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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?

#51

Earlier quoted context omitted.

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 „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.

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

#52
Depends on what you're into:

romance: i would suggest "Looking for Alaska" by John Green or "Pierre et Luce" by Romain Rolland

fantasy: The Way Of Kings by Brandon Sanderson or "Blackout" by Marc Elseberg

life advice ig?: "The Algebra of Happiness" by Scott Galloway

... never been a CTO xd

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

#53

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…

> For some good general material, I'd also recommend the resources that Gergely Orosz makes available for subscribers to his "pragmatic engineer" newsletter. Those are templates for the kind of documents and processes you will most likely need - if you're new to the role, you will not go too wrong by using them

One word of caution: Engineers and EMs read these newsletters and even management books, too.

It’s not hard to see when your leadership is just parroting things they read from a book or newsletter and trying to pass it off as if they had deep leadership experience. Engineers are good at seeing through cargo cult leadership.

I suggest that if you embrace a practice found in a book or a newsletter, be transparent about the source. Encourage people to read more about it in the book or newsletter where you found it. Don’t try to pass it off as a management technique you invented or pulled from deep background experience, because it feels disappointing to the team when someone realizes their CTO is just parroting things from a newsletter or blog and trying to hide the source.

Also, don’t get into the mindset that having read a lot of books or blogs or podcasts or newsletters is a substitute for experience. Some of the worst leaders I’ve had were those who would lord their book knowledge over everyone as though it made them the confident expert on everything, while we could all clearly see that the extents of their knowledge started and stopped with what was contained in the books they read. Books contribute bits and pieces and give suggestions to add to your corpus of knowledge, but if you treat them like definitive, all-encompassing sources of wisdom then it’s going to be clear to people that you don’t really know what you’re doing. Be honest and stay humble.

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

#56
You’ve been chosen to be a CTO, this usually means that you either did well in the company or were hired because of a good track record. So keep doing this + keep things simple, plan ahead, learn from colleagues, share knowledge. Stay humble, confess mistakes, ask for genuine feedback and advice.

Books and blogs have a limited anecdotal value (sometimes it is high but the effort is also high). I’ve learned more from individual HN comments and actual work experience and mistakes than any book.

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

#59
post #44

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.

How/where did you find former CTOs to talk to?

...you just found one and talked to him.

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

#60
post #47

Earlier quoted context omitted.

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.

I don't think the parent comment means only code, never learn. I think their intention was to not worry too much about the "CTO" title and instead focus on building the product at hand.

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.
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