Leading with Sensitivity: How Elanor Boekholt-O'Sullivan Challenged 100 Years of Military Thinking

What does it really mean to lead with strength?

For decades, we've been taught that great leadership is about being loud, decisive and commanding. But what if the most effective leaders are the ones who listen first, lead with empathy and have the courage to challenge the status quo?

In this episode, Osher Günsberg sits down with former Deputy Commander of the Royal Netherlands Air Force (and first female to be promoted to rank of lieutenant general) Elanor Boekholt-O'Sullivan, whose remarkable career has redefined what leadership can look like. Rising through one of the world's most traditional institutions, Elanor transformed military culture by proving that sensitivity, curiosity and authenticity aren't weaknesses, but powerful competitive advantages.

Drawing on more than 30 years of military service, Elanor shares how she overcame resistance, challenged outdated systems, and created lasting change by helping people rethink why they do what they do. From being the only woman aboard a warship with no accommodation for women, to inspiring a new generation of leaders to embrace vulnerability, her experiences offer lessons that apply far beyond the military.

This conversation also explores her extraordinary decision to leave the military after 32 years to take on one of the Netherlands' biggest challenges: helping solve the country's housing crisis as newly appointed Minister of Housing and Spatial Planning. Her deeply human perspective on the importance of creating not just houses, but homes, reveals why purpose should always be at the heart of leadership.

Whether you're leading a business, managing a team, raising a family or navigating your own career, this episode is packed with practical insights on resilience, change, emotional intelligence and leading with courage.

LINKS

• Elanor's book 'Armed With Sensitivity: A General's Perspective On Leadership' is out now
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• Watch full stories recorded live at  Story Club on YouTube
• Get tickets for our next Story Club show
• Get Osher's latest books  here
• Send a pic of what you're looking at to sendosheremail@gmail.com

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