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: Today we are talking about the skip-level meeting. The one-on-one you have with your direct report's direct report. The meeting that makes most new managers more nervous than a performance review. Luna: I remember my first one. I spent the whole twenty minutes worrying about what my direct report would think if they found out what I talked about with their team member. Lucas: Right, and that's the core tension. You're trying to get unfiltered information about how things are going two levels down, without undermining the person who reports to you. It's a delicate balance. Luna: So walk me through it. How do you set one up without making it weird? Lucas: Let's use a concrete example. Say you're a new engineering manager at a mid-sized B2B SaaS company. You manage three team leads, each of whom manages four or five individual contributors. You've been in the role for about six weeks. You've had your one-on-ones with your team leads, but you haven't met the individual contributors beyond a quick intro. Luna: That's exactly the scenario. You don't want the team leads to feel like you're going around them. Lucas: Exactly. So first, you communicate the purpose to your direct reports. You say something like, 'I'm going to start having quarterly conversations with folks two levels down. My goal is to understand what's working, what's getting in the way, and where I can help remove blockers. I'm not there to evaluate anyone. And I'll share general themes with you, but not specific things individuals say.' Luna: That framing is key. You're not checking up on them. You're trying to be a better leader for the whole group. Lucas: Right. Then you schedule the skip-level meetings. Thirty minutes, not an hour. You don't need an hour. And you make sure it's not in a conference room — you want it to feel like a conversation, not an interview. Luna: What do you ask? I remember my first skip-level, I asked the same questions I ask in a regular one-on-one. That was a mistake. Lucas: Different questions. You're not their manager, so you shouldn't be asking about their project status or their career goals at the same level of detail. You're looking for patterns. I like a three-part structure. First, build trust: 'What's one thing you're excited about at work right now?' and 'What's one thing that's frustrating you?' Luna: Those are good because they're low-stakes but can reveal a lot. Lucas: Second, understand team dynamics: 'How would you describe the way your team communicates?' and 'Is there anything your team lead does that you wish they'd do more or less of?' That second question can be uncomfortable, so you have to preface it with, 'I'm not asking to get anyone in trouble. I'm asking so I can help your lead be more effective.' Luna: And you have to mean that. If you then go and say, 'Alex said you micromanage,' you've broken trust. Lucas: You handle that by aggregating. If three people mention the same thing, you say to the team lead, 'I'm hearing from a few people that they'd like more autonomy on certain tasks. Let's brainstorm how to create that.' Luna: That's smart. It's not singling anyone out. Lucas: Third part: surfacing blockers. 'If you could change one thing about how the company operates, what would it be?' or 'Is there something that takes up your time that you think shouldn't?' Luna: Those can yield really actionable insights. I once heard from a skip-level that the team spent three hours a week manually updating a spreadsheet because the reporting tool didn't integrate with their pipeline. That was a quick fix. Lucas: And that's exactly the kind of thing that never makes it up the chain because the team lead might not even know about it. The skip-level is your chance to catch those. Luna: Okay, but what about the follow-through? You have these conversations, and then what? Lucas: You take notes — not on a laptop, a notebook — and you look for patterns. Within a week, you should have one or two actions you can take. Maybe it's removing a process bottleneck. Maybe it's starting a working group. And you communicate back to the team broadly: 'I've heard from a few of you that X is a pain point. Here's what I'm doing about it.' Luna: That closes the loop. If people see that their input leads to change, they'll be more open next time. Lucas: And you also share themes with your direct reports. Not verbatim, but general areas. 'The team is feeling good about the product direction, but there's some confusion about the new sprint process.' That way the team lead can address it without feeling undermined. Luna: There's a risk though — what if someone uses the skip-level to complain about their manager? And you know it's a performance issue, not a systemic one? Lucas: That's the hardest part. If one person has a complaint, you don't act on it. You listen, you empathize, but you don't jump in. If multiple people from the same team have a similar complaint, then you have a conversation with the team lead about leadership style, and you coach them. Luna: So you're not the skip-level's therapist, but you're also not ignoring it. Lucas: Exactly. And you have to be transparent with the skip-level about what you can and can't do. If they tell you something that is clearly a personnel issue, you say, 'I hear you. I can't share what you've told me with your manager, but I will look into the broader picture.' Luna: That's honest. It also sets expectations. Lucas: One more thing: frequency. I recommend once a quarter for each skip-level. More than that and you risk becoming their de facto manager. Less than that and you lose the connection. Luna: And what about the first time? Do you tell them it's your first skip-level? Lucas: I do. I say, 'This is my first skip-level meeting, so bear with me. My goal is to learn how things are going from your perspective.' It disarms them and makes the conversation more natural. Luna: I like that. It's vulnerable, but it builds trust. Lucas: And it's true. If you're a new manager, you're learning. Own it. Luna: Speaking of learning, we should say — we don't run ads on this show. We keep it ad-free because we think career advice shouldn't be interrupted by sponsorship messages. If you find value in these episodes and want to support that choice, you can do so at buy me a coffee dot com slash fexingo. Lucas: Yeah, it's a small way to keep this resource open and independent. Appreciate anyone who chips in. Luna: All right, back to skip-levels. One thing I want to add: after the meeting, send a brief follow-up email summarizing what you discussed and any action items. It reinforces that you listened. Lucas: Good point. And keep it short: 'Thanks for the conversation. I heard X, Y, and Z. I'll be looking into the process issue. Let me know if anything else comes up.' Luna: And cc no one. Not even yourself. Just send it from your personal folder. Lucas: Absolutely. The skip-level meeting is a confidential channel. Don't pollute it. Luna: Let's talk about what not to do. What's the biggest mistake you've seen? Lucas: Using the skip-level to gather ammunition against a direct report. If you go in looking for dirt, you'll find it, and you'll ruin the relationship with your direct report and the trust of the skip-level. The meeting is about understanding the system, not the person. Luna: Another mistake: asking leading questions. Like, 'Do you think your manager is overwhelmed?' That puts words in their mouth. Lucas: Stick to open-ended, neutral questions. 'How would you describe your team's workload?' is better. Luna: What about the flip side — when a skip-level asks you for advice on something their manager should be handling? Lucas: You gently redirect. 'That sounds like a great question for your manager in your one-on-one. If you want, I can help you think about how to bring it up.' You're coaching them to go through the chain, not around it. Luna: That's a good skill to have. It reinforces the hierarchy without dismissing their concern. Lucas: And it models the behavior you want. You're showing them that you respect the chain of command. Luna: I think we've covered the basics. Any final pro tip? Lucas: End every skip-level with this question: 'Is there anything else you think I should know that I haven't asked about?' That's often where the gold shows up. Luna: Great. I'm going to schedule my next round of skip-levels this week. Lucas: Do it. And remember — you're not there to evaluate. You're there to listen, learn, and remove obstacles. If you do that, the trust will follow.