"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
"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 trained 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.
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Keep questioning!
Episode Notes
00:00 Welcome to Curated Questions
01:59 Meet Phil Liebman
03:14 When No Sparks Why
05:05 Mentor Dr Lee Thayer
06:29 A Masterclass in Questions
07:49 Socratic Coaching at Vistage
09:27 Intentional Question Craft
10:37 Path to Question Mastery
11:01 Learning Mode vs Knowing Mode
13:10 Choosing to Be Curious
14:17 Spotting Curiosity Signals
16:29 Certainty Kills Coachability
17:19 School Trains Knowing Mode
18:28 Organic Chemistry Mindset Shift
22:14 College Cramming Observation
26:11 Nonconformists and C Students
27:52 Work Rhythms and Reflection
30:04 Cycle of Curiosity and Certainty
31:00 Four Quadrants in Action
35:54 Powerful Questions and Practice
38:40 A Questioning Approach For Parents
43:03 Leadership Is An Art
48:04 Credentials vs Experience
48:25 Competence Over Degrees
48:57 Music Auditions Story
50:48 Learning Then Practice
51:21 Recovering From Mistakes
52:23 Questions Need Reps
53:21 Client Transformations
54:04 Humility Through Questions
55:30 Rapport In Real Life
56:16 Knowing Mode Limits
57:43 Curiosity Beats Arrogance
58:39 Surround Yourself Smart
59:20 Contagious Learning Mindset
01:01:05 Lighten Up And Laugh
01:01:53 Who Inspires Curiosity
01:02:52 Clients As Teachers
01:04:33 Dr Thayer Influence
01:06:40 Grace Hopper Hero
01:12:07 Vistage Dark Days
01:16:02 The Intersection of Music and Questions
01:20:52 Right Now Question Finale
Resources Mentioned
Lynn Borton's Choose to Be Curious podcast
Leonardo da Vinci quote: "It had long since come to my attention that people of accomplishment rarely sit back and let things happen to them. They went out and happened to things."
Mount Sinai Comprehensive Cancer Center
Phil Liebman on LinkedIn