Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / How to Find a Mentor When You Are a Manager of Managers
Transcript
- Lucas: You've been a manager for a few years. You're good at it. You get promoted again — now you manage other managers. And suddenly, the old rules of mentorship don't apply. Luna: Right — because in theory, you're supposed to be the one with all the answers. Who do you turn to when you're the most senior person in the room? Lucas: Exactly. That's the trap a lot of senior leaders fall into. They've climbed high enough that their internal network is all peers or direct reports. And asking for help feels like admitting weakness. But the reality is, the higher you go, the more you need outside perspective. Luna: So how do you find that mentor when you're managing managers? Let's start with a real example. Who's our case today? Lucas: A VP of Engineering at a mid-stage SaaS company — about 300 employees. She was promoted from Director of Engineering about 18 months ago. She's technically brilliant, her teams ship on time, but she told me she feels like she's 'flying blind' on the strategic side — board communication, cross-functional alignment, how to think about org design. Luna: And she can't go to her CEO and say 'I don't know how to do my job' — even though that's exactly the kind of person who could help her. Lucas: Right. And her direct reports look to her for direction. So her options are limited internally. That's where the concept of 'peer mentorship' comes in — but not peer in the sense of someone at the same company. I mean someone at a similar level in a different industry or company. Luna: So a peer outside your org chart. That makes sense. No power dynamics, no fear of looking weak in front of your own boss. Lucas: Exactly. In her case, she reached out to a VP of Engineering at a different SaaS company — not a competitor, but adjacent space — who she met at a conference. They started a monthly 45-minute video call. No agenda. Just 'what's on your mind?' And within three months, she told me it was the most valuable hour of her month. Luna: What kind of things came up that she couldn't discuss internally? Lucas: Her biggest one was: how do you handle a director on your team who is technically stellar but a terrible people manager? She'd been avoiding the performance conversation because she was afraid of losing the technical output. Her peer mentor had dealt with the same situation and walked her through a specific framework for separating the two roles. Luna: That's huge. And it's the kind of thing that's hard to get from a coach who doesn't understand the engineering context, or from a friend who's not in a similar role. Lucas: Now, if you're a manager of managers and you don't have that conference connection, you have to be more intentional. I recommend building what I call a 'mentor board of directors' — three to five people, each serving a different purpose. Luna: Let's break that down. What are the seats on that board? Lucas: First, the 'industry peer' — someone at a similar level in a different company. They help with role-specific challenges. Second, the 'functional expert' — someone who knows a domain you don't, like finance or marketing, so they can help you think about cross-functional strategy. Third, the 'senior outsider' — ideally someone two or three levels above you, maybe retired, who can give you perspective on your career trajectory. Luna: And you're saying these don't have to be formal, long-term commitments. They can be ad-hoc, as needed. Lucas: Exactly. One of my own mentors I only talk to once a quarter. But when I do, it's a deep dive. The key is knowing what each person is there for. You don't ask your industry peer about career strategy — that's the senior outsider's job. Luna: There's a 2025 Harvard Business Review study that found that 63 percent of senior leaders who maintain a formal mentoring relationship report higher job satisfaction. And the effect was strongest for those who had multiple mentors, not just one. Lucas: That tracks. A single mentor can't cover all your blind spots. And for senior leaders, the blind spots get more expensive. A bad decision at that level affects hundreds of people. Luna: So how do you actually find these people? Cold outreach? Networking events? Lucas: It's a mix. The best way is through warm introductions — someone you respect who can make the connection. But cold outreach can work if you're specific about what you're asking. Don't say 'will you be my mentor?' Say 'I admire your work on X, I'm facing Y challenge, could I buy you coffee for 30 minutes?' The specificity makes it easy to say yes. Luna: And if you do get that meeting, what's the right ask? How do you move from a one-off to an ongoing relationship? Lucas: You don't. Not at first. Let the relationship develop naturally. After that first conversation, follow up with a thank-you note and maybe one insight you took away. Three months later, send them a relevant article or an update on how their advice played out. If they engage, then you can suggest a recurring check-in. But forcing it kills the trust. Luna: That's good advice. Before we go deeper into how to structure those relationships, I want to mention something. If you're finding this episode useful as you navigate your own career moves, we want to keep this show ad-free and accessible. If you're in a position to support us, you can do that at buymeacoffee.com/fexingo. It's a small gesture that helps us keep the conversation going. No pressure, just if it feels right. Lucas: Yeah, and we appreciate every bit of support. It's what lets us dig into topics like this without any sponsor influence. So thank you. Luna: Alright, back to the VP of Engineering. She built her board of directors — she found that peer mentor, plus a former CEO who now does advisory work, and a product leader from a different industry. She told me the biggest shift was in how she approaches her weekly one-on-ones with her directors. She now spends more time asking questions than giving answers. Lucas: Because she realized her job is no longer to be the technical expert — it's to develop other leaders. And that's a muscle you have to build consciously. A mentor who's been there can tell you what to look for. Luna: What's one concrete thing our listeners can do this week if they're a manager of managers looking for a mentor? Lucas: Identify one area where you feel the most uncertainty. Is it org design? Stakeholder management? Strategic planning? Then think of one person you know — even loosely — who excels in that area. Reach out with a specific question. Don't ask for mentorship. Ask for 20 minutes of advice on that one thing. Nine times out of ten, they'll say yes. Luna: And if you don't know anyone? What then? Lucas: Then you go to LinkedIn or industry forums. Look for people who write thoughtfully about that topic. Engage with their content for a few weeks. Then send a message that references something they wrote. That kind of outreach has a much higher success rate than a generic 'I'd love to pick your brain.' Luna: So it's about being prepared, being specific, and respecting their time. Lucas: Exactly. And once you've built that board, you'll find that the loneliness of senior leadership starts to fade. You have people you can be vulnerable with — without it affecting your internal reputation. Luna: That's a powerful outcome. I think a lot of managers of managers feel isolated, but they don't realize there's a structured way to solve it. Lucas: Right. The mentor board of directors isn't just a nice to have. For senior leaders, it's a strategic tool. And the earlier you build it, the better. Luna: Great advice. Thanks, Lucas. Lucas: Thanks, Luna. And thanks to our listeners. We'll see you next time.