Reading list for a new CTO

I always maintain a list of a dozen or so books to read, so this article is updated whenever I finish a new book that makes me say ‘wow’.

Eighteen months ago I stepped into a CTO role, completely unaware of what I was letting myself in for. I was a good software engineer—if only one thing was true about my career until that point, it was that—and I had managed people before, but becoming a startup CTO was another beast altogether.

Transitioning from an engineer to a CTO meant that I was embarking on a whole new career where very little of my prior knowledge would be useful. I was at the foot of Mount Stupid. I knew nothing, had no clue where to gain the knowledge I needed, and no way to validate the knowledge that I did acquire.

Before the big move, the CTO at my previous company, perhaps knowing of my career aspirations, had put The Messy Middle on my radar, and a teammate some years prior had lent me a copy of Peopleware (which I have yet to return to him—sorry David!). It was from those two books that I realised I might learn at least some of what I needed from literature.

Of the books that I have read so far, there are a few that have really stood out. If I was starting again from scratch, these are the ones I would tell myself to read before even thinking about ‘CTO’ as a career move:

The Manager’s Path

The Manager’s Path, by Camille Fournier, covers every stage of technical management, starting with the first time you are given line-management responsibility for one of your peers and ending with managing managers and reporting to a board of executives. Its bluntness about the difficulties faced at each stage makes it essential reading for anyone stepping into any of these roles for the first time (no matter how much experience you may have in other management roles), and the sidebar stories are welcome breaks from each chapter that help to explore related scenarios.

Modern CTO

Modern CTO is a book of bite-sized advice taken from the varied professional life of Joel Beasley, a successful engineer and CTO who has seen it all. The book is short, and that is one of its great strengths. Its chapters are small enough that you can pick one at random whenever you have a few spare minutes and you will learn something new. And the book as a whole is short enough that it can also be read in one sitting.

The Five Dysfunctions of a Team

The Five Dysfunctions of a Team is Patrick Lencioni’s masterpiece fable about a failing company who bring on an unconventional CEO to force the executive team to come face-to-face with their failings and learn to embrace one other as their ‘first team’ (realising that the people you manage are not your primary team is an eye-opener!). It is an enjoyable read that should resonate with anyone who has ever worked in a corporate environment and should be required reading for anyone who wants to climb that ladder.

Managing Humans

Inspired by the many, many blog posts of the author (Michael Lopp, otherwise known as Rands), Managing Humans is a collection of insights and stories covering a variety of topics to do with technical and people management. Rands’s writings are worthy of every manager’s time, if for no other reason than the fact that they have brought together [at the time of writing] over 15,000 leaders in the Rands Leadership Slack group, where individuals from tiny and massive companies alike share advice and guidance. If you only do one thing before taking on a management role, join this group.

Radical Candor

Kim Scott’s Radical Candor was a frustrating read—its lessons are so obvious you will kick yourself for not realising them on your own. After the first few pages, the Randical Candor model was self-evident and the rest of the book almost felt like filler (that’s a definite compliment for this kind of book!). As the name suggests, the book promotes the use of Radical Candor in people management, but perhaps more valuably makes the reader confront the alternatives: the Manipulative Insincerity and Obnoxious Aggression of those awful bosses we’ve all had, and the Ruinous Empathy that I am convinced most of us succumb to the first time we’re put in charge of other humans.

The 4 Stages of Psychological Safety

Most startups pride themselves on having a great culture. When this is taken for granted, those leading the company are prone to making the dangerous assumption that their team feels psychologically safe because they offer a ping-pong table and flexitime. Timothy R. Clark’s The 4 Stages of Psychological Safety breaks down how to build your team up to a place where they feel truly safe: not just to contribute to the status quo but to challenge it. It is a short book that will challenge your core assumptions about how your team truly feel.

The Phoenix Project

The spiritual successor to The Goal (which I suspect may join this list once I have finished reading it), The Phoenix Project by Gene Kim is a work of fiction that follows the newly-appointed and reluctant VP of IT Operations at Parts Unlimited, Bill Palmer, as he races to address the systemic failings that are causing missed deadlines, disastrous PR and low staff morale. Pay special attention to the chapter where Bill takes the time to talk to (and discovers the goals of) the company’s CFO.

Radical Focus

Radical Focus is a fable by Christina Wodtke that tells the story of two young entrepreneurs who are tasked by their investor with implementing OKRs into their tea supply business (and failing along the way, for a refreshing dose of realism). One afternoon of reading this book did more to convince me of the potential of OKRs than years of hearing management types drone on about them. The fable in the first half is short and fun, and the explanations in the second half comprise of real-life stories and templates you can use as a starting point for your own business.