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 and making connection easy 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

Chad works with leaders, educators and events in three primary ways.

Chad leading a conference keynote

Connected Conference Keynote Package

Show your attendees something unique, meaningful, and deeply engaging. People might come once for the content, but they’ll come back again and again for the connection that happens in-between the content. Get in touch when you're ready to push the envelope with your event.

Teambuilding and trust by We and Me

Engage to Educate Live Online Training

Join Chad Littlefield in a series of live, interactive workshops tailor-made for other trainers, educators, and facilitators. Cut your prep and stress time in half with an easy method to design your meetings, events, trainings, and presentations for contribution—not just consumption!

Ask Powerful Questions Workshops

Maximize the opportunity for team and leadership development. Equip your group with essential—yet rarely taught—communication skills. Do this all while facilitating meaningful conversations that will have a positive ripple throughout your entire organization. 

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 with 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 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 500+ video tutorials with over Two Million 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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    Ready to level up your team?

    Gain instant access to our all our FREE resources.

    21 Printable We! Connect Card questions

    10+ video tutorials for group activities (that your team won’t scoff at)

    An excerpt to Ask Powerful Questions, our Amazon #1 Bestseller—in 4 categories

    Coupon codes for free shipping and bulk rates

    You have successfully joined the movement of people around the globe filling their communities and organizations with conversations that matter! Thanks for asking great questions and helping to design the world for contribution—not just consumption.