Field Note: A Double-Edged Sword of Mentoring

Over the last few years, I don’t think I’ve enjoyed anything more than mentoring. It’s been deeply rewarding. I wish I’d invested in it earlier—but I’m here now, and hopefully accelerating.

A few things I’ve learned are non-negotiables.

• The mentee chooses you as the primary decision point. But when you say yes, you also need to see something in them. You can’t do this on autopilot.
• Depth over breadth. Two mentees is my max. With that comes regular space and time—an hour a week, consistently, is ideal.
• Trust, and two-way learning. I’ve learned as much from my mentees as I hope they’ve learned from me. But that only works if it genuinely goes both ways.

So where’s the double-edged sword?

Here it is. One of the biggest outcomes of mentoring is an elevation in confidence, ambition, belief, and the size of someone’s dreams. Being part of that unlock is incredibly rewarding. But sometimes, that growth isn’t entirely in service of what’s directly in front of you.

There may come a day when a mentee tells you—partly because of the work you’ve done together—that they’re ready to move on to something bigger.

That’s awesome. Truly. But when that person is in your team, it cuts both ways.

You want them to fly. And at the same time, you deeply value their contribution, their presence, their irreplaceability in the team you’re building. If forced to choose, I’d support them to fly. Every time. That's the cost of mentoring I'm willing to pay.