What's Next! with Tiffani Bova

RELOAD: Are You Asking the Right Questions with Hal Gregersen

May 22, 2025
Hal Gregersen, Executive Director of the MIT Leadership Center and author of 'Questions Are the Answer', dives into the transformative power of effective questioning in leadership. He reveals how asking the right questions can enhance creativity and drive organizational success. With captivating anecdotes, he illustrates the importance of curiosity and engagement, including a poignant story about how a curious worker unlocked innovation on a citrus farm. Gregersen also discusses AI's role in retail engagement, emphasizing the need for leaders to listen and learn from employees.
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ADVICE

Perform a 24-Hour Question Audit

  • Conduct a 24-hour question audit by noting every question you ask throughout a day.
  • Analyze these questions to understand their purpose and improve your questioning skill.
INSIGHT

Executives Limit Questions With Answers

  • Many executives ask questions but often seek answers they already know, limiting creativity.
  • Longer reflection on questions rather than immediate answers leads to better problem solving.
ANECDOTE

Mark Benioff's Game-Changing Question

  • Mark Benioff challenged the assumption of selling enterprise software only traditionally by asking if it could be sold on the internet like Amazon sells books.
  • This question led to innovative thinking and Salesforce's transformation.
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