Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / Mentorship When Your Mentor Is a Former Competitor
Transcript
- Lucas: You know that person in your industry whose name you see in every pitch you lose? The one who keeps beating you to the same clients, the same budget, the same speaking slot? Luna: I think everyone has at least one name that makes them a little tense. Lucas: Right. Well, today I want to talk about why that person might actually be the best mentor you'll ever have. Specifically, how to turn a former competitor — someone who has cost you real money, time, or status — into a genuine advisor. Luna: That sounds counterintuitive. I mean, the instinct is usually to keep them at arm's length, not invite them into your head. Lucas: Exactly. And there's a reason for that instinct. But I've been looking at a pretty compelling case. A marketing director named Priya — she's in B2B SaaS, mid-market — she was losing deals to a company called CloudSpan for about three years. Same prospects, same quarter-end, she'd get the 'we went in another direction' email, and it was almost always CloudSpan. Luna: That is the kind of pattern that makes you bitter. Lucas: It can. But what Priya did instead was reach out to CloudSpan's co-founder, a woman named Dana, and ask her for a twenty-minute call. Not to complain — to ask Dana how she thought about the market. And that call turned into a mentorship that lasted two years. Luna: What was the initial reaction? I can't imagine Dana said yes immediately. Lucas: She almost didn't. Dana told Priya later that she assumed it was a sales pitch or a competitive intelligence grab. But Priya's ask was very clean. She said: 'I respect the way you've positioned CloudSpan. I'd like to understand how you think about category creation. No pitches, no confidential information. Just your framework.' Luna: That's smart. She defined the boundary upfront. That probably made it safer for Dana. Lucas: It did. And that's the first lesson I want to hold onto today. When you approach a former competitor as a mentor, the single most important move is to make the ask narrow and non-transactional. You are not asking for their secrets. You're asking for their thinking. Luna: So it's more of a learning conversation than a traditional mentor request. Lucas: Right. And there's a three-phase arc that seems to hold across a lot of these relationships. Phase one — and this is the phase Priya and Dana were in for the first three or four months — is what I'd call arm's-length observation. You meet once a month, you talk about a specific framework or a market trend. No personal stuff. No career advice. Just ideas. Luna: That phase lets both sides test whether the other person is operating in good faith. Lucas: Exactly. And if they are, you move to phase two, which is explicit reciprocity. This is where the relationship stops being one-way. Priya, for example, started sending Dana a short monthly note with one data point she had spotted that she thought Dana might find useful. Nothing proprietary. Just a signal from the market that Dana's team might have missed. Luna: So Priya was giving value back. That changes the dynamic from 'I'm a supplicant' to 'we're peers who trade insights.' Lucas: Exactly. And that's crucial because former competitors have a very high sensitivity to being used. If they sense you're only there to extract, the relationship dies. But if you're consistently giving something of real value — a piece of intelligence, a warm introduction, a different perspective — they start to see you as a collaborator, not a scavenger. Luna: What does phase three look like? Lucas: Phase three is what I'd call genuine advocacy. This is where the former competitor starts actively championing you. In Priya's case, after about a year, Dana introduced her to three investors and two potential board members. She also started sending opportunities Priya's way — speaking gigs, partnership conversations — that weren't directly relevant to CloudSpan. Luna: That is the mark of a real sponsor, not just a mentor. Dana was putting her own reputation on the line for Priya. Lucas: Yes. And I think that's the real prize in this type of relationship. A former competitor — someone who has seen you fight — knows exactly what you're capable of under pressure. Their advocacy carries more weight because it's not based on a friendly bias. It's based on empirical observation of your performance. Luna: But I imagine not every former competitor is suitable for this. How do you even pick the right person? Lucas: Good question. I think there are three criteria. One: you need to genuinely respect their thinking. Not just their results — their thinking. Two: they need to operate with enough integrity that you trust them not to exploit the vulnerability you're showing. And three: there has to be enough distance — they're not your direct competitor in your current market anymore. Maybe they moved to a different segment, or you did. Luna: So the relationship works best when the competitive tension has cooled but the memory of it is still fresh. Lucas: Exactly. And there's one more structural thing that helps. When you set up the first meeting, send a one-paragraph agenda. I've seen this fail more often from people who just say 'can I pick your brain?' That's vague and annoying. But if you say 'I'd love to understand how you decided to enter the European market in 2024 and how you thought about the channel trade-offs,' that's specific enough that they can prepare, and respectful enough that they know you've done your homework. Luna: One of the things I wonder about is the emotional side. If someone has been a thorn in your side for years, isn't it hard to flip that switch and view them as a resource? Lucas: It is. And I don't think you should pretend the friction didn't exist. In fact, I think the best opening line acknowledges it. Something like: 'I know we've been on opposite sides of a lot of deals, and I've learned a lot from competing with you. I'd love to learn even more by talking with you directly.' That signals honesty, not amnesia. Luna: I like that. You're not pretending you were friends. You're reframing the competition as a form of learning. Lucas: Right. And that reframe is the core of the whole thing. Because if you can learn from someone who has cost you deals, you can learn from pretty much anyone. The threshold for what feels like a threat becomes much lower. Luna: It also builds a muscle that's useful beyond this one relationship. The ability to separate ego from insight. Lucas: Exactly. And it's a muscle that a lot of people never develop. They stay in the 'us versus them' frame even when 'them' could be the best teacher they ever had. Luna: If today was actually useful to you, the way these stay ad-free is listener support. Buy me a coffee dot com slash fexingo. Lucas: Yeah. It's a small thing, but it genuinely makes a difference. Keeps us independent and focused on content that helps you think differently about your career. Luna: And we mean it — if you've ever used something from this show in a real conversation or a decision, that's exactly the kind of impact we want to keep having. Lucas: Alright. So back to the arc — once you've moved through those three phases, what do you do to sustain the relationship? Because the danger with a former-competitor mentor is that the relationship can drift if you don't have a natural cadence. Luna: Right, there's no built-in reason to keep meeting once the competitive intensity fades. Lucas: Exactly. So the best approach is to create a recurring structure that is low-friction. For Priya, she and Dana settled on a thirty-minute call every six weeks. They had a shared document where they each added one question or observation before the call. That way, the conversation was always anchored in something current, not just 'so how's business?' Luna: That reminds me of what some executive teams do with 'pre-reads' before meetings. It forces preparation. Lucas: Right. And it also signals respect. Because when you show up having written down a thoughtful question, you're telling the other person that their time is valuable to you. And that matters enormously in a relationship where the power dynamic is relatively flat — neither of you reports to the other, neither owes the other anything. Luna: One thing I've noticed in my own network is that former-competitor mentors tend to be more direct. They don't sugarcoat. Maybe because they don't have the same political considerations as an internal mentor. Lucas: Yes. And that's actually one of the biggest advantages. An internal mentor — your boss, your skip-level, a senior leader in your company — they always have an institutional lens. They can't fully separate what's good for you from what's good for the organization. A former competitor has no such constraint. They can say 'that strategy you're pursuing is wrong' without worrying about your company's politics. Luna: That kind of candor is rare and precious. Lucas: It is. And it's also why these relationships can be surprisingly durable. Once the trust is established, they often outlast formal mentoring programs. Priya and Dana still talk, even though both have changed roles and Priya is now a VP at a different company. The relationship evolved from competitive to collegial to genuinely supportive. Luna: So the final takeaway might be this: the person who has been your biggest rival might also be your biggest ally — if you ask the right question in the right way. Lucas: I think that's exactly right. And I'd add one more thing: the next time you find yourself frustrated by a competitor, ask yourself what you could learn from them. The answer might surprise you. Luna: I'm going to think about who that person is for me. Lucas: Good. And if you figure it out, let us know how it goes. We'd love to hear.