[omeze]

This is a pretty classic "managing up" scenario, some notes on stuff IME:

- To convince yourself if this is criticism is any way _only_ self-serving, (not saying it is), ask yourself "would I feel this way if he was doing a great job but I was still underwater in areas XYZ?". If yes, great, proceed

- Note: the above implies you could feel this way even if he was doing an awesome job. The solution would just be to hire or prioritize better.

- Ask for a private of 45-90m with the ask "can we talk about some long-term stuff?". In this chat, do not waste time getting to the point and stay focused on 1 thing: your needs to do the best job you can. No compliment sandwiches and very little catchup, keep the mood focused and productive, not destructive or lighthearted.

- Focus on your needs and the org's needs. You will be criticizing this person, there is no way around it, but you should not be mean-spirited. The source of your frustrations is your needs, so you should not try to criticize, you should try to be productive (if you want this person to stick around).

- Watch this video from YC about how to handle cofounder disagreements, because its the same thing: https://youtu.be/30a5yFBd7Fo?t=263 -- in particular, focus on "Non-violent communication". Yes, it sounds like a meme, but its the only productive way to have these conversations and it works.

- Keep in the mind the end goal is to still work together. Do not burn bridges.

good luck!

[stuntkite]

Second on the NVC thing. A coworker who was an underwater CTO put me on that because he was having a really hard time being under water and dealing with me being an acerbic dickhead. It is really, really effective at making difficult conversations much easier. In general, applying it in daily life makes me a happier person too. Not that I'm a fantastic practitioner or anything. When dealing with sticky situations like OP here, I'll usually write out how I think the conversation might go and try to nail down the NVC language before hand so I don't mess up with a bunch of "It feels like" non feelings language.

[headscientist]

Writing it out beforehand and rehearsing seems like a great idea. So much easier to just end up using non-productive (or violent) communication if you don't rehearse a bit and make an effort to keep your communication and language very purposeful and conscious.

[headscientist]

In the kind of conversation you're proposing, do you think that, in addition to the very concrete asks I would have, there's a place to say something along the lines of "I just generally want to feel like you have our back, that you're fully present, that you're accountable, etc" or is that just too general and too close to coming across like a personal attack?

I could also reframe that as concrete requests like "It would help me if you gave us more of a heads up if you aren't going to be around", "It would help me if you made more of an effort to join meetings that we schedule where your input is needed", "It would help me and the team if you provided more regular updates on work that is in your hands so we can better plan work", etc

[stuntkite]

https://www.audible.com/pd/Nonviolent-Communication-Audioboo...

It's read by the author, which is a good move I think. Really good stuff that I think can help you map out where you're trying to go.

[headscientist]

Thank you! Was going to reply to your other comment because I saw that one first and I could not figure out what NVC referred to haha.

[stuntkite]

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.

[headscientist]

Thank you. Appreciate your thoughts.

> Sometimes the most important thing isn't absolute max productivity.

This is a really great point to keep in mind.

[headscientist]

Thank you, this is very helpful! I like this approach