Coaching for Leaders

David Epstein: Inside the Box

David Epstein is the author of the #1 New York Times bestseller Range and The Sports Gene, both of which have been translated into more than 30 languages. He was previously the host of Slate‘s popular “How To!” podcast and a science and investigative reporter at ProPublica. His TED talks have been viewed more than 12 million times. His newest book is also a New York Times bestseller: Inside the Box: How Constraints Make Us Better (Amazon, Bookshop)*.

It seems like we should be the most focused, creative, and innovative when we are the freest to do whatever we want. Turns out, it’s pretty much the exact opposite. In this conversation, David and I discuss why constraints make all the difference.

Key Points

Myth: we are most creative and innovative when we are most free. In fact, it’s the opposite.

Given complete freedom, we tend to follow the path of least resistance. The Einstellung effect: employing only familiar methods even if better ones are available.

General Magic (the most important technology company that nobody’s ever heard of) had virtually no constraints and ultimately produced nothing.

Write down hypotheses and make commitments visible before you begin. Give people agency in creating constraints.

If your organization or team was being handed off to someone else tomorrow, what’s the first thing the new leader would change? Consider making that change now.

To avoid over-indexing on constraints, ask this question: “Could I still surprise myself?”

Resources Mentioned

Inside the Box: How Constraints Make Us Better by David Epstein (Amazon, Bookshop)*

Interview Notes

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Related Episodes

How to Transform Your Limitations Into Advantages, with Mark Barden (episode 207)

Help Your Brain Learn, with Lisa Feldman Barrett (episode 513)

Get People Reading What You’re Sending, with Todd Rogers (episode 666)

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Leanne ten Brinke: Poisonous People

Leanne ten Brinke is an Associate Professor at the University of British Columbia, where she directs the Truth and Trust Lab. Her research investigates trust, deception, and dark personality traits across diverse populations—from incarcerated individuals to hedge fund managers and politicians. She reveals how dark personality traits shape our institutions and relationships, while offering practical strategies to recognize and counteract their harmful influence. Her book is titled Poisonous People: How to Resist Them and Improve Your Life (Amazon, Bookshop)*.

If you are a leader, you are going to deal with poisonous people. Sometimes they will show up as clients, sometimes your boss, sometimes your peers, and sometimes the people you manage. Regardless of where they show up, this conversation with Leanne will help you handle this tough dynamic.

Key Points

Dark traits exist on a spectrum. While only 1% of the population rises to a clinical level of psychopathology, 10-20% of the population has a dark personality profile.

There are many more people with psychopathy per capita in senior management positions than in the general population.

Poisonous people generally aren’t interested in shifting their personality. As such, you will not change them. Given that reality, aim to better manage the relationship.

Establish clear boundaries with poisonous people and put things in writing you might normally assume. Dark personalities are really good at exploiting unspoken norms.

Find ways to create win-wins with poisonous people. They don’t do well with trade-offs, because they don’t like to lose anything.

Avoid face-to-face negotiations with them. Their charm and charisma will win you over in the moment. Text-based dialogue will help you objectively negotiate better.

Use the carrot instead of the stick. Reward good behavior when it happens (just not by giving them power over others).

Resources Mentioned

Poisonous People: How to Resist Them and Improve Your Life by Leanne ten Brinke (Amazon, Bookshop)*

Interview Notes

Download my interview notes in PDF format (free membership required).

Related Episodes

How to Handle a Boss Who’s a Jerk, with Tom Henschel (episode 164)

How to Start Better With Peers, with Michael Bungay Stanier (episode 635)

How to Show Up Authentically in Tough Situations, with Andrew Brodsky (episode 727)

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Chris Duffy: Humor Me

Chris Duffy is an award-winning podcaster, comedian, and television writer. He hosts the podcast How to Be a Better Human and you can find his comedic TED talk, “How to find laughter anywhere” online. He is the author of Humor Me: How Laughing More Can Make You Present, Creative, Connected, and Happy (Amazon, Bookshop)*.

It sometimes seems like someone with a good sense of humor does everything a bit better. Perhaps leadership is no different – but it’s not about landing jokes. In this episode, Chris and I explore why everyday humor is all about paying attention and generosity.

Key Points

Humor might not make the list of top leadership competencies, but it helps you perform every other competency better.

A good sense of humor is inherently generous.

Effective humor isn’t landing the perfect joke or being the center of attention. It’s noticing the humor is everyday work and bravely calling attention to it.

The first pillar of cultivating humor is simply being present.

Start with times you are least present and most zoned out. Zero in with a “new bathroom” frame of mind.

Celebrate the bad stuff and find humor in it. By doing so, you inherently help people appreciate excellence.

Resources Mentioned

Humor Me: How Laughing More Can Make You Present, Creative, Connected, and Happy by Chris Duffy (Amazon, Bookshop)*

Interview Notes

Download my interview notes in PDF format (free membership required).

Related Episodes

How to Engage With Humor, with David Nihill (episode 235)

Get Better at Deep Listening, with Oscar Trimboli (episode 408)

How to Genuinely Show Up for Others, with Marshall Goldsmith (episode 590)

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Phil Le-Brun: The Octopus Organization

Phil Le-Brun is an executive in residence at Amazon Web Services and a former corporate VP and international CIO at the McDonald’s Corporation. He is a sought-after speaker and has been featured in Harvard Business Review, The Wall Street Journal, and The Guardian. He is the co-author with Jana Werner of The Octopus Organization: A Guide to Thriving in a World of Continuous Transformation (Amazon, Bookshop)*.

Most of us have gone through some version of a reorg. A lot of leaders have also implemented their own reorgs. Sometimes they work. Many times, they don’t. In this conversation, Phil and I discuss what goes wrong with reorgs and how we can do better.

Key Points

Organizations traditionally looked like the tin man from The Wizard of Oz: perfectly planned, many interchangeable parts, not flexible.

An octopus organization adapts, works independently to serve the larger whole, and is innately curious.

A reorg that starts with an org chart misses the complex organic connections you are unlikely to fully understand.

Prioritize structural stability while building internal flexibility.

Nurture the complex informal human networks that deliver value.

Be honest about objectives and communicate a reorg early.

Engage people by starting with smaller-scale change. Clarify the problem to be solved instead of the structural “answer.”

Resources Mentioned

The Octopus Organization: A Guide to Thriving in a World of Continuous Transformation by Phil Le-Brun and Jana Werner (Amazon, Bookshop)*

Interview Notes

Download my interview notes in PDF format (free membership required).

Related Episodes

How to Get the Ideal Team Player, with Patrick Lencioni (episode 301)

How to Approach a Reorg, with Claire Hughes Johnson (episode 621)

How to Help Employees Handle Tough Moments, with Anthony Klotz (episode 777)

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Liane Davey: Thoughtload

For the past 25 years, Liane Davey has researched and advised teams on how to achieve high performance. She is the author of You First and The Good Fight and is a regular contributor to Harvard Business Review. She is the author of the new book Thoughtload: Manage the Madness and Free Your Team to Do Great Work (Amazon, Bookshop)*.

We all love to hate our task lists. However, we can do a lot better with just a bit of strategy. In this conversation, Liane and I explore how to make our task list work for us instead of against us.

Key Points

Often it’s not really the workload that’s crushing – it’s more so the thinking about all the workload. That’s what thoughtload is.

The problem with a to-do list is that everything goes on it. Thus, to-do lists are terrible for managing your attention.

Instead of one task list, keep a limited amount of tasks on three priority lists.

Category 1 list: your most important outputs and outcomes.

Category 2 list: what you do to help others achieve their most significant outcomes.

Category 3 list: administrative stuff.

Four questions determine what gets on your lists:

Important (an activity that will add value to a key output or outcome)?

Urgent (something with growing negative consequences if you wait)?

Targeted (a task that no one can do as efficiently or effectively as you)?

Essential (core to creating the critical value, not just a nice-to-have)?

Resources Mentioned

Thoughtload: Manage the Madness and Free Your Team to Do Great Work by Liane Davey (Amazon, Bookshop)*

Interview Notes

Download my interview notes in PDF format (free membership required).

Related Episodes

The Scientific Secrets of Daily Scheduling, with Daniel Pink (episode 332)

Align Your Calendar to What Matters, with Nir Eyal (episode 431)

How to Take Back Your Evenings, with Guy Winch (episode 783)

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Activate your free membership for full access to the entire library of interviews since 2011, searchable by topic. To accelerate your learning, uncover more inside Coaching for Leaders Plus.