Latest / New Manager Conversations with Fexingo: First 90 Days, Managing Former Peers, and Leadership Basics / How New Managers Can Run a Great Skip-Level Meeting
Transcript
- Lucas: So there's this moment that happens maybe four to six weeks into a new manager role — you get a calendar invite from someone two levels up, and the subject line just says 'chat'. No agenda, no attached deck, and suddenly you're supposed to have a skip-level meeting, and nobody ever told you how to run one. Luna: I remember my first one. I spent the entire night before rehearsing what I thought my boss's boss wanted to hear, and then she just asked me how things were going and I froze. Lucas: Right, because the instinct is to treat it like a status update or a pitch. But a skip-level meeting is actually a completely different animal. It's not about reporting progress — it's about building a relationship with someone who has a much broader view of the organization, and who can advocate for you and your team in ways your direct manager can't. Luna: Okay, so what's the actual goal? Are you trying to impress them, or is there something more specific you should be trying to get out of it? Lucas: I'd say the goal is twofold. First, you want to leave them with a clear, honest picture of what's happening on your team — the wins, but also the friction points, because they're probably not getting that level of detail from your boss's status reports. And second, you want to learn something about the broader business context that can help you make better decisions as a manager. It's a two-way street, and that's the part most first-timers miss. Luna: So you're saying it's not a performance review for you, and it's not a chance to complain about your boss either. Lucas: Exactly. It's a strategic conversation. And the preparation starts long before you walk into the room. I like to think of it in three phases: before, during, and after. Before the meeting, you need to do your homework. That means understanding what your skip-level's priorities are — what are they being measured on, what are the big initiatives they care about? You can usually find this out from company all-hands, their recent emails, or just by asking your direct manager what the skip-level is most focused on. Luna: And during the meeting, what's the right structure? Should you come in with a slide deck or is that too much? Lucas: No slides. This is a conversation, not a presentation. But you should absolutely come in with a mental agenda. I'd suggest opening with a brief update on your team — one or two wins, one challenge you're working through. Keep it to two minutes max. Then pivot to questions. The best skip-level meetings are driven by questions, not updates. Luna: What are the questions that actually work? I feel like generic questions like 'how can I help?' can fall flat. Lucas: Yeah, 'how can I help' is a bit lazy. You want questions that show you're thinking about the business, not just your own team. Here are three I've seen work well. One: 'What's the biggest challenge you're seeing across the department right now?' That gives you context and shows you're not siloed. Two: 'What's something you wish you'd known as a new manager?' That's a bit softer, but it builds rapport and often gets a great story. And three: 'What are the key priorities for the next quarter that I should be aligning my team toward?' That way you're not just reacting to whatever comes down, you're proactively aligning. Luna: That third one is smart because it gives you a reason to follow up later. You can send a note saying, 'Here's how we're adjusting our team goals based on what you shared.' Lucas: Exactly. And that follow-up is the 'after' phase. You should always send a thank-you email within 24 hours, and it shouldn't be a generic 'thanks for your time.' It should summarize two or three key takeaways and any action items you committed to. That shows you're organized and serious about the conversation. Luna: But there's a tricky part here — what if your skip-level raises a concern about your direct manager? Or what if you learn something that might reflect poorly on them? How do you handle that without creating tension? Lucas: That's the delicate dance. The rule I've always followed is: don't go behind your manager's back. If the skip-level brings up an issue that involves your boss, your job is to listen, not to pile on. You can say something like, 'That's not how I've experienced it, but I'd be happy to share more if it's helpful.' And then, if it's a serious concern, you should give your manager a heads-up that the skip-level asked about it. Transparency is key. Luna: So you're advocating for a kind of radical transparency, but isn't there a risk that your manager feels like you're building a separate relationship behind their back? Lucas: There is, and that's why the follow-up matters. If you're transparent with your manager about what was discussed — not every detail, but the general themes — that actually builds trust. It shows you're not hiding anything. And in my experience, most managers are fine with it because they know skip-levels are part of the culture. What they don't like is feeling blindsided later. Luna: That makes sense. Let's talk about what you actually do with the information you get. Say your skip-level mentions a new strategic pivot that your team isn't ready for. Do you bring that to your manager right away, or do you hold onto it? Lucas: Great question. The first thing is to contextualize. Your skip-level has a different vantage point — they might be talking about something that's still in the exploratory phase, not a done deal. So you don't want to run back to your team and cause panic. But you should absolutely share it with your direct manager, because they might not have heard it yet, and that gives them a chance to prepare. Just frame it as, 'I heard this in my skip-level, and I thought you should know.' Luna: And what if the information is about your team's performance — like the skip-level has heard some negative feedback that hasn't reached you yet? Lucas: That's not a pleasant moment, but it's actually a gift. It means you have a chance to address it before it becomes a bigger issue. Thank them for the honesty, ask for specifics, and then go back to your team and look into it. Don't get defensive. That's the fastest way to lose trust with your skip-level. Luna: Let's talk about frequency. How often should you actually have skip-level meetings? Is it a one-time thing or should it be recurring? Lucas: I'd say monthly is a good cadence, at least for your first few months. It gives you enough time to actually act on things you discussed, but it keeps the relationship warm. After you've built that trust, you can shift to quarterly if that feels more natural. The key is to not let it become a box-ticking exercise. If you're just going through the motions, it's going to feel like a waste of time for both of you. Luna: What about the situation where your skip-level is genuinely too busy to meet? Like, you're a new manager and they're an executive with a packed calendar. How do you make that work? Lucas: That's a real constraint. But you can make it work by being flexible and efficient. Offer to meet for twenty minutes instead of the usual thirty. Or propose a walking meeting if they're often on the move. And always come with a clear agenda so they know it's not going to be a rambling chat. If they see you're respectful of their time, they'll be more open to making it happen. Luna: And what if they cancel twice in a row? Do you keep pushing or do you take a hint? Lucas: You keep pushing, but you make yourself easy to reschedule. And you can use that persistence as a signal that you're serious about the relationship. I remember a story from a friend who's an engineering director — as a new manager, her skip-level kept canceling, so she started sending a monthly one-page summary of her team's progress, wins, and challenges. After a couple of months, the skip-level reached out and said, 'I've been reading your updates, let's find time to talk.' The document became the meeting. Luna: That's a great workaround. It shows initiative without being pushy. Lucas: And it leads to a broader point: the skip-level is not just one meeting, it's an ongoing relationship. The more you can make that relationship useful, the more it will pay off for you, your team, and your career. Luna: I want to come back to something you said earlier about not going behind your manager's back. How do you handle a scenario where your skip-level directly asks you for your opinion on your manager's performance? That's a landmine. Lucas: It is, absolutely. The best approach is to stay positive and factual. You can say something like, 'I've been really happy with the support I've received. They've been great at helping me navigate the first few months.' If you have a specific concern, you can frame it as a development area, but you should never badmouth your boss. Not only is it unprofessional, but it also makes you look like a gossip. And it could come back to bite you. Luna: What if the question is more pointed, like 'Is there anything they could be doing differently?' Lucas: That's a classic. And you can answer honestly without throwing them under the bus. For example: 'One thing that could be helpful is more frequent check-ins as I ramp up, but I also understand there are lots of competing priorities.' That way you're giving feedback, but you're also showing empathy and understanding. And you're not saying anything that could be interpreted as malicious. Luna: That's a good middle ground. Now, for the new manager who's listening and feels nervous about their first skip-level, what's the one thing you'd tell them to remember? Lucas: Remind yourself that the skip-level is probably more nervous than you are. They don't know how you're going to react, whether you're going to be defensive or open. So if you walk in with a genuine curiosity and a desire to learn, you'll stand out. The fact that you're even thinking about this means you're probably going to do just fine. Luna: That's a comforting thought. And if you're listening and you've got a skip-level coming up, maybe start with the three questions Lucas mentioned — they really do work. Lucas: And if you've gotten something out of this show, whether it's a tip like this or just a bit of confidence before a tough conversation, a couple of dollars a month is genuinely what keeps these episodes ad-free and coming out every week. If that's worth anything to you, you can buy me a coffee at buy me a coffee dot com slash fexingo. It makes a real difference for a small show like this. Luna: Yeah, even a small contribution helps us cover the costs of editing and hosting. And it honestly feels great to know people are getting value out of these conversations. Lucas: So, to wrap it all up — skip-levels are a chance to build a bridge, not just to check a box. With a little preparation and a lot of genuine curiosity, they can become one of the most valuable relationships you have as a new manager. Luna: And if you've got a story about a skip-level meeting that went well or went sideways, we'd love to hear it. Maybe we'll share it in a future episode. Lucas: Until next time, keep asking good questions.