Stumbling Blocks: How Great Leaders Are Made

Jonathan Block
  • 5.0 (24)
  • Management

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

  1. Jul 30

    Jim Olson, Chief Communications Officer: How to Turn your Setback Story into your Comeback Legacy

    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 Jim was diagnosed with stage 4 melanoma that had spread to his lung and his brain. During treatment he lost his eyesight. He is now legally blind. And he wrote a book about all of it called Tailwind. We talk about the 2am back pain that had no medical explanation and ended up saving his life. The "do hard things" tattoo he got a month before he went blind. And why he now prays in gratitude for the healing that's already happening instead of begging for the healing he wants. If you're carrying something heavy right now, this one is for you. In this episode: 00:00 The monster storm none of us escapes 00:25 Welcome to the Treehouse 02:00 The Dr. David Dao crisis, from the comms chief's chair 06:00 The fog of war, and why the first information is almost always wrong 10:54 Inside the Good Morning America apology 13:00 When your policies get in the way of your values 14:30 Miracle on the Hudson and the three flight attendants nobody named 18:36 The unsung heroes in Jim's own life 20:53 The 2am back pain that saved his life 25:00 Stage 4, and then the brain tumor 29:00 Losing his sight 33:30 "Cancer made me stronger. Blindness made my world brighter." 35:00 Writing Tailwind blind, on short-term disability 38:49 Ambition without purpose is a sailboat without a compass 41:00 Why me? Oscar Munoz and the two kinds of patients 44:49 Faith, gratitude, and a letter to God 47:37 Praying for what's already being made Get Jim's book, Tailwind: https://www.amazon.com/Tailwind-Compass-Turning-Setback-Comeback/dp/B0GXCCZ1QY Hear the Oscar Munoz episode referenced throughout: https://podcasts.apple.com/us/podcast/oscar-munoz-ceo-united-airlines-why-its-never-too-late/id1849573843?i=1000744337146 Stumbling Blocks explores the stumbles, crises, and formative moments that forge great leaders. Hosted by Jonathan Block and recorded at the Treehouse Studio. Questions? Comments? Email me: Jonathan@Blockleadershipgroup.com

    Jim Olson, Chief Communications Officer: How to Turn your Setback Story into your Comeback Legacy

  2. Jun 29

    Kelli Arena, CEO, Nat'l Cryptologic Foundation: How I Helped NSA Find Its Voice

    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 voice. Kelli has remade herself across four worlds: journalism, academia, government, and now the nonprofit sector, where she just became President and CEO of the National Cryptologic Foundation. A few things she gets into, worth your time even if you never press play: She took six months of maternity leave, three separate times, as an on-air correspondent. Everyone said it would end her career. It didn't. Younger women in the newsroom started thanking her, because she'd quietly given them permission. She earned back America's trust at the NSA the boring way: Through Consistency. Relationships. A rule that every reporter got a callback within 30 minutes, even when the answer was "no comment." And her advice for anyone starting over: "Listen more than you speak. Every single time I have listened to others before making a decision, it has been a better decision." 0:00:00 The Stumble that nearly ended my career 0:01:33 Meet Kelli Arena 0:02:52 A new chapter: President and CEO of the National Cryptologic Foundation 0:03:25 What cryptology is, and 500,000 open cyber jobs 0:05:30 AI's impact “can't be overstated” 0:07:30 Who gets displaced, and how we reskill them 0:08:40 Getting cyber smart as citizens 0:10:05 Becoming CNN's justice correspondent, then 9/11 0:12:05 Six months of leave, and the warnings that proved false 0:15:00 A day in the life: news as the ultimate team sport 0:18:10 Inside the Moussaoui trial 0:21:45 “I am Al Qaeda”: chaos in the courtroom 0:23:35 Why the jury chose life over death 0:25:16 Laid off: the 2009 budget cuts 0:27:25 Reinvention: teaching journalists to hold power accountable 0:30:15 The women who risked everything just to drive 0:32:50 Advice to young reporters in a hostile climate 0:35:20 A story Jonathan had never told on air 0:38:05 Inside the NSA: secrecy meets a journalist 0:42:00 Taking “no such agency” public 0:43:45 Re-earning America's trust after Snowden 0:48:00 Knowing when it's time to leave 0:49:30 What she's most proud of 0:51:30 Myron Kandel and the bag of work clothes 0:55:10 The reinvention lesson: listen more than you speak New here? Follow Stumbling Blocks so you don't miss what's next. A quick review is the best way to help other leaders find the show.

    Kelli Arena, CEO, Nat'l Cryptologic Foundation: How I Helped NSA Find Its Voice

  3. May 29

    Shalene Gupta, Editor, Fast Company: The Manager's AI Survival Guide

    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 it, and it matches what I find in my own work. People will walk through almost any change, AI included, when they trust that their leader has their back. In this episode: 0:00:00 The question every manager is asking 0:01:20 The one-line takeaway from the AI Survival Guide 0:02:30 Two universes: the AI race vs. where most of us work 0:04:53 Ethan at Meta: "If you think they'll replace you, they probably will" 0:06:07 The math: a person vs. $200 to $500 a month in tokens 0:07:36 ClickUp's "100x more productive" memo 0:08:40 Are we weighing the human cost? (Dimon at Davos) 0:09:49 What it feels like to be a middle manager today 0:11:48 What the excited managers had in common (and a Georgia-Pacific surprise) 0:14:10 Advice for leaders taking teams through AI 0:16:26 Advice for the rest of us 0:17:07 My takeaway, and a look at next week Links: "The Middle Manager's AI Survival Guide" (Fast Company): https://www.fastcompany.com/91531056/the-middle-managers-ai-survival-guide The Power of Trust, by Sandra Sucher and Shalene Gupta: https://amzn.to/4xdcxUK The Cycle, by Shalene Gupta: https://www.amazon.com/Cycle-Confronting-Pain-Periods-PMDD/dp/1250882893 Shalene Gupta: https://shalenegupta.com Shalene Gupta is the staff editor for Fast Company's Work Life and Leadership section, co-author of The Power of Trust with Harvard's Sandra Sucher, and author of The Cycle. Stumbling Blocks: How Great Leaders Are Made is hosted by Jonathan Block, founder of Block Leadership Group, recorded in the Treehouse Studio in Georgia. If this was worth your time, follow the show and leave a review. It's the best way to help other leaders find it. Next week: Retired Vice Admiral Mark Harnitchek, who led the Defense Logistics Agency, on loss, grief, and leadership as a mirror. I'll see you then on The Stumble.

    Shalene Gupta, Editor, Fast Company: The Manager's AI Survival Guide

  4. May 6

    Dana Perino, White House Press Sec. & Bestselling Author: "Purple State" & Crossing Party Lines

    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 in recent history. Dana talks about the personal story behind the book: The time a dear friend said, "Do not pass up the chance to be loved." She almost didn't listen. Dana tells the story of sitting in the Oval Office with President Bush just before walking out to face a press corps hungry over a tell-all memoir from her predecessor. She was furious on his behalf. He told her something about forgiveness that changed her. Purple State is out now. Pick it up today here:* https://amzn.to/4tRzGcZ CHAPTER MARKERS 0:00:00 Welcome to the Treehouse Studio 0:01:13 The 2007 Phone Call 0:02:35 Life After the White House 0:04:58 Purple State: The Book 0:06:59 Why I Wrote a Novel 0:10:42 Wearing Your Politics Lightly 0:12:57 The Oval Office and the Forgiveness Lesson 0:15:52 68% of Young People Won't Date Across Party Lines 0:17:29 Do Not Pass Up the Chance to Be Loved 0:19:00 Peter, the Proposal, and the Open-Ended Ticket 0:20:05 Dinner With the Queen's Staff 0:21:46 There Is Freedom in Being Disciplined 0:23:41 Closing Thoughts on Purple State 0:24:49 Outro KEYWORDS / TAGS Dana Perino, Purple State, leadership, Fox News, The Five, White House Press Secretary, forgiveness, discipline, political fiction, women in leadership, Minute Mentoring, President Bush, Jonathan Block, Stumbling Blocks, career resilience, love, faith *Amazon affiliates receive a small commission from Amazon for purchases made through this link. Commissions do not impact editorial decisions.

    Dana Perino, White House Press Sec. & Bestselling Author: "Purple State" & Crossing Party Lines

  5. Apr 23 ·  Bonus

    Outtakes: Sue Gordon Meets My Parents

    My parents were visiting me the day I interviewed Sue Gordon, former Deputy Director of National Intelligence. So they joined me in the Treehouse Studio to say a quick hello to her. Here's their conversation.

    Outtakes: Sue Gordon Meets My Parents

  6. Apr 22

    Sue Gordon, Deputy Director of US Intelligence: What America Needs From Its Leaders

    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 and patriotism, not preference. You should have your team. Godspeed, Sue." Since then, life has come at her hard. Both parents died. Her husband Jim, the love of her life for 43 years, died unexpectedly. She has faced two rounds with cancer, the second one far more deadly than the first. And she says she's the most blessed woman in the world. In this conversation, Sue goes deep on: The U.S. strikes on Iran and what she sees that most Americans don'tWhat the Epstein files actually reveal about how power protects itselfWhy she almost ran for PresidentWhy she quit the CIA with two weeks' notice to be a better momHow the Trump administration publicly excoriated a 40-year career civil servant, and what she chose to do instead of fighting backWhy she thinks America needs to fix a system the Founders never designed for this much speedWhat she wants every woman in a man's world to know, and what she wants the good men to finally do about itThe doorways of grief, and how to move through them This is Sue Gordon in full: the spy, the mom, the widow, the patient, the patriot. Unfiltered. Funny. Occasionally heartbreaking. Always worth your time. Find her podcast, Understandable Insights here: https://podcasts.apple.com/us/podcast/understandable-insights-information-to-intelligence/id1827249845 Books and Works Mentioned: A Severe Mercy The Price We Pay An Immense Journey Sue's Resignation Letter If this episode is worthy of your time, please share it and leave a review. It's how we grow.

    Sue Gordon, Deputy Director of US Intelligence: What America Needs From Its Leaders

  7. Apr 22 ·  Bonus

    Outtakes: The President's Advice I Didn't Want

    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 third is about what shaped my decision to work for Attorney General Gonzales as a political appointee. If you haven't heard Parts One and Two yet, start there. This bonus episode will mean more after you've heard their full story. Content warning: Like part 1, this episode touches on childhood trauma and may not be suitable for all listeners. If you'd like to support the show, please follow Stumbling Blocks on your favorite podcast app and leave a review. It's the best way to help other leaders like you.

    Outtakes: The President's Advice I Didn't Want

  8. Mar 28

    Attorney General & Rebecca Gonzales, Pt 2: Leadership, Loss, and Love

    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. Friends vanished. Job opportunities disappeared. And the pain was so deep they sat side by side in silence, because words wouldn't come. But strangers showed up in ways you won't expect. And President Bush wrote a handwritten note that says something every leader needs to hear. And eventually, it becomes clear where home is. It's a political love story unlike any you've heard before. If you missed Part 1, start there first: https://podcasts.apple.com/us/podcast/exclusive-attorney-general-alberto-gonzales-becky-gonzales/id1849573843?i=1000757588087 Next episode: Sue Gordon, 30-year CIA veteran and former Deputy Director of National Intelligence. 0:00:00 Introduction & Part 1 Recap 0:03:30 The U.S. Attorney Scandal 0:07:45 "People Will Do Anything to Get Power" 0:09:50 President Bush Defends His Attorney General 0:11:45 The Call to Resign 0:15:30 The Phone Stopped Ringing 0:18:00 "We're Rich in Love" 0:22:15 President Bush's Handwritten Letter 0:27:30 The Wilderness Years 0:34:15 "It's Got to Work Out" 0:40:50 Finding Home in Nashville 0:45:35 Advice for Your Own Wilderness 0:51:00 Outro & Next Episode Preview TAGS/KEYWORDS: leadership, resilience, Attorney General, Alberto Gonzales, George W. Bush, public service, marriage, faith, political crisis, Washington DC, wilderness, Belmont University, trust, Rebecca Gonzales

    Attorney General & Rebecca Gonzales, Pt 2: Leadership, Loss, and Love
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About

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

Information

  • Creator
    Jonathan Block
  • Years Active
    2025 - 2026
  • Episodes
    25
  • Rating
    Explicit
  • Copyright
    © 2025 Jonathan Block