Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / How to Find a Mentor Who Challenges Your Thinking
Transcript
- Lucas: So we talk a lot on this show about finding a mentor who believes in you, who opens doors, who vouches for you. And that's important. But there is a quieter, less flattering version of mentorship that I think a lot of professionals actually need more — and that is the mentor who challenges you. Who pushes back. Who tells you your idea is half-baked. Luna: The kind of mentor who makes you a little uncomfortable before you leave the coffee meeting. Lucas: Exactly. And I want to be clear — I'm not talking about someone who's just contrarian for sport. I mean someone who genuinely tests your assumptions because they want your thinking to be stronger. There's actually a term for this in organisational psychology — a 'disconfirmer.' Someone who deliberately presents counter-evidence to your hypothesis. Luna: I love that word. It sounds clinical, but it captures exactly the function. Disconfirming, not just disagreeing. Lucas: Right. So today I want to drill into how you find that person, how you signal that you actually want friction, and how you handle it when the friction feels personal. And I have a concrete case that I think illustrates this really well. Luna: Let's hear it. Lucas: A product manager I know — let's call her Priya — was working at a large enterprise software company. She was a high performer, getting promoted fast. She had a mentor who was essentially her biggest fan. But she realised she was only getting better at what she was already good at. She wasn't being stretched. So she deliberately sought out a mentor in a completely different division — operations, not product. And she told him, 'I want you to tell me why my roadmap is wrong.' Not 'can you give me feedback,' but specifically 'tell me why it's wrong.' Luna: That takes guts. Most of us are trained to present our best case to a mentor. She's basically inviting criticism. Lucas: And that's the key move. Because what happened is, the operations mentor looked at her roadmap and said, 'You're assuming your engineering team can deliver this in two quarters. Based on their velocity, they can't. You need to cut scope by forty percent or push the timeline.' That was not something her product-side mentor would have said. He would have said, 'That's ambitious, let's figure out how to sell it.' Luna: And that saved her from overpromising and burning credibility with engineering. Lucas: Exactly. So the first step in finding a disconfirmer mentor is to look outside your silo. If you're in marketing, look for someone in finance. If you're in engineering, look for someone in sales. You want someone who has a fundamentally different lens on what 'good' looks like. Luna: And if we've helped you think through a career move or decision — whether it's finding a mentor or handling a tough conversation — consider supporting the show. It keeps this content ad-free and available for everyone. You can do that at buy me a coffee dot com slash fexingo. No pressure, just an option. Lucas: Yeah, that genuinely helps us keep going. So back to the search — how do you actually signal that you want challenge, not comfort? I think the language matters a lot. Luna: What do you say? Like, 'please disagree with me'? Lucas: Close. I think the most effective phrase is something like: 'I have a hypothesis I'm testing, and I'd love for you to stress-test it.' That frames it as intellectual rigor, not personal vulnerability. Or you can ask a specific 'pre-mortem' question: 'If this project fails six months from now, what do you think the most likely cause will be?' That invites honest critique without making it about you. Luna: That's a great technique. And it also signals to the mentor that you're not fragile. That you can handle the heat. Lucas: Exactly. And the mentor you want will actually rise to that. The wrong mentor — the one who just wants to be nice — will deflect. They'll say, 'Oh, I'm sure it'll be fine.' That's a red flag. You want someone who pauses and says, 'Well, let me think about that... Actually, here are three things that worry me.' Luna: So part of the process is also knowing who not to ask. If someone consistently avoids giving you constructive friction, they're not the right mentor for this purpose. Lucas: Right. And there's another angle — sometimes the person you need is not more senior. It could be a peer who sees your blind spots because they work alongside you. One of the most challenging mentors I ever had was a colleague who was two years behind me in tenure but had a completely different cognitive style. She would look at my recommendations and say, 'You've assumed everyone is rational. They're not.' Luna: That's a blind spot many of us have. We build logical arguments and forget that organisations are emotional systems. Lucas: So don't restrict your search to people above you. Look for lateral mentors, even reverse mentors. Sometimes the most valuable challenge comes from someone who doesn't owe you anything — because they're not invested in your ego. Luna: What about when the challenge starts to feel personal? There's a line between constructive friction and just being demoralising. How do you tell the difference? Lucas: That's a crucial question. I think the test is: does the feedback make your thinking sharper, or does it make you want to shrink? A good challenging mentor asks questions that open up new possibilities, even if they're uncomfortable. A bad one delivers verdicts that close doors. 'Your plan has a flaw in the timing' is challenge. 'You're not strategic enough' is judgment. One is about the work, the other is about you. Luna: And if you feel the latter, you should probably back away from that relationship. Or at least recalibrate. Lucas: Right. And the best way to recalibrate is to be explicit about what you need. You can say, 'I really value your perspective, and I'm looking for specific, actionable pushback. Can we focus on that?' That often resets the dynamic. Luna: I want to talk about something that I've seen trip people up — how to thank a mentor for criticism without sounding defensive. Because a lot of us respond to challenge by explaining why we're right, which defeats the purpose. Lucas: Yes. The instinct to justify is strong. The counter-instinct is to say, 'That's a really interesting point. Let me sit with that.' Or 'I hadn't considered that — can you tell me more?' Those responses signal receptivity. They also buy you time to process without sounding attacked. Luna: And they give the mentor the signal that their challenge landed well, which encourages them to keep doing it. Lucas: Exactly. And this is where the relationship builds trust. The more you show that you can absorb challenge and come back with a stronger idea, the more the mentor will invest in you. It becomes a virtuous cycle. Luna: So let's get practical. If someone is listening right now and thinking, 'I need a disconfirmer mentor,' what is the one thing they should do this week? Lucas: I'd say identify one assumption you're making in your current project — something you've never questioned. Then find one person in your network who has a perspective that would naturally counter that assumption. It could be someone from a different function, a different level, or even a different industry. Reach out with a specific request: 'I'm testing an assumption about X. Would you be willing to play devil's advocate for twenty minutes?' Luna: And if they say yes, you've got yourself a potential mentor. Lucas: You've got the beginning of a relationship that's built on intellectual honesty, not just affinity. And that's often where real growth happens. Luna: Lucas, I think this is one of those episodes that's going to make some listeners uncomfortable — and that's exactly the point. Lucas: I hope so. Because the best career advice I ever got was not 'believe in yourself' — it was 'your plan has a hole in it, and here's why.' I want more people to have that experience.