Podcast Summary

Podcast: Redefiners
Episode: The Leadership Lessons That Shaped Us: Celebrating 100 Episodes of Redefiners
Hosts: Marla & Simon (Russell Reynolds Associates)
Date: August 27, 2025

Overview

This special milestone episode celebrates the 100th episode of Redefiners by distilling the most powerful leadership insights shared by bold, inspiring guests over four years. Hosts Marla and Simon curate 11 key lessons—backed by memorable stories, candid advice, and remarkable moments—from business titans, global changemakers, and industry rule-breakers, offering a real-world playbook for extraordinary leadership.

Key Discussion Points & Leadership Lessons

1. Leave Your Door Open to New Opportunities

Guest: Ruth Porat (CFO, Alphabet & Google)

• Ruth challenged the traditional “grand career plan” narrative, instead embracing flexibility and ongoing self-reflection.
• Her pivotal question: “What’s your highest and best use?”

  "If you keep addressing that question...and you don’t have blinders on, you will find that leaders eventually say, wow, if you did X and Y and A and B, you can probably do something else as well." – Ruth Porat [04:06]

Notable Moment:

• Ruth never expected to reach the C-suite, focusing instead on growth, learning, and impact over a strict plan.
• Marla called it “a phenomenal piece of advice… the opposite of what most people tell you.” [04:33]

2. Take Risks: Deliberately Throw Yourself in the Deep End

Guest: Adena Friedman (CEO, NASDAQ)

• Adena volunteered for projects outside her expertise, intentionally building resilience and capability.

  "If you see jobs that you find really compelling in five years...figure out a path to get there...If you look forward in five years and...you don't want any of those jobs...maybe this isn't where I should be." – Adena Friedman [06:04]

Notable Moment:

• Marla highlighted Adina’s courage and “record-breaking” episode in the studio [05:21].

3. Develop Grit: Unshakable Determination to Succeed

Guest: Deborah Martin Chase (Hollywood Producer)

• Pivoted from Harvard lawyer to leading Hollywood producer through sheer faith in herself and relentless work.

  “I made up my mind that I was gonna succeed…you are willing to do work harder, you know, be better and not give up to succeed.” – Deborah Martin Chase [08:05]

Notable Moment:

• Marla: “The sheer determination in her voice, you can hear it, can’t you? That’s someone who refused to let the world dictate what she was going to do.” [08:38]
• Simon: “If you want to know what glass ceilings sound like as they shatter, those were the words that capture it.” [08:51]

4. Stay Curious: Leap in Order to Learn (Especially with AI)

Guest: Brad Smith (President, Microsoft)

• Learning on the fly is critical—especially in areas like AI.

  “Do people need to learn before they leap? I actually think they need to leap in order to learn." – Brad Smith [10:13]

Notable Moment:

• Marla: “You can’t figure out AI by reading about it...you have to start using it…learning as you go.” [09:38]
• Simon reflects on how this reverses conventional wisdom. [10:55]

5. Treat Failure as a Superpower

Guest: David Rubenstein (Co-founder, Carlyle Group)

• Through interviewing icons like Oprah, Buffett, and Bezos, Rubenstein distilled the secret:

  “They typically had failures early on...picked themselves up and got back into the arena...persistent...shared credit and took blame...had humility." – David Rubenstein [13:29]

Notable Moment:

• Marla emphasized the power of resilience and how RRA specifically assesses for it. [14:00]

6. Have the Courage to Make Unpopular Decisions

Guest: Dee Caffari (Record-Breaking Yachtswoman)

• Leadership is lonely—sometimes you must prioritize tough calls over being liked.

  “It’s pretty lonely at the top, and that’s why you pay the bucks to make the big decisions...you have to make those difficult decisions and take responsibility and own them.” – Dee Caffari [15:48]

Notable Moment:

• Simon: “Being alone on the dark ocean, in Dee’s case, not a metaphor, that was an incredibly powerful story...” [16:37]

7. Never Accept Impossible: Break Through Boundaries

Guest: Dr. Ngozi Okonjo-Iweala (Director-General, WTO)

• “No” is not an acceptable answer when the stakes are high.

  “Not accepting no for an answer and just being determined...trying to focus people that these things really matter and we've got to find a way to break through.” – Ngozi Okonjo-Iweala [18:08]

Notable Moment:

• Marla recalled Ngozi negotiating after her mother’s kidnapping—a testament to inner strength and resolve. [19:13]

8. In Times of Crisis, Your People Come First

Guest: Tony Capuano (CEO, Marriott)

• Navigated CEO transition during COVID-19 and the loss of a beloved predecessor.

  “They are natural and appropriate emotions, but to compartmentalize them a bit...tomorrow morning, 800,000 people are going to...look to you to lead them out of this...That was a way to sharpen my focus on the task ahead.” – Tony Capuano [20:31]

Notable Moment:

• Marla: “Your personal pain...becomes secondary to the needs of those that are depending on you...” [22:48]

9. Take Responsibility, Share Credit

Guest: Bill Roedy (Former Chair/CEO, MTV International)

• Military principles shaped his business leadership:

  “First on the battlefield, last to leave...slow to take credit, quick to take blame.” – Bill Roedy [24:17]

Notable Moment:

• Marla emphasized these principles as building deep organizational loyalty. [25:24]

10. Lead Authentically: Own Your Story

Guest: Sarah Mensah (President, Jordan Brand)

• Blending motherhood and work in a male-dominated, high-pressure environment.

  “I was going to entitle myself...the right to work as hard as I was working...and to be unabashedly a mom...I just owned it.” – Sarah Mensah [27:42]

Notable Moment:

• Sarah’s playful but firm assertion of identity influenced the culture, inspiring other women. [28:30]

11. Innovate and Empower with Purposeful Culture

Guest: Will Guidara (Former co-owner, Eleven Madison Park)

• The “$2 hot dog” story: putting guest experience over convention, then embedding this attitude institutionally.

  “I started to approach the business from a very different perspective.” – Will Guidara [31:12] “They come up with a great idea, they give their team the idea, but...don’t back it up with the resources to make it a plausible part of the culture.” – Will Guidara [32:08]

Notable Moment:

• Simon: “It wasn’t just a one-off...he took and internalized it...and gave his team permission and resources to innovate.” [32:12]
• Marla: “Not just about grand gestures, but meaningful culture, and empowering teams.” [32:18]

Notable Quotes Recap

• “What’s your highest and best use?” — Ruth Porat [04:06]
• “Leap in order to learn.” — Brad Smith [10:13]
• “Resilient leaders pick themselves up again day after day.” — Marla [14:00]
• “Lead authentically. Own your story.” — Sarah Mensah [27:42]
• “First on the battlefield, last to leave.” — Bill Roedy [24:17]
• “It’s pretty lonely at the top...you have to make those difficult decisions...” — Dee Caffari [15:48]

Episode Flow & Timestamps

• 00:00–02:20 | Introduction, milestone reflections, show purpose
• 02:20–04:46 | Lesson 1 (Ruth Porat): “Highest and best use”
• 05:21–06:38 | Lesson 2 (Adena Friedman): Career courage
• 07:20–08:38 | Lesson 3 (Deborah Martin Chase): Grit
• 09:38–10:55 | Lesson 4 (Brad Smith): Curiosity & AI
• 11:31–14:00 | Lesson 5 (David Rubenstein): Failure as Superpower
• 14:55–16:37 | Lesson 6 (Dee Caffari): Decisions & loneliness
• 16:37–19:13 | Lesson 7 (Ngozi Okonjo-Iweala): Impossible isn’t
• 19:54–22:48 | Lesson 8 (Tony Capuano): Crisis responsibility
• 23:07–25:24 | Lesson 9 (Bill Roedy): Accountability & loyalty
• 25:44–29:18 | Lesson 10 (Sarah Mensah): Authentic leadership
• 30:12–32:18 | Lesson 11 (Will Guidara): $2 Hot Dog, culture
• 32:42–33:37 | Closing reflections, connecting the lessons

Language and Tone

The episode is characterized by warmth, admiration for guests, and a pragmatic optimism. The hosts maintain an engaging, conversational tone and a mix of awe, humility, and curiosity throughout as they draw out each lesson’s relevance and accessibility.

Conclusion

Redefiners’ 100th episode offers a deeply human, practical manual for leaders at every stage, grounded in real-world stories of courage, authenticity, resilience, and the unending journey to learn and lead boldly. The enduring message: these are skills and values—openness, grit, accountability, innovation—anyone can purposefully build.