The CTO Toolbox

The Missing Book for experienced and new CTOs



Stepping into the role of a CTO was like navigating a labyrinth in the dark, filled with unexpected twists and unforeseen challenges. And the labyrinth gets bigger, and the pitfalls deeper. I needed a blueprint, a guide that could illuminate the path ahead and equip me with the tools for success and since I could not find one, I wrote it.

This book does GOOD. All the proceeds from the book sales fully dedicated to the following NGOs who use technology to help people.

Who is “The CTO Toolbox” for?

  • Software engineers who want to progress in the management track
  • Seasoned CTOs who want a collection of tools or get new ideas on how to solve complex problems
  • VPs of Engineering looking to take the next step.
  • CEOs who want to give a gift to their CTO
  • But really, anybody interested in Technology leadership in general!

Book Preview

The Book – Content

The book is structured in five collections of tools that are the fundamental toolbelt for a CTO. In each “toolbelt” I give you an overview of those things that I consider critical for managing a team of engineers. Not everything will be useful at once and you need to pick the relevant ones for you but at least you have the full portfolio!

Some articles have been written by seasoned CTOs and friends who are more experts than me in the topic. Each of the chapters is just an overview on how to work with it and how to apply it. But there are lots of books written on each individual element. So consider the book as a compendium of the syllabus for a CTO.

  • Tools for Technology
    • Blameless Detailed Postmortem Reports
    • Full DevOps philosophy following the “4 types of work”
    • TDD when possible and available. Otherwise good test coverage
    • Security, Scalability, Maintenance and Governance by Default
    • You build it you run it
    • QA embedded in teams
    • Tech Debt is a Tech Lead responsibility
    • 3 Legged Stool framework for new development
    • 5 Ideals of work
    • Deleting code is GOOD
    • Guilds
    • CI/CD
    • Observability – Knowing what is going on before it happens
    • On-Call rotations – Keeping your systems alive
    • Architects are a “role”, not a position
    • Definition of done
    • Training is not optional
    • Everything managed
    • Research VS Implementation
  • Tools for Product Management
    • Agile
    • Priority Buckets
    • Break the Silos, Engineers should meet customers
    • Cross Functional teams with product owners
    • Product Owner Responsibilities
    • Story Points
    • Task Forces
    • The Glue
  • Tools for Team Leadership
    • 90 First days of a CTO
    • OKRs
    • People growth: Career Ladder & performance reviews
    • Tech Leads vs Engineer Managers
    • Weekly Leads Catch Up
    • Hiring
    • Hire Slow, Fire Fast
    • Teams phases formation
    • The Trade-Off Matrix
    • The Nemesis
    • Communication, communication, communication
    • The CTO Readme
    • Multi Cultural Environments
    • Remote: It works…
    • Full autonomy, Full accountability
    • Be Compassionate
    • Managing Up: Your boss, the CEO, or the board
    • Outsourcing, Offshoring and Nearshoring
    • Budgeting and Control, Money for What Matters
  • Tools for Corporate and M&A
    • Cloud Partnerships
    • Working With The Board
    • Toolbox for Due Diligence
    • The Aftershock. Culture change after selling your company
  • Tools for Taking care of yourself
    • Your Support Group. Anonymous CTOs
    • Disconnect. Completely
    • Keep Learning
    • Your Own Performance Review
    • Learn to Communicate and Present
    • The Advisor CTO, Coaching Startups
    • Your Job is to Look into the Future
    • How to accept or not a CTO job
    • Time to Go. When and how to leave your current CTO gig

About the Author

My name is Sergio. You can read more about me here. I have been a CTO for more than 15 years in different company sizes, industries and countries. I have been in tiny startups, big startups, scaleups, corporations and NGOs. I have taken CEO and Product roles. I have been teaching, investing, traveling, sharing, talking and learning continuously. And I have make a lot of mistakes in every single step I’ve taken.

Testimonials from readers

“Hi Sergio, I’ve just finished your book. I think it’s super cool, good job 🙂 I’ve learned quite a few things. I like the ‘toolbox’ format because although in these books sometimes you forget the topics I think I can always go back and re-read one of the chapters when I need it.”
— Jordi Gimenez, CTO, Bugfender

“I’m only 25% in and I’ve already extracted more value out of it than in the last 10 business books combined. I love to measure content in wisdom nuggets per minute, and this one ranks very high in my list. Proceeds go to non-profits, so you’ve got to buy this one if you’re a leader in technology. It makes me want to drop my CEO role to become a CTO”
— Àlex Rodriguez Bacardit, CEO, MarsBased

Convinced yet? Spend some money, learn the trade and help Teaming and Migracode 🙂