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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?

#81
"An Elegant Puzzle" by Will Larson[0] is revelatory when it comes to leading a software engineering team. There is a solution to every organizational problem I've encountered in companies from single digits to thousands. That book alone, along with its intentional and organized bibliography is one of the best investments you can make in a tech career. Even without context on the size of your company, Larson's new "The Engineering Executive's Primer"[1] will surely make a valuable introduction too.

[0] https://press.stripe.com/an-elegant-puzzle [1] https://lethain.com/eng-execs-primer/

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

#82

Earlier quoted context omitted.

Yep. When building a startup you’ll find a lot of well-meaning people (in books or in person) who really do nothing but distract you. YC got it right, you should make something people want. Everything that’s not either making something or finding out what people want is just going to slow you down.

Too reductionist. You must "sharpen the saw". This takes many forms including adequate learning / training for self improvement as well as investment in your tooling that will pay dividends on delivering faster or with higher throughput. These are second and third system effects that require intention to monitor or measure but the effect is real.

I'd say the time for sharpening the saw was before you started the company. The next opportunity to invest into best practices / long-term is when the company actually has some traction.

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

#83

Earlier quoted context omitted.

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 „buil…

Tbf I believe this depends a lot on the product category. Uber could do this in their first few months but eg Retool couldn’t.

Obviously some ideas can’t be tested without writing some code, but it’s more of a mindset than a strict playbook–many programmers (myself included) tend to bias towards wanting to write code and avoid sales conversations until the thing feels “done”. Tech message boards are littered with programmers trying to justify why their app has to have a full polished build that will take a year before they can begin selling it.

When you get in the habit of asking yourself, before building, how you can learn the most about what people want with the least amount of code, clever ideas often come to mind.

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

#85

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 :-)

:-)

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

#87
You might find my survival guide for founders who depend on devs to get things done useful. It covers topics like how not to lose key information if a dev leaves, preventing endless rebuilds and framework switching, keeping devs busy vs. keeping them productive, and ensuring product builds don't go off the deep end.

As an example, here's the chapter on estimates: https://superstruct.tech/blog/estimates

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

#88
Given the diversity of the "CTO" role in terms of responsibilities and scale - what you should be reading will vary depending on your current size, composition, industry and your own personal experience level.

One I find no trouble recommending regardless of these however is High Output Management by Andy Grove (of Intel). Not a new book, but chalk full of what I consider absolute truths when it comes to optimizing middle management (which is predominantly your role as a CTO, once the org reaches 50+ people and your direct reports all have direct reports). The fact it is still very relevant to organizational challenges today when it was written 40 years ago is a testament to this. It is a shame there are so few books that focus on this very-ignored (and honestly largest) segment of management and arguably where you get the most traction as a company.

I've yet to meet two CTOs that share the same skillset or strengths, or who work in the same org structure.

I would recommend doing some executive courses and trainings (with our other execs) to learn some common language and techniques/methodologies around team management and execution - this has been the thing which helped me most in embracing a CTO role (even one with other CTOs from separate business units reporting into). It is ironic but the best blend for a high level CTO is actually people and organizational skills moreso than pure technical aptitude. You need to be able to fact check your people and ask the right technical questions and understand the fundamentals of technical debt and TCO analysis, but honestly you'll be using your people/organizational skills and trying to hire people that know the technology better than you for the most part.

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

#89
post #82

Earlier quoted context omitted.

Too reductionist. You must "sharpen the saw". This takes many forms including adequate learning / training for self improvement as well as investment in your tooling that will pay dividends on delivering faster or with higher throughput. These are second and third system effects that require intention to monitor or measure but the effect is real.

I'd say the time for sharpening the saw was before you started the company. The next opportunity to invest into best practices / long-term is when the company actually has some traction.

The entire point of sharpening the saw is that it is continual though. It doesn't have to be a major investment or long-term, in fact it explicitly references "Daily Self-Renewal". I believe the original comment branch just meant don't worry about "what's applicable to the CTO".
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