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

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 for "an elegant puzzle" by Will Larson.

Or does "CTO" mean that you switched from being an engineer to managing a team of engineers? Then everything for new managers applies, for starters I'd recommend "Becoming an effective software engineering manager" by James Stanier, or "Engineering management for the rest of us" by Sarah Drasner.

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, and if you want to create your own they are excellent starting points.

Your best bet is to see if your company is willing to pay for you to take some Dale Carnegie classes (Specifically the ones on Effective Communication). It will help you more than anything technical.

So many managers and higher fail terribly at being effective because they believe all they need to do is encourage/enforce the practices in the books on the engineering teams, and that is the path to failure and the death of morale.

Take the books as guidance, but listen and engage with your reports (and their reports) to find the problems that need to be solved. Don't dictate or drive people, let them use their expertise in the direction you lead.