AUGUST 23, 2025

Why designers rarely make great CEOs

It is telling that among all Fortune 500 companies, only Brian Chesky at Airbnb comes from a design background.

Why designers rarely make great CEOs

Brian Chesky is the only Fortune 500 CEO with a design background. Out of 500 of the world’s most powerful companies, only one is led by a designer. That fact alone says something about the gap between design and leadership.

I have felt this gap firsthand. A few years ago, I was in a workshop that looked like a parody of itself. The walls were covered in sticky notes. We had empathy maps, personas, journey maps, lo-fi wireframes, and multiple iterations of the same flow taped up. It looked impressive, like we were doing “real design.”

But when I looked at what we actually shipped to users, it was… fine. Not great. Not memorable. Definitely not the thing people would love and keep coming back to.

I recently realized that design is no longer about creating products people love. Too often, it has become more about proving that we followed the process. That we matter.


The process trap

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Jenny Wen captured this perfectly in her piece, Don’t trust the design process.

We stopped doing the real thing that would be the most empathetic, useful, and that would actually serve business outcomes best: building stuff that worked well and that people would love.

Between 2014 and 2020, design became obsessed with The Process. Instead of showing great products and designs, portfolios were filled with flows, personas, user stories, and concept tests. We became servants to the process.

And it made sense at the time. Ten years earlier, design was mostly about making things pretty. We needed to evolve, to prove we were serious about understanding users, business outcomes, and complex systems.

But in proving that, we lost something. The craft. The product. The thing people actually touch.

We convinced ourselves that good design was about following the steps. That if we just trusted the process, we would get to the right outcome. But some of the best work I have seen has come from skipping steps, backtracking, starting from a solution, or simply building something because it felt right.

The process was supposed to serve us. Instead, we started serving it.


Where workshops still matter

None of this means that process or workshops are useless. I still run ideation sessions often, and I think they are one of the best tools we have for driving alignment.

When you bring a mix of stakeholders into a room, you get their thinking, their perspectives, and their ideas on the table. Even if you already know the direction, the act of engaging people creates ownership. It is often the fastest way to drive the conversation forward and ensure everyone feels heard.

The risk comes when the workshop becomes the outcome instead of the input. The value of an ideation session is not in the sticky notes on the wall or the perfectly documented flows, but in the alignment it creates. Its purpose is to open up the conversation, surface different perspectives, and give people ownership of the direction. Once that alignment is in place, the real work begins: turning those discussions into something people can actually use and love.


Why this matters for leadership

This obsession with process is also why many designers struggle when they step into leadership roles.

Designers are trained to perfect the details. To sweat every pixel. To prove the process. But CEOs do not win by obsessing over process. They win by zooming out, seeing the big picture, and moving fast when something works.

When you are running a company, you do not get credit for having the perfect persona. You get credit for putting something in people’s hands that actually works.

Pixel perfection is not strategy. Process perfection is not leadership.


Beyond the pixels

The challenge in design was never really about building. AI has simply made that impossible to ignore. Today it is easier than ever to create designs, spin up end-to-end flows, and even ship full products with tools like Lovable or V0. The craft of building has become the easy part.

The harder part is deciding what to build. Choosing the right problems. Knowing when to copy what already works. Knowing when to skip the process. And knowing when to zoom out far enough to see the bigger picture.

This is also where AI should be helping us most. Not just in drawing screens faster, but in making better decisions. In running ideation sessions that surface stronger options. In reverse-engineering competitors to see how they monetize features or structure their funnels. Tal Raviv has even shared prompts that help teams break down the business logic of a product.

I think this will become (or already is ) the future of design. Using AI as a copilot to move faster, to ideate more broadly, and to make smarter decisions about what problems to solve. Which is why Raviv’s framing of the “Super IC” hit home for me.

The leverage of an individual contributor has never been higher. The job now is not to build more pixels. It is to know which pixels are worth building at all.


Knowing what to build

AI has made the tension between speed and quality sharper.

On one hand, it gives us incredible leverage. You can wireframe in minutes, generate copy instantly, and prototype full flows before your coffee cools. The pace of an individual contributor has never been higher.

But speed is not the same as good design. The faster we move, the more important it becomes to pause at the right moments and make sure what we are building still feels human.

So how do you know when to pause? Here are three practical ways I use with my team:

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  1. Use the Decision Spectrum to categorize impact
    Not all decisions deserve the same attention. A color tweak can move fast. A change to user flows or access logic requires slowing down.

    My PM and I often talk about this in terms of quick wins. After an ideation session, the obvious, low-impact fixes or ideas usually reveal themselves right away. We group those together and start tackling them while giving the high-impact decisions the time and focus they deserve.

    If time is tight, we often push the quick wins forward first. It buys us breathing room and keeps developers moving while we run research or take more time to shape the bigger, bolder moves.

  2. Set decision timers and thresholds
    Urgency can bring clarity. Sometimes we give ourselves 30 minutes to make a choice, like picking a layout pattern. If the timer goes off and the decision still feels shaky, that is our cue to slow down and dig deeper.

  3. Maintain decision provenance, especially with AI
    Every step, even the ones AI suggests, should have a reason behind it. If you cannot explain why a choice was made, you probably moved too fast. We make a point to keep track of our reasoning so we can revisit or reverse a decision later.

    AI makes the craft easier. What it cannot do is provide judgment. That is still our job as designers: knowing when to move quickly and when to slow down enough to make something people will actually love.


Where I have landed

When I mentor younger designers, I see the same mistake over and over again. They trust the process more than the product. They spend weeks inventing flows, frameworks, or problem statements that look great in a portfolio but fall apart when real people use them.

And I tell them the same thing every time: the process is just a tool. Not the goal.

If you want to grow as a designer, stop worshipping the process. Learn how to bend it. Skip steps when they do not matter. Start from the solution if it gets you closer to something people love.

Because whether you are leading a product or a company, nobody will remember the process you followed. They will only remember the thing you built.

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