Episode 91 of The Informed Life podcast features a conversation with conversation designer, consultant, and coach Daniel Stillman. Daniel is the author of Good Talk: How to Design Conversations That Matter and the host of The Conversation Factory podcast.

This is a special episode of The Informed Life: it’s the first recorded in person, while Daniel and I attended UX Lisbon earlier this year. Fittingly, it’s an experiment: a freeform, less produced conversation about how we converse.

Few interactions are as meaningful as conversations. In many ways, the quality of our conversations affects the quality of our lives. This is the crucial question, as Daniel put it:

Is the way that I am designing my conversations getting me what I want out of life? Is it working for me?

Good Talk features a framework for designing better conversations — what Daniel calls a “conversation operating system.” I wanted to learn more about this OS and how we might implement it.

It’s hard because conversations are so integral to daily life that we don’t step back to examine our performance — especially in those critical conversations that change the course of our lives. Daniel used an evocative image to make the point:

If you watch movies or like any kind of TV drama, the music tells you if it’s an important moment. The music tightens, and you tighten up; you’re like, “this is an important moment! Something’s going to happen.” And that is not present in life. It’s up to us to decide whether or not a moment is important and if we’re going to take advantage of that moment or let it, as they say, slip through our fingers.

But if we know we’re heading into an important conversation, we can be more intentional about establishing conditions that lead to success. This is where Daniel’s practice of conversation design comes in:

I’m designing for what I think people want and like and enjoy. And that’s being an intentional designer of, “what would you think they would say it was like? Was it deep? Was it cool? Was it fun? Was it fast? Was it impressive? Was it stultifying?” Nobody says that! Nobody says like, “you know what I want? I want people to be bored out of their minds, so I’m going to ram a hundred slides down their throat and have no exercises.” I’m like, how’s that a workshop? Right? So I design for a conversation.

I loved talking with Daniel about this subject. Not only was it very “meta,” but was also a bit of an experiment. Because it was an in-person conversation about conversation, I was less focused on timing and staying focused on the subject and more on being present with Daniel. I’d love to hear your thoughts about this format for future TIL episodes.

The Informed Life episode 91: Daniel Stillman on Conversation Design