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Sunday, May 31, 2026

The Companion of Leadership? Problems

Whether flourishing or failing, problems will follow.

Going great? Around the corner is Pat Riley's "Disease of Me."

Not going so well? Problems seem like wolves at every door.

Types of Problems 

Accept the reality of Chuck Daly's "48" - minutes, shots, million - and see that coaching and economics demand "allocation of scarce resources."

  • Minutes. Players decide the lineup via performance. It's human nature for players, family, and friends to place blame on coaches. 
  • Roles. Clarify roles. Encourage people to excel in theirs. "Problem personalities" create problems. Have hard conversations before a crisis.
  • Recognition. Everyone wants appreciation. That arrives in different forms - playing time, praise, publicity. "You catch more flies with honey than vinegar." Spread recognition to "lesser luminaries" who contribute. Dean Smith leveraged that at Carolina. 
Identifying Problems

Problems fall into knowns, known unknowns, and unknown unknowns. Communication via assistants and captains helps identify both smoldering fires and "black swans." 

Black swans are the "unknown unknowns," the 'out of the blue' potential catastrophes that can derail teams. They could be ethical, moral, health, or other. Nobody could predict the impossible coincidence Jayson Tatum, Tyrese Halliburton, and Damian Lillard (all wearing "0" tearing their Achilles. 

Known unknowns are many - variance of player and team performance, team chemistry, substance abuse and off-field issues, and so forth. 

Knowns are expected issues of competition. In military terms, "The enemy gets a vote" and "No plan survives first contact with the enemy." Or Mike Tyson's, "Everyone has a plan until they get punched in the mouth." 

Into the Abyss

Stay humble; stay hungry. I knew a doctor who boasted that he could keep anyone alive for twenty-four hours. Then he ran into acute trauma victims during the Gulf War. Hubris meet humility. 

1. "Dot b" is a mindfulness concept to stay under control. Stop and take a breath. Think about conventional and out of the box solutions.  
2. Get help. "No man is an island." Find the 'foxhole guys' who can help.
3. Dig deep. Train players to expect and to confront adversity. Make an "I" problem into a "We" issue. "We can do this."

Anticipate Problems - The Premortem Examination

Know that anything can block our journey. The Premortem Examination can improve projected outcomes about 30 percent, according to Gary Klein. 
  • Depth helps pre-empt fragility. Playing young players helps mitigate future crises of "lack of experience." 
  • Mindfulness increases resilience. 
  • Video study lifts sport-specific IQ. 
  • Reflection on a team's "condition," both physical and mental can help prevent fatigue-based degradation. 
  • Study failure. (see Lagniappe)
Problems are inevitable. Coping with them well is not. It's on us. 

Lagniappe. Study failure. I share an AI consult. I have read the first four books on the list and also recommend David Epstein's bestseller "Range."

Success is a poor teacher.

Failure is data.

The challenge is that failure is often wrapped in:

  • ego,
  • emotion,
  • blame,
  • and hindsight bias.

The goal is not merely to endure failure but to study it systematically.

The Four Levels of Failure

I would suggest coaches examine losses through four lenses:

1. Execution Failure

Did we fail to do what we intended?

Examples:

  • missed free throws,
  • poor blocking footwork,
  • turnovers,
  • missed assignments.

These are often the easiest failures to diagnose.

2. Decision Failure

Was the decision itself sound?

An athlete can:

  • make the right decision and fail,
    or
  • make the wrong decision and succeed.

This distinction is crucial.

This is one reason you appreciate Ed Smith's Making Decisions.

3. System Failure

Did our environment contribute?

Examples:

  • practice design,
  • communication systems,
  • scouting process,
  • leadership structure.

Many coaches stop at player mistakes and never examine the system.

4. Assumption Failure

What did we believe that wasn't true?

These are often the most valuable lessons.

Examples:

  • "Our ball pressure is good enough."
  • "This player learns best through instruction."
  • "Experience equals leadership."

Every season contains hidden assumptions waiting to be exposed.

Books Every Coach Should Read on Failure

1. Black Box ThinkingMatthew Syed

Probably my first recommendation.

Central thesis:

High performers learn faster because they study mistakes more effectively.

The comparison between aviation and medicine is unforgettable.

Sports application:

  • film review,
  • error analysis,
  • learning culture.

A basketball team can create its own "black box."

2. Think AgainAdam Grant

One of your favorites.

Key concept:

Develop a "rethinking scorecard."

The best coaches update beliefs.

Sports application:

  • lineup decisions,
  • offensive systems,
  • player evaluations.

3. Making DecisionsEd Smith

A hidden gem.

Focus:

  • outcome versus process.

Sports application:
After every match ask:

Was our process good?

rather than:

Did we win?

4. The Success EquationMichael Mauboussin

Essential reading on:

  • skill,
  • luck,
  • randomness.

Coaches often attribute too much to either.

Sports application:
Understanding variance.

Sometimes:

  • the ball rims out,
  • an official misses a call,
  • an opponent shoots 60%.

Not every loss is diagnostic.

5. Being WrongKathryn Schulz

A fascinating exploration of:

  • why humans resist being wrong,
  • how certainty blinds us.

Sports application:
Humility.

6. The Logic of FailureDietrich Dörner

Perhaps the most underrated book on the list.

Dörner studied why intelligent people fail in complex systems.

Sports application:
Teams are complex systems.

Common coaching mistakes:

  • solving yesterday's problem,
  • overreacting,
  • ignoring unintended consequences.

Articles Worth Reading

"The Weakest Link" — Atul Gawande

Part of his broader work on systems thinking.

Failure often results from:

  • process breakdowns,
    not
  • individual incompetence.

NASA Challenger Disaster analyses

Sports lesson:

Normalization of deviance.

Small mistakes become accepted.

Then catastrophe occurs.

Basketball examples:

  • poor communication,
  • poor warmup habits,
  • sloppy transitions.

Practical Framework

After every match:

What happened?

Facts only.

Why did it happen?

Avoid blame.

What assumption failed?

Most important question.

What will we do differently?

Action step.

What should we continue doing?

Many postmortems ignore successes.

A Final Thought

One of the most profound ideas comes from Matthew Syed:

"The reason aviation became safer is not that pilots stopped making mistakes. It's that they became better at studying them."

The same is true in sports.

Championship cultures are not cultures that avoid failure.

They are cultures that:

  • detect failure quickly,
  • discuss it honestly,
  • learn from it systematically,
  • and move forward without ego.

That idea fits beautifully with your long-standing interest in journaling, rethinking scorecards, metacognition (thinking about thinking), and teaching athletes how to think rather than merely what to do (they're not cattle).