HOW TO CTO EST. 2025

Hi, I'm Alexander Timofeev.

Learning out loud as a CTO — notes, interviews, and the messy bits in between.

This is my public notebook. No playbooks — just things I'm figuring out.

Now Shipping CTO Spotlight · Drafting lessons on 1:1s

Editor's note

Why this exists

I spent most of my career as an engineer and then stepped into leadership. The CTO role turned out to be part strategy, part people, part systems — and not at all tidy. How To CTO is where I keep notes on what helped me, and sometimes how other leaders actually work.

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CTO Spotlight

Real routines and decisions from other leaders — use what fits, ignore the rest.

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Sarah Chen

CTO · TechFlow

"The best 1:1s happen when you stop talking about work and start talking about the person."

People Routines 1:1s

Marcus Rodriguez

VP Engineering · DataCorp

"I learned to say 'I don't know' more often. It's liberating and builds trust."

Leadership Culture Trust

Emily Watson

CTO · StartupXYZ

"Technical debt isn't just code — it's also processes, meetings, and decisions we avoid."

Technical Strategy Process

Field Notes

Stories from the field. Personal takeaways, not advice.

Jul 2026 2 min read

Your card is already on file

Imagine paying for the agentic system of your choice the way we paid for software decades ago. A boxed perpetual license, version 1.0, yo...

Jun 2026 2 min read

Sloppy code hides. Sloppy UX doesn't.

Vibe-coded interfaces (the ones spun up from scratch, not deliberately guided by a human) look pleasing at first glance, yet are very har...

Apr 2026 1 min read

Perfectionists gonna perfectionate

Perfectionists are going to perfectionate :P Instead of "polishing" my code, now I'm bettering the PRD for a week or so (in my defence — ...

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Short, useful, irregular.

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