Crazy Good Questions

Embrace the small talk. Discover others’ stories.

Networking events. Class reunions. Holiday office parties. Conferences. Those moments when you and just one other co-worker show up early to a meeting….


All of these are opportunities to take small talk deeper. Instead of focusing on filling the awkward silence with something… anything… we can use these moments to connect with the humanity of others. To do that, we have to ask the right questions because that gives people a fighting chance to respond with interesting stories. 


“When discussions focus on listing accomplishments,” says a participant in our annual Kellogg Reunion workshop, “there isn’t much to talk about once you go through the list. Setting my outlook to offer my stories over my stats set the stage to elicit a similar response in people I talked to, which led to deeper connections.”

Seamlessly incorporate thought-provoking questions into your everyday conversations:

A Sample of Crazy Good Questions

1.    What motivated/prompted you to [______]? [For example: What prompted you to move to Chicago? ]

2.    What has surprised you the most? [What has surprised you the most about becoming a parent? Or a CEO, provost, board member...?]

3.    What do you make of [______]? [Did you watch season two of Stranger Things? What did you make of it? ]

4.    When you are not here, what do you like to do?

5.    Tell me more.  

© 2019 by Leadership Story Lab

820 W Jackson, Suite 210

Chicago, IL 60607 | 312.324.3830

Ready to start telling stories? Connect with us:

  • White Twitter Icon
  • White Facebook Icon
  • White Instagram Icon
  • White YouTube Icon
  • White LinkedIn Icon
  • goodreads
  • Forbes

Subscribe to our resource guide "Better Every Story":

By subscribing, you are agreeing to our privacy policy.