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Coach Them Until It Hurts

3 min readSep 29, 2019

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“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…

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The Startup
The Startup

Published in The Startup

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Alessandro Desantis
Alessandro Desantis

Written by Alessandro Desantis

Technology leader and strategic advisor. I work at the intersection of people, software and words.

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