Ask HN: How can I approach our CTO who seems checked out?

I joined a mid-size startup about two years ago as a very hands-on VP of engineering. My responsibilities including managing about 25 engineers, half of whom are out of the country and half of whom are here in the US. I also do a lot of infrastructure/devops type work, I write technical specs, manage our Linear board, handle releases. This is all in addition to writing code and submitting PRs...basically in the trenches with the rest of the dev team when I'm not doing higher level work.

Through the original interview process, it was clear that more hands-on management was needed and that I'd be taking over a lot of the day-to-day management to free up the CTO who was desperately under water. Since then, the CTO has seemed pretty checked out. Very frequently, he will message me to tell me he can't make it to the standup (which he stopped joining altogether for a while, which I was fine with). There's never really a reason given. To me, it feels like he believes he's in semi-retirement.

Part of me is trying to empathize and imagine what it must be like to be in his shoes where someone comes in and very effectively takes over a lot of his work. And the truth is there is a ton that he can do to help the team. I'm not suggesting it's all on me — it very clearly isn't — but perhaps he doesn't have clear idea on how he can continue to help and I haven't gone to him and told him explicitly. I'd hope I wouldn't have to do that, but it might be an awkward spot for him to be in. I don't know.

In any event, this puts me in a weird position where what I feel like communicating to him is something along the lines of:

- you seem checked out, you're often absent and we don't know why - we can't rely on you for any concrete work because you aren't accountable to anyone - the rest of us are working 10x as hard as you are - part of your job should be to teach people, but you don't

and to implore him to recommit himself to the company or acknowledge he really is checked out and that it might be best to just leave.

But, I know that's not a constructive way approach the conversation; I probably wouldn't respond positively if I was approached that way.

So, how can I bring this up? What's an effective way to air my grievances and work towards resolving this situation?

When I approached the CEO, he basically acknowledged it's a problem and put it on me to bring it up with the CTO however I see fit.

Any recommendations on how I should approach this?

Thanks in advance.

I am completely unqualified to answer this question, but it seems to me the CEO should be handling this.

You, as a VP of Engineering handling this could put the CTO on major defense, as it'll make you look like you're vying for their job.

I didn't flesh this out enough in the original post, but the CEO isn't actually dismissing it casually. He actually said this is really serious and said he thinks we should address transparently sooner than later. It's more that he's leaving it to me to figure out the right way to approach it. On the one hand, I appreciate him giving me some time/space to figure out how I'd like to approach it. On the other hand, I feel he's kind of shirking his responsibility and pitching it of to me.

Right, I've thought this too. I mentioned in another reply that, on the one hand, I appreciate the CEO giving me some time/space to figure out how to approach this delicately. On the other hand, I feel he should be providing more support to me in this scenario. How exactly though is kind of a good question.

Fella's gotta go. You deserve to be CTO.