Chad Littlefield

Co-founder, Speaker, Author, and Creator of We! Connect Cards

Ready to make connection easy?

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Forbes calls Chad aglobal expert on asking questions that build trust and connection in teams.”


Great leaders and educators know that investing in their people boosts results and increases retention. That’s why they contact Chad when they want to amplify a culture of connection, belonging, and trust.

Trusted by educators, businesses, and events everywhere.
Trusted by JetBlue, Penn State, Cigna, We Work, Univeresity of Notre Dame, Johnson & Johnson, Starbucks
Trusted by Conscious Capitalism, George Mason Univeresity, ASU, Typeform, TedX, Indiana University, Embry-Riddle, Goodwill

Ways to engage with Chad


Hit “refresh” on remote. 


Make Connection Easy


Tools You Can Use Tomorrow

Chad Littlefield, M.Ed.
Co-founder & Chief Experience Officer

Chad Littlefield colorful portrait

Chad Littlefield is the co-founder and Chief Experience Officer of We and Me (—an organization whose mission is to help leaders, educators, and events make connection easy.

Forbes calls Chad a “global expert on asking questions that build trust and connection in teams.” He is a TEDx speaker, bestselling author, and creator of Connection Toolkit, which is now being used to create conversations that matter on campuses and companies in over 80 countries around the world. Chad and his late partner Will Wise are the authors of Ask Powerful Questions and How to Make Virtual Engagement Easy.—both #1 Amazon Bestsellers. 

Chad has led workshops, trainings, retreats, and interactive keynotes at Crayola, JetBlue, Starbucks, Conscious Capitalism International, Johnson & Johnson, Penn State, Notre Dame, George Mason University, Typeform, Goodwill, and hundreds of events. Feel free to connect Chad via his free resources and weekly videos or follow him on LinkedIn.

Chad and the We and Me team believe…


    Leaders accomplish more by asking powerful questions than by commanding and controlling


    Smart and authentic human connection fosters more engagement and better performance


    People, purpose, and planet are just as important as profit


    Interactive experiences have more impact than PowerPoint slides because people learn by doing

    Chad’s most requested virtual and in-person speaking topics 

    Speaking Topics

    Connection Before Content

    We! Connect Cards from We and Me, Inc.

    Google found that the #1 indicator of high-performing, innovative teams is the psychological safety and trust that develop through largely social connections. 

    In this fun, interactive session, Chad Littlefield, TEDx speaker and bestselling author, will share how to make the research above come true in your world with three essential ingredients to “connection before content.” 

    We’ll get a chance to experience Chad’s We! Connect Cards, which are being used in 80+ countries to create conversations that matter.

    This session will: 

    Increase the culture of psychological safety (which heaps of research shows increases performance)

    Strengthen leaders’ ability to foster a sense of belonging (which impacts retention and the decision to stay or leave an organization)

    Equip attendees with a set of practical tools to take the heavy lifting off of them to lead effective and engaging meetings (which increase job satisfaction)

    How to Make Virtual Engagement Easy

    How to Make Virtual Engagement Easy Book

    Ready to hit “refresh” on virtual?

    In this fun, interactive session, Chad Littlefield, TEDx speaker and bestselling author, will share practical tools on making engagement and connection easy, whether you’re virtual, hybrid, or in-person.

    During this session, you will:

    Get immediately practical ideas to strengthen remote culture and offset video call fatigue

    Experience The 5 Ingredients for Engagement to enliven your everyday gatherings

    Leave re-energized at the possibility to gather with purpose—online and off

    🎥 Note: Being video and mic ready is highly encouraged, as breakouts and interaction will be a key component of this session (i.e., wear pants).


    Ask Powerful Questions

    How many questions do you ask in a day?

    In a world where answers are cheap and we can easily ask Google the distance from Timbuktu to Kathmandu, Chad Littlefield, TEDx speaker and bestselling author, will share how the questions we ask matter more than ever. 

    During this session, you will:

    ✅ Get tips to redesign meetings for contribution—not just consumption

    ✅ Takeaway instantly useful tools to ask smarter questions that can transform transactions into meaningful and memorable interactions

    ✅ Experience the essential mindsets and tools from the Ask Powerful Questions Pyramid™ to build and maintain relationships of trust


    View one of Chad’s 200+ video tutorials with over 1,000,000 views across the channel!

    To catch the latest videos…

    Start a Conversation

    Chad or someone on his team will respond within 48 hours with pricing and availability or an answer to your question.

    Chad speaking with big We! Connect Conversation Starter Cards
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    Video screenshots from Video Series

    5 Essential Ingredients for Virtual Engagement

    Gain instant access to our FREE video training.

      ✓ Prevent video call fatigue

      ✓ Learn the Do’s and Don’ts of Virtual Meetings

      ✓ Turn your virtual meetings from exhausting to energized

      ✓ Create meaningful, unique experiences for staff and students online

    You have successfully joined the movement of people around the globe filling their communities and organizations with conversations that matter! After you confirm your subscription, you'll receive a link to our video series on the 5 Essential Ingredients for Virtual Engagement.