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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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43. The Four Questions That Transform Leadership Conversations: What, What Is, What If, and What Now
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What if the quality of your leadership came down to the quality of your questions?
And what if shifting just one word in how you frame a question could completely change the direction of a conversation?
Most leaders ask questions to get answers. But the real power lies in asking questions that unlock thinking, creativity, and action in others.
This episode introduces a practical framework for asking better questions – four simple categories that can transform how you lead meetings, drive strategy, and navigate complexity. Whether you're facilitating a team discussion, making a tough decision, or trying to move beyond surface-level conversations, these questioning techniques will shift what's possible.
You'll discover:
- The four types of questions every leader needs to master: "what", "what is", "what if", and "what now"
- Why "what" questions clarify focus and set the stage for meaningful dialogue
- How "what is" questions help you uncover the real issues beneath the surface
- Why "what if" questions ignite creativity and open up new possibilities
- How "what now" questions drive action and accountability
- A practical quadrant model you can use to structure any conversation
- Simple techniques for naming shifts in your questioning to enhance clarity
- Why progression matters more than perfection when developing your questioning practice
This is a short, practical episode designed to give you an immediately useful tool. The goal isn't perfection – it's progression. Pick one type of question, experiment with it in your next conversation, and notice what shifts.
Whether you're preparing for a strategic discussion, wanting to deepen team engagement, or simply curious about how to facilitate better conversations, this framework offers a clear path forward.
Related Episodes
- KP on Breaking Out of 'Answer Mode': https://dig-deeper.captivate.fm/episode/26-breaking-out-of-answer-mode-building-collective-wisdom-and-the-village-that-raises-leaders-kirsten-patterson/
- Kate Christiansen on Escaping the 'Answer Trap': https://dig-deeper.captivate.fm/episode/32-escaping-the-answer-trap-and-why-slowing-down-speeds-you-up/
- Simon Dowling on Why Creating Space Matters More Than Efficiency: https://dig-deeper.captivate.fm/episode/18-why-creating-space-matters-more-than-efficiency-simon-dowling-on-intentional-leadership/
The Questions Toolkit: digbyscott.com/questionstoolkit
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