Coach Them Until It Hurts

Published on September 29, 2019 · 4 mins

“I think I can run the demo on my own, you don’t need to be there.”

That’s when I knew she didn’t need me anymore. Somewhere, deep inside, I felt a novel, weird sensation: it was pride and… what else?

At the time, I was the CTO of a tech startup, and I had been training Carmen, our frontend lead, for well over a year now. Carmen was a brilliant engineer who now led a team of eight, tasked with developing three different products. She had never considered being a manager, but since the company needed someone to fill the role and she was the most experienced engineer, she promptly rose to the challenge.

However, Carmen lacked any management experience whatsoever, so she turned to me for guidance and mentoring. The process was long and often unpleasant, as we went through her strengths and weaknesses and tried to fit them into her new role.

And now she didn’t need me anymore.

As I took a second to collect my thoughts, I slowly came to the realization that resentment was what I was feeling. Right there, along the pride for seeing one of my people finally take the wheel and lead a critical demo, I resented her for daring to leave me.

What Management Is About

Mama’s gonna keep you right here under her wing, She won’t let you fly but she might let you sing.

As a manager, it feels good when people turn to you for guidance. It makes you feel respected, looked up to and, above all, useful. It makes you happy that you can help someone grow, and it makes you sad when they don’t need you anymore and can continue to grow on their own.

This feeling is quite natural, and there’s nothing wrong with it, but you must never forget the one fundamental truth of management:

Management is about enabling people.

It’s not about project management, performance reviews, hiring pipelines, meetings agendas or conflict resolution. Those are all tools you employ to reach your one and only goal, which is to allow the people you manage to become their best selves and then get out of their way.

If you fail to do this, if you become possessive and hinder their growth out of fear, you are doing your reports, your company and yourself a disservice:

  • your reports will not be able to reach their full potential, because you will always be there to guide and correct their every step;
  • your company will eventually be full of followers rather than leaders;
  • you will be stuck dealing with the exact same challenges for years.

When you don’t give people the space they need to grow, they will leave the company at best and resent you at worst.

What You Should Do Instead

Instead of holding everyone’s hand indefinitely, your job should be to scale your vision to an ever-higher level, becoming a better manager and magnifying the impact of your actions more and more every year.

As your people learn to walk on their own, start considering what the next big thing will be for you: is it time to start hiring and coaching new people? Can you help out with strategy definition? Would you benefit from spending a bit more hands-on time and get your skills up to date, now that you don’t have to do as much management anymore? Your own manager should be able to help you out.

When people don’t need you anymore, it feels scary. You can’t help but wonder whether you’re becoming useless to the company. While natural, this fear is irrational: no one will want to get rid of you just because you’ve done a great job of mentoring your employees. Learn to stay with the fear. It will fade eventually, and all you’ll be left with is pride.

See you soon?
© 2025 Alessandro Desantis