Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Handle a Boss Who Keeps You on Standby
Transcript
- Lucas: We got an email this week from a listener we'll call Jenna. She's a senior marketing manager at a mid-size tech company, been there about eighteen months. And her boss, the VP of marketing, has a habit that on its face sounds small but over time is driving her crazy. Luna: Let me guess. He schedules meetings but never shows up on time. Lucas: Close but worse. Jenna's boss keeps her in a state of standby. He'll ping her late afternoon with something like 'Hey, can you hop on a quick call at seven?' and then seven comes, nothing happens. Eight o'clock, still nothing. She's sitting there with dinner on the counter, laptop open, waiting for a meeting that never materializes. And this happens two, three times a week. Luna: That is a specific flavor of disrespect. It's not just that he's disorganized — it's that he treats her time as infinitely elastic. Lucas: Exactly. And Jenna's not alone. I've seen this pattern in a lot of orgs, especially in roles where you're expected to be 'responsive' but there's no formal on-call structure. You're not a doctor getting paged for emergencies. You're a knowledge worker whose manager just assumes you'll be available whenever they happen to think of something. Luna: There's a term for this actually. Some HR folks call it 'time theft' in reverse — the employer stealing your personal time without compensation. But most companies don't frame it that way. Lucas: Right. So let's talk about what Jenna did, because she tried a few things before she got to a workable solution. First, she tried the direct approach. She said, 'I'm happy to support urgent needs, but can we schedule a standing window each evening in case you need me?' And her boss said, 'That makes sense theoretically' — and then nothing changed. Luna: The 'theoretically' qualifier. That's a red flag in itself. It means the person is agreeing at the conceptual level but has no intention of altering their behavior. Lucas: So Jenna escalated slightly. She started putting a hard stop on her calendar at 6:30 PM every day, labeled 'Personal commitment — do not disturb.' And her boss ignored it. He'd ping her at 7:15 and say, 'Hey, I know it's after hours, but can you just take a quick look at this?' And she'd cave because she felt guilty. Luna: And also because 'quick look' is the classic foot in the door. You look, you have a thought, then it's a thirty-minute back and forth. Lucas: Precisely. That's the standby trap. The manager isn't asking for a huge block of time. They're asking for five minutes, which then expands because the context isn't there. And the employee is the one absorbing all the friction. Luna: So what was the move that actually worked for Jenna? Lucas: She tried something counterintuitive. She started treating her own availability as a scarce resource — even when it wasn't. She told her boss, 'I'm blocking off Tuesday and Thursday evenings from 7 to 9 for focused project work. If you need me, please Slack me before 6:30 with the topic and I'll respond by 9 AM the next day.' And she physically turned off notifications on her phone during those hours. Luna: So she created a boundary that looked like a productivity optimization rather than a personal preference. That's smart because it's harder for a manager to argue with 'I'm using this time to get work done' than 'I want to eat dinner with my family.' Lucas: And it had an interesting side effect. Her boss started sending fewer of those late-night pings because now there was a cost — he had to think ahead. The standby behavior was partly laziness. He'd remember something at 7 PM and fire off a message because it required zero planning. Once Jenna forced him to plan, the volume dropped by about 70 percent. Luna: But I'm guessing the remaining 30 percent were still problematic. Because some managers genuinely believe their team should be available on demand. Lucas: Yeah. For the ones that didn't go away, Jenna started using what I call the 'two-hour rule.' If her boss pinged her after 7 PM with something that wasn't a true emergency, she would respond at exactly 9 AM the next day with a simple: 'Saw this — I'll have a draft to you by end of day.' No apology, no explanation. She just treated it as a regular morning task. Luna: And that normalizes the delay. The longer you do it without apologizing, the more the manager adjusts their expectation. Lucas: Exactly. And here's the key — Jenna never explicitly said 'I'm not working after hours.' She just behaved as if her workday ended at 6:30. And because she was otherwise reliable, her boss eventually adapted. It took about six weeks. Luna: That's a long time to feel anxious every evening though. Not everyone can tolerate that ambiguity. Lucas: No question. And that's where we need to be honest about the limits of boundary-setting. If your boss is the kind of person who will hold a grudge or retaliate for you not being available, no script or rule will fix that. In those cases, the move is to start documenting and looking for a new role. Luna: Right. The boundary conversation only works if the manager is fundamentally reasonable but disorganized. If they're controlling or punitive, the boundary becomes a target. Lucas: I want to pause here for a second, because I think this connects to something bigger. When we talk about managing up, we often frame it as a set of tactics — use these words, set this calendar block. But the underlying question is: do you have a boss who sees you as a person with a finite amount of time and energy, or do they see you as a resource that should be maximized? Luna: And that's the question Jenna had to answer for herself. She eventually realized her boss fell into the second camp. He wasn't malicious — he just genuinely thought 'if she's a good employee, she'll be available.' Lucas: And that's a philosophy you can't negotiate with. So Jenna updated her resume, started networking, and within three months she had an offer at a company whose VP of marketing had a Slack status that literally said 'I respect your time — please do the same for me.' She took that as a green flag. Luna: I love that. It's a cultural signal. And it's worth remembering that in a tight labor market — and we're still in one as of June 2026, at least for experienced marketers — you have leverage. The standby boss is a retention risk, and smart companies know that. Lucas: If today's episode helped you think through a similar situation — or gave you the language to name what's happening in your own workday — honestly, if it was worth a coffee to you, that link is buy me a coffee dot com slash fexingo. It's the smallest ask we can make, and it's what keeps this show ad-free and independent. Luna: Yeah. We don't run ads, we don't have sponsors, we just have listeners who find value in the conversation. That's the model. And if you ever want to support, that's the place. Lucas: So back to the standby problem. One thing I didn't mention is that Jenna's situation also points to a structural issue. In many companies, there's no policy around after-hours communication. It's left to individual managers, and that creates inconsistency. One team might have a 'no Slack after 6 PM' norm, another expects you to respond within the hour. Luna: That's a classic HR blind spot. They'll have policies about harassment and discrimination but nothing about time expectations. And yet time is the thing employees care about most. Lucas: Right. So if you're in a position to influence policy — even just on your own team — you can propose something like a 'responsiveness agreement.' It's a one-pager that says: here's when you can expect a response, here's what counts as urgent, here's the escalation path. It removes the ambiguity that the standby boss exploits. Luna: And it's a concrete deliverable. You're not complaining about your boss, you're proposing a system that benefits everyone. That's a harder argument for them to resist. Lucas: Exactly. And if your boss still resists, that's useful information. It tells you that the standby isn't accidental — it's intentional. And then you have a decision to make. Luna: I think the biggest takeaway from Jenna's story is that the boundary is not about winning a battle with your boss. It's about clarifying your own line and then acting consistently. If you treat your off-hours as non-negotiable, other people eventually will too. Maybe not immediately. But eventually. Lucas: And if they don't — if six weeks of consistent boundary-setting gets you nowhere — you have your answer. The standby was never about the schedule. It was about control. And you can't negotiate control away. You can only leave it. Luna: Jenna left. And she's now in a role where she actually looks forward to the occasional late-night message because it means something urgent and important, not just a manager who didn't plan. Lucas: That's the goal. Not zero after-hours work, but work that's genuinely worth your time. Thanks for listening, and we'll see you next episode.