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substack.com - Handling Pressure Is a Skill Three Lessons from The Art of Learning

How to Perform under Pressure in High-stakes Work and Leadership Roles

Section titled “How to Perform under Pressure in High-stakes Work and Leadership Roles”

I picked up The Art of Learning expecting a book about learning how to learn.

It isn’t.

Josh Waitzkin writes about the world he knows well: competitive chess and martial arts, but his lessons apply well beyond these sports.

Despite years of reading, practicing and observing high performers under pressure, a few ideas in this book changed my thinking.

When competing in one of the kung fu championships, a competitor broke Waitzkin’s right hand. Given a complex fracture, the doctor advised complete rest, which meant that Waitzkin would have to skip the Nationals scheduled seven weeks later.

Sensible advice. I give the same to my own children when they get injured.

Waitzkin ignored it. He trained with a cast.

Forced to rely on his weaker left side, he learned to control his opponent’s two limbs with one arm. That discovery became one of the staples in his fighting style. Later, when his right hand recovered, it was free to do decisive damage. This advantage would never have emerged without the constraint.

Waitzkin explains that non-athletes treat injury as downtime. Athletes cannot. If he sat out every injury, he would spend most of the year on the couch. Instead, he learned to train through limitation and extract value from it.

Constraints don’t slow high performers down. They force advantages that would never appear otherwise.

Early in my career, I was selling document-management software. I arrived at a large bank for the first round of a formal tender. The woman who showed me in looked worried.

“Is it just you?” she asked. “Your competitor brought two senior guys with beards. And even they struggled.”

Great. I had already wondered whether people did not take me seriously due to my age.

When the decision-maker walked in, polished and confident, I made a judgement call. I decided not try impress him with the product. I did not even move past the first screen of the demo. Instead, I asked him about their problems and listened.

And he talked and talked. Man, this guy loved to talk.

Later that day, the same woman called me. “He was very impressed by your presentation,” she said.

I chuckled to myself. The lack of beard was not a disadvantage after all.

The constraint was perceived lack of status. I stopped trying to prove myself, put him on the pedestal, and let him admire his own thinking.

Once you embrace the constraint, you can often walk straight through it.

One of Waitzkin’s central ideas is “study numbers to leave numbers”.

I sometimes refer to it as the study of numbers to leave numbers, or form to leave form. A basic example of this process, which applies to any discipline, can easily be illustrated through chess: A chess student must initially become immersed in the fundamentals in order to have any potential to reach a high level of skill. He or she will learn the principles of endgame, middlegame, and opening play. Initially one or two critical themes will be considered at once, but over time the intuition learns to integrate more and more principles into a sense of flow. Eventually the foundation is so deeply internalized that it is no longer consciously considered, but is lived. This process continuously cycles along as deeper layers of the art are soaked in.

-Josh Waitzkin

The same progression appears in martial arts. A novice executes techniques step by step. An expert moves as one integrated pattern.

In cognitive terms, this is the shift from System Two to System One, as described by Daniel Kahneman. System Two is slow and deliberate. System One is fast and automatic. Most world-class performance happens in System One. There is no such thing as a slow world champion.

Waitzkin makes two points. First, if you want speed, you must rely on System One. Second, System One is trainable. Feed it good data. Give it many repetitions. Over time, effort translates into flow.

Flow is not talent. It is accumulated practice.

This is exactly how Amazon’s Bar Raiser program works. Candidates go through interview after interview, shadowed by experienced mentors who provide them feedback. Reps and feedback. Reps and feedback. It often takes a year or more to complete the program. By graduation, most Bar Raisers have conducted over 200 interviews.

Early in my own training, I shadowed a very experienced Bar Raiser. Her interview was a masterclass. She put the candidate at ease within minutes. She asked a single question, then unpacked the story until she had everything she needed. It felt effortless and authentic. All three of us enjoyed it. Watching her was like watching Joshua Bell perform. Pure flow. Years of practice.

Principle 3: Handling Pressure is an Acquired Skill

Section titled “Principle 3: Handling Pressure is an Acquired Skill”

Being able to handle pressure is not a personality trait. It is a skillset.

For senior leaders, pressure shows up everywhere. A boss gives you two weeks to fix a failing initiative. A weekly high-stakes review demands crisp answers and sound judgment. Decisions stack up through the day faster than your brain can recover.

Waitzkin describes two skills that matter most.

The first is stopping the downward spiral.

The initial mistake is rarely fatal. What causes damage is the second, third, and fourth mistakes that follow, once you realise what you’ve done.

Experienced performers learn to catch themselves early and reset.

I can spot an experienced Amazonian in a big review by how they handle a question they cannot answer. New Amazonians often try to hand-wave their way through, because that worked elsewhere. They get pressed until the gap is obvious. Experienced Amazonians say, “I don’t know,” and take a follow-up. They know they are in a hole, so they don’t dig.

The second skill is the recovery routine. High performance requires sustained energy. In championships, it is match after match. At work, it is meeting after meeting.

Generic advice like “take a deep breath” rarely works on its own. Athletes build deliberate recovery routines. At first, these routines can take 30 or 45 minutes.

Snack. Meditation. Stretching. Music.

Over months of repetition, the routine is compressed until it produces the same effect in seconds.

Waitzkin trained himself to recover with a single deep inhalation and release. The “deep breath” works for him because he earned it.

All in all, it is an excellent book. It also made me want to try tai chi. Maybe one day.🙂

That’s it for today! Thank you for reading. If you know someone who operates under pressure for a living, share this newsletter with them. Your support keeps me writing.