Latest / New Manager Conversations with Fexingo: First 90 Days, Managing Former Peers, and Leadership Basics / How New Managers Can Run Their First Skip-Level Meeting
Transcript
- Lucas: You've been a manager for maybe two months. You've got your one-on-ones with your direct reports dialled in. Then your boss says, 'I want you to start doing skip-levels with the team.' And you think — wait, isn't that my boss's job? Luna: I remember that moment. It felt like I was stepping into my boss's territory. Lucas: Exactly. But skip-levels are one of the most underused tools in a new manager's kit. They're a direct line to the people two layers down — the folks who actually do the work. And they can surface problems no one else will tell you. Luna: Let's back up. What exactly is a skip-level meeting? Lucas: It's a one-on-one between you and your direct report's direct report. So if you manage Sarah, and Sarah manages Alex, you meet with Alex directly — skipping Sarah. The goal isn't to check up on Sarah. It's to understand Alex's experience and see if there are patterns Sarah might be too close to notice. Luna: And you're doing this without undermining Sarah, right? That's the tricky part. Lucas: Right. The first rule: you never use a skip-level to evaluate your direct report. If Alex says something that reflects poorly on Sarah, your job is to coach Sarah, not punish her. But more on that later. Luna: So who should a new manager skip-level with first? Lucas: Start with the most junior people on the team — the ones who might feel invisible. They're often the ones with the most unfiltered perspective. Also, anyone who's been on the team less than six months; they can spot the gaps between what's promised and what's delivered. Luna: And how do you set it up without making people nervous? Lucas: Transparency. I tell the skip-level: 'I'm meeting with everyone on the team one level down to understand how work is flowing. Nothing you say will be attributed to you. I'm not checking on your manager — I'm checking on the system.' And I copy my direct report on the invite so there's no secrecy. Luna: That's smart. Now — what's the actual agenda? A skip-level shouldn't be a status update. Lucas: No, it's about three things. First: what's working well that we should keep doing? Second: what's getting in the way of your best work? Third: what could your manager — my direct report — start, stop, or continue doing? That last one is the gold. Luna: And if they clam up? Blank stares? Lucas: I ask for a specific example from last week. 'Tell me about a time you felt blocked.' Or 'What's one process you'd change if you could?' People find it easier to talk about a situation than about a person. Luna: What about the elephant in the room — what if the skip-level starts venting about their manager? About your direct report? Lucas: That happens. And the instinct is to jump in and fix it. Don't. Instead, say something like: 'Thank you for being honest. I want to make sure we address this in a way that protects the relationship. Let me think about how to bring this up constructively.' Then you do bring it up with your direct report — but framed as a pattern, not a complaint. Luna: So you anonymize it. Lucas: Always. I say 'a few people on the team have mentioned that project hand-offs feel unclear' — not 'Alex said you're dropping the ball.' The skip-level has to trust that you'll protect their identity. Luna: What if the feedback is about you? Your decisions? Lucas: Then you listen. Thank them. And actually consider it. If a skip-level tells me a policy I championed is creating busywork, I owe it to them to revisit it — or at least explain the reasoning. That builds enormous trust. Luna: How often should a new manager do these? Lucas: Every six to eight weeks. Monthly is too frequent — you'll struggle to find new things to talk about, and it starts to feel like surveillance. Quarterly is too infrequent; you lose continuity. Every six weeks hits the sweet spot. Luna: And how long should each meeting be? Lucas: Twenty-five to thirty minutes. Enough time for depth, but not so long that it drains the skip-level's day. And I always let them end early if they've said everything. Luna: One thing I struggled with — when I heard a problem during a skip-level, I wanted to fix it right away. But that made my direct report feel undermined. Lucas: That's the biggest trap. The skip-level isn't your channel for operational fixes. It's an information channel. You take what you learn and feed it back to your direct report in a coaching conversation. You empower them to make the change. Otherwise, you're just doing their job. Luna: Okay, so let's say I've done a few skip-levels. I've gathered patterns. Now what? Lucas: You summarize themes — not names — and share them with your direct report. Then ask: 'What do you think is driving this? What's one thing you'd like to try?' Then let them lead. Your role is to support, not override. Luna: And if the pattern is something your direct report can't fix alone — like a resource issue or a cross-team bottleneck? Lucas: Then you escalate together. You say to your direct report: 'This seems like something we need to bring to the leadership team. Do you want to present it, or would you like me to?' That builds their credibility, too. Luna: This is really helpful. I think a lot of new managers skip skip-levels because they're afraid of the awkwardness. Lucas: The awkwardness fades after the first one. And the payoff is huge — you catch problems early, you build trust across the org, and you get a reputation as a manager who actually listens to the people doing the work. Luna: If today was actually useful to you, these conversations stay ad-free because of listener support. You can help keep them going at buy me a coffee dot com slash fexingo. Lucas: Yeah, that really does make a difference. Every contribution helps us keep the show focused on practical advice, not sponsors. Luna: So, Lucas — any final piece of advice for someone about to run their first skip-level? Lucas: Yes. Remember that you're there to learn, not to audit. Go in curious. Ask open questions. And then actually do something with what you hear. Nothing kills trust faster than a skip-level where nothing changes.