channel. And it forces the boss to think: is this actually an emergency? Because most things aren't. Lucas: Exactly. And if the boss still can't respect that, then you have a bigger problem — a boss who fundamentally doesn't believe you have a right to time off. And that might be a sign to start looking for a new role, because that pattern rarely changes without a formal complaint or a leadership shift. Luna: Yeah, and that's hard to hear. But better to know early than to burn out over two years of never really being on vacation. Lucas: If today was actually useful to you — maybe you're planning a vacation and dreading the Slack messages — the way these episodes stay ad-free is listener support. You can head to buy me a coffee dot com slash fexingo. No pressure. Just if you found value and want to help keep this going. Luna: Yeah, it really does make a difference. Even a small contribution helps us keep the lights on and the episodes free for everyone. So thanks to anyone who's considered it. Lucas: All right. Let's get back to tactics. One more thing I want to mention: the 'out-of-office autoreply' is your friend, but you have to craft it carefully. Instead of saying 'I'm on vacation and will respond when I return,' which invites urgent people to find a workaround, you say: 'I'm out of the office until July 25th. For urgent matters, please contact Sarah at sarah@company.com. Otherwise, I'll respond when I return.' That redirects without leaving a loophole for your boss to decide what's urgent. Luna: I love that. And you should also set up a Slack status that says the same thing, with Sarah's name. Maybe even temporarily mute notifications on your phone. Lucas: Yes. And here's a pro tip: if you use Slack, you can set a custom status that automatically snoozes notifications for the duration of your PTO. That way, even if your boss sends a direct message, it won't ping you. You'll see it when you come back, but it won't interrupt your day. Luna: So the theme here is: preparation beats hope. You can't just hope your boss won't bother you. You have to build a system that makes it easy for them not to. Lucas: Exactly. And the beauty is, that system also helps your team. When you document your processes and set up coverage, you're making everyone less dependent on you. That's a career win in the long run — you become more promotable because you're not a bottleneck. Luna: Let's take a listener question that came in via email. Ryan from Chicago asks: 'What if you're the only person who knows a critical process, and your boss knows that, and that's why they expect you to be reachable on vacation? Isn't that kind of your fault for not documenting it earlier?' Lucas: I think that's a fair question, but I'd push back gently. Yes, you should document, but the responsibility also lies with the organization to ensure there's redundancy. If you're the only person who knows something, that's a management failure, not an employee failure. But practically speaking, you have to fix it for your own sanity. So do the documentation, but don't blame yourself for the situation. Luna: I agree. And I'd add: if your boss uses that as a reason to keep you tethered, they're not managing well. They're exploiting a weakness they should have fixed. Lucas: Right. So to Ryan: do the documentation, but also have a conversation with your boss about why it's not sustainable for one person to be the sole knowledge holder. Frame it as a risk to the business — if you get hit by a bus, the company is screwed. So let's cross-train someone. Luna: That's a strong argument. 'I want to protect the company from my absence.' Hard for a boss to argue with that. Lucas: Exactly. So let's wrap with a quick checklist. Before your next vacation: one, do the out-of-office email audit and create a FAQ. Two, identify a backup person and brief them. Three, set a clear threshold with your boss for what counts as urgent. Four, update your out-of-office autoreply and Slack status to redirect. Five, mute notifications on your phone. Six, actually enjoy your vacation. Luna: That last one is the hardest, but it's the whole point. If you can't enjoy it, what's the point of taking it? Lucas: Exactly. And if your boss makes that impossible, you have a decision to make. But try the boundary-setting first. You might be surprised how much they respect it if you present it professionally. Luna: I hope Priya and everyone else listening gives it a try. Thanks for the conversation, Lucas. Lucas: You too, Luna. See you next episode.