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.
- 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!
I think the CEO needs to pay more attention to this. A bit of a red flag that the CEO dismissed this casually unless they think you are being unreasonable. If my team member brought to my attention that the CTO is not doing good, I would take that very seriously.
Having said that, you could try to understand what's going on with the CTO and that depends a lot on your own relationship with them. I would tread carefully though.
You, as a VP of Engineering handling this could put the CTO on major defense, as it'll make you look like you're vying for their 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.
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.
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?”
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.
The best approach is to stop doing this, and quickly! Deal with the problems that are facing you and your team, and leave the leadership to deal with the CTO. “Not my monkey, not my circus” - as I understand they say in Poland.
If you need more resources, work with your leadership to get that help in-place. If you need a specific bit of assistance from the CTO, then make a clear request for it and follow it up if you don’t get it. You’ve mentioned that you feel there are areas where he could be helping, and you haven’t communicated that. At your level, you have the responsibility for seeking out the support you need from management. Focus on getting the things that you need, and avoid a fuzzy and unmeasurable metric of “my boss seems too checked-out”.
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.
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.
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.
>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.
I am sure that there is a more positive way to approach this.
Maybe something along the lines of: "I think that there is some uncertainty regarding roles and responsibilities. Some details never have been discussed, so there is a bit of confusion. Can we clarify this?"
If he is only available 1/10 should not really matter. What really matters is that everyone gets the input that they need.