Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Set Boundaries with an Always-On Boss
Transcript
- Lucas: So there's this moment from about eighteen months ago that I still think about. A marketing director I know — let's call her Priya — was on a family vacation in the Finger Lakes. She's at a lake house with her husband and kids, no cell service in most of the cabin, and she's driving twenty minutes each way to the nearest town with a signal just to check Slack. Luna: I've been that person. The 'Wi-Fi hunting' vacationer. It's miserable. Lucas: Right. And the worst part? Her boss wasn't a monster. He wasn't sending angry messages. He'd just fire off questions at 9 PM on a Saturday because he was working — he genuinely couldn't understand why she wouldn't also be working. He had this 'we're all in it together' mentality that completely ignored the fact that she had, you know, a life. Luna: So how did she handle it? Because that's the kind of boss who's hard to push back on. He's not abusive, he's just — always on. Lucas: Exactly. That's the distinction we're talking about today. Not the toxic manager who yells or steals credit. The one who's personally high-performing and assumes everyone else shares that same 24/7 drive. And it's surprisingly common — especially in mid-size growth companies where the culture is still being shaped by a few key people. Luna: I've definitely seen that. The boss who sends an email at 11 PM and then follows up at 7 AM the next morning because they're 'just getting to their inbox.' It sets this implicit expectation that you're supposed to be working in the margins too. Lucas: And that's the trap. Because if you respond at 11 PM once, you've trained the algorithm — and the person — that you're available at 11 PM. Priya realized that after she got back from that vacation and found she'd actually answered a few non-urgent messages from the lake. She'd inadvertently reinforced the pattern. Luna: So what did she do differently? I'm guessing the standard 'just set boundaries' advice didn't cut it. Lucas: It did not. She tried that at first. She had a conversation where she said, 'Hey, I'm trying to protect my evenings for family time.' And her boss nodded and said he totally understood. Then two nights later, he pings her at 8 PM about a slide deck. Because in his mind, this was urgent — and 'family time' didn't override urgency. That's the problem with traditional boundary-setting language. It sounds personal, like you're asking for a favor. It doesn't reframe the business logic. Luna: So she needed a structural fix, not just a conversation. Lucas: Exactly. She came up with something she called a 'communication charter.' She drafted a one-page document that defined response-time expectations by channel and time of day. Email: 24 hours. Slack during business hours: same hour. Slack after 6 PM: next business day, unless marked with a specific emergency tag. And she framed it as a productivity optimization — not a personal request. She said, 'I want to make sure I'm giving focused attention to the highest-priority work, not fragmenting my day by jumping into every notification.' Luna: That's smart. It's harder for a boss to argue with 'I'm optimizing my focus for the company's benefit.' How did her boss react? Lucas: He was initially skeptical. He said, 'But sometimes I need you at 9 PM.' And she asked him to define what 'need' meant. Because in the previous six months, exactly two after-hours requests had been genuinely time-sensitive — like a client presentation the next morning that changed last minute. The other forty or fifty were things that could have waited until morning. She proposed a system: if it's truly urgent, email with in the subject line and she'd respond within two hours. Otherwise, it lands in her next-day queue. Luna: And he agreed to that? Lucas: He did — with one tweak. He wanted a 10 PM cut-off instead of 6 PM. And she took that deal. The key was that she gave him a concrete mechanism for genuine emergencies while removing the ambient expectation. And over the next month, the number of after-hours messages dropped by about 70 percent, because most of the stuff he'd been sending wasn't actually urgent. He just hadn't been forced to think about it. Luna: It's almost like he needed a forcing function to sort his own priorities. Which makes sense — a lot of always-on bosses are reacting to their own anxiety, not to real business needs. Lucas: That's the insight I think is worth holding onto. The always-on manager is often operating from a scarcity mindset — they're afraid they'll miss something, or that the company will falter if they're not constantly driving. So when you set a boundary, you're not just protecting your own time. You're forcing them to confront their own relationship with work, which can be uncomfortable for them. Luna: It's like you're asking them to trust the system. And if they're a control-oriented person, that can feel like a loss of control. Lucas: Exactly. Which is why Priya's second move was important. She didn't just set the charter and disappear. She started sending a brief end-of-day summary every evening — three bullet points of what she'd accomplished and what she'd pick up tomorrow. That gave her boss a sense of closure. He could see she was on top of things, so he didn't feel the need to check in. Luna: That's a great tactic. You're proactively providing the visibility they would otherwise try to extract through random late-night messages. Lucas: Right. And it worked. Within about three weeks, the late-night pings were almost nonexistent. And Priya told me something interesting — her boss actually started sending his own end-of-day summaries. He'd copy her on a note saying, 'Here's what I wrapped up, see you tomorrow.' He was modeling the behavior she'd introduced. Luna: That's a win-win. And I think it points to a broader lesson — that sometimes the boss who seems impossible to manage is actually just lacking a clear framework. They're not malicious, they're just operating on default settings. Lucas: Yeah. And the moment you offer a better default — one that still serves their need for control or information — they'll often take it. But you have to be the one to design it, because they won't. They're too busy sending Slack messages at 9 PM. Luna: So let me ask you this — what about the bosses who don't respond to a rational framework? The ones who see a communication charter as insubordination or a lack of commitment? Lucas: That's a real category. And in those cases, you're not dealing with a communication problem — you're dealing with a values mismatch. The boss believes that availability equals dedication. And no amount of clever framing is going to override that belief if it's deeply held. Then your options narrow: you either find a way to tolerate it while you build leverage, or you start looking for a manager whose values align with yours. Luna: And that's hard to hear, but I think it's honest. Not every boss can be managed into being reasonable. Lucas: Exactly. But I'd say it's worth trying the structural approach first, because a lot of people skip straight to either resentment or resignation without testing whether the boss simply needs a better system. And in my experience, about sixty to seventy percent of always-on managers will respond to a well-framed structural change — if you do it the way Priya did. Luna: Okay, so let's break down the specific steps for someone listening who's dealing with this right now. What's the playbook? Lucas: Step one: audit the pattern. For two weeks, keep a log of every after-hours communication from your boss. Note the time, the channel, and whether it was truly urgent or could have waited. You need data, because your boss will likely say 'I don't do that that often' — and you'll have receipts. Luna: Data is the antidote to perception. I love that. Lucas: Step two: design your proposed charter. Decide your response-time tiers. What's your cut-off hour? What constitutes a true emergency? Write it down as a one-page proposal — and phrase it in terms of focus and productivity, not personal time. Luna: And stress-test it. Run it by a trusted colleague first to make sure it doesn't sound unreasonable. Lucas: Great point. Step three: have the conversation. Schedule a one-on-one dedicated to 'optimizing communication,' not 'setting boundaries.' Use your data: 'Over the last two weeks, I noticed about 15 after-hours messages, of which two were time-sensitive. I'd like to propose a system that ensures I'm responsive to the urgent ones while protecting my deep-work time during the day.' Luna: And then leave room for negotiation. Your boss might want a different cut-off or a different emergency signal. That's fine. The goal is a mutual agreement, not a unilateral demand. Lucas: Exactly. Step four: over-deliver on the proactive communication piece. Send that end-of-day summary. Show them you're on top of it. That builds trust and reduces their impulse to check in. Step five: if the pattern returns, re-audit and have a follow-up conversation referencing the agreement. Most bosses will self-correct if they've explicitly agreed to the system. Luna: I want to add one more thing — and this is from my own experience. Sometimes the always-on boss is also responding to pressure from above. So if you can understand their stressors, you can frame your proposal as something that helps them look good to their boss too. Like, 'If I'm focused during the day, I'll deliver higher quality work on the big projects, which reflects well on both of us.' Lucas: That's a really smart addition. You're aligning your boundary with their incentive. And that makes it almost impossible for them to say no. Luna: Right. And if they still say no — if they insist on 24/7 availability and treat any pushback as a lack of commitment — then you have your answer. It's not a communication problem. It's a culture problem. And you have to decide whether you can live with that culture. Lucas: And that decision is valid. No one should feel trapped. But I'd encourage people to try the structural approach first, because it might surprise you. Priya's boss turned out to be a reasonable person who just needed a better operating system. And she was the one who built it. Luna: That's a great note to end on. And honestly, if this episode helped you think about your own situation in a new way, that's exactly what we're here for. We do this show because we believe that navigating a difficult boss is a skill — and it's one you can get better at. Lucas: And we keep it ad-free, so there's no sponsor pressure to stretch the content or cut corners. A small group of listeners already chips in monthly through buy me a coffee dot com slash fexingo, and that support is what allows us to keep making episodes exactly the way we want — focused on what's actually useful, not what sells. If that resonates, you know where to find us. Luna: Yeah, it's a simple model, and it works. No ads, no tracking, just the show. We're grateful for everyone who's part of it. Lucas: Alright — next episode, we're going to talk about something I've been getting a lot of listener questions about: the boss who withholds information as a power play. How to recognize it, and how to work around it without triggering a confrontation. Luna: That's a good one. See you then. Lucas: Take care.