Host Ken Woodward talks with Kevin Kelly, who shares his insights on the power of questioning for personal and societal growth, discussing the role of questions in driving innovation and fostering understanding. He emphasizes the importance of inefficiency and exploration in formulating impactful questions, contrasting this with AI's tendency to provide average answers. Kelly also discusses his long-term projects, such as the 10,000-year clock with the Long Now Foundation, emphasizing the importance of long-term thinking and striking a balance between stability and adaptability. The discussion highlights the value of embracing disequilibrium for intellectual and technological advancement and challenges the notion of productivity by suggesting that waste and failure are integral to the discovery process.
#30 Tim Molnar: Intentionally Cracking Love's Enigma Through Analytics
Host Ken Woodward talks with Tim Molnar, who shares how he developed his strategic dating framework by applying research principles to dating, emphasizing the importance of asking better questions about ourselves and potential partners. He explores how traditional metrics like "feeling a spark" can be misleading compared to questions about safety, visibility, and energy levels after being with someone. The conversation highlights how self-awareness, intentional action, and thoughtful questioning can increase the probability of building fulfilling relationships while also creating space for continued growth and evolution within partnerships.
#29 Dave Reynolds: Cultivating Transformational Growth Through Questions
Host Ken Woodward talks with Dave Reynolds, CEO of the Rumin8 Group, about the impact of purposeful questioning in leadership and coaching. Reynolds shares his journey of learning the value of questions through his mentor Pablo, emphasizing transformation over transactional leadership. They discuss the importance of preparing for coaching conversations, asking in-depth questions, and fostering a culture of coaching and accountability in organizations. Reynolds also introduces concepts from his new book "Radicle Growth," which focuses on using questions to drive personal and organizational growth. The episode highlights the need for leaders to go beyond surface-level interactions, commit to ongoing development, and engage more deeply with their teams through strategic questioning.
#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.