Coaching for Leaders

Academy alum Dev Baldwin joins Dave to share how he leveraged the power of learning from peers.

Are you at an inflection point? Apply to the Coaching for Leaders Academy by Friday, September 11th.

Simone Stolzoff: How to Not Know

Simone Stolzoff is an author and journalist who explores big questions about work, meaning, and identity. A former design lead at the global innovation firm IDEO, his work has been featured in The New York Times, The Atlantic, The Wall Street Journal, The Washington Post, and on the TED stage. He is the author of How to Not Know: The Value of Uncertainty in a World that Demands Answers (Amazon, Bookshop)*.

I’m not sure about you, but I very much dislike uncertainty. And yet, basically the job of leadership is to not only deal with it but to help others thrive in the midst of it. In this conversation, Simone and I explore how to build your tolerance for uncertainty so you can lead much more effectively.

Key Points

We love certainty and our tolerance for uncertainty is decreasing due to the internet, smartphones, and AI access.

Organizations with higher uncertainty tolerance tend to be more innovative and adaptable.

We assume unwavering confidence breeds credibility, when in fact, research shows that those who admit what they don’t know are perceived as more credible.

Professional athletes have the same threshold for pain but a higher pain tolerance. We can develop a similar tolerance for uncertainty.

Find your anchor points. By knowing the key boulders you can hang onto in a storm, you are vastly better able to weather uncertain times.

Build to learn. Progress depends on uncertainty.

Row through the fog. Maintain faith that you will discover the next step by continuing to row.

Sometimes what we feel is most uncertain is actually more certain than we realize.

Resources Mentioned

How to Not Know: The Value of Uncertainty in a World that Demands Answers by Simone Stolzoff (Amazon, Bookshop)*

Interview Notes

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

Related Episodes

How to Lead Better Through Complexity, with Jennifer Garvey Berger (episode 613)

Notice Disruption and Innovate Through It, with Steve Blank (episode 761)

The Counterintuitive Secret to Creativity and Focus, with David Epstein (episode 789)

Discover More

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.

Neal Schore: The 25th Hour

Neal Schore is the founder and CEO of 25th Hour Group, an executive coaching and leadership events firm. Previously, he served as the founder, president, and CEO of Triton Digital, a global technology, data, and services leader in the digital audio and podcast industry. He is the author of The 25th Hour: How to Thrive (And Gain Ridiculous

Amounts of Time) By Getting Out of Your Own Way (Amazon, Bookshop)*.

No productivity approach can negotiate with physics. How we manage time is really how we manage ourselves. In this conversation, Neal and I explore a key question to help us shift from ordinary to exceptional.

Key Points

Swirling shows up for all of us when we ruminate on an interaction in a way that’s not helpful.

Most people don’t think to ask about others’ intent.

The key question to shift our thinking: “What’s the intent?”

Ordinary thinking goes with the flow. Exceptional thinking pauses and allows us to consider the intent behind the interaction.

To free time each day, pause before responding in a complex situation and ask yourself, “What’s the intent?”

This question becomes powerful when you can ask and answer yourself without needing to say it out loud.

Resources Mentioned

The 25th Hour: How to Thrive (And Gain Ridiculous Amounts of Time) By Getting Out of Your Own Way by Neal Schore (Amazon, Bookshop)*

Interview Notes

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

Related Episodes

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

How to Help Difficult Conversations Go Better, with Sheila Heen (episode 655)

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

Discover More

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.

Jia Jiang: Easy Discipline

Jia Jiang is an award-winning speaker, entrepreneur, and the bestselling author of Rejection Proof. His TED Talk is among the top 1% most viewed of all time, and he has spoken to over 400,000 people worldwide. He is also the creator of Rejection Therapy, a platform designed to help people overcome fear and build resilience, and is the author of Easy Discipline: An Unconventional Way to Achieve Ambitious Things (Amazon, Bookshop)*.

No pain, no gain. We’ve all heard that before – and it’s true that one way to achieve is through a lot of pain. Good news: there are other ways, too. In this conversation, Jia and I explore how to harness the ambition you already have through easy discipline.

Key Points

Pain tolerance is admired and celebrated. When greatness comes through pain, our society cheers it. When greatness comes through loving work, we are suspicious.

Hard discipline and easy discipline both produce results, but easy discipline does so with more joy and sustainability.

Ambitious people often suffer from High Eyes, Low Hands Disease. Higher ambitions create higher expectations that make a gap seem harder to transcend.

In the game of Catan, it’s not the lucky players that win; it’s the most active players. Professional learning follows the same pattern.

The momentum loop is the practice of early action generating greater fuel for later action. Even wrong movements are almost always superior to standing still.

Resources Mentioned

Easy Discipline: An Unconventional Way to Achieve Ambitious Things by Jia Jiang (Amazon, Bookshop)*

Jia Jiang’s speaking

Interview Notes

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

Related Episodes

How to Change Your Behavior, with BJ Fogg (episode 507)

How to Get Out of a Rut, with Anne-Laure Le Cunff (episode 747)

How to Help People Flourish, with Marcus Buckingham (episode 778)

Discover More

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.

Chris Bailey: Intentional

Chris Bailey is an author and lecturer who explores the science behind living a more productive and intentional life. He has written hundreds of articles on the subject and is the bestselling author of The Productivity Project, Hyperfocus, and How to Calm Your Mind. His newest book is Intentional: How to Finish What You Start (Amazon, Bookshop)*.

Starting is often a lot easier than finishing. Our mindsets and our tactics can make a big difference in how far we really go. In this conversation, Chris and I discuss the best ways to finish what we begin.

Key Points

Procrastination is triggered by six characteristics of aversion: boring, unpleasant, frustrating, far off in the future, unstructured, and/or meaningless.

The more we activate the logical centers in our brain, the less aversion we run into.

Almost everything can be more fun if we put the right structure around it. Gamification, countdown timers, and artificial deadlines can drive our behaviors in substantial ways.

Make goals about others. Rather than simply “reading 10 pages,” shift to “reading ten pages to be a better mentor.”

Most of us have a preference for either performance goals or learning goals. Identify which works better for you and for the people you lead.

Define a target pace and map your progress against it. We often do this with organizational projects, but rarely for our own goals.

Pair joyful tasks together with the ones that don’t bring joy as a means to keep you moving.

Resources Mentioned

Intentional: How to Finish What You Start by Chris Bailey (Amazon, Bookshop)*

Interview Notes

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

Related Episodes

How to Become the Person You Want to Be, with James Clear (episode 376)

How to Change Your Behavior, with BJ Fogg (episode 507)

Make Your Task List Work for You, with Liane Davey (episode 785)

Discover More

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.

Ludmila Praslova: The Canary Code

Ludmila Praslova is a Professor of Industrial-Organizational Psychology at Vanguard University of Southern California and regularly writes for Harvard Business Review, Fast Company, Psychology Today, and Forbes. She’s the recipient of the 2025 Talent Award from Thinker50 and has been named a LinkedIn Top Voice. She is the author of The Canary Code: A Guide to Neurodiversity, Dignity, and Intersectional Belonging at Work (Amazon, Bookshop)*.

We’ve all seen career paths that sound like this: analyst 1, analyst 2, senior analyst, lead analyst, manager of analysts, etc. Those paths to leadership work for some people, but they don’t work for others. In this conversation, Ludmila and I explore how to create leadership paths that work for everyone.

Key Points

Canaries were used in coal mines because they were more sensitive to early indicators of problems – in a way that helped everyone. The same is often true for neurodivergent leaders in organizations.

The “ideal leader” is a myth. If we are honest, no individual fits the ideal profile.

Having different paths to leadership makes more sense in a complex world. Many of the best leaders are specialists in something.

Instead of looking for “culture fit,” challenge yourself and your organization to do a “culture add.” Neurodiverse leaders can be less susceptible to bias and have higher levels of divergent thinking – huge benefits strengths for many organizations.

In addition to people management, consider paths for leadership that focus strength and skill on system and process, strategy, expertise, though leadership, global leadership, and creative ideation.

Making the workplace more accessible and equitable for one population almost always makes it better for everyone.

Resources Mentioned

The Canary Code: A Guide to Neurodiversity, Dignity, and Intersectional Belonging at Work by Ludmilla Praslova (Amazon, Bookshop)*

Interview Notes

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

Related Episodes

The Mindset Leaders Need to Address Burnout, with Christina Maslach (episode 608)

The Neurodiversity Edge in Organizations, with Maureen Dunne (episode 694)

How to Motivate Younger Employees, with David Yeager (episode 775)

Discover More

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.

Joanna Stern: I Am Not a Robot

Joanna Stern is an Emmy Award-winning technology journalist who was previously the personal technology columnist at The Wall Street Journal. For many years, she has been one of the most recognizable and entertaining voices in consumer tech, and she just recently launched her own media company and YouTube channel called New Things. Her new book is I Am Not a Robot: My Year Using AI to Do (Almost) Everything (Amazon, Bookshop)*.

What if you decided to go to AI first for virtually everything in your life? Joanna Stern decided to do exactly that and captured it all in her recent book. In this episode, we explore how those implications are showing up for a lot of us in the workplace.

Key Points

Customer service functions are one of many places where organizations are already using AI to supplement or replace work that people used to do.

Some aspects of AI work are preferred by both customers and employees. For others, having people in the loop is essential.

AI may eliminate some jobs and hiring. It also presents an opportunity to create work that is more interesting.

For many aspects of work and research, AI is useful as a “first pass” that helps the human spend more time doing the things that humans do.

The AI pushback is real and helpful. It allows us to grapple with how we use new technology and the best way for it to show up in our work and lives.

Resources Mentioned

I Am Not a Robot: My Year Using AI to Do (Almost) Everything by Joanna Stern (Amazon, Bookshop)*

New Things by Joanna Stern

Related Episodes

Principles for Using AI at Work, with Ethan Mollick (episode 674)

Becoming an AI-Savvy Leader, with David De Cremer (episode 710)

Using AI to Make Networking Easier, with Ruth Gotian (episode 766)

Discover More

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.

Daniel Coyle: Flourish

Daniel Coyle is the New York Times bestselling author of The Culture Code, which was named Best Business Book of the Year by Bloomberg, BookPal, and Business Insider. He has served as an advisor to many high-performing organizations, including the Navy SEALs, Microsoft, Google, and the Cleveland Guardians. His newest book is Flourish: The Art of Building Meaning, Joy, and Fulfillment (Amazon, Bookshop)*.

When teams really thrive, it isn’t about luck or simply optimizing systems. Instead, it’s about intentionally creating spaces for connection, agency, and shared growth. In this conversation, Daniel and I discuss where to begin to help a team flourish.

Key Points

Life (and leadership) is treasure creation, not a treasure hunt.

Flourishing environments encourage experimentation, agency, and even mistakes, allowing ownership and innovation to thrive.

If leaders think like designers, using questions and constraints, they will more likely unlock people’s full potential.

Simple acts such as little “thank you’s” build psychological safety and lay the foundation for flourishing groups.

Some of the world’s greatest innovations emerged from environments that welcomed surprise, cross-pollination, and flexibility.

Value the art of asking good questions over having all the answers.

Resources Mentioned

Flourish: The Art of Building Meaning, Joy, and Fulfillment by Daniel Coyle (Amazon, Bookshop)*

Interview Notes

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

Related Episodes

What Innovative Leaders Do Differently, with Linda Hill (episode 774)

How to Help People Flourish, with Marcus Buckingham (episode 778)

The Counterintuitive Secret to Creativity and Focus, with David Epstein (episode 789)

Discover More

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.

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

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

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)

Discover More

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.