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Ask Powerful Questions: Create Conversations That Matter

Key insights from

Ask Powerful Questions: Create Conversations That Matter

By Will Wise, Chad Littlefield

Audio available 16 minute read Published Apr 22, 2017

What you'll learn

This book was born of social awkwardness and frequent failure. International speaker Will Wise felt like an outsider until he discovered the power that good questions have to unlock life experiences and form meaningful connections with others. Since then, he and Chad Littlefield have teamed up to run workshops for a variety of organizations around the world, with the goal of building cultures of trust and belonging. 

Key insights

  1. 1 The reward of initiating conversations that matter far outweighs the risks.
  2. 2 Intention, rapport, openness, listening, and empathy are the building blocks of conversations that matter.
  3. 3 Intention is the foundation of deep connection and strong relationships.
  4. 4 Fear of rejection and looking stupid are the two most common obstacles to trying to connect with people.
  5. 5 To convey genuine openness, start your questions with “how” and “what”—never “why.”
  6. 6 True, reflective listening is a gift as rare as it is powerful.
  7. 7 People become useless to themselves and others when they mix up empathy and sympathy.

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