What to Talk About at a Leadership Retreat

As I was filming a video about why things always get in the way of what we care about, I got kicked out of the lobby of the Omni San Diego hotel. After 17 years as an executive coach, I’ve had a lot of practice on what to talk about at a leadership retreat. I like to focus on three deep questions that help leaders and teams strengthen their personal identity.

What do you care about?
Do you own it?
What’s stopping you?

These questions might seem odd at first, but just as Jennifer Potter agrees in her recent HBR Article, sometimes you have to go slow to go fast. Most teams want to just dive right into planning for the next quarter or year or discuss goals, but without strong self-awareness and a sense of identity around what you care about, no one will follow you. Learn more about why I ask these questions at leadership retreats. A bonus question is one I experienced recently while I was volunteering which is, what is relevant to you? Deep questions create a strong identity to strengthen teams.