Stumbling Blocks: How Great Leaders Are Made

Stumbling Blocks: How Great Leaders Are Made

Here, leaders share the moments along the way that have shaped them most deeply. Their stumbling blocks. You'll hear leaders as they really are: challenged, battered, and deeply flawed. And you'll see them picking back up, dusting themselves off, and leading again. Because if we let them, stumbling blocks make us better. Welcome to Stumbling Blocks: How Great Leaders are Made. I’m your host, Jonathan Block. I've spent the last 20 years studying leadership, and I ask leaders to take us back to the moments that aren't on highlight reel: • The day they got laid off. • The crisis that almost broke them. • The loss that re-shaped how they see the world. Join me to uncover the stumbles that make leaders great. Welcome to The Stumble. Subscribe today. Questions? Comments? Linkedin: www.linkedin.com/in/jonathanfblock Insta: @JonathanFBlock Twitter: @JonathanFBlock Email: Jonathan@BlockLeadershipGroup.com

Episodes

October 13, 2026 • 43 mins

In 2016, a former PEOPLE reporter named Natasha Stoynoff said Donald Trump attacked her during an interview at Mar-a-Lago. Sandra Sobieraj Westfall, the Washington Bureau Chief for PEOPLE Magazine, made a business and editorial decision: She would stand by her friend and colleague. The magazine would cover the President's policies, but it would not cover his family the way it had covered every other First Family.

This is the story o...

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Tim Creasey: Chief Innovation Officer, Prosci: How to Lead Change

Why do smart, well-run companies keep leading big changes that fail? Tim Creasey has spent 25 years at Prosci studying change management and shares the answer on this podcast.

Tim is Chief Innovation Officer at Prosci, the research firm behind the ADKAR Model, one of the most widely used change management frameworks in the world. We talk about why change is so ...

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On 9/11/2001, Scott Stanzel was 28 years old, working his dream job at the White House when Secret Service agents came running down the halls, throwing open doors and shouting at everyone to get out. They had two minutes.

For twenty-five years, Scott has said almost nothing publicly about September 11th. "Over the years I've struggled with how to talk about my experiences or even acknowledge that day," he wrote once.

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Most crisis experts have never actually sat in the room when everything fell apart. Jim Olson has. He was head of communications at US Airways when Flight 1549 landed on the Hudson. He was at Starbucks when its flagship store in Jakarta was bombed. And he was at United Airlines the night Dr. David Dao was dragged off a plane and it became one of the first viral crises in business history.

Then the crisis came for him. In 2024 Ji...

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Kelli Arena spent her career at CNN telling the public what powerful people would rather keep quiet. She covered the Justice Department, won an Emmy, and reported the Moussaoui trial, the only 9/11 case tried in an American civilian courtroom.

After Kelli left journalism, she went into another form of public service, serving as Chief of Communications for the National Security Agency, spending eight years helping the Agency find its...

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Shalene Gupta, staff editor for Fast Company's Work Life and Leadership section, interviewed 35 middle managers at some of the biggest companies in the world for her piece "The Middle Manager's AI Survival Guide." What she found is that the contradictory headlines about AI at work aren't actually contradictory. There are two different worlds, and which one you're working in makes a world of difference.

One idea sits under all of...

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Dana Perino's new book is called Purple State. It's a political romance novel set in a gerrymandered Wisconsin district, about three young women who discover that love and friendship don't stop at party lines.

Coming from the 26th White House Press Secretary and co-host of The Five on Fox News (the most-watched show on cable news!), it's a book worth paying attention to. Especially as we find ourselves more divided than any time...

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Sue Gordon once oversaw 100,000 women and men of the U.S. intelligence community as Deputy Director of National Intelligence, the number two role in American spycraft.

She briefed Presidents Reagan, HW Bush, Clinton, W Bush, Obama, and Trump. She managed a $100 billion budget.

And in August 2019, she handed Vice President Pence her resignation letter with a handwritten note: "I offer this letter as an act of respect...

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A few times during my two-part interview with Judge and Rebecca Gonzales, they turned the tables on me. They listened. And they drew three stories out of me that I've rarely shared.

The first is a story that never made it into the main episodes: the Oval Office advice I didn't want that... changed my life.

The second is about what happens when your Quaker mother and your Jewish father sit down together at Hanukkah.

The thi...

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Part 2 of this exclusive conversation with Attorney General Alberto Gonzales and his wife Rebecca. It is a conversation about love, political betrayal, faith, and what it means to keep going when the wilderness feels endless.

Judge Gonzales describes the political firestorm that ended his time as the nation's top law enforcement officer.

What followed were years Rebecca calls "the wilderness." The phone stopped ringing. ...

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Excerpts from Attorney General Gonzales and Rebecca Gonzales's interview with Stumbling Blocks on ICE Actions, Immigration, and the Epstein Files



Excerpted Quotes from Attorney General Gonzales On ICE Actions and Immigration

Based on what I've observed… it seems like we're going through an unprecedented, dangerous time. I worry about what's going on in our country, and I think a lot of Americans are worried about it.

Th...

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EXCLUSIVE: This is a story two decades in the making. For the first time since leaving office 19 years ago, Attorney General Alberto Gonzales and his wife Rebecca Gonzales sat down together for an interview.

In Part 1, the Attorney General and Rebecca speak candidly about ICE, immigration, and the Justice Department's handling of the Epstein files.

They talk about Al's rise from a two-bedroom house in Humble, Texas to the Oval O...

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Conor Grennan is CEO of AI Mindset and until recently, Chief AI Architect at NYU Stern School of Business. He's trained teams at Google, NASA, Microsoft, JP Morgan, and many more.

He's a New York Times bestselling author, a MasterClass Instructor, co-host of the AI Applied podcast, and a recipient of the Dalai Lama's Unsung Hero of Compassion Award.

Conor has become one of the most sought-after speakers and strategi...

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In this episode, I welcome Rear Admiral Tim Ziemer, the former chief of the President’s Malaria Initiative (PMI) and former CEO of World Relief.

Admiral Ziemer explains how and why he saved 12 million people from death by malaria, and prevented another 2 billion cases of the disease.

He reflects on a life of disciplined service bookended by tragedy, from the 1968 attack in Vietnam that killed his father and left hi...

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A conversation with former Reuters Canada Bureau Chief Steve Scherer on job displacement, the gig economy, and America’s identity crisis.

Steve was once a high-level journalist, a Reuters Bureau Chief for Canada, who interviewed world leaders like Justin Trudeau and covered global financial markets. Then, a budget cut cost him his job, his work visa, and forced him to move his family out of Canada.

Now, he&rsqu...

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Brent Beshore made his first million at 28. Visited the White House. Got ranked 28th on the Inc. 500. Got everything he wanted.

And realized he had summited the wrong mountain.

In this raw conversation, Brent—CEO of Permanent Equity, a private equity firm that owns 16 companies generating $400M in revenue with zero debt—goes places most CEOs do not.

He talks about weighing 252 pounds while everything he...

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In this episode, I sit down with Linda Rutherford, former Chief Administration Officer of Southwest Airlines for the second half of our conversation.

Linda, described as the "keeper of Southwest's corporate soul," provides a rare, behind-the-scenes look at how one of the world’s most iconic brands survived two of the most disruptive forces in its 50-year history: Winter Storm Elliott and the hostile takeover by Elliot...

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In this episode, Linda Rutherford, the former Chief Administration Officer at Southwest Airlines, shares insights into the secret sauce that makes Southwest the 'LUV airline.' She discusses the legacy left by the airline's founding CEO, Herb Kelleher, and president, Colleen Barrett, as well as her role as a growth catalyst for the airline.

Linda also reflects on her early life, resilience, and the impact of generosity and vulnerabil...

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When Oscar Munoz stepped in as CEO of United Airlines, he didn't head for the executive suite. He headed for a Houston hangar at 2:00 AM to jump on a picnic table and listen to 500 angry aircraft mechanics.

In part two of this deep-dive conversation, Oscar reveals why he threw out the "business school rule book" to save an airline with a broken spirit. We discuss:

  • The Power of the Listening Tour: Why he told Wall Street "...
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The viral video that changed aviation—and the CEO who broke the rules to fix it.

On April 9, 2017, United Airlines faced the world’s first truly global viral crisis when a passenger, Dr. David Dao, was forcibly dragged off a flight in Chicago. The internet exploded, calls for resignation mounted, and the airline’s initial response—calling the incident a "re-accommodation"—only poured gas on the fire.

In ...

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