The Skill You Think You Have (You’re Probably Wrong)
The Skill You Think You Have (You’re Probably Wrong)
PLUS: 33 Ways To Break Your Routine This Month
October 04, 2026
“We can be blind to the obvious, and we are also blind to our blindness.”
\- Daniel Kahneman
If you're a leader, your quality of thinking is your single most important capability.
The irony is that it's also one that you've probably never thought about training.
That’s normally because you’re certain you know why you did what you did. Most people are. Some of you will be wrong.
That was definitely the case with me.
For years, I believed that my curiosity, my intellect and my experience were good enough.
I learnt on the job. I drew on the mental lessons that my years in Taekwondo and boxing had taught me.
I sought out mentors. I devoured everything from The 7 Habits of Highly Effective People through to The Tao of Jeet Kune Do.
On one level it paid off. I consistently delivered results. I rose in responsibility and status. I was working with clients like Nike, HSBC, BMW, Marriott and Facebook (now Meta).
Then in 2017, I was headhunted to join VICE Media. At that time it was a global powerhouse, which had just reached a valuation of $5.7 billion.
I was appointed MD for the Middle East and Africa, and tasked with building a team and a business from scratch in the region.
I knew this challenge would stretch me more than ever and so I signed up to INSEAD's first ever executive coaching cohort.
This wasn’t about preparing for a career change. It was about investing in myself as a leader.
I was approaching the new role in just the same way I’d approached fight camp. Knowing that the work I put in here could mean the difference between success and failure.
The training I underwent was in the psychodynamic model, which focuses a lot on unconscious behaviours.
It opened my eyes to blind spots. It also opened a doorway to exploring the quality of my own thinking.
I learnt the power of metacognition - the ability to monitor, evaluate and direct your own thinking.
The outcome? Maximising your potential to think, learn and create.
THE PROOF
While I was at INSEAD, a peer who knew my love of reading recommended Principles by Ray Dalio.
Dalio founded Bridgewater Associates in 1975, out of a two-bedroom apartment in New York.
The philosophy behind his work is what he calls radical transparency - building an entire culture around deliberately examining your own thinking, and everyone else's, in real time.
Every mistake at Bridgewater gets logged, by the person who made it, in what's called the Issue Log. It’s data to learn from.
Meetings get recorded too, so everyone in the firm can go back and examine exactly how a decision got made, not just what the outcome was.
Then there are ‘Baseball Cards’ - a running, evidence-based profile of every employee's actual thinking patterns. Showing where they're reliably strong and where they consistently get things wrong.
Again, this is based on real data, not on how people see themselves.
Dalio's obsession has been about creating an environment where the best thinking wins, regardless of who's in the room or how senior they are.
It’s metacognition in action, at scale.
If you thought metacognition sounded a bit ‘woo-woo’, I’ll point you to the fact that Bridgewater is now the largest hedge fund in the world.
THE SCIENCE
Research supports the instincts Dalio built Bridgewater on.
Our brains are prediction machines, and as a leader, you're forecasting constantly.
We tend to assume that being good at your job and being good at judging your own decisions are the same skill.
They're not.
In one of the largest forecasting studies ever run, backed by the US intelligence community, tens of thousands of people were asked to predict real-world events such as elections, market movements and conflicts.
A small group consistently outperformed everyone else. Researchers called them ‘superforecasters’.
You’d probably guess these individuals had a higher IQ or some kind of shared intellectual expertise.
In reality, it was something researchers call calibration.
The superforecasters' stated confidence matched how often they were actually correct. If they expected to be right, they usually were. If they weren't sure, they usually weren't either.
This was in stark contrast to the majority, who were either overconfident about their calls that turned out wrong, or too unsure about ones they actually had right.
The most important takeaway for you is that this skill is trainable.
Researchers taught people to use base rates instead of gut feel, to update their estimates in proportion to new evidence, and to recognise their own common biases. This produced a tangible improvement in accuracy.
Forecasting is a measurable version of metacognition.
THE APPLICATION
The single most powerful word in my locker is why.
So many of you are locked into an always-on world. If I asked you a direct question about your thinking, your first answer would come easily.
If I asked you why again, that's often the first time you'll have to pause and actually think about it.
And we wouldn’t stop there.
One of our clients on the Prime Performance Program built her entire identity around being ‘the fixer’. The one the team brought every problem to because they trusted her to deal with it.
She works in a fast-growth start-up and has been integral to its success.
However, growth brings its own challenges - roles evolve, responsibilities expand and the behaviours that built the business aren't always the right ones to hyper-scale it.
In this case, her greatest strength was at risk of becoming her biggest constraint.
Her team kept defaulting to her for everything, even when they could have worked it out themselves.
Other stakeholders, including the co-founders, kept on giving her more to do, because they trusted her to get it done.
The result was that ‘the fixer’ was struggling to stay on top of everything.
When we started working together I asked her why she was saying yes to everything. The answers I got were about duty of care to the team.
About doing what she knew worked best for the business. About it being “the right thing to do”.
As we dove deeper, it surfaced issues around identity, and a fear of how she'd be perceived if she stopped being the one who always had the answer.
Once she could see that, she could act on it differently.
Deliberately stepping back so her team had room to learn how to solve things themselves - caring enough to let them fail, as that is an essential part of their own growth.
When you’ve built your reputation on being the fixer, it’s hard to step out of the engine room and into the wheelhouse.
You can feel like you’re leaving a piece of you behind. You tell yourself stories to rationalise why you need to remain present.
The cognitive athlete uses metacognition to recognise the danger of this kind of self-sabotage.
Monitor what you're actually doing. Evaluate what's really driving it. Direct it differently.
Start with asking yourself ‘why’.
Go well.
J.
LIVE BETTER, LEAD BETTER
The best content I researched this week:
1. This week was perfect timing for neuroscientist and author Nicole Vignola to show up with an article on how to access genius level thinking. A 4-minute read packed with practical insights and tips.
2. Management thought leader Dave Kline shares the 3 questions every leader needs to answer before their team can succeed.
3. Saving the best to last, I’m a huge fan of Brad Stulberg’s work and I love the thinking behind his latest article. As the man says: “Your life needs quests”. Here he’s listed 33 ways to break your routine this month.
Share this with a fellow leader - we’re stronger together.
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