About the Guest: Carlos Gonzalez de Villaumbrosia has been building teams and digital products for 10+ years. He also founded Product School, which has trained tens of thousands of PMs. Throughout that journey, he’s watched PMs destroy potential mentor relationships by asking all the wrong question at the outset. His insight: most people approach mentorship like it’s a transactional service you can request, when in fact it’s something that only emerges organically from genuine usefulness.
Here’s something I’ve watched happen dozens of times. Someone finds a product leader they genuinely admire (as a person, not just their LinkedIn). They work up the courage, draft a careful message, and ask: “Would you be willing to mentor me?”
And then nothing. Or worse, a guilty yes, and one conversation before the whole thing evaporates.
I used to think the problem was the ask itself (bad timing, wrong person, clumsy execution), but that’s not it; those explanations barely scratch the surface. The real mistake is treating mentorship like a transactional service: something you can request and commit someone to, when it’s actually something that only emerges from repeated usefulness.
This is the key insight from my conversation with Carlos. His observation: you’re confusing mentorship (free, organic, relationship-based) with coaching (paid, structured, transactional). Mixing those up creates friction for everyone involved, especially the person you’re asking.
Mentorship vs. Coaching
There’s a sharp distinction that most people miss, and it’s the reason formal mentorship requests almost always fail.
Mentorship is free. It’s organic. You admire someone. They help you occasionally because they see something in you worth investing in. It’s relationship-based and fundamentally non-transactional.
Coaching is paid. You hire someone for their time and expertise. There’s a defined relationship with clear expectations. You’re buying someone’s attention.
These are completely different things. And when you ask someone to be your mentor, you’re accidentally treating it like a transactional engagement. You’re asking them to commit to something they didn’t negotiate. You’re asking them to take on an obligation they never agreed to. Most people say yes out of obligation, then ghost you when life gets busy.
Carlos distinguishes mentorship (free, organic) from coaching (paid, structured)
One emerges naturally. The other is a service you purchase. Confusing the two creates friction for everyone, especially the person you’re asking.
Finding Your Mentor (It’s Closer Than You Think)
Start with your actual network. Not LinkedIn influencers. Not the people with the most followers. The people you genuinely admire, as a person. Someone in your orbit, or someone you’ve been paying attention to. Someone whose judgment you respect. Someone whose career decisions intrigue you.
Carlos points out something critical here: the best mentors often aren’t famous. In fact, they’re usually not trying to be. They’re just solid people doing interesting work, and they’re probably not drowning in mentorship requests because they don’t have a personal brand to maintain. Your cousin’s boss. Someone from a previous company. An investor you met once. A peer who’s three years ahead of you. These are the people who are likely to respond and stick around for a sustained mentorship.
Carlos on identifying people you actually admire and reaching out in a way that respects their time
And here’s what’s important: the people you’re looking for aren’t chasing followers or building personal brands. They’re doing real work, and most of them aren’t drowning in mentor requests.
Carlos on why the best mentors aren’t famous or seeking followers
When you reach out, don’t ask them to be your mentor. That’s the ask that creates all the friction. Instead, be specific. Small. Bounded. “I’ve watched how you navigated X and I’m facing something similar. Could we grab coffee?” Or: “You’ve always had clarity on prioritization in a way I want to understand. I’m facing a tough call and would value your perspective.”
Someone can commit to a single conversation. They can commit to 30 minutes. They can’t commit to a nebulous, open-ended obligation they never negotiated.
So if you’ve gotten that first coffee, what do you actually do next?
