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.”


Our Crazy Good Questions will give you a playbook for enriching conversations so that you walk away learning new things, hearing vivid stories and building stronger relationships.

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.  

Let the Story Do the Work Book Cover
If you find these questions useful, you’ll find further insights in Esther Choy’s book, Let the Story Do the Work—including a chapter on networking that turns dreaded mixers into meaningful exchanges.  Read the first chapter for free!
Esther’s book is based on years of experience of training and coaching managers in storytelling techniques to help them become more engaging and persuasive communicators. Whether you would like to stand out in the interview process, add punch to a presentation, or make a compelling case for a new initiative, we can help. Schedule a complimentary session with us today!

© 2019 by Leadership Story Lab

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Chicago, IL 60611 | 312.324.3830

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