I’ve mentored engineers who became executives. I’ve also mentored engineers who would have been better served by a different approach from me — giving advice when they needed space, or autonomy when they needed direction.
Mentorship is not a single skill that you either have or don’t have. It’s a practice that gets better with reflection and deliberate effort, and one I’ve had to revise repeatedly over the course of my career.
Here’s what I think I understand now that I didn’t when I started.
What Mentorship Is Not
It’s not telling people what you would do. The advice that comes most naturally to experienced leaders — “here’s what I did in a similar situation” — is often the least useful. Your situation and theirs differ in ways that matter. Your instincts were shaped by your specific experiences, which they don’t have. What worked for you in 2005 in a large enterprise may not translate to their context in 2026 at a startup.
This doesn’t mean your experience is worthless. It means that framing your experience as instruction rather than one data point among many is usually a mistake. At best, the advice doesn’t fit. At worst, they follow it anyway.
It’s not having an answer for every problem. One of the most valuable things a mentor can do is model comfort with not knowing — demonstrating how to approach ambiguity, how to ask good questions, how to evaluate options without false certainty. Mentees who watch you pretend to know things you don’t learn to pretend, not to think.
It’s not a transaction. Mentorship is a relationship, and relationships take time. A single conversation can be useful, but the mentees who developed most were those I engaged with over years, through different challenges and phases of their careers. The accumulated context matters. Without that continuity, what you offer is perspective, not development.
What Actually Helps
Listening before advising. Most mentors listen less than they should. Before you can give useful guidance, you need to understand the actual problem — which is often not the problem as first presented. People frequently open with a surface-level question when the real question is deeper.
Asking questions that open things up rather than close them down. “What have you already considered?” and “What’s the version of this that works out well?” are more useful than “Here’s what you should do.” Questions that help someone think more clearly about their own situation are often more valuable than answers.
Giving increasing responsibility with a safety net. The best mentorship I’ve provided has involved giving people real, meaningful work that stretched them beyond their current capabilities — while ensuring that the consequences of struggling were manageable. This differs from throwing people in at the deep end — which is not mentorship — and from protecting them from any challenge, which is not mentorship either. The tension between support and stretch is where growth actually happens.
Naming what you observe. Mentees often lack perspective on their own patterns — the strengths they underestimate, the habits that limit them, the way they’re perceived by others. An honest observer who can name these things — with care, not as criticism — provides something that’s very hard to get elsewhere. This requires trust in the relationship and skill in delivery, but it’s one of the highest-value things a mentor can do.
Following their agenda, not yours. The mentorship relationship serves the mentee’s development, not the mentor’s desire to share wisdom. If you find yourself excited to talk about something because it’s interesting to you, check whether it’s actually what they need right now. The most useful question at the start of any mentorship conversation is: what do you most want help thinking through?
What I’ve Learned From Mentoring
The common wisdom is that mentorship benefits the mentee. What’s underappreciated is how much the mentor gets from it.
Being asked to explain why you do something — really explain it — forces a clarity about your own reasoning that you don’t get from just doing it. I’ve changed my own practices more than once because a mentee’s question revealed that I couldn’t actually articulate a good reason for what I was doing.
Junior engineers see things that senior engineers have stopped seeing. The organizational dynamics that experienced leaders have normalized, the friction points that veterans work around automatically, the things that seem strange from outside the culture — mentees surface all of this.
After years of mentorship, you realize you’re watching someone develop their own leadership identity — not a copy of yours, but something that emerged partly from the conversation and partly from everything else they are. That is genuinely rewarding.
The Legacy That Outlasts the Work
I’ve been at this long enough to watch people I mentored early in their careers now mentor others. The ideas, the frameworks, the ways of thinking about problems — they don’t disappear when the conversation ends. They propagate in ways that neither the mentor nor the mentee fully controls.
This is the real reason to invest in mentorship. Not as charity, and not as a way to build loyalty within a specific organization, but because developing the capacity of the people around you is genuinely the highest-leverage work a senior leader can do.
The most valuable professional legacy isn’t the technology you built or the company you helped grow. It’s the people who are doing better work, in more places, because at some point you showed up consistently and took their development seriously.
That’s a return worth investing in.