If They Never Outgrow You, Are You Even Leading Them?

Welcome back to The Moat.

This edition touches upon something most founders don’t talk about. What happens when someone grows so much, they’re ready to move on?

It’s about handling that moment with clarity and understanding that letting people outgrow you might just be the biggest leadership win of all.

All that and more…

TL;DR

• Leadership is about graduation, not retention. When talented employees outgrow their roles and leave for bigger opportunities, it signals you've succeeded as a leader.
• Taking departures personally is leadership insecurity. Great mentors develop people to surpass them, just like sports coaches prepare players for higher leagues.
• Your "alumni network" becomes your biggest asset. Former employees who left on good terms become referral sources, customers, and brand ambassadors.
• Real mentorship focuses on growth, not control. Effective leaders provide continuous learning, honest feedback, and genuine opportunities that push people beyond their comfort zones.

You know what nobody tells you when you’re building a company?

That people will leave. And not just leave—outgrow you.

And it doesn’t always feel okay. At least not in the beginning.

When you spend time mentoring someone, pouring effort into their employee growth plan, and giving them every opportunity to level up, it’s only natural to feel a bit sad when they decide to move on.

Especially when you’ve invested so much in their journey.

But if you’re doing your job right, people will outgrow their roles. And eventually, that means outgrowing you.

It took me a while to accept that. To realize that someone choosing to move on doesn’t mean you’ve lost them or that they were disloyal. It means you’ve done your job.

Growth is progress. And if people feel ready to move on to bigger things, that’s not something to resent. It’s the opportunity to celebrate their professional development.

What’s important is to make sure that during their time with you, they’re continuously growing, leveling up, and seeing value.

Because the real win lies in helping them reach a point where they can take what they’ve learned from you and multiply it elsewhere.

So, why do so many leaders still take it personally when people leave? Why does it feel like a loss instead of a win?

The Part No One Prepares You For

When people join an organization, they start from scratch. They don’t know the culture, the processes, the expectations.

And everyone around them pitches in to help them get there—mentors, managers, teammates.

Growth starts from that very first day. And if you’re doing things right, it doesn’t stop.

At first, it’s all about learning the basics, getting comfortable, and figuring out how to deliver good work. But eventually, people start leveling up.

They take on more. They master what they’ve been taught. And then, naturally, they start looking for the next challenge.

That’s how it’s supposed to work.

If you’ve created an environment where someone can reach their potential, they’re going to want more. And sometimes, that “more” isn’t something you can provide.

Maybe it’s a higher role, a different environment, or just a fresh challenge. The point is, if people stay stagnant, something’s gone wrong.

Honestly, it’s like being a good sports coach. Your job isn’t to keep players on your team forever. It’s to prepare them to compete at the highest level, whether that’s with you or somewhere else.

The best leaders develop leaders, ready to move on and make an impact, wherever they go.

Mentorship is Leadership, Not Control

If I’m being honest, holding people back just to keep them around isn’t mentorship. It’s leadership insecurity.

As founders, mentors, or leaders, it’s natural to want the people you’ve invested so much into to stick around. It feels like validation when they stay.

It feels personal when they leave.

But, at the end of the day, it’s about giving people the skills and mindset to grow even if that growth means moving on.

When mentorship works, it looks like this:

• Making Learning Continuous: People should always feel like there’s something new to learn. That doesn’t stop just because they’ve mastered their current role.
• Creating Real Opportunities: Giving people new challenges and responsibilities—things that actually push them to grow, not just keep them busy.
• Providing Honest Feedback: Not sugarcoating things just to keep them comfortable. The best mentors are direct, because real growth requires real feedback.
• Celebrating Their Progress, Not Just Their Presence: A good leader doesn’t just hold onto talent. They acknowledge when someone’s outgrown their role and support them in moving forward.

Mentorship is a continuous process of adding value. And if someone leaves, that doesn’t erase what you’ve taught them.

When Employees Leave, You Don’t Lose Them

Even when people leave they don’t just disappear. Unless you burn the bridge, they’re still connected to you.

They’re just on a different path. And that’s a good thing.

If you’ve done mentorship right, your ex-employees are some of your biggest assets and the employee life-cycle goes on. Because they take what they’ve learned from you and apply it elsewhere.

They refer talent your way. They bring you business. They speak highly of the culture you built focusing on skills development and offering personnel performance evaluation.

In other words, people remember how you made them feel when they left.

Here’s what actually works:

1. Make exits a positive experience. If someone’s leaving, don’t make it awkward. Celebrate their next move. Acknowledge their growth. Wish them well. It’s basic decency, but you’d be surprised how many companies mess this up.
2. Keep the door open. Some of the best hires are boomerang employees—people who leave, gain experience, and come back stronger. You don’t get that if you’re petty about them leaving in the first place.
3. Stay connected. Just because someone isn’t on your payroll doesn’t mean they’re out of your network. Check in. Support their new journey. Keep the connection alive.

If You’re A Real Leader, You’ll Let Them Grow

So, the next time someone on your team moves on, ask yourself:

• Did you do everything you could to help them grow?
• Did you leave the door open for them to come back?
• Did you make it easy for them to leave on good terms?

If the answer is yes, then you didn’t lose them. You helped them win. And that’s true mentorship.