Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / How to Find a Mentor When You Are Changing Careers
Transcript
- Lucas: Let me tell you about Sarah. She taught eighth-grade English for nine years. Great at it — won a teaching award. Then in early 2025, she decided she wanted to move into tech sales. Not a small pivot. And her first instinct was to find a mentor who was a senior sales leader at a SaaS company. Luna: That sounds logical, right? Go straight to the target. Lucas: It does. But it's almost always the wrong first move when you're changing careers. Sarah spent three months sending LinkedIn messages to VPs of sales. She got two replies and zero actual mentorship. The problem wasn't her — it was the ask. She was approaching people who had no frame of reference for her background. To them, she looked like a risk. Luna: So what did she do differently? Lucas: She shifted her target. Instead of the VP of sales, she started looking for what I call 'transferable skill translators' — people who had themselves made a similar jump from education or another non-sales background into tech sales. She found a guy named Dan who had been a high school history teacher and then moved into a sales development role at a CRM company four years earlier. Luna: And Dan got it immediately. Lucas: Exactly. He didn't need her to explain why teaching skills mattered in sales. He'd lived it. So the first rule for career-change mentoring: don't seek the person at the top of the mountain you want to climb. Seek someone who's already made that same climb. Luna: I think that's counterintuitive for a lot of people. We're told to 'go straight to the decision-maker.' But in mentorship, that backfires because they can't relate to your trajectory. Lucas: Right. And the second rule builds on that. Sarah's next step was to create what I call a 'career change mentor map.' She listed three categories. One: people who had made the exact same transition she wanted — teacher to tech sales. Two: people in her target role who had come from a different industry altogether — not necessarily education, but maybe retail or hospitality — so they understood the generic pivot challenge. And three: people outside her target industry who could serve as a career advisor, not a technical mentor — someone who knew her strengths and could advocate for her across a transition. Luna: So a mentor map with three tiers. That's a really concrete framework. How many people ended up in each tier? Lucas: She aimed for three to five per tier. She ended up with three in tier one, four in tier two, and two in tier three. The tier-three people were actually former colleagues from her teaching days who had moved into HR and training. They couldn't teach her how to cold-call, but they could write her a recommendation that said 'She is a fast learner who thrives under pressure' — which is exactly what a hiring manager in sales wants to hear. Luna: So the career advisor — tier three — is almost like a character reference for a career change. They vouch for your ability to adapt, not your specific skills. Lucas: That's a perfect way to put it. And that leads to the third rule, which is about how you ask. Sarah's cold email to Dan — the teacher turned sales rep — was brilliant. She wrote three sentences. Sentence one: 'I'm a former teacher exploring a move into tech sales, and I saw you made the same transition.' Sentence two: 'I'm not asking for a regular mentorship — I'd love to hear about one specific moment in your first year that was harder than you expected and how you handled it.' Sentence three: 'Would you have 15 minutes for that one story?' Luna: That's so specific. She's not asking for a lifelong commitment. She's asking for one story. Lucas: And that lowered the barrier to entry enormously. Dan said yes. The call lasted 40 minutes because he wanted to keep talking. And by the end, he offered to do a monthly check-in. That's how a career-change mentorship starts — not with a formal ask, but with a low-stakes request for a single piece of wisdom. Luna: I love that. And I think a lot of people in career transition feel like they need to prove they're worthy of mentorship first. But this approach flips it — you're saying 'I value your experience enough to ask for one specific insight.' Lucas: Yeah. And it also shows you've done your homework. You're not just copy-pasting a generic message. You've thought about what that person uniquely can offer. That respect goes a long way. Luna: Before we go deeper, I want to circle back to something that's been on my mind. We talk about mentorship a lot on this show, and we deliberately keep it ad-free because we believe this advice should be accessible to anyone, whether you're a teacher considering a career change or a seasoned executive. If you find value in these episodes and want to support that choice, you can do so at buy me a coffee dot com slash fexingo. It's a simple way to help us keep the show exactly as it is. Lucas: Yeah, and we really mean that — no ads, no sponsors, just the content we think is useful. So if you've ever gotten something out of an episode, that link is there for you. Luna: Okay, back to Sarah. So she had her map, she had her low-stakes ask. What came next? Lucas: She started having these conversations. And here's something interesting that happened. One of her tier-two contacts — a woman who had moved from retail management into a customer success role — told Sarah that she should apply for a specific sales development program at her company. That program was designed for career changers and didn't require a sales background. Luna: So the mentor actually became a sponsor. She didn't just give advice — she opened a door. Lucas: Exactly. And that's a key distinction when you're changing careers. A mentor tells you what to do. A sponsor uses their credibility to get you in the room. Sarah's tier-two contact referred her directly to the hiring manager. Sarah got an interview, and she got the job. She started in January of this year. Luna: Wow. So within about six months of starting her mentor map, she had a new career. That's a pretty compelling case study. Lucas: It is. But I want to be honest about the emotional side too. Sarah told me that the first two months of her mentor search were brutal. She got ignored, she got a couple of patronizing replies — 'Why would you leave teaching? You're so good at it.' She almost gave up. Luna: That's the part people don't talk about. The rejection when you're already feeling vulnerable because you're leaving a known identity. Lucas: Right. And that's why the tier-three career advisors are so important. Sarah's former teaching colleague who moved into HR — she was the one who said, 'You're not crazy. This is a smart move. Keep going.' That emotional support is undervalued in the mentorship conversation. Luna: So the mentor map isn't just about skills. It's also about resilience. Lucas: Exactly. And I'd add a fourth rule based on Sarah's experience. You have to be willing to offer something in return, even as a career changer. Sarah didn't have sales experience, but she had curriculum design skills. She helped Dan — her tier-one mentor — redesign the onboarding presentation for new sales hires. That was a real contribution. Luna: So it was a reverse mentorship within the mentorship. She was bringing something to the table. Lucas: Yes. And that made the relationship sustainable. Dan wasn't just giving — he was getting. That's the hallmark of a good mentorship, whether you're changing careers or not. Luna: I want to zoom out for a second. You've given us a four-part framework: find transferable skill translators, build a three-tier map, make a low-stakes ask, and offer value in return. But what about people who are changing careers and don't have a clear target yet? They know they want out, but they don't know what's next. Lucas: Great question. For that group, I'd say skip tier one entirely at first. Focus on tier three — career advisors who know you well and can help you brainstorm. And add a new tier: informational interviews with people in industries you're curious about. Not asking for mentorship, just asking 'What does your day actually look like?' That's even lower stakes. Luna: And those informational interviews can lead to mentorship organically. You're essentially doing market research on your own future. Lucas: Exactly. Sarah actually did a few of those before she settled on tech sales. She talked to someone in project management, someone in operations. Each conversation clarified what she didn't want. That's valuable too. Luna: So the key is to start before you have clarity. Don't wait until you know exactly what you want. Lucas: Right. Because the clarity comes from the conversations. The mentor map is not a static document. It evolves as you learn. Sarah's map changed three times in four months. That's fine. Luna: I think that's a really freeing way to think about it. It takes the pressure off having to get it right the first time. Lucas: Absolutely. And it also takes the pressure off the mentor. They're not responsible for your entire career transition. They're just a piece of the puzzle. Luna: One last thing — how do you know when a career-change mentorship has run its course? Is there a natural endpoint? Lucas: I think it's when you no longer need that specific person's perspective to make decisions. For Sarah, that happened around month six, after she'd been in the job for three months. She and Dan transitioned to an occasional check-in rather than a monthly call. And that's healthy. Luna: So the mentorship served its purpose. It got her through the transition. Lucas: Exactly. And now she's starting to mentor other career changers herself. That's the full circle. Luna: That's a great note to end on. Thanks, Lucas. Lucas: Thanks, Luna. And to everyone out there making a change — the map is yours to draw.