The Engineer who became CTO and quit after 6 months to join my team
What happens when your dream role becomes a nightmare and what I learned from it.
👋 Hey, it’s Stephane. I share lessons, and stories from my journey to help you lead with confidence as an Engineering Manager. To accelerate your growth see: 50 Notion Templates | The EM’s Field Guide | CodeCrafters | Get Hired as an EM | 1:1 Coaching
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Alex looked like he had it all figured out.
(That’s not his real name, I’m using a pseudonym to respect his privacy.)
A very smart engineer, working at an awesome startup for a couple of years. He led a complex cloud migration, built a couple of brand new web dashboards and even invented 2 patents.
Everyone was looking up to him and was going to him with the most complex projects.
When the CTO position at his Series A startup opened up, he applied. Who wouldn’t? It felt like the next natural step and he got it!
But what happened next almost broke him.
The unfortunate story
The startup had 60 people. 20 permanent engineers and some contractors.
The board agreed on an ambitious roadmap in which everything was agreed before he became CTO. Everything was top priority and a big part of it relied on hiring more engineers. That was part of the plan.
Then COVID hit.
Sales dropped instantly and everyone was panicking. The CEO very quickly decided to let go off 50% of every department. Alex had to fire half of his team - 10 engineers gone overnight just like that.
But the roadmap didn’t change.
And suddenly, what looked like a dream job turned into a nightmare. Alex was being asked to deliver a plan built for 30 engineers... with just 10. He tried to push back, suggest different ideas, but no one would budge.
The board wanted all of it - or else the company would be in even more trouble.
He completely burned out.
How I met Alex
I met Alex while this was happening. We got chatting at a leadership meetup. He shared with me his story, and honestly, I was shocked.
We often glamorize fancy titles. CTO. VP of Engineering. But these roles can put you in impossible situations.
During that time, I was also working for a startup and truth is we were also struggling. Had a layoff just weeks before and a restructure.
Part of our restructure included prioritizing a key project for my team that none of us had experience with really. And that was a key risk.
As we spoke more with Alex, I realized that his experience made him the perfect fit for our coming project!
I discussed it a bit with him and he had loads of insights immediately.
So, I decided to push for it. I made a case to our CEO for a new hire, miraculously got it approved and connected Alex to my company.
We ended up making him an offer which he accepted and joined my team but this process taught me a lot!
Bias is real - I liked Alex. I wanted him to join my team. That made me push harder than usual because I thought it was worth it.
Reputation risk - After I vouched for him, I felt some pressure. If it didn’t work out, it could reflect badly on me and I didn’t really have a plan B.
Genuine connection > job boards - On reflection, Alex didn’t pitch himself. We just talked. Real networking creates real opportunities.
Being a CTO is damn hard
It’s not as glamorous as you might think.
Still, it’s the job I would like to get one day.
I don’t romanticize the title. I couldn’t care less about it to be honest.
For context: My dad is a C-level exec at a major insurance firm. One year, his target (set by the board) was to shrink the org by 40% while keeping the same output. When I heard that from him my heart started racing.. That kind of pressure can break people. I’ve seen it firsthand.
So why do I still want it?
Because real leadership shows up when things get hard. When you’re forced to make ugly decisions. I’ve seen leaders handle that with coldness. I’ve also seen it done with care.
I try to be the kind of leader who still creates chances for people, even when that is on a path outside of the company I happen to work with.
I believe that we need more leaders who put people first, not just the company’s interests. That’s who I want to be. And I want to do it at scale, so I’m working hard to earn the right to be in that position.
Call it naive. I call it my purpose.
As much as I love the journey, one day I know it will become my reality and I am getting more and more ready for it day by day.
I hope you are also walking and enjoying the journey towards something bigger and would love to know what this is..
See you in the next one,
~ Stephane
PS. How I feel when everyone is saying they want to be a CTO one day.