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The Best Leaders Don't Have the Most Answers — They Ask the Best Questions | The Olympic Minds
44 minutes Posted Jun 8, 2026 at 12:15 pm.
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What if the leadership skill your team needs most from you right now isn't decisiveness, strategy, or vision — it's the ability to stop talking and truly listen? In this episode of Olympic Minds: Leadership Beyond Limits, we tackle the hard truth about what separates leaders who build great teams from leaders who simply manage them.

Host Sherry Winn, two-time Olympian, national championship basketball coach, and CEO of the Winning Leadership Company, sits down with Rachel Rogers — Salesforce MVP Hall of Famer and Principal Business Strategy lead at Northwell Health — a leader who has spent her career designing people-first organizations in the middle of rapid technological change. Rachel brings refreshing honesty about work-life integration, the real opportunity hidden inside AI disruption, and the listening-first coaching approach that has helped her develop some of the most effective teams in her industry.


In this episode you will learn:

  • Why work-life balance is a myth — and the integration mindset that actually allows high performers to show up fully at work and at home

  • How the most effective leaders use AI as a leveling-up tool for their people rather than a replacement threat

  • Why the single greatest coaching skill you can develop as an executive is learning to stop talking and listen with intention

Whether you're leading a team of three or three hundred, this episode will give you a practical framework for showing up more intentionally — at work, at home, and everywhere in between. Tune in, subscribe, and share this with the leader in your network who needs to hear that slowing down is not falling behind.

#ExecutiveLeadership #CsuiteLeadership #WorkLifeIntegration #LeadershipDevelopment #HighPerformanceTeams #EmotionalIntelligence #AIWorkplace #LeadershipCoaching #SelfAwareness #MentalToughness


Guest: Rachel Rogers https://www.linkedin.com/in/rachelvrogers/Host: Sherry Winn https://www.linkedin.com/in/thewinningleadershipcompany/

Sound: Mahesh R.

Producer: Archita Puranik