I am not yet a CTO of a medium or large business, but here is a collection of books, resources and thoughts I think will be relevant to any new CTO.

This is a work in progress. Feel free to contribute.

See also: my pins tagged with ‘cto’

Management

An Elegant Puzzle - Will Larson

By far my favourite book of all time. An absolute treasure chest of effective engineering management strategies, from managing individuals, to managing teams, to forming teams, to recruiting, to time management. Includes strategies for what to do when you’re sinking or barely staying afloat (pay off debt and let your investments snowball).

Strongly strongly recommended. I love this book so much.

Delegation

Turn the Ship Around! - L. David Marquet

I’m only half-way through but this is a great book about how to delegate, and how it often starts from the smallest change, enabling people to do their best work - and trusting them to do it.

It assumes that you have the power/authority/structure to delegate, however.

Being effective

Fierce Conversations - Susan Scott

One of my top-rated books on having effective conversations, both at work and outside. I’ve struggled with being direct, it wasn’t until this book I learned that to be direct is to be kind, if done in the right way. Highly recommended!!

Measure What Matters - John Doerr

The source of truth guide on OKRs (Objectives and Key Results).

Good OKRs are not 100% trickle down, they are social contracts that your teams publish.

Burnout

Beyond Burnout - Suzi McAlpine

Beyond Burnout is definitely the best book I’ve read on the topic. It covers how to identify burnout, how to stop it, and how to prevent it, from three different perspectives:

As an individual who may have burnout,
As a manager of others who may have burnout, and
As a leader of an organisation.

Generally it is not the quantity of work that impacts burnout, but the quality. Humans need validation and acceptance and to feel fairly rewarded. Trying to do too much with too little is a recipe for burnout.

Amazingly this book was released in mid-2021 from a New Zealand perspective. It’s suitable for software professionals, execs, and medical staff.

Still to read

I still want to read and potentially add to this list:

[Crucial Conversations: Tools for Talking When Stakes are High ](https://www.amazon.com/gp/product/1260474186/ref=as_li_tl?ie=UTF8&tag=jevonorg-20&camp=1789&creative=9325&linkCode=as2&creativeASIN=1260474186&linkId=f01ed351c74e3f16529f37796bc36646
Cynefin framework (I have already read this, it’s a good framework)