I am writing a guide for first time CTOs and trying to understand what the role actually feels like in practice.
There are plenty of articles about architecture, scaling systems, and choosing the right stack. But most of the CTOs I talk to say the hardest parts are things they never expected. Things like managing engineers, hiring the wrong people, navigating founders, technical debt under pressure, or being responsible for everything when something breaks.
If you have been a CTO, especially for the first time, what were the things that surprised you the most?
What nearly broke you in your first year?
What mistakes did you make that you wish someone had warned you about?
And what advice would you give to someone stepping into the role for the first time?
There are plenty of articles about architecture, scaling systems, and choosing the right stack. But most of the CTOs I talk to say the hardest parts are things they never expected. Things like managing engineers, hiring the wrong people, navigating founders, technical debt under pressure, or being responsible for everything when something breaks.
If you have been a CTO, especially for the first time, what were the things that surprised you the most?
What nearly broke you in your first year?
What mistakes did you make that you wish someone had warned you about?
And what advice would you give to someone stepping into the role for the first time?