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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?

#92
This isn't a book or blog, but I recommend two different communities:

CTOlunches.com, which is an in-person group that meets for lunches around the world. It also has an active mailing list, with hundreds of engineering leaders there.

The rands leadership slack (Google for it) is an invite only slack with thousands of engineering leaders across the world. Great for asynchronous conversations across a wide variety of topics; they even have an anonymous q and a channel.

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

#93

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 :-)

Haha, for sure. I wrote about that contrast here a few years ago: https://www.mooreds.com/wordpress/archives/2555

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

#94
Camille Fournier: the manager's path

Eye-opener (worst take away / for me - you can't be friends with devs-under-you anymore. Or with anyone techie it seems. Probably depends on company-founders' culture - if small and new - or politics - if older and/or bigger)

some more of hers here: https://skamille.medium.com/an-incomplete-list-of-skills-sen...

Also.. you can't be everything. Choose your poison (or if it has been pre-chosen, find out what it is sooner than later), hire other people for other stuff:

https://www.allthingsdistributed.com/2007/07/the_different_c...

more on the topic:

https://news.ycombinator.com/item?id=20642423

And... think/assess very-very well - all-the-time - How much trust you have got.. and for what. YMMV. Sometimes "CTO" is only a parrotizing label for investors to flock on. Sometimes it's for real.

have fun

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

#95
post #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…

I mean this is decent advice, but slightly odd given you could easily have plugged your site here AND actually given the OP what they asked for :-) Maybe it’s some reverse psychology thing. Ok I’ll do it, you evil genius… https://hackernewsbooks.com PS CTOs aren’t always chosen, many are self-appointed as founders or co-founders (possibly in this case too). Chosen implies you’ve been subject to external assessment, s…

That is a very interesting line of thinking, my comment was kind of the opposite - I find that after reading a couple of good books on a certain topic, the rate of learning goes down rapidly compared to the steady amount I get from HN comments and experience. About hackernewsbooks - it's not mine since many years and I am not affiliated with it, I am just the one who built it and sold it. It's still nice though.

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

#96
post #26

So, does a CTO need to know about: - Dev/ML/X Ops - System Architecture - DB design? etc?

My expectation as a lead-role in DevOps is that my CTO understands what I am saying, if I were to present a business case to him for evaluation or raise a concern with the company tool stack. Shortly put I want somebody with decision making powers to also have the knowledge to make those decisions. I don't need them to be able to implement any of the changes, but I need them to be able to know why the change needs to happen and what business value it does or does not give.

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

#97

Camille Fournier: the manager's path Eye-opener (worst take away / for me - you can't be friends with devs-under-you anymore. Or with anyone techie it seems. Probably depends on company-founders' culture - if small and new - or politics - if older and/or bigger) some more of hers here: https://skamille.medium.com/an-incomplete-list-of-skills-sen... Also.. you can't be everything. Choose your poison (or if it has been…

A CTO can't have friends in their department?

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

#98

Camille Fournier: the manager's path Eye-opener (worst take away / for me - you can't be friends with devs-under-you anymore. Or with anyone techie it seems. Probably depends on company-founders' culture - if small and new - or politics - if older and/or bigger) some more of hers here: https://skamille.medium.com/an-incomplete-list-of-skills-sen... Also.. you can't be everything. Choose your poison (or if it has been…

A CTO can't have friends in their department?

I think it is really tough for execs to have friends in the same department, not just the CTO. Sometimes the business has needs that conflict with people's needs/desires and a good exec should choose the business.

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

#99
I don't know if I qualify for a CTO though people call me one (people have called me names since I was a kid but Mom always said to ignore them...) But let's tuck at that first word -- "Chief". In many cultures Chief meant the one who held the final responsibility for whatever went bad. They were also the ones who had to negotiate with opposing forces. With that in mind, learn your opposing forces and what can go wrong. Ask the dreaded Marketing tribe for their books and learn shamanic things like how long it takes to get something into the media or a retail store. Negotiate with someone in nursing to learn the mystical art of dealing with angry people you are actually trying to help. You will learn more from a nurse or a clothing buyer than you will learn from the best coding book.

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

#100

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.

Yes, so much is contextual and it's really hard to get that from books. But conversations, whether with peers or a coach, can help you because they have that context.
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