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Curated Questions

Celebrating The Power Of Questions

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#75 Phil Liebman: It's Not The Answers — It's Having the Questions

"It's not having the answers I teach people — it's having the questions. And that just upsets the entire architecture of safe thinking." - Phil Liebman

Phil Liebman spent years being mentored by one of the most relentless questioners he'd ever encountered. It changed everything about how he leads and coaches. In this conversation, Phil unpacks the difference between knowing mode and learning mode, why most of us were systematically educated out of curiosity, and what it actually takes to form a powerful question.

He introduces his cycle of curiosity and certainty, a four-quadrant framework that explains why three-quarters of the best thinking happens before any action is taken.

Phil shares hard-won lessons from decades of executive coaching, traces his intellectual foundation back to mentor Dr. Lee Thayer, and makes the case that leadership is a performing art, not a management science.

The episode closes with a personal health scare that became an unexpected masterclass in what curiosity can do when fear shows up uninvited.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)

Keep questioning!

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tags: Curated Questions, Ken Woodward, Phil Liebman, curiosity, powerful questions, learning mode, knowing mode, leadership development, executive coaching, question formation, safe thinking, Vistage, Lee Thayer, Grace Hopper, intentional questions, leadership mindset, curiosity in leadership, coaching questions, question mastery, learning vs knowing, leadership transformation, curiosity and fear, cycle of certainty, leadership consciousness, question craft, coachability, humility in leadership, performing arts of leadership, leadership curiosity, open-ended questions, organizational leadership, contagious curiosity
categories: Connection, Leadership, Listening, Personal Growth, Imagination, Strategy, Coaching, Creative Thinking, Legacy, Mentoring
Wednesday 03.18.26
Posted by Kenneth Woodward
 

#42 Ashley Kirsner: Want Connection? Skip The Small Talk

"It is much safer to be vulnerable than you might think." - Ashley Kirsner

Ashley is the founder and director of Skip the Small Talk, and believes in the efficacy of high-quality person-to-person interaction for improving psychological health. She has conducted research with professors at prestigious organizations such as Cornell University, the Harvard Decision Science Lab, and the Harvard Business School, on social and clinical psychology topics ranging from decision-making and implicit biases to facial expressions in borderline personality disorder patients.

Ashley gained hands-on therapeutic experience as a suicide hotline phone responder and as a peer counselor at Cornell. Ashley received her B.A. in Psychology from Cornell University and turned down acceptances to doctorate programs in order to devote her time to Skip the Small Talk. She received a fellowship from the Harvard Divinity School for individuals who have demonstrated a social impact in the domain of creating meaningful communities. Skip The Small Talk events are regularly held internationally, as well as an online options.

In this engaging episode of 'Curated Questions,' host Ken Woodward sits down with Ashley Kirsner, the founder and director of 'Skip the Small Talk.' They explore the transformative power of meaningful conversations, the science behind vulnerability, and the surprising benefits of structured social interactions.

Ashley shares her experiences from the suicide hotline, her inspiration for starting 'Skip the Small Talk,' and how intentional question design can foster deeper human connections. The conversation also delves into the physiological benefits of social interactions, ethical considerations in community building, and the importance of creating safe spaces for vulnerability. Tune in to learn how these insights can help you build stronger, more authentic relationships in your own life.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

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tags: Ken Woodward, Curated Questions, Ashley Kirsner, Skip The Small Talk, vulnerability, meaningful conversations, suicide hotline, active listening, human connection, loneliness epidemic, social anxiety, open-ended questions, community building, authentic relationships, emotional safety, conversation starters, deep sleep benefits, social psychology, Cornell University, Harvard research, mental health, depression support, anxiety relief, interpersonal connection, question prompts, vulnerability gym, stranger conversations, empathy skills, social skills training, conversation techniques, relationship building, emotional intelligence, social isolation
categories: Listening, Community, Connection, Gratitude, Relationships, Belonging, Mental Wellness, Personal Growth, Social Impact
Wednesday 07.30.25
Posted by Kenneth Woodward
 

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