The Systems Behind Steven Bartlett’s Fast Moves and Big Wins

You don’t get to 13 million+ Youtube subscribers by guessing. Steven Bartlett has systems — and they work.

He’s built and exited companies, invested in dozens more, authored bestsellers, and become a go-to voice on modern leadership and performance.

As host of The Diary of a CEO, one of the most-watched business podcasts on the planet, Steven has interviewed more than 500 of the sharpest minds in business, neuroscience and performance, decoding what truly drives excellence at scale. 

Having spent years myself interviewing global leaders, elite athletes, and high performers across industries, I’ve found there are common threads that keep showing up — patterns I explore more deeply in my book, The Leading Edge. 

So, when I sat down with Steven virtually for Growth Faculty I was especially curious to speak with him — given he is a fellow interviewer and thinker who’s had a front-row seat to greatness in so many forms.

I asked him: What patterns has he noticed? What, in his view, actually sets the best apart?

His answer:

“The most successful leaders aren’t the smartest. They’re the ones with systems and principles that drive faster decisions and keep them focused on the long game.”

 It reminded me of a quote I love from James Clear:

“You don’t rise to the level of your goals. You fall to the level of your systems.”

Big visions are inspiring. But without systems, they’re just hopeful PowerPoints.

Steven’s point is the same: the leaders who stay ahead are building repeatable systems that help them make faster, smarter decisions — every time the game changes. And the game is changing…fast.

You Can’t Outrun Change. But You Can Fish Smarter.

So just how fast is the game changing?

In our conversation, Steven pointed to a prediction by futurist and author of ‘The Singularity Is Near’, Ray Kurzweil, who says we’re on track to experience 20,000 years of progress in this century alone, driven by the accelerating pace of innovation. Yes, twenty thousand.

Put another way:

If you’re 40 today, by the time you’re 60, you’ll experience a year’s worth of today’s change roughly every 90 days.

Let that land: every quarter, the equivalent of a year’s worth of transformation—technology, consumer behaviour, geopolitical disruption, business models—all shifting faster than most leadership teams can plan, decide, or respond.

So how do you keep up? 

Steven’s answer: Don’t give people fish. Teach them how to fish.

As he put it:

“If I gave you the right answer today, that’s a fish. But what you really need is a fishing rod—a system to keep finding the right answer 100 days from now, when everything’s changed again.”

Why Smart Leaders Fail on Purpose

One of Steven’s go-to fishing rods? 

Deliberate, structured experimentation.

He explained that over the years, he’s become “religious” about the value of failure. Not because failure itself is fun or inspiring—but because it’s often the only way to unlock breakthroughs that can’t be planned or predicted.

He’s become, in his words, “religious about the value of failure.” Because it’s often the only path to the insights you can’t predict.

He gave one standout example from his own experience with The Diary of a CEO podcast. His team made a small change — just 10 seconds shaved or shifted in the podcast’s structure — tested over a short period of time. That seemingly minor tweak ended up being the difference between 2 million and 13 million subscribers on YouTube.

“That one change outperformed hard work, hiring well—everything.”

But there’s a catch (yes, pun intended). According to Steven:

“If you want to double your success rate, you have to double your failure rate.”

At first glance, that might not make sense. Surely not all failure is created equal? Surely there’s a more efficient way?

So, I asked Steven…what does smart failure actually look like?

The Systems Behind Smart Failure

Everyone loves to say “fail fast.” But speed without systems is just chaos in a hurry.

That’s what separates Steven Bartlett’s approach from the usual “move fast and break things”. He’s not just encouraging failure. He’s designed for fast, practical learning—on purpose.

Below are two ways he’s built smart failure into the fabric of how his company works:

System #1: Know Which Bets Cost You Nothing (Which Ones Might Cost Everything)

Smart failure isn’t about throwing things at the wall. It’s about knowing which bets are worth making—quickly—and which ones aren’t.

One of the decision-making models Steven often returns to comes from the author of Atomic Habits, James Clear (who Steven had just finished interviewing when we spoke).

Clear explains that most decisions fall into three categories: Hats, Haircuts, or Tattoos.

• Hats are low risk. Try them on, take them off.
• Haircuts might not be great, but they grow out with time.
• Tattoos are permanent. Think twice.

However, most leaders treat every decision like a tattoo — overthinking, over-approving, and over-engineering.

When in reality, Steven says, “99% of the things that we do are hats or haircuts.”

Steven’s seen this play out firsthand. While working with a billion-dollar family business early in his career, he dealt with a father and son leading two different brands under the same roof. 

Pitching ideas to the father meant nine months of sign-offs from procurement, legal, and whoever was back from annual leave.

But when he pitched to the son, he’d interrupt Steven halfway through the pitch and say: “Do it now.”

That speed paid off. One experiment Steven pitched—a $20,000 test—ended up delivering 15 million new followers to the son’s brand.

Over five years, Steven watched two leadership strategies play out in real time.

One treated every decision like a tattoo—slow, cautious, and over-engineered.
The other treated most decisions like hats—easy to test, easy to change.

The result? 

“The son’s business overtook the father’s. Because he intuitively knew that in business, the biggest risk when you’re dealing with hats and haircuts isn’t being wrong—it’s the time you waste making a decision.”

Why This Matters For Leaders

Steven’s story is a reminder: most decisions are reversible. Yet many teams treat small bets like they’re make-or-break moves. That mindset kills momentum.

So ask yourself:

• Are we spending 6 months debating what we could learn in 6 days?
• Are approvals slowing us down more than risk justifies?
• Do our systems support pace—or stall it?

Which brings us to Steven’s second system…

System #2: Reward Experiments, Not Just Outcomes

Here’s where most “fail fast” cultures actually fail: they say they celebrate failure, but they still promote and pay bonuses to people based on results.

So what happens? People only run experiments they’re confident will succeed, which means they’re not experiments at all.

For instance, his company has:

• A dedicated Failure & Experimentation Team whose job is to drive the company’s failure rate UP, not down. At the helm is Grace Beverly Miller, the team’s leader and, in Steven’s words, “the best hire I’ve ever made.”
• A second team tasked with figuring out how to kill the business—before a competitor can. 
• A bonus and promotion structure based on the volume of experiments, not just their outcomes.

Importantly, Steven notes: “We incentivize the input, not the output.”

Steven pointed out Jeff Bezos’ 1-in-10 rule: one in ten bets pays for the graveyard. But you only get to the one if you’re willing to run the nine.

“I reckon we have two good experiments every year that change the game,” Steven told me, “and we have to run through these other 25 things that were a waste of time, but the two pay for the graveyard.”

Amazon’s graveyard? It includes the Fire Phone, pets.com, and a dozen other flops. But AWS — originally a side project out of Cape Town — is now a $150 billion business. It paid for all of them.

Why This Matters For Leaders

This is about having infrastructure for curiosity. You don’t need to run a podcast or a tech business to apply this. 

You just need to ask three questions about your current systems:

1. Are we making it easy to test new ideas? (Or are ideas dying in committee?)
2. Are we rewarding people who move fast, even when outcomes are unclear? (Or only rewarding those who succeed?)
3. Are we recognising pace, learning, and boldness—not just results? (Or are we still promoting based on who plays it safest?)

You get what you reward. If you reward caution, you’ll get cautious teams.

If you reward experiments, you’ll get velocity.

And velocity, right now, is the only competitive advantage that compounds.

What You Can Do Starting This Week

Steven’s systems sound impressive. But how do you actually start building this in your own organisation?

Because most of you reading this aren’t running a podcast empire or a venture-backed tech company. You’re leading teams inside larger organisations, managing constrained budgets, and answering to boards who expect results, not experiments.

So where do you begin? Here are two places to start:

1. Test “Hat or Haircut” Thinking in Everyday Approvals

At the start of every project or proposal, build in a quick classification step:

• Is this a hat (easy, reversible)?
• A haircut (minor impact, manageable)?
• Or a tattoo (irreversible, major risk)?

Then match the sign-off process to the level of risk. Don’t over-engineer hats.

2. Run a “Kill the Company” Exercise Once a Year

As you kick off the calendar year in 2026, you might want to run a team session focused on finding ways to disrupt, undercut, or outcompete your own business or team. 

Ask:

• What would a competitor do to beat us tomorrow?
• What are we not seeing?
• Where are we most vulnerable to being slow or blind?

Why it works: You train your team to seek change before disruption forces it. And you get sharper to your own blind spots — fast.

Fail Smarter, Move Faster, Stay Ahead

Steven Bartlett isn’t telling leaders to fail more for the sake of it. He’s saying that in a world moving at the pace of 20,000 years of change in a single century, the only sustainable advantage is learning faster than everyone else.

That means failure isn’t something to avoid. It’s something to design for.

Not reckless failure. Not chaos. Deliberate, incentivised, systematised failure that’s small enough to be safe, fast enough to learn from, and bold enough to push the business forward.

And the leaders who get this right? They don’t just stay in the game. They rewrite the rules.

🎁 As a thank you to my Conversations That Matter subscribers, I’ve created a hands-on team exercise designed to spark curiosity, speed up learning, and reduce the fear of failure for you to download. Head back to the email that brought you here to download it and get started!