#26 Chad Littlefield: The Catalyst for Collaborative Conversations

Chad Littlefield is the co-founder and Chief Experience Officer of We and Me (www.weand.me). The organization aims to help leaders, educators, and events make connection easy. His successful 2015 Kickstarter for We! Connect Cards: Create Conversations that Matter, which is comprised of cards with questions on the front and a stretch on the back intended to make conversations fun and meaningful. 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 worldwide.

Chad and his late partner Will Wise launched their books How to Make Virtual Engagement Easy and Ask Powerful Questions: Create Conversations that Matter, both #1 Amazon Bestsellers. Chad's YouTube channel has over a million views, and he hosts the annual Connectors Summit in December to bring people together to hone their skills and meet like-minded people leading the vital work of connecting. He lives and delivers the enthusiasm you expect for someone trying to change the world through intentional connection.

The conversation delves into the transformative power of asking meaningful questions and building connections. Chad shares his journey of discovering the impact of questions, We Connect Cards' origin, and intention's role in effective questioning. The discussions also explore practical strategies for fostering deep connections and the societal impact of genuine curiosity. Full of insights and practical advice, this episode is a must-listen for anyone interested in enhancing their communicative skills and fostering stronger relationships.

#25 Seth Godin: Embracing Tension & Unleashing Questions Strategic Potential

Seth Godin is a bestselling author of 22 books in 39 languages, entrepreneur, and speaker. In April of 2025, he will upload his 10,000th daily blog post to one of the most popular blogs in the world; yeah, that's over 27 years of daily writing. Seth founded Squidoo and Yoyodyne (acquired by Yahoo!) and is credited as the inventor of email marketing (the good kind).

Seth has given five TED talks, including two that rank as the most popular of all time. By teaching about everything from effective marketing and leadership to the spread of ideas and our responsibilities as leaders, Seth has motivated and inspired people worldwide.

The conversation delves into Seth's background, achievements, and philosophy behind the power of asking questions. They discuss how questions can create tension, drive more profound understanding, and foster meaningful connections. Seth shares anecdotes from his experiences, offering practical examples of strategically using questions in various contexts, from personal interactions to professional settings.

The episode underscores the necessity of intentionality in asking questions to effect change, highlighting the strategic importance of inquiry in personal growth and leadership. It concludes with reflections on empathy, systemic challenges, and the enduring significance of caring and trying to make a difference, no matter the state of the world.

#24 Ken Woodward: Impactful Questions: Are You Better Off...

This episode dives into the significant political question posed by Ronald Reagan during the closing moments of his 1980 presidential debate with Jimmy Carter: 'Are you better off than you were four years ago?'

Ken Woodward explores the context of the 1980 political climate, marked by economic difficulties, high inflation, unemployment, and international issues such as the Iran hostage crisis and concerns about U.S. global standing and nuclear threats. Reagan's question, which became iconic in U.S. political discourse, was noted for its simplicity, personal relevance, emotional resonance, and strategic timing. The question invited voters to reflect on their circumstances rather than abstract policies, ultimately contributing to Reagan's landslide victory.

The episode details six crucial lessons for crafting influential questions, emphasizing audience perspective, engagement, simplicity, timing, self-reflection, and a call to action. Listeners are encouraged to consider how such questions have shaped their decisions and to apply these insights in personal and professional contexts.

#23 Ken Woodward: Right Now Questions Explored

This episode explores 'Right Now Questions,' a concept introduced in an earlier 2024 podcast episode. The episode compiles various interviews where individuals share their current pressing questions.

Featured guests include author Chazz Scott, who discusses life post-book release and physical recovery, and sisters Shreyaa and Esha Venkat from the nonprofit NEST4US, who are considering their future plans and educational transitions. Other contributors include educator Kwame Sarfo-Mensah reflecting on his roles, business leader Bill Reed sharing deep questions on emotional triggers and passions, and multi-hyphenate EbonyJanice Moore contemplating her priesthood journey. Art Historian and problem solver Amy Herman ties in personal and professional life experiences, and Executive Coach Jerry Colonna speaks on his transitional stage. The audience is invited to share their own Right Now Questions, fostering a continuous journey of learning and inspiration.

#15 Kwame Sarfo-Mensah: The Vocabulary of Identity & Creating Culturally Affirming Classrooms

Kwame explores the concept of identity, including personal and social identities, and how these can affect one's experience in the world. The conversation delves into the challenges of addressing identity in educational settings and the importance of diversity, equity, inclusion, and accessibility. Kwame shares his experiences and insights on the power of questions in navigating contract negotiations, understanding student backgrounds, and self-growth. The dialogue also touches on unlearning ingrained biases and recognizing privileges. The discussion concludes by reflecting on the role of questions in fostering a more inclusive and understanding society.

#14 Bill Reed: Questions At The Heart Of Leadership, Mentorship and Relationships

The discussion delves into how questions have shaped Bill’s parenting, leadership, and mentoring approach, emphasizing the importance of curiosity and intentional relationship-building. We also explore the impact of effective questioning in meetings and mentoring relationships, focusing on Bill's current endeavors and insights into fostering a culture of transparency and authentic inquiry.

#12 Jimmy D. Smith: Navigating Leadership, Friction, Mentorship, and Legacy

Smith shares his inspiring career journey from an aspiring pilot to a guardian of the nation's nuclear arsenal, highlighting the importance of persistent inquiry, mentorship, and community engagement. He discusses his unique work habits and strategies for career advancement and introduces the 'Talk Backwards' methodology for relationship building. Smith also emphasizes selflessness, integrity, and his initiatives in STEM programs, particularly with HBCUs, providing scholarships, internships, and job opportunities. Personal anecdotes and life lessons from his mentor, Vice Admiral Paul Sullivan, are woven throughout, encouraging listeners to question, grow, and help others succeed.

#10 Nikki Giovanni: Reflections On Life, Galaxies, & A Poetic Exploration of Questions

The conversation explores Nikki's reflections on the significance of the power of words, influential librarians, and growing up Black in America. Giovanni shares impactful moments and discusses age, curiosity, societal challenges, and learning philosophies. The dialogue delves into her deep understanding of history, human nature, black women's significance, and space exploration. Giovanni's personal anecdotes and poems provide a rich narrative on societal issues, the beauty of nature, joy, curiosity, and the importance of chosen relationships over familial ties.

#09 Derek Sivers: Challenging Conventions, Reframing, & The Intentional Path

Derek delves into his experiences with questioning assumptions, pushing boundaries, and the role of journaling for self-reflection. The conversation encompasses topics like the importance of reframing perspectives, cultural differences in questioning, and Sivers' embrace of minimalism. He advocates for reframing situations and adopting beliefs that are useful over what is "true." Practical advice and anecdotes underscore the value of curiosity and inquiry, offering valuable insights into leading a more examined life through the transformative power of questions.

#05 Jenny Hegland: Being a Listening Poet, Grief, and Questions as a Pathway to Healing

Jenny opens with heroics in Saipan in the aftermath of a typhoon, then recounts how community engagement and outreach fueled activism and making a difference in the community. Jenny explains the role of the listening poet and the impact it has had on her and those she serves. We discussed her parents' role in encouraging questions and how questions can be a pathway to healing. Other topics include community, grief, and loneliness. Jenny also shares two of her listening poet poems and the backstory that inspired them.

Episode #2: Pat Ennis

“Oftentimes people know their solutions, it is in them, we just have to ask the right questions for them to say what the solutions are.”

— Pat Ennis

Pat Ennis is a founder and President of ENNIS Legacy Partners. He helps business owners build sellable business value, control their exit, and leave their desired legacy. Pat has extensive executive leadership experience in wealth management and the non-profit sector. Additionally, Pat is a host of the Exit Readiness Podcast

I have known Pat for over 20 years and have experienced his skill at asking targeted and meaningful questions. His model of humility and patiently asking questions has been beneficial over the years. Our discussion provides a tangible example of the path curiosity can take a conversation.

We cover a lot of ground in our discussion. Pat explains how sales and serving his clients is first and foremost about being curious and taking a genuine interest in the individual sitting across the table. He talks about using questions to test assumptions and how asking meaningful questions is a means of loving others.