Dealing with Confusing Feedback from my CTO in a pre-seed stage startup

Exit Criteria

• This is a fancy way of saying "signs you should leave the company".
• Synergy is so important with early-stage companies. If after all this, this is still genuinely bothering you and you feel like the CTO isn't acting strongly in good faith to make you feel better, I think you should leave. It's worse than letting this misalignment fester and blow up the company. The CTO and Engineer #1 absolutely have to get along incredibly well.
• Doing product direction and execution work is hard: I've been there. This is why as I grew to a leadership role within Instagram, my manager told me to write less code and just delegate it away. It is simply not reasonable to expect someone to do as much execution work as you and also expect them to come up with ground-breaking ideas to really level up the company at the same time: There's not enough hours in the day. I think you should definitely be a strong voice in the room when it comes to company vision, but when it comes to PMF, that is mostly the job of the CEO (and maybe CTO as well if they're the classic technical cofounder). If they're demanding both of this from you, I think that's another reason to leave.
• If you have landed new ideas on your own, can show the impact, and they're still giving you this feedback, that's another sign to leave. It means that you're not getting full credit for your contribution.

I decided to leave this job, my last day will be next Friday.

I’m absolutely happy about my decision. I’m not so happy about being unemployed with this market, but I can afford it.

Thanks for helping me out!

Sorry to hear this - It always sucks when you're working super hard (which you clearly are), and you feel like your work isn't fully appreciated. First, I recommend these 2 other discussions where the engineer and their manager didn't see eye-to-eye:

• "Manager and I were misaligned about my promotion - How do I remedy this?"
• "My manager and I don't see eye-to-eye. How can I improve this relationship?"

There's a lot to unpack here, so I'll split up my response in multiple parts:

1. How to work better with your CTO
2. How I'm deciphering the feedback
3. Exit criteria

How To Work Better With Your CTO

Here's my core points here:

• Figure out their perspective - Right now, what you have from them seems pretty vague. "Think more about how the business should succeed" is literally something that every employee at a startup as small as yours should be doing, so that's effectively nothing. Ask clarifying questions like:
  • What avenues of success should I be thinking about? - This can be growth, retention, marketing, product performance, new features: There's so much an early stage startup can work on.
  • What's a good idea example I can model off of? - I assume the CEO/CTO are regularly coming up with ideas to improve the company. If there's an idea (or better yet, a suite of ideas), they're proud of, make them tell you, so you can use it as an anchor.
• Flip it back to them - After you figure out exactly what their perspective is, you can find the delta between their expectation and what you're actually doing. Ask questions about this delta until you figure out how to improve or prove that you are doing what they supposedly expect. Show proof if you're aiming for the latter of course.

At the end of the day, this is a classic exercise in delicate communication, so I 200% recommend watching my Effective Communication series if you haven't already.

How I'm Deciphering The Feedback

• I assume your company is <10 people, probably even <5 people as you're the only engineer. At this stage, it's often expected for every employee to have a huge impact on product direction, especially if they're a senior engineer like yourself.
• You mentioned that you're suggesting new ideas on what to do, but a lot of what you outlined is embedded in execution. My guess is that they want you to spend more time on the brainstorming aspect.
• There's also a depth component to suggesting ideas - This could be what they think is lacking. It's very easy to be "the idea guy" and just suggest a bunch of ideas (this is really annoying in startups and in general); the next level is to actually make a real case for your ideas. You can do this with the following:
  • Make a formal presentation doc. It could also be a deck.
  • Show metrics and case studies demonstrating that your idea has concrete data vouching for its potential effectiveness.
  • Attaching a detailed execution breakdown and an engineering estimate in terms of time, which is something you are specially equipped to do.

@Alex (I wish tagging works, but I bet that’s on the backlog already 😄), thanks SO much for your response; I’m going to watch/read your suggestions over the weekend to start my new week on the right foot!

I love what you said in the exit criteria section specifically speaking: “…it’s simply not reasonable to expect someone to do as much execution work as you and also expect them to come with ground-breaking ideas to level up the company at the same time”; sadly I think I’m on that boat right now :/

I talked to my CTO yesterday (Thursday), and after a long talk, we ended up with a plan…which, well…sounds like what I mentioned above (do 100% great technical work + share ideas on a specific date), and now that I think about it, it makes me think that it sucks.

I’ll give this a try and try to adjust the expectations.

I’ll be back to this post to update you about my situation!

Thanks ❤️

How can I "draw a line" here? Or should I draw it at all?

That's a great question! Unfortunately this is really hard to do as it isn't something you can really measure (as with many complex issues in tech like this).

I think my main piece of advice here is to make your best effort following the advice I gave before about pushing to understand their viewpoint and deepening your contributions and from there, follow your gut. If you're simply being overworked, and you're pulling far more of your weight than the cofounders, your gut will let you know.

However, you can be a little more scientific about it and keep a track record. Even at such an early stage startup, it helps to write things down so you always have that historical "bird's eye" view. In terms of what to write down:

1. Idea contributions + impact - Let's say your startup has tried 10 things in the past quarter. Who was the primary driver behind each idea? More importantly, who was the primary driver behind the most impactful ideas? If it turns out that you are the main person behind 80% of the best ideas, that signals drastic action to me. Either you should get far more equity or you should just leave as you're probably good enough to start your own company and the cofounders clearly aren't very good at their job (i.e. figuring out the direction of the company and getting PMF).
2. Execution record - When it comes to actually building stuff out, who's doing it? Let's say you're doing 80% of the raw execution: I think it's fine in your case to only be responsible for 20% of the big ideas moving the company forward. High-quality ideation takes a lot of effort: If someone is doing the heavy lifting coming up with the best ideas, it's fair to not expect too much execution from them (and vice versa).

Again, there's no hard math to this, so I recommend just writing and maintaining that historical record of company contributions, plug away at things for another 1-2 months, and use your analysis + your gut to go from there.

I wonder if you could discuss how you plan to spend your time in each 1 or 2 week planning cycle? This way you get some implicit buy-in from the CTO that those areas are the highest priority for the business.

@Rahul, thanks!

Yes, I understand that finding PMF should be the priority because the company will die without it, and it makes sense that it's the only thing that matters in the end.

I have some following questions about what you (you suggested this in your video) and @Alex said:

There's also a depth component to suggesting ideas - This could be what they think is lacking. It's very easy to be "the idea guy" and just suggest a bunch of ideas (this is really annoying in startups and in general); the next level is to actually make a real case for your ideas.

I agree with that, and the plan we came up with after our meeting was basically for me to suggest ideas after the next development cycle (2 weeks). And that makes sense, and I think that that's what it means to be the founding engineer. But I'm having trouble with this point in the Exit Criteria section that @Alex mentioned:

...but when it comes to PMF, that is mostly the job of the CEO (and maybe CTO as well if they're the classic technical cofounder). If they're demanding both of this from you, I think that's another reason to leave.

And I say, "I'm having trouble" because I see them as "conflicting" to some extent. That said:

How can I "draw a line" here? Or should I draw it at all? What I'm trying to figure out is when do you think (I know this is a super tough question) it is reasonable to say, "Well, I think I'm almost taking over the CEO/CTO's role here in terms of product direction I better stop" or "I think that they're just asking too much from me, this is not my role."

To add more color to this situation:

• The CTO is also writing code and acting as an engineer most of the time.
• We're three people, the two co-founders, the CEO, the CTO, and myself.