CTO Challenges
You're not the first CTO to face this. Here's the map.
After coaching 80+ CTOs, I’ve noticed something: the problems keep repeating. Different companies, different industries, different stages - but the same fundamental challenges.
Everyone has the same problems, just different!
You’re not broken. You’re not uniquely bad at this. You’re facing problems that every tech leader faces at some point. The difference is whether you recognize them early and get help, or whether you burn out trying to figure it all out alone.
I’ve mapped out the 10 challenges I see most often. Find yours. Read about it. Then decide if you want to tackle it alone or with someone who’s been there.
Career Stage
Where you are in your journey matters. Each stage brings different challenges.
First-Time CTO - You were a great developer. Now you’re an executive. Nobody gave you a manual. The transition is brutal without support.
Developer to Manager - The hardest transition in tech. What got you here won’t get you there.
VP of Engineering - Between CTO and teams. Strategy meets execution.
Personal
Leadership is lonely. The higher you go, the fewer people understand what you’re dealing with.
Imposter Syndrome - That voice telling you you’re about to be found out? Every tech leader knows it. You’re not alone.
The Lonely Leader - You can’t share doubts with your CEO. Your team looks to you for certainty. Who do you talk to?
Scaling
Growth breaks everything. What worked at 5 engineers doesn’t work at 50. What worked at 50 doesn’t work at 150.
Scaling Pains - More engineers, slower velocity. Dependencies everywhere.
The Bottleneck CTO - Everything needs your approval. Nothing moves without you.
Tech Turnaround - You inherited a mess. Where do you even start?
Technical Debt Crisis - The codebase is crushing you. Every feature takes longer.
Strategic
The big decisions. These are the moments that define your tenure as CTO.
Strategic Decisions - Rewrite or refactor? Hire or outsource? Platform or products? The decisions nobody can make but you.
What Connects These Challenges
They all share something: you can’t solve them alone. Not because you’re not smart enough - you are. But because these challenges need perspective from someone who’s been there. Someone who can see the patterns you can’t see from inside.
The best CTOs I know have coaches, mentors, or peer groups. They have people they can talk to confidentially. They don’t try to figure everything out from first principles.
Ready for Support?
I’ve coached 80+ CTOs through exactly these challenges. If you want someone in your corner who’s been there - let’s talk.