Latest / New Manager Conversations with Fexingo: First 90 Days, Managing Former Peers, and Leadership Basics / How New Managers Can Host Effective Skip-Level Meetings
Transcript
- Lucas: So you've been a manager for maybe ninety days. You've got your one-on-ones down, you're delegating without hovering, you've survived your first performance conversation. But there's one meeting type most new leaders never schedule, and it might be the highest-leverage thirty minutes on your calendar. Luna: I'm guessing you mean skip-level meetings? Because I've seen managers avoid those like the plague. Lucas: Exactly. And it makes sense — they feel awkward. You're meeting with someone who reports to your direct report. The potential for crossed signals, for undermining your own team member, is real. But Google's Project Oxygen found that managers who run regular skip-levels see about twelve percent higher team retention compared to those who don't. That's not trivial. Luna: Twelve percent — that's huge. But I think the hesitation comes from not knowing what to actually do in that room. Is it like a one-on-one? Is it a casual coffee chat? Lucas: It's structurally different. A one-on-one with your direct is about their priorities, blockers, and growth. A skip-level is about the broader team's health, the work environment, and things that might not surface when the middle manager is in the room. I learned a framework from a product VP at HubSpot that I love. Three questions: 'What should I know about your work?', 'What's one thing the team should stop doing?', and 'What do you need from me that you aren't getting?'. Luna: The third question is the money one. Because it gives you permission to address something that might be uncomfortable — without it being framed as a complaint about their manager. Lucas: Right. And that's the tightrope. You want candor, but you don't want to create an us versus them dynamic. So the first rule is: never ask a question in a skip-level that you wouldn't be comfortable asking your own manager in a one-on-one. If it feels like you're prying, you probably are. Luna: I actually had a bad experience with this early in my career. A senior leader scheduled a skip-level with me, and within ten minutes it was clear he was trying to figure out if my manager was dropping the ball. I felt like I was being used as a spy, not heard as a team member. Lucas: That's exactly what kills skip-levels — when they become surveillance. The best ones are transparent. You can start by saying, 'I'm not here to evaluate your manager. I'm here to understand how the team is functioning and how I can support you.' That sets the tone. Luna: Do you take notes during a skip-level? I've seen that go both ways. Lucas: I take notes openly, but I always say, 'I'm going to jot a few things down so I don't forget — and if you share something that might affect your manager, I'll ask your permission before I act on it.' That builds trust. Because if you take notes behind closed doors and then something changes, people know where it came from. Luna: That's smart. And it gives the employee a sense of control over what gets escalated. Lucas: Exactly. Now, frequency — I recommend once a quarter for each team member who's two levels down. More than that and it starts to feel like you're bypassing the middle manager too often. Less than that and you lose continuity. Luna: And what about the manager in the middle? Do you tell them you're having these conversations? Lucas: Absolutely. You should tell your direct report, 'I'm planning to do skip-levels with your team. I'll share general themes back with you, but I'll keep individual conversations confidential.' That way there's no sense of an end-run. It's a partnership, not a secret check. Luna: I like that. So the manager in the middle feels included, not circumvented. Lucas: And here's a practical tip: keep it to twenty-five minutes. That's enough time for three good questions and a bit of off-topic chat. Anything longer and it drifts into performance-review territory. Luna: Twenty-five minutes — I'm writing that down. Now, what if you get a piece of feedback that's clearly about the manager? Like, 'My manager never gives me feedback.' How do you handle that without breaking trust? Lucas: First, thank them and say, 'I appreciate you sharing that. I'd like to check in with your manager about team-wide feedback practices without mentioning you specifically.' Then you go to the manager and say, 'I've heard from a few people that feedback is a growth area for the team. Can we talk about your process?' You never breach the confidence. Luna: So you aggregate themes. That's the safe play. Lucas: It's the respectful play. And it makes you a better leader because you're seeing the team's reality, not just the filtered version your direct report presents. Which brings me to something I think about a lot. Luna: What's that? Lucas: If we've helped you think through a leadership move or a tricky team situation, and you find yourself coming back to these conversations, that's the kind of signal that tells us this show is hitting the mark. We keep the show ad-free, and listener support at buy me a coffee dot com slash fexingo is what makes that possible. It's a small way to keep the conversation going. Luna: Yeah, I think a lot of listeners use these episodes as a kind of playbook and I love that. It means we're giving you real frameworks, not just theory. Lucas: So back to skip-levels — one more nuance. If you're managing former peers, skip-levels can feel even trickier. Because you used to be at their level, and now you're meeting with someone who's a level below them. That dynamic can breed distrust if you're not careful. Luna: Right, because the person you're skip-leveling might think, 'Oh, she's just trying to find out if her old buddy is slacking.' Lucas: Exactly. So in that case, you lean extra hard on the transparency piece. You say, 'I used to work alongside your manager, and I want to make sure I'm supporting the whole team, not just my old relationships.' That honesty actually builds more trust than pretending the history doesn't exist. Luna: That's a good point. Acknowledging the elephant in the room. Lucas: Now, what about the opposite scenario — when you're a new manager and your own boss wants to skip-level your team? That can feel threatening. My advice: lean into it. Offer to set up the meetings yourself. Say, 'I think it's great you want to connect with the team. Let me schedule them and give you context on each person.' That puts you in the driver's seat. Luna: And it shows you're not afraid of what they might hear. Lucas: Exactly. Confidence breeds confidence. If you're defensive about skip-levels, it looks like you have something to hide. If you welcome them, it signals that you're secure in your leadership. Luna: So let's say I'm a new manager and I want to start doing skip-levels next week. What's my action plan? Lucas: Three steps. First, tell your direct report about the plan and get their buy-in. Second, schedule twenty-five minute meetings with each person two levels down — spread them out over two weeks so you're not doing five in one day and getting fatigued. Third, prepare three open-ended questions and commit to not taking any action that would reveal an individual's identity without permission. Luna: That sounds doable. And I'd add one thing: after the first round, share an aggregate summary with the whole team — like, 'Here are three themes I heard, and here's what I'm going to do about them.' That closes the loop. Lucas: That's a fantastic addition. It shows you listened and you're acting. Which is ultimately the whole point — skip-levels aren't a check the box exercise. They're a tool for building a healthier organization, one honest conversation at a time. Luna: So next time you're tempted to skip the skip-level, think about that twelve percent retention number. Lucas: And think about the signal it sends. You're saying, 'I care enough to hear from everyone, not just the people who report to me directly.' That's the kind of leadership that makes people want to stay.