Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Manage a Boss Who Schedules Back-to-Back Meetings
Transcript
- Lucas: So we are going to talk about a specific kind of boss today, and I guarantee almost everyone listening has either had this boss or is working for one right now. Luna: Let me guess — the boss who schedules back to back meetings all day long and then wonders why nothing gets done? Lucas: Exactly that. The calendar-packer. The person who sees a thirty-minute gap and immediately fills it with a check-in, a sync, a 'quick touch-base.' And the result is that you, as the employee, spend your entire day moving from one video call to the next, with zero time to actually think, let alone do the work those meetings are supposedly about. Luna: It's exhausting. And it's not just annoying — there's real data on this. Microsoft put out a survey last year, in 2025, and found that 68 percent of employees said they don't have enough focused work time. That's more than two out of three people. Lucas: Yeah, and Microsoft is in a unique position to measure this because they own the tools — Outlook, Teams, all of it. They can literally see how many hours people spend in meetings versus in deep work. And their own data suggests that the average knowledge worker spends nearly sixty percent of their week in meetings or on instant messages. Luna: So the boss is part of the problem, but they're also probably not doing it maliciously. Most managers I've met who over-schedule aren't trying to torture their teams — they're just operating on autopilot. Lucas: Right. And honestly, if today was worth a coffee to you, that's the link — buy me a coffee dot com slash fexingo. It keeps the show ad-free and lets us keep digging into these specific workplace problems. Luna: Absolutely. And it's a small way to say this topic matters to you. So back to the calendar-packer — what's the actual move here? Lucas: So the first step is what I call a 'meeting audit.' And I know that sounds administrative and boring, but it's the most effective tool I've seen. You literally create a one-page document — a spreadsheet, even a notebook page — and you list every recurring meeting on your calendar for two weeks. Luna: Every single one? Including the ones your boss isn't on? Lucas: Every single one. Because the goal is to see the full picture. For each meeting, you write down three things: one, the stated purpose. Two, who really needs to be there. And three, what actually happens in the meeting — is it decision-making, information-sharing, or just status updates that could be an email? Luna: Okay, I like that. So you're building evidence. Because if you go to your boss and say 'I have too many meetings,' that's a complaint. But if you go with a document that shows 'I spend 23 hours a week in meetings and only 4 of them are decision-making,' that's data. Lucas: Exactly. And the data is hard to argue with. Now, the tricky part is how you present it. You don't want to accuse your boss of being the problem — even if they are. You want to position it as a shared problem: 'I want to be more productive for you and for the team, and I think we could streamline our calendar.' Luna: That's the managing-up script. Can you give a specific example of what that sounds like? Lucas: Sure. Something like: 'Hey, I've been tracking how I spend my time, and I noticed I'm in meetings for most of the day. I want to make sure I'm focused on the highest-impact work. Could we look at my calendar together and see if there are any meetings I could attend less frequently or get updates from instead?' Luna: That's good because it frames it as you wanting to be more effective, not as you complaining about your boss. But what if the boss pushes back? Some managers hear that and say, 'No, I need you in every meeting because if something comes up, you need to know.' Lucas: Then you need a second tactic. Suggest a 'meeting-free block.' This is a recurring chunk of time — say, Tuesday and Thursday mornings from nine to noon — where you are not available for meetings. You put it on your calendar as 'Focus Time' and you defend it. Luna: And what if your boss schedules over it anyway? Lucas: Then you have a conversation about priorities. You say, 'I see you scheduled a meeting during my focus block. I can make that work, but I'll need to push my project deadline back by a day. Is that okay?' You make the trade-off explicit. Most bosses will start to respect the block when they see that overriding it has a real cost. Luna: That's a subtle power move, actually. You're not saying no — you're saying 'yes, but here's what it costs.' And that puts the decision back on them. Lucas: Exactly. And if they still don't respect it, then you have a bigger problem — a boss who fundamentally doesn't value your time. At that point, you might need to think about whether staying in that role is sustainable. Luna: Let's talk about the cultural piece, though. Some organizations just have a meeting-heavy culture. It's not just the boss — it's the norm. Everyone sends calendar invites for everything. Lucas: Right. And in those cultures, you have to be more strategic. One thing I've seen work is the 'meeting-free Wednesday' — a team-wide agreement that no one schedules internal meetings on Wednesdays. It has to come from leadership, but if you can get your boss on board and then they pitch it up the chain, it can spread. Luna: So the strategy is: start with the audit, present it as a productivity improvement, then introduce a focus block, and if that fails, try a team-wide change. That's a pretty clear ladder. Lucas: It is. And I'd add one more thing: be honest about your own habits. Sometimes we accept meetings we don't need to attend because we feel obligated. If you're in a meeting where you're just listening, and you don't need to contribute, you can ask to be taken off the invite. Most bosses won't notice, and the ones who do will respect the initiative. Luna: So the real takeaway here is that managing a meeting-heavy boss isn't about confrontation — it's about using data and framing to shift the conversation from 'I'm overwhelmed' to 'Here's how we can be more productive together.' Lucas: Exactly. And the best part is, once you start doing this, you're not just helping yourself — you're modeling better behavior for your boss and your team. That's real leadership, even if you're not the manager. Luna: Alright, I think we've given listeners a concrete playbook. Next time someone's boss sends a meeting invite for 4 PM on a Friday, they'll know what to do. Lucas: Or at least have a better script than just 'ugh, another meeting.' That's it for this episode. We'll be back with another difficult boss scenario soon.