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Comment by cientifico | Hacker News Reader

I recently became CTO, and one of the biggest struggles I have is communication with the CEO. (Sorry if covered by the book, just read the index)

On 8 months so far, the CEO:

  * Don't want to have any alignment meeting.
  * Don't want to plan anything.
  * Don't want to drive vision.
  * Want to focus only in the killer feature.
  * Don't want to build mockups or prototypes to test with users.
  * If we do, they have to be beautiful.
  * Don't want to work on anything that takes more than a week.
  * Rejected to have any effective meeting.

</Frustration>

What I want to say in this message is that I miss exactly the things that are not in the book.

Edit: we are just 3 cofounders!

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I've seen that before. At least in my context, this happened because the CEO did not see the CTO as anywhere near equal at all. Instead, the CTO was the CEO's "tech guy". And because he was considered the best or most important tech guy, the CTO got his title.

Sorry about that, but it sounds like you should consider the possibility that the CEO sees you as just another employee (with a fancy job title). In that mental state, it would mean a waste for the CEO to include you into his decisions.

Indeed. Recommendation is to make this clear to the CEO and if he doesn’t understand (likely outcome) just leave.

That's the plan.

I had a job offer recently and it's very obvious that the CEO does way too much CTO stuff than they should. It was my biggest red flag (against everyone's recommendations, since the job offer came with a very generous package)

I've been in this situation. The CEO did not listen to his "tech" people about product, marketing or business issues. The company ultimately collapsed, leaving him with 2 options 1) go out of business, 2) fire sale acquisition. Well, he got "acquired" for pennies on the dollar. None of the original investors, himself included, got anything.

Here I take the blame. I ask from day one to work on some kind of vision. She said that we can't talk for days, so better do it fast.

I said yes (instead doing what I wanted that was to invest the time needed to agree on a vision).

Then I continued saying yes again and again, until without realizing it, I put my self in an employee mindset. Waiting for her to decide what I work as she blocked everything.

I need to move back to founder mindset and start setting some boundaries.

Long ago, when I was young(er), I made the trek to YC's Startup School one year. I was sitting in the audience when someone asked Marc Andreessen how they should go about deciding when to break up with their cofounder.

I still remember Marc's answer exactly: "If there's any doubt, then there's no doubt."

I know it's such a huge decision that I, as a random Internet commenter, won't be able to convince you. Let me try anyway: It's been eight months. Presumably, you've tried everything you're going to try to fix this. What else is left that you haven't tried? What are you logically expecting to have happen here?

And how much more of your life are you planning to invest in a situation like this, when you could easily go elsewhere and be working in a productive situation instead?

I still have a couple of things to try... But you are right. If it doesn't work so early...

Thanks for your comment.

I'll relay a quote from my mother -- "If you're feeling bad about this. Don't worry. It will only get worse! Hahahaha! (phone click)"

In all seriousness -- what you're running into is exactly what makes the job challenging. Here are a couple places to start, having been both in your shoes, and the shoes of those on the other end:

1. Executive 1:1s -- who are the other executives you work with outside of the CEO if any? Try to get 1:1s scheduled so you can get some more context about what you're walking into. Get a sense of what their needs are, which will give you a sense of what the broader organization's needs are. Remember, you're being hired to make the CEO's problems go away /without/ their asking you. Being able to integrate into their executive team is one of the best ways to prove you know what you're doing, and all it takes is some consistency, diligence, an open mind, and a desire to earnestly ask helpful questions.

2. Executive alignment meetings -- Is your CEO and executive team meeting regularly? If so, ask to join. If not, take the initiative to plan it -- ideally after you've aligned with the other executives beyond the CEO. Even if the CEO cannot make every (or even most) of their meetings, they'll greatly appreciate the initiative and it will build credibility. I know you mentioned they don't want to have these meetings, so it may be required to work indirectly through other executives first, based on who has the CEO's ear.

3. CEO 1:1 -- if you're the CTO, your CEO likely wants to have some degree of a regular 1 on 1 catchup, if at least to make sure you don't leave. You can figure out a cadence to make this work on said CEO's calendar -- whether it's once a week, biweekly, monthly, etc. The purpose of this meeting is to ensure that you are able to align with the CEO and collect feedback from them about what areas you're doing well on and around what areas you can improve. If you can't get this scheduled, I don't think you're in a place where you're set up to succeed and I'd advise you to leave. If it's hard to get this scheduled, try pushing on the first two approaches first to get the rapport to get here.

Most importantly -- if you can't get any of these scheduled, you should really re-evaluate whether this is the right role and whether you shouldn't move. If you are the CTO and you cannot get some kind of regular time, no matter how infrequent, with the CEO and other executives, you are not really the CTO and you should consider leaving. Just my 2c.

Seems like you're being treated as more of a founding engineer (as others have written).

I wrote about the difference here: https://www.mooreds.com/wordpress/archives/2555

That said, I'd worry about the lack of planning or driving vision. Those are two critical parts of any early stage CEO position. Do you know why they are so focused on the near term? Is it because they're trying to drive an MVP so they can fundraise or sell? Because they don't have a vision? I'd probably dig into that and try to understand why. (Or, as others have suggested, leave.)

Hey, that's my last job..!

Are you up to the point where you outline necessary short-term steps that must be taken, and the CEO says "Yeah ok, here's what we're doing <totally unrelated stuff>"?

Or the cool part where you push for SOC2 accreditation, the CEO says "not yet" but still talks about how you're "working towards SOC2 accreditation" in sales pitches?

Don't worry, its not you that's schizophrenic.

Devils advocate: it sounds like you’re seeking for too much affirmation from your boss and instead, they want you to be a leader of your division.

Which means, you should be informing your boss (CEO) what the product vision is and executing on it. Not seeking their approval to do so.

Unsolicited advice: you probably don’t want to be calling out your CEO when people know who you are (HN profile).

I have worked with a few CEOs like this; the last was an old company (25 years) in dire need of a digital transformation to survive. The company had more than 300 employees and was still using Excel and Lotus Notes on-prem server room. I started a move to Office365 and Azure Cloud .NET, but the CEO showed no interest in the technology and gave me a few months to complete the transition. He came up with some unrealistic ideas for accomplishing the move when timescales were not met.

After a year, I left the company after delivering a few things. Recently, I visited their website and found only a single home page with several PDF documents embedded within it and no sign of any client-facing solution. Assume they are back in Excel again.

There are plenty of CEOs / Founders out there that would love to find a great CTO / CIO so don't give up looking :)

My advice is to start looking for a new job or go freelance. I started doing fractional CTO work - which is interesting but challenging to find new clients.

I see two possible situations here; but, IMO, both situations imply that you should probably walk away.

In general: Most people can't start a tech business. Starting a tech business is like being a professional athlete: Most people can't be a professional athlete either!

Situation one:

Early stage businesses need to try a lot of different things against potential customers, and see what sticks. (Look up product-market-fit.) If you aren't at the product-market-fit stage, it doesn't make sense to work on anything that takes longer than a week. (Or a month.)

This is because, if you build something that takes longer than a week (or month,) you're probably building the wrong product.

IE, if this is the situation you're in, you might be better suited to working for a company (startup) that generally has product-market-fit, because you like to build a known thing. There is nothing wrong with this, because this describes the vast majority of technical work.

Situation two:

The CEO probably is a lousy CEO. There is nothing wrong with this, because most people can't be a CEO of a successful startup. It's up to you and your other founder (and investors) to recognize this and figure out what to do. (Replace the CEO, walk away...?)

This is also hard to recognize: I spent over a year of my life working unpaid with someone who initially appeared to be a good CEO. At the end, I realized this person was better off building a sales organization instead of being the CEO. (The big issue was the person I was working with would constantly let their imagination run away, which made it very difficult to plan anything.)

I also more recently spent time with two founders investigating if I should be their CTO. Again, great people and appeared very promising; but, in one of our last conversations, one of them made some off-the-cuff remarks that made me realize they didn't know how to start a "tech" business. Although I wish them the best, I don't think they're going to meet their market window because they're just working on the wrong thing for their talents. (IE, they didn't want to invest enough time in me to build appropriate trust among us; and they didn't know how to hire the right people to build the product they needed.)

Founder issues are the #1 reason for companies to fail. And mismatched founders are very common. Especially with inexperienced founders. And with startup accelerators being biased to young and inexperienced founders, you can blindly assume this to be the case for most startups in such programs.

From reading your comment, my conclusion is that you are not a CTO but a lead engineer employed by your two co-founders. This company is probably going to fail and it isn't your fault necessarily. Or very fixable. If your CEO can't delegate things he's not good at that you are supposed to do, that means either you are the wrong person for the job or they are. It's that simple. Figure out which it is. And have that conversation with them ASAP and not in two years. It will save both of you lots of time and money.

I see this a lot in the startup world: non technical founders involving a CTO because they believe they need a tech person to take care of the pesky tech thingies they don't understand. Tragically, a lot of companies end up picking the wrong person for this job because they simply lack the capability/judgment of picking the right person. And a lot of would be CTOs end up wasting a lot of time dealing with a rudderless co-founders and companies that they are not actually empowered to fix.

Such companies founding with a CTO is a ticket for disaster. Either you are a tech startup in which case the CTO should be the main founder of the company and the largest shareholder that has the final say in what the product is and does. The CTO should be seeking out a good CEO/CRO to manage the business side. Not the other way around. Classic example here is Google with effectively two founder CTOs eventually getting Eric Schmidt to lead the business. Worked out great. Mark Zuckerberg maybe should have done the same thing with Facebook.

Alternatively, you are some kind of non technical company where tech just is a means to an end (we need a website, an app, and a thingy and some hand wavy slide compatible aspirational buzzwords). That's completely valid of course. Such companies need technical and operational leadership and managers but these aren't founders necessarily. Amazon is the classic example here. Jeff Bezos was the business guy building a market place. Involved lots of tech of course. But in the end it was a simple (ugly) website and logistics operation. AWS bootstrapped much later out of that. The right person to get would be somebody that can execute and lead. Somebody like Werner Vogels who wasn't a co-founder of Amazon. And the reality is that you end up replacing some of these people over time as well. Early engineering teams with 2 or 3 people are very different from later stage companies.

I actually get the question if I know a decent CTO a lot from would be founders. My standard answer is: you don't need one and you should avoid getting one. I always recommend other founders to look for a good VP of engineering instead but not immmediately and maybe start with just a few good engineers and a project/product manager. Maybe one of the existing people can step up in an interim role. Don't slap the CTO title on anyone unless you really need one. And if you do, make sure the equity is appropriate and plan for that person to leave or disappear at some point. The person that does your app and website initially is unlikely to be your long term dream CTO.

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