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I like translating such interactions into kindergarden-emotion-language to distill the intention.
“You checked out! Explain self!” Will raise defenses.
“Hi human. I human, you human. I friend. (Stay here for a while) I notice thing. How you?
You human. I friend. I help. What happen?
I worry. You help understand?”
This is the problem, I wouldn't call myself an expert in leadership, but if your CEO doesn't have the emotional fortitude to bring this up with the CTO it is a leadership fail. If your leadership team cannot have candid feedback with each other is it not going to work out well.
I have no idea how big your startup is besides the engineering staff you said and where exactly you fit into the org chart (VP of Engineering -> P of Engineering -> CTO?), but being a leader means holding other leaders accountable.
Do you have a regular dialogue with your CTO? If so, I'm sure that: > 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 Might go away almost overnight. If he knows what's going on on a day-to-day (or regular) basis, he might be able to insert himself and his knowledge when tactically relevant or useful.
Right. No, we don't. 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 when I'm working on those types of tasks, which means providing updates to the team, tracking my progress openly, giving info in standups, etc. I have a good relationship with the CTO, but it still…
Your example though, sounds like a conversation a manager has with their reports. In your position, you would be better off communicating in terms of what you expect from them and what can they do to help you do your job better. The CTO's performance is ultimately the CEO's responsibility and your part is to pass on your feedback to the CEO and be clear that you expect them to take care of the situation, however they see fit.
I personally think you should discuss it with him, maybe first over a drink in a more casual setting figuring out how he will give up his role (to you for instance) and what he will do after, leaving his ego intact while putting the company first. He can then suggest it himself publicly and be done with it.
If yes, then he probably agrees with you about being in semi-retirement.
But he has been “needed” in this company since day 0, so this new feeling of not being needed (because of the great job you’re doing) is strange and uncomfortable. He probably hasn’t worked out how to explain to his co-founders and CEO (let alone to you) that it’s time for the next thing.
If it’s in the company’s interests for him to launch a new product or revenue stream, that could be an exciting and engaging project for a while.
But ultimately it’s gonna work best if you make it easy for him to let go and move on to his next project. Encourage him to explicitly take a vacation and have someone else (or you) act in his role. This will make it easier to realize that his work is done, when he returns.
If no, ignore all this.
Source: I was once this CTO. Had an awesome VP Eng and CTO-in-waiting who helped me hand things over. Happy to discuss more candidly over email.
- 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!
This sounds familiar! Is the CTO also the (co)founder? If yes, then he probably agrees with you about being in semi-retirement. But he has been “needed” in this company since day 0, so this new feeling of not being needed (because of the great job you’re doing) is strange and uncomfortable. He probably hasn’t worked out how to explain to his co-founders and CEO (let alone to you) that it’s time for the next thing. If…
Fella's gotta go. You deserve to be CTO.
That's the thing. It seems self-serving (and I guess it is), but I am handling an increasingly huge area of responsibility and working around the clock, while he seems only half-committed at best. At some point, this does just point to me being the CTO tbh.
> At some point, this does just point to me being the CTO tbh.
Do you want to take over from him? If you silently feel you can do a better job than him and you want his job, it helps getting clarity for yourself about that. You envision how he should do his job if he was you. Maybe he is burnt by the past work load. Maybe he is letting you burn down, knowingly or not. Try to make a connection on a level where you don´t judge anymore.
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 hir…