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

Great question. If he were fulfilling what I view as his responsibilities, I would not necessarily feel it imperative to take over for him. If he were to leave — whether voluntarily or forced out — I would gladly take over the role. I'm qualified for it and I'd be the natural choice. Not sure if that answers your question. I generally have ambitions to continue to level up and that definitely involves being in the CTO spot somewhere, but I don't feel it has to be here and now. But if they wanted me to take over, I'd very excited to do so.

I think you're right in general though that I really do need to do some soul-searching to figure what I want.

Oh and yes, I do think he's "trying" to recover in a sense. The thing I'm unsure about — and maybe he himself is unsure of — is whether that ship has sailed and he's either unable or unwilling or unmotivated to recover.

If I was the CTO I would hire another vp with a different style and pit you against them and slowly move you out but he can't afford that so he is stuck with you for now.

Expecting the CTO to show up to standup meetings, expecting the CTO to help you do day to day tasks, and generally placing expectations on what your boss should be doing nevermind going to the CEO gently stab him in the back are things you shouldn't be doing. It is not your job to manage the CTO, why would the CEO give you that position knowing you will judge their performance at some point and go to the board the next time you feel overworked.

Tell the CEO there is too much work and you need more resources. Hire people to lighten your load. Take the new time/space to create a vision. Leverage your positive relationship with the CTO to get their support for new vision and use that to win the CEO over. Succeed with your vision and you will receive credit. When CTO moves on after you get purchased you move into that role.

Whatever you are doing now you better walk it back somehow and never share the nonsense you shared here with him/her. Think about it logically.. if the CEO fired the CTO and replaced them with you.. they lose historical knowledge plus a relationship that goes back to founding. You may or may not be able to replace them skillwise but it looks bad to investors. You would need to hire a replacement for yourself who will not be as good as you are. In the short term increased risk, less productivity and this is a startup so longterm doesn't matter because you hope to get bought out. Any CEO who would do this is foolish. Which is why you heard: "this is a concern you talk to him.." The CEO knows you are doing a great job and wants you to keep doing it but promoting you to CTO is a bad idea.. even if the CTO left chances are they go outside.

Your only strategy is to use the vacuum to do something impressive, then get people to replace your tasks and wait for an opening and you will be in a good position to land that role. Telling your boss he isn't working hard enough is not going to go well.

I am in a completely opposite situation as yours. I joined as VP Engineering at a startup and my CTO refuses to pass any responsibilities. I tried to communicate him multiple times to let me take care of day-to-day management stuff which he agrees to but jumps back right in. I think part of the reason is his passion about the product and expertise but that is definitely getting in way of me doing my job.

I wish I was in your place as you are getting more autonomy and that will definitely help you get to the next level.