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

No problem. Good luck with your convo. I'd bet that homie has been burnt out for a while and might have some personal shit going on.

As someone who's been a founding partner CTO a couple times, I'll tell you that sometimes you put everything you have into the initial run and then the growth finally happens and then something else happens and life attacks. You're having issues sure, but his history with the company probably means he's entitled to bum out for a while and come back. Likely his partners don't know how to bring it up and hope he'll just sort it out, not realizing that it would be more effective to just tell him to bow out for a month or few and come back when he's ready. Maybe he has a personal issue where the only thing keeping him going is showing up and half assing this job some times.

It might on the surface appear to you that he should just quit, but if he's burnt out that means he probably isn't ready to go do another thing and very likely he likes and is proud of what he's built. You very probably don't know the details of his terms in his partnership contract as well. He might be entitled to do whatever he wants. He could even be doing this on purpose to fuck with the other founders for some reason. You are walking into a complex situation nearly blind. If there's internal founder stuff, no one aside them would know aside from spouses and maybe lawyers. It might even be a contractual breach for anyone to inform you.

If I could offer just a little advice. Do your best not to put yourself in too much judgement of him. The initial run for startups is really hard. He's been in a foxhole with the other founders. Sometimes the most important thing isn't absolute max productivity. But handled correctly, if you talk with him and do your best to understand who he is and how you can help give him enough space to re-engage without risking his livelihood, you'll do well. Tread lightly though. Coming between a man and his meal is a good way to get wrecked. You could very easily step in some shit and end up the perfect scapegoat for.... whatever. I've seen a lot of weird stuff go on with founders. In fact, startups this size without really crazy internal C suite shit would be abnormal.

Lots of things to unpack here and there was quite a delay in my response. But here it is.

>Right. No, we don't.

You're (in a sense) his boots-on-the-front-line guy and you two don't have a regular dialogue? Yikes.

>He messages me when he needs help with things since I'm holding a lot more in the hands-on stuff. One of the problems is that he tends to work in a silo whereas I prefer to act as just another engineer...

So there's a difference in working style which could be the root of the issue. Have you ever brought this up to him?

I used to PM with an engineer who was like this. Since it was a small team and he was very good at his job, I let it go at first but had to eventually pull his leash a bit because he wasn't truly acting part of the team. You have to have a discussion about this with him.

Do you even know what he's doing at a given point in time, even if he's working alone? As part of your team's processes you should know or have an idea, because without an idea he or another of your team members might be doing redundant work. That's not good for anyone. Even a quick message from him to the rest of the team on a regular basis simply stating "hi, today I'm working on X" might be really useful.

>* Perhaps he'd love to hear from me things like "We could really use your help on X" or "It would be great if you did Y." Maybe he really doesn't know how/where he can be helpful.*

Try that. Or go to him more regularly at the beginning of his day and say "hey, we're having problems with ABC or XYZ, can you devote a chunk of time to helping us solve it?". If you can get in front of problems and put work on his plate quickly, it might prevent him from being able to go off and do his own thing....because if he's truly burnt out or just DGAF anymore you'll be able to tell quickly.

The other factor is that you seem to be quite good at your job and he might be worried that he's stepping on your toes (and hindering your abilities or your team's progress) if he gets too involved, or worse - he's realized that with you being involved, he doesn't really have to care anymore.

I don't know if your job is in-person or remote, but I've seen this happen when companies are fully remote - the team aspect is killed and people feel less like a team and more like individual contributors....which is fine in some ways but when combined with the right type of personalities, the work becomes so fragmented and siloed that people "check out" to various degrees if they are able to. I've seen executives do this frequently.