165. Anna Wintour: Culture, Influence, and the Power of Decisive Leadership

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Dec 8, 2025

Anna Wintour, the influential editor-in-chief of American Vogue, shares her unique insights on leadership shaped by fast decision-making and resilience. She discusses how her upbringing in a media family influenced her career and the importance of mentorship in building strong teams. Wintour reflects on the cultural power of fashion, whether it's reviving cities through events like Vogue World or adapting the magazine's aesthetics. She also reveals the lessons learned from her career setbacks and why she prefers celebrating creativity over controversy.

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INSIGHT

Decisive Speed Beats Slow Perfection

Fast decision-making sustains momentum and clarifies direction in fast-moving industries.
Anna Wintour prioritizes speed and decisiveness over prolonged deliberation to keep a global newsroom agile.

ADVICE

Build Leaders Not Clones

Surround yourself with creative people who challenge and improve your ideas.
Mentor and promote others so they develop their own leadership rather than creating 'AW light' replicas.

ANECDOTE

Tarzan Lawsuit And The Hoodied CEO

Anna recalled a copyright lawsuit over a Tarzan story that panicked her but taught resilience.
Cy Newhouse reframed crises as publicity and modelled calm decisive leadership during office protests.

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Why should everybody get fired at least once? As the former Editor-in-chief of American Vogue, how does Anna Wintour use fashion as a cultural and economic force? Why is Anna’s leadership style defined by the speed of her decision making?

Rory and Alastair are joined by Fashion icon Anna Wintour to answer all this and more.

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