Ask HN: What are good books/blogs to read for a first time CTO?

The best advice is probably to learn as much as you can from different sources but also keep a pragmatic point of view that helps to select the things that apply to your situation. Very often, new leaders follow a recipe without paying attention to the organization's problems. (check the book “The First 90 Days” by Watkins; it may give you ideas to organize your initial approach).

As someone who went from engineering to product design, I observe that CTOs without a product vision are challenging to work with. For example, at a previous company, a CTO tried to implement the hard rule that every UI component should be in the shared UI library. But, even when I was leading the design system, that rule didn’t match how a product design process works. It caused delivery slowdowns and a degradation of the UX. I can bring up other examples, and the typical pattern is a leader looking at only one aspect or two without balance. Try to go beyond engineering and learn more about business and product design, which will help you prioritize engineering decisions. Some product-related books: Inspired by Cagan and Well-Designed by Kolko. Beyond engineering and product, as a C-level executive or director, people and hiring will be your primary concern. There are many management books, and I don’t have any particular to recommend (all of them will provide tools, but none is perfect: The Advantage and The Five Dysfunctions of a Team by Lencioni, The Phoenix Project by Gene Kim). I also enjoy taking ideas from biographical stories like Creativity Inc. by Ed Camull or Creative Selection by Ken Kocienda. Finally, a book I found funny and cynical but depicts big corps very well is “Management Stripped Bare” by Jo Owen.

Of course nothing is black and white, but if you have limited time/money then you want to get to ramen profitability fast and you simply don’t have time for business model canvases, the perfect employee option scheme, a scalable k8s setup or a perfect CI/CD pipeline.

There’s so much stuff that feels important and valuable, but so little of it really cannot wait until after your wheels are off the ground.

When you read postmortems of startups that didn't get enough customers, often it’s this stuff that actually went wrong. Too much time spent on other stuff than “build something” and “that people want”.

To my experience, it’s difficult to resist all that good advice that’s all over the internet, books, accelerator programs and the like, and saving it all for later. People will tell you “you should get $PETPEEVE right from the start” for every imaginable pet peeve (all the way from legal stuff to unit tests to SEO) and they’ll be very convincing. Trying to resist this is not reductionist, it’s super hard.

Doing short courses (executive training) might be better. Assuming you have the Technical Domain side covered, my suggestion would be to focus on the following;

1) Behavioural Psychology - https://en.wikipedia.org/wiki/Behaviorism

2) Organizational Behaviour - https://en.wikipedia.org/wiki/Organizational_behavior

3) Evidence-based Management - https://en.wikipedia.org/wiki/Evidence-based_management

I think the #1 thing when you become part of an exec team is that you should be optimizing for the _business_, and not your function. The working assumption is that you will keep your function executing and delivering, but what is really hard is helping to figure out what the right decisions are for the business. Should we invest more in product or sales? What if there’s a huge top of funnel problem — what can we do about it? Your job is to bring that technology perspective to the discussion.

I’ve been an exec, founder, CEO, and board member at various stages of successful (IPO) /unsuccessful companies (acqui-hire) companies. And the common thread at every stage is that the most successful companies had management teams that worked well together to optimize for the business.

So instead of spending your energy on reading / learning more about tech, I’d recommend you spend your energy learning more about business (I’d probably start by asking the CEO & the rest of the mgmt team for advice on what to learn.)

This might be a bit contrarian, but don’t read engineering oriented books. Read up on selling, marketing, and product design. These are the things that will help you make better decisions about what you will build. My bet is that you got the technology parts covered, and the management things will start to matter once you have a team of 8+.