Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / How to Find a Mentor When You're a Middle Manager
Transcript
- Lucas: So Luna, you know that feeling when you're a middle manager stuck between your team and the executive floor, and everyone assumes you already have all the answers? Luna: Oh, absolutely. It's like you're supposed to translate strategy into action, but you're also the one who has to explain to your team why the new policy makes zero sense. Lucas: Right. And that's exactly why today we're talking about finding a mentor when you're a middle manager. Because the usual advice — go find a senior executive to guide you — often misses the mark. You need someone who gets the unique squeeze of being both boss and subordinate. Luna: And before we dive into the strategies, I just want to say — we're glad you're here. We keep this show ad-free because we think that's the right way to have these conversations. If that matters to you, and you want to support that choice, you can find us at buy me a coffee dot com slash fexingo. No pressure, just knowing you listen is enough. Lucas: Exactly. It's a small way to keep this free for everyone. Anyway, let's dig into the middle manager mentorship gap. Lucas: First, let's name the problem. A lot of mentorship advice assumes you're early in your career and just need someone to show you the ropes. But as a middle manager, you've already got a solid skill set. What you're missing is perspective — how to navigate the political landscape, how to influence upward, and how to develop your own leadership style without losing your identity. Luna: And that's not something your boss can always provide, because they're the ones evaluating you. You need someone outside that line of sight. Lucas: Exactly. So the first strategy is to look for a mentor who's been in your exact seat before — someone who's now a senior leader but still remembers what it was like to manage a team while also reporting to a director. They can offer the 'been there' wisdom that's so much more useful than generic advice. Luna: But how do you find those people, especially if you're not naturally connected to the C-suite? Lucas: You can start with your own network of peers from previous jobs or industry events. Look for someone who's a level or two above you but not in your direct reporting chain. A good way to approach them is with a specific question about a challenge you're facing — like 'how did you handle your first budget cut as a manager?' That kind of specificity makes it easy for them to say yes. Luna: That's smart. It's less intimidating than 'will you be my mentor?' and more likely to get a genuine response. Lucas: Right. And don't overlook the power of peer mentorship. You might think you need someone above you, but other middle managers in different departments or even different companies are facing the same struggles. You can form a 'peer mentor circle' — four or five of you meet once a month, share dilemmas, and give each other honest feedback. Luna: I love that. It's like a mini advisory board for your career. And it's more reciprocal, which can feel less awkward than a traditional mentor-mentee dynamic. Lucas: Exactly. And here's a counterintuitive one: consider reverse mentoring with one of your direct reports. You get a younger person's perspective on technology, trends, or even how your team perceives you. They get exposure to leadership thinking. It's a win-win. Luna: That's a great way to build trust too. It shows you're humble enough to learn from anyone. Lucas: And it can be as simple as setting up a monthly coffee chat where you ask them about their generational cohort's take on a work-related topic. You're not looking for them to solve your problems, but to broaden your lens. Luna: So, what about the elephant in the room? If you work in a company that's really hierarchical, asking for a mentor at all might feel risky. How do you navigate that? Lucas: Good question. In a rigid culture, you might keep your mentorship search outside the company. Professional associations, alumni networks, even LinkedIn can be a safe space. You can also approach someone you trust in HR who might informally connect you with a mentor in another division. Luna: And if you're in a startup or a flat organization, there might be fewer obvious senior people. But you can still find mentors among founders or investors, right? Lucas: Absolutely. In a startup, you might have more direct access to the CEO than you'd think. A lot of founders appreciate a manager who wants to grow strategically. You can ask for advice on a specific business challenge, not just your career. That's a mentor relationship that benefits both sides. Luna: Let's talk about the ask itself. How do you actually approach someone without sounding like you're just using them? Lucas: The key is to make it about a specific problem, not a vague 'please mentor me'. So instead of 'I want to learn from you', say 'I'm facing this challenge with my team's morale, and I'd love your perspective on how you handled a similar situation'. That gives them a clear way to contribute, and it's flattering because it shows you respect their expertise. Luna: That makes sense. And you're not asking for a long-term commitment right away. It's more like an informational conversation that can grow into something more. Lucas: Exactly. And if that conversation goes well, you can suggest meeting again. But always be respectful of their time. A good mentor relationship is built on mutual value, not just one person taking. Luna: So, what are some specific things you should be looking for in a middle manager mentor? Is there a checklist? Lucas: I'd say three things. One, they should be someone who has successfully managed a team while also navigating upward influence. Two, they should be willing to give you honest feedback, even if it's uncomfortable. And three, they should be connected — maybe not to the C-suite, but to a network that can open doors for you. Luna: And how do you vet for those qualities before you invest time? Lucas: You can start by asking them about their own career journey. If they talk about their team with pride and also mention challenges they faced with senior leadership, that's a good sign. You can also ask a mutual connection about their mentoring style. And remember, you're not looking for a friend; you're looking for someone who will push you to grow. Luna: That's a good reminder. And I feel like there's a special challenge for first-time managers who are now managing former peers. That's a whole different beast. Lucas: Oh, for sure. That's one of the toughest transitions. If you're in that boat, you might want a mentor who specifically has experience with that transition — someone who can help you set boundaries and re-establish authority without ruining relationships. That's a niche but valuable mentorship. Luna: So, how do you actually structure a mentorship relationship once you've found someone? Is it just a monthly call? Lucas: It depends on the person, but a good rhythm is a monthly 30-minute call or coffee. You should come prepared with an agenda, even if it's just three bullet points. And you should always follow up with a thank-you email summarizing what you discussed and what you're going to do differently. That shows respect and makes the relationship more effective. Luna: And what about setting expectations? Should you be explicit about what you hope to get? Lucas: Yes, but gently. In that first conversation, you can say something like 'I'm looking for guidance on navigating middle management, and I'd love to get your perspective over the next few months'. That sets the stage without making it formal or heavy. Luna: And if the chemistry isn't right, you're allowed to move on, right? It's not a marriage. Lucas: Absolutely. If you're not getting value after two or three sessions, it's okay to politely end it. You can say 'I've really appreciated your time, but I think I've got what I needed from this for now'. That's professional and honest. Luna: Let's also not forget the sponsor angle. We talked about sponsors in episode 152, but for middle managers, a sponsor is often more impactful than a mentor. How do you find a sponsor? Lucas: That's a great point. A sponsor is someone who uses their political capital to advocate for you when you're not in the room. For a middle manager, that can be the difference between getting that promotion or being overlooked. Finding a sponsor is similar to finding a mentor, but you're looking for someone who's willing to put their reputation on the line for you. Luna: And how do you make yourself sponsor-worthy? Lucas: You need to be visible and reliable. Take on high-visibility projects, deliver results, and make sure your successes are known to the right people. A sponsor is more likely to advocate for someone who's already making them look good. It's about building trust through performance. Luna: So, for someone listening right now, what's the one action they can take today to start this mentor search? Lucas: I'd say: pick one person you admire who's a level or two above you, and send them a concise, specific message asking for a twenty-minute coffee conversation. Mention a specific challenge you're facing. That's the first step. And don't be afraid if they say no — you've already practiced the ask, and there are plenty of other people out there. Luna: That's a solid plan. And I think the biggest takeaway is that middle managers need a different kind of mentorship — one that understands the unique pressures of being in the middle. It's not just about climbing the ladder; it's about learning to navigate the rungs that are already under you. Lucas: Well said. So next time you're feeling stuck between your team and your boss, remember that you're not alone. There are people who've been exactly where you are, and they're often willing to help if you approach them the right way. And maybe that's the real mentorship lesson: it's not about finding a perfect guide, but about building a network of people who can see your path from different angles.