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43. The Four Questions That Transform Leadership Conversations: What, What Is, What If, and What Now
Episode 4328th October 2025 • Dig Deeper • Digby Scott
00:00:00 00:13:03

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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.

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The Questions Toolkit: digbyscott.com/questionstoolkit

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