Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / How to Ask a Senior Leader to Be Your Mentor
Transcript
- Lucas: There's this specific moment in a lot of careers where you know you need mentorship from someone with real seniority — like a vice president or a director three levels above you — but you have no idea how to actually make the ask without feeling like you're bothering them. Luna: And a lot of people just never send that message. They draft it, stare at it, and then close the tab. Lucas: Exactly. So I want to look at a real example that worked. A product manager at Microsoft — let's call her Priya — wanted mentorship from a vice president in a different division. She didn't know him at all. No warm intro, no shared Slack channel, nothing. Luna: So she cold-emailed him? That feels like it'd go straight to the trash. Lucas: She didn't email. She sent a 30-second video message through LinkedIn. And in that video, she said three things: her name, one specific thing she admired about a product decision he'd made two years ago, and a single ask — 'Could I have fifteen minutes of your time to hear how you think about product strategy?' That's it. Luna: That's so much shorter than I would've guessed. No life story, no resume highlights. Lucas: Right. And he said yes. The reason, he told her later, was that the video showed she'd done her homework — she referenced a real decision, not generic praise — and the ask was tiny and specific. Fifteen minutes, no agenda beyond learning how he thinks. Luna: I think the 'no agenda' part is key. A lot of us feel like we need to show up with a full presentation of what we want from the relationship. Lucas: And that pressure kills the ask. Senior leaders get pitched all day. They're exhausted by people who want something concrete — a job, a intro, a decision. What they almost never get is someone who genuinely wants to understand their mental model. That's refreshing. Luna: So the ask is really about curiosity, not need. Lucas: Exactly. And the structure for the ask — whether it's a video, an email, or even a dm — is basically four sentences. Sentence one: who you are, briefly. Sentence two: one specific thing you've learned from them or observed about their work. Sentence three: the ask — fifteen minutes, no prep needed from them. Sentence four: a simple 'thank you' and a suggestion for a time. Luna: That's a script I can actually use. But what about the fear that the person is just too busy? That they'll ignore it. Lucas: They might. And that's fine. But here's the thing — if you send that message to ten senior leaders you genuinely admire, and two say yes, you've just opened two doors that didn't exist before. The cost of a no is a few minutes. The value of a yes is potentially years of career acceleration. Luna: That's a good reframe. So it's a numbers game, but with high-quality, specific asks. Lucas: Yes. And the specificity does the heavy lifting. Priya didn't say 'you're a great leader.' She said 'the way you handled the transition from on-premise to cloud for your product line in 2020 — I've studied that playbook.' That shows she's done the work. Luna: And then once they say yes — what do you do in that fifteen minutes to make sure they want a second conversation? Lucas: You prepare three questions. Not ten. Three. And they should be about the leader's decision-making process, not advice for you. For example: 'When you're evaluating a new market opportunity, what's the first signal you look for?' or 'How do you decide which projects to kill?' Those questions show you're trying to learn their framework. Luna: So the goal isn't to get them to solve your problem. It's to learn how they think so you can solve your own problems better. Lucas: Exactly. And if you do that well, at the end of fifteen minutes, they'll often offer a second call. Or they'll say 'send me anything you're working on and I'll give you feedback.' That's the transition from a one-off chat to an ongoing mentorship. Luna: Do you think there's a difference in how you pitch this to someone inside your company versus someone outside? Lucas: Great question. Inside your company, you can be a little more specific about context — you can reference internal projects or teams. But the core structure is the same. Outside your company, you'll lean more on their public work: podcasts they've done, talks they've given, product launches. But the ask is still fifteen minutes to learn how they think. Luna: And you've mentioned video messages a couple times. Is that really better than email? Lucas: In my experience, yes. A short, well-lit video where you're looking into the camera and speaking naturally — it conveys confidence and warmth in a way text doesn't. It's harder to ignore a face. But if video feels too awkward, a thoughtful email works too. The same four-sentence structure. Luna: It's almost like you're giving them a low-friction way to say yes. The barrier to entry is almost zero. Lucas: That's the whole game. And look, this takes practice. The first few videos you send will feel strange. But I've seen people get mentors — real, active mentors — from cold outreach like this. And the key is always the same: be specific, be brief, and be curious. Luna: You know, everything we've been talking about — the four-sentence script, the preparation, the mindset — it's the kind of practical advice that takes time to produce and share. And honestly, one of the reasons we can keep these episodes ad-free and focused is that listeners who find them useful sometimes chip in a few dollars. Lucas: Yeah, it's a small thing that makes a big difference. A couple of dollars a month is genuinely what keeps these going — buy me a coffee dot com slash fexingo, if you've gotten something out of them. Luna: And it really does help us keep the lights on without any sponsors. So back to the mentorship part — you mentioned that after that first call, you want to send a follow-up within 24 hours. Lucas: Yes. A thank-you note that references one specific insight from the conversation. Not just 'thanks for your time.' Something like 'I loved your point about killing projects early — I'm going to apply that to my current roadmap review.' That reinforces that you were listening and that their time had impact. Luna: And then you wait before asking for another meeting. Lucas: Right. A month is usually good. And when you do ask, reference the last conversation. 'You mentioned you'd be interested to see how my project went — here's a quick update. And if you have fifteen minutes, I'd love to hear your thoughts.' That's how a single ask turns into a long-term advisory relationship. Luna: So the whole process starts with one very specific, very brave message. Lucas: Exactly. And the best time to send it was yesterday. The second best time is today.