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

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

#34
I've been a CTO a couple of times (VMware, startup), I don't think I'm a good one (I am better as an individual contributor, rather than as a manager), but I have one piece of advice for you: ignore books, or use them as secondary source of truth.

You should instead TALK to long-time or former CTOs and ask them for advice. You won't find that advice in any book. It's invaluable.

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

#36

Depends a lot on your situation: Does "CTO" mean you are the tech lead of a small (single team) engineering organization? Then everything written for staff engineers applies. E.g I've heard good things about "Staff engineer's path" by Tanya Reilly. Does "CTO" mean you are leading an org that is too large to be hands-on with tech, and need to build an effective structure and culture? Then I second the recommendation f…

And maybe CTO means “the founding programmer of a new startup” in which case my advice would be to stop reading and start coding :-)

There's always time to read, you can't only code. E.g. I run a lot so I get through a hell of a lot of audio books.

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

#38
I was CTO of a startup from pre-seed stage ($0 raised, bootstrapping) thru Series A + B stages ($millions raised, scaling). I then promoted a senior engineer to the CTO role, around the time that we had ~20-30 engineers organized into sub-teams with engineering leads. As part of that, I ran an engineering management book club internally for the new CTO and engineering leads (which was also open to any engineers to join). I then published that reading list as a neatly organized blog post.

The team wrote web / SaaS / analytics software in Python and JavaScript, deployed on Linux + AWS, using lightweight planning tools like GitHub and Notion. It was also a fully distributed team long before the pandemic. Over time, the company (Parse.ly) gained hundreds of enterprise customers and established itself via profitable growth in a straightforward SaaS business model. In 2021, less than a year after this blog post was published, the company was acquired by one of the largest open web internet companies (Automattic, creators of WordPress.com).

"Managing software teams: the definitive reading list"

https://amontalenti.com/2020/11/28/definitive-reading-list

The blog post is organized into a few sections, each featuring a few relevant books:

- Management as a high-leverage activity

- Product marketing and product management

- Debugging dysfunctional product cultures

- The psychology of deep work

- Fully distributed teams

- Programmer mindset and philosophy

It's easy to skip around to find a good starting point or make your own (smaller) reading list. Hope that helps. Good luck!

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

#39
For a startup, focus on shipping faster. The only thing that matters in a startup is finding the product market fit.

If you don’t get to this point, the startup will die. So spending time optimizing the performance or arguing which code formatting standards to follow is just a waste of time and resources.

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

#40

Depends a lot on your situation: Does "CTO" mean you are the tech lead of a small (single team) engineering organization? Then everything written for staff engineers applies. E.g I've heard good things about "Staff engineer's path" by Tanya Reilly. Does "CTO" mean you are leading an org that is too large to be hands-on with tech, and need to build an effective structure and culture? Then I second the recommendation f…

And maybe CTO means “the founding programmer of a new startup” in which case my advice would be to stop reading and start coding :-)

And honestly, pre product-market fit my advice would be not even coding, but iterating in an extremely scrappy way (read: Google Sheets, Jupyter Notebooks, no-/low code, handwritten invoices) until you have people paying for your product and not churning after the first month. Everything else comes secondary. For every company that didn‘t manage to scale their tech and teams fast enough, there‘s 100 that die by „building and they will come“ a polished app with great UX through 4 ecosystems that get launched to deafening silence.
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