8/23/25

How Do You Lead Better Conversations? | Matt Chmiel, Head of Discourse at On_Discourse

Matt Chmiel, Head of Discourse at On_Discourse, works with executives, founders, and investors to spark deeper, more thought-provoking conversations. In this interview, he explains how he provokes dialogue, why the best discussions start with powerful questions, and how active listening can transform your interactions.

🎙 Topics Covered:

  • What it means to be “Head of Discourse”

  • How to challenge people to think beyond their answers

  • Examples of provocative icebreaker questions

  • Why listening is the most important skill in conversation

  • Advice for teenagers on working with people and leading dialogue

If you’ve ever wondered how to ask better questions, create meaningful exchanges, or work in a role that’s all about people, this interview offers valuable insight.

Next

Can You Really Make a Living Going Out to Dinner? | Danny Fishman, The Room