Ask HN: How can I approach our CTO who seems checked out?
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
[ 5.0 ms ] story [ 95.6 ms ] thread>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 have a good relationship with the CTO, but it still feels a bit awkward for me to be telling him or even suggesting to him what to do, but maybe that's my own issue. 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.
I think you're right that more regular communication would help. He just hasn't been great about this. He provided no onboarding to me, didn't teach me anything and I basically had to pick up everything by myself. I'm a bit worried I'm up against a behavior that has become very entrenched or that he really just doesn't have the motivation he once did.
>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.
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 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.
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.
> 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.
I think you're right in general though that I really do need to do some soul-searching to figure what I want.
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?”
The top two or three answers on this post are the way to go - talk, explain the issues, sure, see if there is something that could be done to help, but ultimately just look after OP’s own and OP’s organisation’s interests. It doesn’t matter if CTO is put out or not.
We are all very very clever, but often miss the emotional part.
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.
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!
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
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.
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.
> Sometimes the most important thing isn't absolute max productivity.
This is a really great point to keep in mind.
This is a fantastic question and good way to think about the issue. It may very well be that if I were to write down what I think he ought to be doing, that it would differ greatly from his own perception of what his role. But at least by identifying the divergence, we can work to rectify the situation.
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.
More power to this guy if he thinks he can make a move and make it work out.
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”.
I wish I was in your place as you are getting more autonomy and that will definitely help you get to the next level.