Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / How to Find a Mentor Who Actually Challenges You
Transcript
- Lucas: We talk a lot on this show about finding a mentor who supports you, who opens doors, who gives you advice you can actually use. And all of that matters. But there's a type of mentor that's actually more valuable — and harder to find. The mentor who challenges you. The one who pushes back, who tells you your idea isn't good enough, who makes you uncomfortable. Luna: Right, the 'yes-mentor' versus the 'constructive friction' mentor. I've definitely had both. Lucas: Exactly. And the research backs this up. A study from Harvard Business Review a few years ago found that professionals who had mentors who provided both career support and what they called 'challenging assignments' — meaning the mentor actively pushed them into discomfort — advanced faster and reported higher satisfaction than those whose mentors only offered emotional support. Luna: So it's not just about feeling good. It's about actual career velocity. Lucas: Right. And I want to ground this in a specific story. I was talking to a product manager at HubSpot — let's call her Sarah. She's been there about six years, and she told me her biggest promotion came after she started working with a senior director who was famously blunt. Sarah said her first few feedback sessions were brutal. The director would say things like, 'This roadmap is incremental thinking. You're not solving a real problem.' And Sarah was used to getting praise. Luna: Ouch. That's the kind of feedback that stings in the moment but sticks with you. Lucas: Exactly. And Sarah told me she almost quit that mentorship after two sessions. But she stayed, and she started rethinking how she approached product strategy. She said the turning point was when the director told her, 'I'm not being hard on you because I don't like you. I'm being hard because I see potential, and I don't want you to settle.' That reframed everything. Luna: That's a powerful reframe. And it's also a big ask — to trust someone who's making you uncomfortable. Lucas: It is. And that's why most of us default to mentors who are affirming. They're easier to be around, they validate our choices, and they make us feel smart. But the data suggests that the mentors who actually move the needle are the ones who create what psychologist Adam Grant calls 'constructive friction.' Luna: So how do you find that kind of mentor? Because you can't exactly ask on LinkedIn, 'Hey, will you make me uncomfortable?' Lucas: You can, actually. But you have to be strategic about it. The first step is to look for people who have a reputation for candor — not rudeness, but directness. In most organizations, those people are known. They're the ones who speak up in meetings, who ask hard questions, who don't let bad ideas slide. Luna: So you're saying seek out the person who's a little intimidating. Lucas: Exactly. But the next step is to approach them in a way that signals you're ready for that. When you ask for mentorship, you frame it as: 'I'm looking for someone who will tell me what I need to hear, not what I want to hear. I want to grow faster, and I think your perspective could help me see my blind spots.' That's a very different ask than 'Can you give me career advice?' Luna: That's smart. You're essentially giving them permission to be candid before they even start. Lucas: Right. And you also need to be specific about the areas where you want challenge. Not a vague 'help me get better.' But something like, 'I'm working on my strategic thinking, and I'd love for you to poke holes in my logic on this upcoming project.' That gives them a concrete place to start. Luna: And what about when you're already in a mentorship and you realize it's too comfortable? Like, your mentor is great but they never really push you. Lucas: That happens. And it's not necessarily a bad mentor — they might just have a different style. But you can actually ask for more friction. You can say, 'I feel like I'm plateauing a bit. Could you be more critical of my assumptions next time we meet? I really want to stress-test my thinking.' Most good mentors will respect that request. Luna: So it's not about changing the mentor, it's about changing the terms of the relationship. Lucas: Exactly. And if they can't or won't adapt, that's a signal you might need a second mentor who plays that role. Because one mentor doesn't have to be everything. You can have a supportive mentor and a challenging mentor. Luna: That's a good point. Diversify your mentorship portfolio. Lucas: Right. And the challenging mentor doesn't even have to be in your industry. Sarah at HubSpot told me her most transformative mentor was actually a former engineer who had moved into product — but from a completely different domain, like hardware. He didn't know the SaaS playbook, so he questioned everything. Luna: That's interesting. A mentor from a different industry can challenge you in ways an insider can't, because they don't take the same assumptions for granted. Lucas: Exactly. And they're often more willing to say, 'Why are you doing it that way?' without worrying about office politics. So one practical tip: if you want constructive friction, look outside your direct function or industry. Luna: Okay, but let's talk about the downside. What if the challenge becomes too much? When does constructive friction turn into destructive friction? Lucas: That's a crucial question. The line is crossed when the feedback is no longer about your work or your growth, but becomes personal, demeaning, or consistently negative without any constructive path forward. A good challenging mentor will also point out what you're doing well. They'll say, 'This part is strong, but this part needs work.' They don't just tear you down. Luna: So it's about balance. The criticism should feel like it's coming from a place of wanting you to succeed, not just wanting to be right. Lucas: Exactly. And you also need to gauge your own capacity. If you're in a period of high stress or low confidence, a highly challenging mentor might not be what you need right now. It's okay to take a break and come back to that kind of relationship later. Luna: That's a really important caveat. Self-awareness matters here. Lucas: Absolutely. And one more thing: when you get that kind of hard feedback, the way you respond matters. The best reaction is to pause, say 'Thank you, I need to think about that,' and then actually reflect. Don't get defensive. Don't explain away. Just absorb it. Luna: Harder than it sounds, but that's the growth moment. Lucas: It really is. And here's something I've noticed: the people who benefit most from challenging mentors are the ones who are already pretty good. Because if you're early in your career, you need more foundational support. But once you're solid, the thing holding you back isn't a skill gap — it's a blind spot. And only someone willing to point it out can help you see it. Luna: So this is particularly relevant for mid-career professionals, or high performers who are already getting positive feedback. Lucas: Exactly. And that's where a mentor who challenges you becomes a differentiator. The people who get promoted to senior levels are often the ones who sought out that friction. Luna: That reminds me of something one of our listeners mentioned — that they actually found a challenging mentor through a professional development program at their company. The mentor was assigned, and they were nervous at first, but it turned out to be the best thing for their career. Lucas: Yeah, formal mentorship programs can be hit or miss, but if you get paired with someone who has a reputation for being direct, lean into it. Don't shy away. Luna: So to wrap up the practical side: how would you recommend someone start looking for a challenging mentor this week? Lucas: Three steps. First, identify someone you respect who has a track record of asking hard questions — in meetings, in reviews, wherever. Second, reach out with a specific request that signals you want candor, not comfort. Third, once you start the relationship, give them explicit permission to be critical. And then — this is the hardest part — actually show you can take it. Follow up on their feedback. That builds trust. Luna: And if you don't have access to senior people in your own company, you can find them through industry groups, alumni networks, or even on LinkedIn — just be clear about what you're looking for. Lucas: Exactly. And one more thing — we talk a lot about giving back on this show. And one way to do that is to be that challenging mentor for someone else, once you have the experience. It's a gift that keeps giving. Luna: Speaking of giving back — and this ties in because we're talking about people who invest their time and candor — we want to say a quick thank you to the listeners who support this show. It's a small group, but it makes a real difference. Lucas: Yeah, genuinely. If the conversations on this podcast have helped you think through a career decision or find a mentor, and you want to keep it going, a handful of listeners chip in monthly through buy me a coffee dot com slash fexingo. And that's literally what keeps this ad-free and sustainable. Luna: It's not a big ask — just if it's added value for you, it's a way to ensure we can keep having these conversations. Lucas: Right. And back to the topic — one thing I want to emphasize is that the best challenging mentors are often the ones who've been challenged themselves. They know what it feels like to be pushed, and they do it from a place of empathy. Luna: So it's not about being harsh for the sake of it. It's about caring enough to be honest. Lucas: Exactly. And that's the kind of mentor we should all aspire to be.