“What is the kindest thing anyone has ever done for you?”
Patrick O’Shaughnessy ends every Invest Like the Best podcast with this question and the answers are stunning. Despite talking for an hour, guests stop in their tracks, think deeply, and often the best conversation of the whole show follows.
Questions like these are magic because they do all the following:
- Invite others to join in a conversation
- Show genuine curiosity in topics and people
- Expand on discussions instead of ending them
But it doesn’t end there. Thoughtful questions are important, but they’re really just the first step. After you’ve asked a question, focus fully on the response. Put everything else out of your mind, just listen, and you’ll be amazed what you learn and how people open up.
This approach to conversations is called empathetic listening and it’s one of the most powerful skills anyone can learn. It was used by Eric Maddox to find Sadaam Hussein and is also advocated by Chris Voss (the former FBI’s lead hostage negotiator) in his book Never Split the Difference.
Remember every great conversation starts with thoughtful questions and deep listening. Though each question is context dependent, here a few favorites I often fall back on to kickstart conversations:
- What’s the kindest thing anyone has ever done for you?
- What are your top three books?
- What are you most proud of in your life?
- What is a time (in the past month) you’ve overcome a fear of yours?
- What is one thing I can do differently to help you?