What if the key to building stronger connections with the people we work with started with asking powerful questions? Today’s inspiring expert guest on Finding Brave has made it his life mission to “gently eradicate small talk” in the hopes that it will bring us all closer to what really matters to us all.  

Chad Littlefield is the co-founder of We!™ and creator of We! Connect Cards, a tool to spark conversations that matter in 50+ countries around the world. He has spoken at TED, and most recently he and his partner Will Wise launched their new book, Ask Powerful Questions: Create Conversations that Matter, now a #1 Amazon Bestseller.

As you’ll hear, it all starts with gaining a deeper awareness of our intentions, as well as a genuine curiosity and touch of bravery to get to truly know the people around us. It just takes ones step on our part, but even a tiny act can have profound effects.

And you’ll explore with us the idea that small talk can keep us from forging the true bonds we’re longing for, but our efforts at making connection can backfire if we’re not more careful and conscious.

Highlights from this Episode:

  • Why the questions we ask will determine how we are able to build trust and connection [4:15]
  • How having the right intentions will set you up for a positive interaction [10:13]
  • Examples of the right, and wrong way to use start building trust with others [11:05]
  • The role of biases in our day-to-day interactions [17:20]
  • What are “positive social risks” and why it’s such a valuable concept to comprehend [19:05]
  • How our intuition may steer us towards connecting with people around us [25:30]
  • How Chad’s trainings may affect introverts differently than the extroverts he works with [27:48]
  • Why his mission is to “gently eradicate small talk” and the way he received this message [31:05]
  • What “small talk” really is and when it can be a good thing [34:58]
  • Chad’s tips for achieving more meaningful and valuable conversations in our lives [38:25]
  • The power of listening and how he reminds himself to do this in every single conversation he has [42:25]

For more information:





Resources Mentioned:

Free Tools, Including 12 Engaging Questions That Build Trust

We! Connect Cards

Connection Toolkit

Chad’s Books, Pocket Guide to Facilitating Human Connections & Ask Powerful Questions: Create Conversations that Matter

His TEDx Talk, Positive Social Risks!

JASON Project

Start With Why by Simon Sinek

Kathy’s Forbes Post, Alan Alda Shares Indispensable Communication Insights From His Life As An Actor


“Questions are the core element of human communication, and human communication is messy, so laying the foundation of intention is super important.” [8:45]

“Most often we have intentions that affect other people, but so rarely do we actually share those intentions with the people they affect.” [10:23]

“I’m never willing to preach or share something that I’m not willing to practice myself.” [12:59]

“The actual risk of a social interaction is almost always lower than the perceived risk.” [21:55]

“If a conversation adds value to both parties, then I would say it matters.” [36:34]

“I think the root of just about every argument is that somebody doesn’t feel heard.” [42:50]


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  1. Listening With Curiosity at Forbes - We! - […] Caprino, senior contributor. Kathy connected with Chad while first interviewing him on her podcast, Finding Brave. Catch the episode…


Kathy’s new book The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss shares vital information on the 7 most damaging power gaps that 98% of professional women face and how to overcome them. Boost your power and confidence today!


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