Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / How to Find a Mentor When You Keep Picking the Wrong Person
Transcript
- Lucas: So you've decided you need a mentor. You've read the articles, you've asked around, maybe you even approached someone. And then... nothing. Or it was awkward. Or the person gave you generic advice and you felt like you were wasting their time. Luna: Right, and you start wondering: is it me? Am I just bad at this? Lucas: Exactly. But here's the thing — most of the time it's not about you being bad at mentorship. It's about picking the wrong person. And we don't talk enough about how to do that well. Luna: We've done episodes on finding a mentor when you're an introvert, when you're a new manager, when you're changing industries. But I don't think we've ever addressed the question: 'What if I keep choosing the wrong mentor?' Lucas: That's today. And I want to start with a number. I came across a study from the Association for Talent Development — they found that roughly 40 percent of formal mentoring relationships end prematurely. Not because the mentor was bad, but because the fit was off. Luna: Forty percent. That's huge. And that's just the ones that formally end — think about all the ones that just slowly die. Lucas: Right. The ones where you stop scheduling calls, or you both get busy, and you never address it. So the question becomes: how do you vet a mentor before you officially ask them? Luna: I think a lot of people skip the vetting. They see a senior person they admire, they ask them to be their mentor, and they expect magic. Lucas: And that's the mistake. The ask itself should come after a period of exploration. I call it the 'pre-mentor conversation.' It's a low-stakes coffee chat — no formal ask, just curiosity. You want to see if there's chemistry. Luna: So you're basically test-driving the relationship before you commit. Lucas: Exactly. And during that conversation, you're looking for three things. I call them the three-filter rule: expertise, chemistry, and availability. Luna: Break those down for me. Lucas: Filter one: expertise. Does this person have the specific knowledge or experience you need? Not just 'they're successful.' I mean, do they know the industry you're trying to break into? Have they managed the kind of team you want to lead? Have they navigated a career pivot? Luna: I've seen people pick mentors who are incredibly accomplished but in a completely different field, and then they wonder why the advice doesn't translate. Lucas: Right. Filter two: chemistry. Do you feel comfortable being honest with this person? Can you tell them you're struggling without feeling judged? Do they listen more than they talk? Luna: That's a big one. I had a mentor once who spent the entire first meeting telling me about their own career. I left feeling like I knew everything about them and nothing about what I should do. Lucas: That's a red flag. A good mentor asks questions. Filter three: availability. This is the one people ignore the most. Someone can be brilliant and warm but have zero bandwidth. If they travel constantly or have three mentees already, it's not going to work. Luna: So how do you assess availability without being rude? Lucas: You ask directly. In that pre-mentor conversation, say: 'What does a typical mentorship commitment look like for you? How often do you like to meet?' And pay attention to their answer. If they say 'I'm really busy but I'll try,' that's a no. Luna: Interesting. So you're basically giving them permission to say no upfront. Lucas: Exactly. And if they say no, that's fine. You've saved both of you time. I want to share a story about a marketing manager I spoke with recently. Let's call her Priya. Luna: Okay. Lucas: Priya was in her early thirties, working at a mid-size tech firm. She wanted to move into product marketing. She found a senior director at another company who was a well-known speaker. She reached out, he agreed to mentor her. First meeting was great. Second meeting, he was distracted. Third meeting got rescheduled three times. After six months, she had had maybe two real conversations. Luna: Classic mismatch. He had the expertise but not the availability. Lucas: Right. So she tried again. This time she picked someone from her own company, a VP she'd worked with on a project. They had chemistry, she thought. But it turned out this VP's advice was all about internal politics — who to befriend, which meetings to attend. Priya wanted skill-building, not office politics. Luna: So the expertise filter failed. The person had experience but not the right kind. Lucas: Exactly. Third time, Priya did the pre-mentor conversation. She found a product marketing lead at a different company through a mutual connection. She asked about her background, how she learned product marketing, what a typical mentorship looked like for her. The woman said she met every two weeks for thirty minutes, and she had room for one more person. Priya said yes. That relationship lasted two years and led to her landing a product marketing role. Luna: So the third time worked because she used the filters. She checked expertise — yes, this person had done the exact transition. Chemistry — yes, they clicked. Availability — yes, it was clear and consistent. Lucas: That's the framework. And I think it's especially important now, in mid-2026, when so many of us are working in hybrid or remote setups. You can't rely on bumping into a mentor in the hallway. You have to be intentional. Luna: That's a good point. In a remote environment, the pre-mentor conversation might be a Zoom call, but the filters still apply. Lucas: Totally. And one more thing I want to add: don't be afraid to end a mentoring relationship that isn't working. We put so much pressure on ourselves to make it last, but if it's not serving you after a few sessions, it's okay to say, 'Thank you, I think I've gotten what I needed for now.' Luna: That's actually liberating. Because a lot of people feel obligated to keep meeting out of politeness. Lucas: And that wastes everyone's time. A good mentor would rather you be honest than ghost them. Luna: Speaking of being honest — I think this conversation about choosing the right mentor is really valuable. And if you've gotten something out of this episode, or out of the Career Mentor Podcast in general, we do have a way you can support the show. It's a small thing, but it makes a difference. Lucas: Yeah. If today was worth a coffee to you, you can buy us one at buy me a coffee dot com slash fexingo. That's it. No tiers, no perks, just a simple way to keep this ad-free and focused on content like this. Luna: And we really appreciate it. Now, back to the filters — I want to talk about one more aspect: what if you find someone who passes all three filters but you're still not sure? Is there a fourth filter we're missing? Lucas: That's a great question. I think the fourth filter is alignment of values. Do you share the same basic principles about work? If your mentor believes in aggressive self-promotion and you're more collaborative, that's going to create friction. Luna: So values are part of chemistry? Or separate? Lucas: I see it as a subset of chemistry, but it's worth calling out. You can have great rapport with someone but fundamentally disagree on what 'good work' looks like. That will show up in the advice they give you. Luna: So to recap: expertise, chemistry, availability, and values alignment. That's a pretty solid checklist. Lucas: And the pre-mentor conversation is the tool to check all four. Don't skip it. It's the difference between a 40 percent failure rate and a relationship that actually accelerates your career. Luna: I think a lot of people will breathe a sigh of relief hearing this — knowing it's not their fault, they just needed a better process. Lucas: Exactly. And if you've had a mentorship that didn't work out, I'd love to hear about it. We may do a follow-up episode with listener stories. Luna: That sounds great. For now, I think the key takeaway is: vet before you commit. Your mentor is too important to leave to chance. Lucas: Absolutely. Thanks for listening, and we'll talk next time.