Morale of the story: don’t apply for a CTO position. Apply for CEO: more money, less pressure, and you get to be as incompetent as you want.
What I don't get is it sounds like he accepted the CEO's edicts unquestioningly: > This one time, for example, when our deployment crashed halfway through right before a major release. The CEO emphasized how important this project was, so we were all hands on deck, trying to get it back up, fearing the worst, that the client would go ballistic if he found out we were delaying the release. I was stressing big time, th…
Agreed wholeheartedly on both points, though I'd say a general problem with people new to leadership positions rather than make it about age. Society as it exists now (at least as I've experienced it) is very strong on rule following and it's a pretty massive shift to be the person setting the rules.
The CEO should've been empowering, too, and it might well be a symptom of the same malady: imagining the way you want things done, then pushing harder and harder until the world is that way regardless of cost. Human psychic cost is real and will cost you your best people.
Consider instead if the CEO said to the team "We definitely need this done, but I don't want you to burn yourselves out. Please keep at it as your top priority during working hours, all other goals are on pause until we have a release, and keep me up to date at the end of each day with progress until we're there. I don't want anyone working after hours. Don't worry about the client; I'll handle them." When the story unfolds from there the client doesn't even notice, the team feels supported and heard, and the work still gets done. Everyone wins.