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

16 pointsby headscientist4 anni fa40 comments

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.

42 comments

omeze4 anni fa

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!

stuntkite4 anni fa

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.