262. Why the CEO is the most dangerous person in a tech startup

Most startup CEOs think they’re the visionary.

But in today’s episode, you’ll learn why the CEO is often the single biggest threat to team productivity — and how to avoid becoming one.

Based on a real conversation with a seasoned CTO and a sales leader who’ve scaled startups to exit, this episode dives into the blind spots that trip up even well-meaning founders.

Whether you’re a CEO, part of a startup team, or investing in one — this lesson will help you lead smarter, build better, and waste less time.

Listen to learn: 

• Why startup CEOs are more dangerous than corporate CEOs (and it’s not about ego)

• What “Seagull CEO Syndrome” does to your roadmap and morale

• How developer paralysis destroys velocity — and how to fix it

• What smart founders, teams, and investors can do to keep priorities on track

Lesson mentioned in this episode: 

Why MVPs are Always Late, Why That's Okay, and What to do About It

Chapters

00:00 — The Real Threat: Why Startup CEOs Kill Productivity

02:10 — Power Without Process: How CEO Impulses Go Unchecked

04:30 — Seagull Syndrome: How CEOs Derail Roadmaps

09:15 — Nothing to Do? Why Bored CEOs Delay MVPs

14:10 — Bottlenecks in Human Form: When CEOs Bypass Their Own Leaders

Growth Through Innovation

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Transcript

Sophia Matveeva (00:00.534)
Most startup CEOs think that they're the visionary, but actually they're often the biggest threat to their team's productivity. And in this lesson, I'll show you why this happened and what to do about it.

Welcome to the Tech for our Techies podcast. I'm your host, tech entrepreneur, executive coach at Chicago Booth MBA, Sophia Matheva. My aim here is to help you have a great career in the digital age. In a time when even your coffee shop has an app, you simply have to speak tech. On this podcast, I share core technology concepts, help you relate them to business outcomes, and most importantly, share practical advice

on what you can do to become a digital leader today. If you want to have a great career in the digital age, this podcast is for you. Hello smart people. How are you today? If we haven't met yet, I am Sophia Matveva. I'm a non-technical founder who has built tech businesses from scratch and helped governments and Fortune 500 upskill for the digital economy. And this show is where we help non-technical innovators learn how to build tech ventures.

without drowning in jargon. If that is your goal, then hit subscribe. Today's lesson is actually built on a conversation that I had at home with a couple of friends at dinner last week. So both of these friends had worked at startups and one of them was on the sales side and the other one had been a CTO at various companies. And they had both worked at companies that weren't from being quite small to exit. So they basically know what they're talking about. And at dinner, they both concluded

that the CEO is the most dangerous person in a startup and that actually is the CEO who is most likely to disrupt things when things are going well. So basically if the CEO didn't spoil things, then things would have been better. They both concluded and they worked in very different startups in different geographies and kind of had the same experience. And the thing is, I'm sitting there and I've actually been the CEO of two startups in my last company.

Sophia Matveeva (02:08.174)
called NT, I was the CEO, that was a tech startup, and at this one, a tech from Techies. And unfortunately, I actually agreed with them because I recognized a lot of the destructive behaviors that they talked about. And frankly, I knew that I had done them. So today, we're going to cover why the CEO is the biggest threat to startups productivity, and what you can do about it, whether you are the leader yourself, or whether you are in the startup team, so you're having to deal with this person.

or whether you're funding startups. So I've got four main lessons for you. And then we've got to wrap up about basically what you can do about these things. So first of all, let's talk about what happens in a large corporation. So in a large corporation, the CEO is much more constrained because they've got lots of layers. So basically, you know, there's the CEO and the people who are doing the actual work, you know, the client facing people, the people doing the grant work.

They are really far removed from the CEO. And moreover, the CEO, you know, if they come up with an idea, it has to go through a strategy department. If it's really big, it has to go through board approval. The board might not approve. They have to convince the board, investors and so on. So basically the CEO is much, much more controlled. In startups, the CEO can literally walk up to a developer and say, build this and then somebody will do it. So essentially in a startup, they have this unchecked power.

And even when there is a board, it is not the same as it would be in a large company. And so basically this unchecked power can destroy velocity. And it's not necessarily because the CEO is a bad, bad person. So insight number one for you is that because in startups that infrastructure to temper the CEO's impulsiveness does not exist and the CEO can literally double somebody's salary or just sack them on a whim.

Basically, nobody says no to the startup CEO in general. So a startup CEO can walk up to a developer and say, do this, that developer will literally stop doing what they're doing and start working on this other thing. And that can be really, really bad. So if you are the CEO, if you are the leader watching this, make sure to build a culture where you can be challenged. And I'll give you an example. So.

Sophia Matveeva (04:32.44)
In my last company, Ente was a fashion tech company. We had a very strong CTO, so my chief technology officer, he himself was a very strong character and also he was very well respected in the industry and I really respected him. And also as a non-technical founder, I knew that technology is his domain and that I had a lot to learn from him on that side. And equally he respected my domain. And so when I would come up

with a feature idea. you know, as a startup CEO, I would see like a TechCrunch article or I'd see a competitor's feature, I'd like, we need to have this, this is a great idea. Yes, let's do this and we'll make millions. Anyway, so when I would have one of these ideas and I wanted to create a feature that we hadn't discussed and had not yet been in our plan, my CTO would say, okay, fine, we can do this, but we already have a plan.

So if we start working on this new thing, that means the plan is going to stall. So do you really want the plan to stall or what bits of our plan do you want to remove so we can do this new thing? And so essentially, he cleverly didn't actually say no to me. He basically just explained the trade-offs. And once I understood the trade-offs, then I could make a decision. And a lot of the time I'd think, you know what, this feature is a good idea, but we can...

put it in development much later on. We also need to test it. And actually our plan right now is pretty good. Let's carry on doing that and then we'll get to this later. So I needed somebody who was essentially strong enough to say to me, look, this is the plan. What do you want to take out of the plan? Because without that explanation, essentially we would have been all over the place. And you know, I would say I was a first time CEO then. I think I hope I do this less now.

But I definitely noticed this tendency. you know, I listened to my CTO and I had respect for his expertise. And this is another thing that, you know, if you are the leader, then hopefully you have respect for the, you have professional respect for the people that you've hired, right? So listen to what they have to say and also empower them, you know, like the way you empower them to say stuff is you ask them, do you think this is a good idea? Should we do this? And tell them, you know, maybe get them to listen to this episode. Okay.

Sophia Matveeva (06:55.843)
Insight number two, the CTO guy who was at dinner, he told me about the CIGAR CEO phenomenon. Basically, he says that, okay, what would happen if the development team, they're all working on something, they're writing code, and then the CEO who's usually at like investor meetings and talking to media or customers or whatever, the CEO just swoops in, as he said, poos all over the place.

like poos all over what you're doing, I stopped doing this, start doing this, basically completely disrupts momentum and then disappears. So basically like a seagull, go in, everywhere and then fly off. And so he said that as the CTO, this happened to him several times in companies that he's worked in. And he said that as the CTO, he would be left cleaning up the mess because essentially they'll be working, they know they would have things.

in their sprint, say they've got a plan, this is what we're going to release within the next week. Then the CEO comes in, all of that basically gets disrupted. And the CTO somehow has to make sure that their timelines are not slipping and people are not completely demoralized. this is really hard. So developers call this requirements churn or even worse, developer paralysis. And also another thing that he told me about is that, you know,

This year wasn't always around to make all of the decisions, which is correct in a scale up. And there will be other senior leaders who would say, okay, we need this in the product roadmap. But he said that developers would actually stop listening to the senior leadership team and stop listening to their ideas because he said that, you know, this year would come in and they would say, okay, no, no, we don't want to do this. We want to do this instead. And developers would think, well, why do I want to start working on one thing?

because the main guy is going to come along and change everything anyway. So why bother? So actually, when you have this situation, it completely destroys productivity because people are actually not doing anything. And also the people who are not doing anything, they are very expensive and often really highly educated. So if you annoy people like that, they will leave and they can have other options and replacing them is difficult and expensive.

Sophia Matveeva (09:16.953)
The rule here is do not derail your own product roadmap if you have a fancy new idea. Use a structured product review process. Remember the story that I told you about above. So essentially think about the trade-off. So if you have a product plan, so you have agreed that within the next couple of months, these are the features that you are going to create. You know why you're going to create them. You're going to create them because your customer said that they wanted them. We have some sort of commercial idea for why it's a good idea.

So you have this plan and what you really don't want to do is just be like, no, no, no, this is all rubbish. Let's do this. If you are going to derail your own product roadmap, essentially your entire company is going to be all over the place and so is your team. now insight number three, there is little to do for the CEO before the product is ready. And this is one I find the CEO can be really, really annoying. And I speak from personal experience. So

Have you ever seen on LinkedIn when somebody says that they're a founder and it says, you know, the company is in stealth mode. Stealth mode basically means that, okay, the company exists, you might've raised some money. You actually have people working on the product. So the product is being made, you know, the app, the algorithm, whatever is being created, but it doesn't yet exist. It hasn't yet been released. So at this point,

for the CEO, especially if they're a non-technical founder, they kind of don't have much to do because they can't raise any more money before the product is ready. They don't have any customers and they can kind of go around and recruit customers to a point, but before your product is ready, you're very limited in what you can do. You can't really promote it and you can't really raise money and the team are developers, so you can't really supervise them.

So basically that's when as the CEO, you are kind of being like, okay, I'm the most important person in theory, there's like, can't really add value. So this is when CEOs try to busy themselves, basically by trying to get involved in things that either they should not be getting involved in, or by creating new features for the first version of the product. So this is another thing that the CTO told me, said, well, I've been in several situations where

Sophia Matveeva (11:41.935)
We are working on the first release, so the minimum viable product. We're working on that. And then the CEO is kind of restless and has nothing to do and keeps on coming up with new ideas. And we say, yes, yes, yes, these ideas are good, but this needs to be in version two or in version three, because if we keep on being distracted and we keep on putting in new features into the minimum viable product, we're not going to release it on time. And so there is a video actually I have on why MVPs are always late. And this is one of the reasons.

One of the reasons that the requirements keep on slipping because somebody often this year was like, no, we need to this and we need to have this. So this delays shipping. That does not look good to customers, to investors, also to your team because, you know, they need motivation. I find that the entire team is kind of restless before the product is released. So basically what can you do about this?

Focus basically, be an adult, be the guardian of priority. as you can tell so far, I just keep on saying to you, know what your priorities are and keep on focusing on them. And essentially don't be distracted by shiny object syndrome. Key insight four, that's the last one for you. The CEO can be a bottleneck in human form. So this actually happens most often when you are not in a remote team. So you'll hear.

You'll understand what I mean. What can happen, and it should not, is that the CEO has an idea and wants something done. And they walk into the office and they know the developer that would work on it. So let's say, I don't know, the CEO wants something changed on the website and they know who the front end developer is. So they'll just go straight to the front end developer. Instead of going through the chain of command, which should be the CTO, and then the CTO would apportion the tasks.

But they're like, why bother? I don't want to distract the CTO. I can just go to the person who I know is going to do this. This breaks the chain of command and it causes confusion and obviously undermines the senior leadership. But also what happens is what I described to you is in my situation is that I had a very strong CTO who essentially would say to me, you know, he was very polite, but even when he was thinking this is complete nonsense, he would say, we've got a plan. What do you want to take out of the plan?

Sophia Matveeva (14:09.941)
And he was old enough to do this. Basically, he was experienced and really respected in the industry. So he had that confidence of a very experienced person. Now, often when the CEO bypasses that experienced person with that gravitas to push back and they go straight to somebody who's junior, that junior developer is like, my God, the CEO is talking to me. If I don't do this, they'll fire me. Or, you know, they're just a bit like, my God, the CEO is talking to me. I better do everything I can to impress them.

Which is totally normal, right? I behaved like that when I was a junior employee too. You know, if an important person swoops in, I'd be like, I'm going to drop everything and do what they say. So this is why it's so important for the CEO not to break the chain of command. Because the CTO has probably given that developer things to do. They probably have a timeline. And if that developer, the front end developer doesn't do their bit.

that maybe they can't release the entire thing. So the entire team's work is disrupted because one person has stopped working on what they're doing. And often the CTO might not even know because they haven't been told. this, you know, the chain of command exists for a reason. And the chain of command is broken in startups because I think people want to be like kind of cool and like we're all friends and we're in this great startup team. But the chain of command was

exists for a reason. I'm not talking about bureaucracy, like don't create needless bureaucracy. But in order for your products to be released, you need a whole team basically working cohesively. So if you as the senior person go and distract the junior people, the team is no longer working cohesively. So if you are the CEO, then speak directly through your chief technology officer. And if you're in the team, and if you are a junior person, I know this is going to sound scary.

but just say, basically ask them, this a priority? So you can say to them, I am working on this, know, the boss, the CTO told me to work on this. Shall I put this aside and do your thing? And if they say, yes, this is really important, then okay, frankly, what can you do? They're the CEO. But often they might think, yeah, okay, literally, I just had this idea on the taxi coming over here. I didn't really think it through.

Sophia Matveeva (16:32.557)
I was just kind of like saying things that are on my mind. I didn't really expect everybody to drop what they're doing. So, I mean, that has definitely happened to me and I know that's happened to other leaders. So here's our wrap up. What can be done to make the CEO less dangerous to make the entire team more productive? So if you are the CEO, be aware of your own weight because your words are interpreted as instructions.

You might've just read something in an article and you might think, yeah, this is something we should do. This sounds really cool. But people are going to drop what they're doing and start doing it. So be aware of that. So filter your input and ask yourself, is this a useful comment to say now to this person? Often, frankly, it's not. If you're on the startup team, I suggest that you learn to push back strategically. Basically do what my CTO did. Say,

So, okay, well, I'm working on this. And so how does this thing fit into our current priorities? And if the CEO says, you know what, this is super important, drop everything else. Well, you got to do what you got to do. But basically help them understand that they're a trade off. And obviously use your own judgment because if this CEO is a reasonable person, then okay, they're going to think, oh, you know what? Yes. Okay, fine. Let's put this into as priority number three, not priority number one. Sometimes.

you're just going to have a massive egomaniac who's going to throw a fit. So it was, it was that kind of person. Obviously pushing back is not a good idea, but if they're a complete weirdo egomaniac, maybe you a job somewhere else. That's it. That's another lesson. Anyway, if you are an investor, I just want you to know that this happens. And if you're an investor, you are, you know, mostly speaking to the CEO and you might not know that this is an issue. So

Pay attention to founder behavior, to just product market fit. Because a well-meaning but chaotic CEO who does not respect the chain of command, essentially doesn't respect his senior leaders. And if senior leaders don't feel respected, what do think they're going to do? So that's the end of today's lesson. I hope you found it useful. If you did, then I would love to hear from you. So please write me a comment or a rating or a review or if you're watching this on YouTube then

Sophia Matveeva (18:59.099)
press like and maybe write a comment, be super generous. And obviously subscribe because especially if you're a non-technical innovator who wants to succeed in the digital age, this show is definitely for you. And by the way, if you are a non-technical founder building your first venture, then you should definitely take our Tech for Non-Technical Founders course. It is not currently open for enrollment because it's summer and I want you to have some time off and enjoy yourselves, but it is going to be...

open in autumn, in the fall when it's back to school. So basically stay tuned. And on that note, I'm going to love you and leave you, wish you a wonderful day and I shall be back in your delightful smart ears next week. Ciao.