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

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!

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

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

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.

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.

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.

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.

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.

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.

"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."

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 didn't flesh this out enough in the original post, but the CEO isn't actually dismissing it casually. He actually said this is really serious and said he thinks we should address transparently sooner than later. It's more that he's leaving it to me to figure out the right way to approach it. On the one hand, I appreciate him giving me some time/space to figure out how I'd like to approach it. On the other hand, I feel he's kind of shirking his responsibility and pitching it of to me.

I am completely unqualified to answer this question, but it seems to me the CEO should be handling this.

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.

Right, I've thought this too. I mentioned in another reply that, on the one hand, I appreciate the CEO giving me some time/space to figure out how to approach this delicately. On the other hand, I feel he should be providing more support to me in this scenario. How exactly though is kind of a good question.

I am in a completely opposite situation as yours. I joined as VP Engineering at a startup and my CTO refuses to pass any responsibilities. I tried to communicate him multiple times to let me take care of day-to-day management stuff which he agrees to but jumps back right in. I think part of the reason is his passion about the product and expertise but that is definitely getting in way of me doing my 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 have been in this situation (I was burnt out and knew it) as CTO (and co founder) and suggested to my right hand to replace me and find something better for me.

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'm torn on this. It's possible he would be very receptive and appreciate the frank conversation. It's also possible he will wonder where I get the gall to suggest to him, in however a constructive or trying-to-help way, that maybe he doesn't actually want to be CTO anymore and should consider giving up his role. He's not the type to freak out on me or anything like that, but it could sour the good relationship we have.

Slow down a bit. Give yourself time to enter his world learn about his experience and meet him there without passing judgment.

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?”

I know you’re not trying to be, but this is very childish.

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.

I sometimes call this puppy language or toddler-speak - intentionally beyond childish. With extreme emphasis on emotion and attitude - which I believe is often the missing component.

We are all very very clever, but often miss the emotional part.

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 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.

That would be great. I'll send you an email later this evening. Thank you!

Based on some of your comments, you’re kind of gunning for the CTO role and trying to manage upwards.

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”.

This is great feedback. Thank you.

If I was the CTO I would hire another vp with a different style and pit you against them and slowly move you out but he can't afford that so he is stuck with you for now.

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.

So executives can play politics but everyone else should just know their place? This is a bootlicker attitude.

More power to this guy if he thinks he can make a move and make it work out.

What I suggested is playing politics. Being so direct and about your ploy won't get you in the club. Create leverage before you try a power move.

Two years is a long time, even more so for a startup. In a 25 people team there's not much room for two heads and such situations are rarely comfortable. If the CEO acknowledges but hasn't done anything about it, maybe they are shirking hard decisions.

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.

> CEO, he basically acknowledged it's a problem and put it on me to bring it up with the CTO however I 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.

If a junior employee was to write up job descriptions for all of the roles on the org chart, what would the CTO's role and responsibilities be? They hired you to run the engineering department, so the CTO could focus on other work. What is that other work? Is that work enough to keep the CTO fully engaged? Is the CTO the right person for that role? The CEO has acknowledged there is a problem. If the CEO understands why the CTO is checked out, the CEO can engage you in the solution. It's their responsibility though.

> If a junior employee was to write up job descriptions for all of the roles on the org chart, what would the CTO's role and responsibilities be?

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.

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 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.

Lots of things to unpack here and there was quite a delay in my response. But here it is.

>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 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

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.

This is a good point. You're right that it really does come down to getting from him the things that I think the team and I need in order to succeed. Sometimes, however, I worry that I'm not getting the point across if I dance around an issue or "soften" it up too much. I'm sure there's a middle ground though where I can get my point across while keeping the conversation practical, focused and constructive. I just need to give some more thought as to how to do that.

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.

Wasn't the issue that the CTO was underwater and you were brought in? So, could it not be the case that he is trying to recover?

> 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.

Great question. If he were fulfilling what I view as his responsibilities, I would not necessarily feel it imperative to take over for him. If he were to leave — whether voluntarily or forced out — I would gladly take over the role. I'm qualified for it and I'd be the natural choice. Not sure if that answers your question. I generally have ambitions to continue to level up and that definitely involves being in the CTO spot somewhere, but I don't feel it has to be here and now. But if they wanted me to take over, I'd very excited to do so.

I think you're right in general though that I really do need to do some soul-searching to figure what I want.

Oh and yes, I do think he's "trying" to recover in a sense. The thing I'm unsure about — and maybe he himself is unsure of — is whether that ship has sailed and he's either unable or unwilling or unmotivated to recover.