Think Like a CTO - The Book

When I became a CTO, nobody handed me a manual. I asked around, I phoned CTOs I trusted, and I made a lot of mistakes, mostly because I did not know what I was supposed to be doing. Years later I was advising CTOs who had been thrown into the role through private equity investment, an acquisition or plain rapid growth, and I watched many of them walk the same road.

So I wrote the book I needed. Think Like a CTO took two years, a global pandemic and a great deal of patient editing from the team at Manning. It was published in February 2023, with a foreword by Ankit Mathur, and it is now in print in English, Russian and Japanese.

Get your copy. Buy on Amazon or buy direct from Manning, in print or as an eBook. Want to know what other readers made of it first? Read the reviews.

Title	Think Like a CTO
Author	Alan Williamson
Foreword	Ankit Mathur, Cofounder and CTO at Roundtrip Health
Publisher	Manning Publications, February 2023
Length	320 pages, 15 chapters
ISBN	9781617298851
Languages	English, Russian, Japanese

What it is for

It is not a leadership book, and it is not a technology cookbook. I will not tell you to pick Java over C#, Amazon over Azure, or the cloud over a data center. What you get instead are the considerations to weigh when you make company-sized decisions, because those decisions often outlive your time in the role. Small case studies run throughout to show the thinking, and every chapter ends with a checklist you can put to work straight away.

The book answers the questions you may have asked yourself but never dared ask your CEO, for fear of looking like you do not know what you are doing. How do I read this budget? How do I judge this vendor? What do I do when we are under attack? And through all of it, one rule: a decision based on data, not gut instinct, is always defensible.

You will learn how to:

• Work well with the rest of the C-suite, from the CEO to the CFO

• Set a long-term vision while still delivering the short-term goals

• Hire, onboard and, when it comes to it, let people go

• Negotiate salaries and handle promotions

• Design systems that are built to last

• Respond to security breaches and ransomware

• Build budgets and work with the CFO

• Choose and manage outsourced vendors

• Deliver bad news with data, not emotion

• Lead in a way that earns your team's trust and respect

Who should read it

From a two-person startup right up to an organization with thousands of employees, the responsibility is wide. This book is for:

• The engineer or development manager who has just been handed the CTO title, and no instructions

• The seasoned CTO who wants to sharpen their skills and spot the gaps

• The CTO stepping into the shoes of the one who just left

• The VP of Engineering on the road to becoming a CTO

• The CEO or founder deciding whether the company needs a CTO at all. (It does. Chapter 1 will help you make the case.)

I like to think of the CTO as the rook (the castle), the next most powerful piece, because they provide the support for the rest of the pieces to move around the board, clearing paths into the distance.

From the preface

Fifteen chapters

Each chapter takes one major area of responsibility and goes deep. Not every chapter will be relevant to you today, but every one of these areas is somebody's responsibility, and that somebody will be your peer, so it never hurts to know what they are contending with.

Chapter	What is covered	Page
1	The Chief Technology Officer What makes a CTO, the four kinds of CTO, whether a company needs one, your first 100 days, and the top 10 qualities.	1
2	Managing Up Your CEO, your CFO and your peers. Taking over from another CTO, presenting to the board, internal politics and change management.	15
3	Visionary Planning The grand vision, long-term planning, seismic shifts, the elevator pitch, and putting together a budget.	45
4	Building a Team Full-time, contract, onshore, offshore or outsourced. Knowing when to hire, sourcing candidates and writing the job description.	70
5	Interviewing, Choosing, and Onboarding Phone, in-person and video interviews, scoring candidates, saying no, and getting new hires up to speed.	94
6	Team Management Charters, team structure, titles, reporting, one-on-ones, training and communication.	112
7	Annual Reviews The skill matrix, handling failure, termination and remote working.	135
8	Technology Decisions Avoiding lock-in, build vs. buy, cloud vs. on-prem, disaster recovery, data, microservices vs. monoliths, open source, languages and frameworks.	153
9	Development Project planning, standards, version control, QA, CI/CD, technical debt, releases and client requests.	187
10	Contract Management Service agreements, SOWs and SLAs, evaluating vendors, software licensing and support contracts.	207
11	Documentation Why to document, what to document and who it is for, from owner's manuals to network diagrams.	217
12	Security Patching, penetration testing, social engineering, data leakage, developing with security, what to do when "we are under attack", and when you need a CISO.	231
13	Housekeeping Hardware, support, monitoring, backup and restoration, and budget oversight.	249
14	Company Growth Investment groups, the impromptu pitch, preparing for integration, due diligence from both sides of the table, and handing over or taking the reins.	260
15	You, Inc. Reviewing yourself, finding a mentor, keeping pace, succession planning, career success and stepping up.	277

A taste before you buy

If you want a flavour of the thinking first, these pieces live in the same territory as the book:

• The Chief Technology Officer - what the role actually is

• Vision without a plan is just a dream - visionary planning

• Technical Debt - A visual guide - development

• Quality - development

• Security isn't something you ... add - security

Read it in your own language

The problems we face as Chief Technology Officers are the same no matter the location, so it was a humbling moment to see the book come back to me in other languages. The Russian edition is titled Настоящий CTO and the Japanese edition CTOの思考法. I wrote about the day the Japanese edition arrived on my doorstep.

What readers say

Comprehensive and insightful views on becoming, and thriving as, a technology executive.
Ankit Mathur, Cofounder and CTO at Roundtrip Health, from the foreword

Interesting and very useful. I could have used this as I moved into CTO roles early in my career.
Jothy Rosenberg, Dover Microsystems

An awesome collection of strategies and real-life stories! Every paragraph describes a situation many of us have experienced or an actionable step to deal with it.
Matt Ferderer, Mighty Gnomes

There are plenty more, from Amazon, LinkedIn and my inbox, on the reviews page.

The long version and the short version

The book is the long version. ThinkLikeACTO.ai is the short version. Read the book if you have a weekend. Talk to us if you have a problem this quarter.

Ryan Burch and I run the firm that grew out of the book: AI readiness assessments, leadership foundations, dev team enablement and product integration work. We are deliberately small and take on a limited number of engagements each quarter so we can do the work properly. If that sounds like your situation, talk to us.

Free: the AI Pulse Check. Twenty-four yes-or-no questions on how you use AI, protect your data, run your engineering, manage vendors and lead. It takes about five minutes, your score appears the moment you finish, and there is no email to hand over. Check your pulse.

And if you are ready for the long version: get it on Amazon or direct from Manning.