Great series. One thing I'm missing though, but it could just be me, is that being the CTO in my experience is often a lonely job.
Everyone else is focused on either business or tech. You're usually the only one that sees both. There's nobody to spar with on the whole picture, you have to make decisions with far reaching consequences on your own.
That's definitely not true where I am. Probably half our devs care about the business side. My co-founder and I are both techies who care about business, so we spar often.
On the far reaching consequences side, I didn't realize how important the choices we made in the first month were. Some of those are still with us.
I can only follow on arohner. We discuss business with all of our developers all the time. Totally depends on the people, but in our team we specifically select for people who see the bigger picture and want to talk business as well.
Especially the first hires need to understand all parts of the business, not just their specifics
That really depends on the company. I see a lot of instances (in SV) where the executive team mostly cares about the technology and product and tunes the business side accordingly.
Everyone else is focused on either business or tech. You're usually the only one that sees both. There's nobody to spar with on the whole picture, you have to make decisions with far reaching consequences on your own.