I Have Some Questions... cover art

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I Have Some Questions... — 203 episodes

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Title
1

205: AI Will Disrupt Tasks, Not Entire Jobs

2

204: "How To Coach Through The Delegation Mess" ft. Alli Murphy

3

203: Eric Wiklendt: "What No One Talks About in M&As About Adding Value"

4

202: Vincent Azzolina: "What Does It Take to Lead in a Zero-Mistake Environment?"

5

201: "Vision First Or Tools First: The Hidden Step Before Any AI Implementation" ft. Justin Coats

6

200: "Need Vs Want: The Abundance Shift That Changes Everything" ft. Alli Murphy

7

199: "How Do We Actually Get ROI From AI?" (reflections on Lauren Cappell)

8

198: Lauren Cappell: "Time Kills Deals: How Faster Legal Work Creates Real Revenue"

9

197: Jason Robinovitz: "What Happens When Students Outsource Their Thinking To LLMs?"

10

196: "Agent Collaboration Should Look Like Co-Working, Not Hand-Offs" ft. Justin Coats

11

195: Rocky Batzel: "What It Means To Be Ready For Manufacturing At One Million Units Per Month"

12

194: Quinn Rose: "What Really Makes Journalism Worth Trusting In The Triple-Check Era?"

13

193: "How Permission Culture Keeps Us Small Without Us Noticing" ft. Alli Murphy

14

192: "Psychological Safety As The Real Happiness Strategy: Seek, Speak, Listen" (reflections on Scott Crabtree)

15

191: "What If Retention Has Less to Do with Product and More to Do with Belonging?" (reflections on Anthony Badalian)

16

190: Scott Crabtree: "What Google Found In Project Aristotle That Changes How You Lead Teams"

17

189: Anthony Badalian: "Why Is Fitness So Hard to Sell When Everyone Needs It?"

18

188: "Why Do We Feel Guilty Taking Rest Even When We Deserve It?" ft. Alli Murphy

19

187: "When Did Trust Between Patients and Physicians Begin to Break Down?" (reflections on Cameron Sabet)

20

186: "What Are the Real Reasons Healthcare Workers Leave? (reflections on Christopher Sund)

21

185: Cameron Sabet: "The Real Breakdown Happening Inside Healthcare"

22

184: Christopher Sund: "Is Healthcare Staffing Broken Beyond Repair?"

23

183: "Kids Are Intuitively Hacking AI With Their Voice, Not Their Keyboard" ft. Justin Coats

24

182: "What is Being Hyper-Responsive Actually Costing You?" ft. Alli Murphy

25

181: "The Best Businesses Solve Recurring Problems" (reflections on Bill Dowd)

26

180: "What If Your Team Already Knows What’s Broken, But Won’t Say It?" (reflections on Josh Frantz)

27

179: Bill Dowd: "Why Are So Many Entrepreneurs Ignoring Businesses Like This?"

28

178: Josh Frantz: "The Value Behind Extracting Knowledge From Frontline Employees"

29

177: "Is Typing Becoming Old-Fashioned in the AI Age?" ft. Justin Coats

30

176: "Is Talking to Your Boss the Same as Talking to a Brick Wall?" ft. Alli Murphy

31

175: "Are You Leading Conversations… or Just Waiting to Talk?" (reflections on Nicole O'Sullivan)

32

174: "Ownership Builds Trust Faster than Success Does" (reflections on Zia Mohi)

33

173: Nicole O'Sullivan: "What If a Mindset Shift Could Add $56M to Your Sales?"

34

172: Zia Mohi: "Are You Leading… or Just Taking Credit?"

35

171: "Can Companies with 5 Employees and 50 Digital Employees Thrive?" ft. Justin Coats

36

170: "What Changes When You Start Leading Leaders?" ft. Alli Murphy

37

169: "Are We Really Preparing Like it Matters?" (reflections on Scott Anderson)

38

168: "Building Culture That's Actually Lived, Not Just Talked About" (reflections on JD Hilzendager)

39

167: Scott Anderson: "What Does Leadership Look Like When Lives Are Actually on the Line?"

40

166: JD Hilzendager: "Building a Business is More About How You Think Than What You Think"

41

165: "What Caused AI to Skyrocket in 2026?" ft. Justin Coats

42

164: "How Do You Engineer Your Exit Without Burning Bridges?" ft. Alli Murphy

43

163: "You Are the Weather on Every Room You Enter" (reflections on Lisa Even)

44

162: Lisa Even: "What Kind of Ripple Effect Are You Creating as a Leader?"

45

161: "How Should Companies Think About AI That Has Agency To Act?" ft. Justin Coats

46

160: "What To Do When Your Boss Breaks The Boundaries They Set Themselves?" ft. Alli Murphy

47

159: "Is Your Current Sales Process Working Against You?" (reflections on Daniel Schmidt)

48

158: Daniel Schmidt: "Selling is a System, Not a Personality Trait"

49

157: "You've Probably Just Scratched the Surface of AI" ft. Justin Coats

50

156: "Delegation Without Scaffolding Can Break Your People" ft. Alli Murphy

51

155: "Are You Managing Parts Intead of Leading the Whole System?" (reflections on John Dues)

52

154: John Dues: "What Does a System of Profound Knowledge Really Look Like?"

53

153: "Are We Misunderstanding AI Job Loss Completely? ft. Justin Coats

54

152: "What If Your Team’s Feedback Is the Wake-Up Call You Need?" ft. Alli Murphy

55

151: "Does External Chaos Really Create Internal Opportunity? (reflections on Adam Plouffe)

56

150: Adam Plouffe: "What Does Great Leadership Look Like When the Ground Keeps Shifting?"

57

149: "Vague Thinking Produces Weak Outputs, Specially with AI" ft. Justin Coats

58

148: "What Do You Do When Your Boss Isn’t Doing Their Job—But You Could?" ft. Alli Murphy

59

147: Are Misaligned Incentives Shaping the Outcomes We Complain About? (reflections on Addison Hosner)

60

146: Addison Hosner: "Can the Legal System Be Both Profitable and Ethical?"

61

145: "What Would You Want From Your Manager If You Survived a Layoff?" ft. Alli Murphy

62

144: "Are We Going About Measuring Success All Wrong?" (reflections on Patrick Guerette)

63

143: Patrick Guerette: "Are We Measuring Success in Athletes the Wrong Way?"

64

142: "What Happens When Your Team Suddenly Doubles in Size?" ft. Alli Murphy

65

141: "True Buy-In Comes From Involvement" (reflections on Ashley Falsafi)

66

140: Ashley Falsafi: "Leadership Skills Are Mostly Portable"

67

139: "What Happens When Efforts Don't Translate to Outcomes?" ft. Alli Murphy

68

138: "The Key to Knowing How to Develop Mutually Beneficial Relationships" (reflections on Charles Byrd)

69

137: Charles Byrd: "Mastering Follow-Ups Is a Necessity"

70

136: "Should You Avoid or Plan For Conversational Landmines?" ft. Alli Murphy

71

135: "Sometimes You Don't Need The Final Roadmap; a Destination Will Do" (reflections on Andrea Brown)

72

134: Andrea Brown: "If You Don't Know Where You're Going, Any Path Will Get You There"

73

133: "Are You a Great Chaser of Vanity Metrics?" ft. Alli Murphy

74

132: Clarifying Your Intentions Before Asking Will Change Everything" (reflections on Steve Toomey)

75

131: Steve Toomey: "Are You Asking to Understand, or to Respond?"

76

130: "Can You Tell The Difference Between Growth Stress and Burnout Stress?" ft. Alli Murphy

77

129: "Are You Riding Your Career Train Intentionally?" (lessons from Pattie Dale Tye)

78

128: "What Is It to Go from Ordinary to Extra-Ordinary?" ft. Pattie Dale Tye

79

127: "Psychological Safety is Making Disagreement Safe" ft. Alli Murphy

80

126: "Do Catalytic Moments Really Exist?" (lessons from Jake Stahl)

81

125: "Can You Win a Deal Before the Close?" ft. Jake Stahl

82

124: "Are You Climbing a Ladder You Don’t Even Want to Be On?" ft. Alli Murphy

83

123: "Should Your Frontline Contribution Eventually Drop to Zero?" (lessons from Staci Lynn)

84

122: "What If Leadership Isn’t About Being the Expert?" ft. Staci Lynn

85

121: "What If What Got You here is now Burning You Out?" (ft. Alli Murphy)

86

120: "Can Trust Be Digitized—and How?" (lessons from Tony Camero)

87

119: "Do We Exchange Trust Before We Exchange Money?" ft. Tony Camero

88

118: "Is There Actually a Playbook for Building Trust as a New Leader?" ft. Alli Murphy

89

117: "AI Doesn't Remove the Human Layer—It Amplifies It" (lessons from Parth Vaghasiya)

90

116: "Is India Quietly Redefining Scalable AI Leadership?" ft. Parth Vaghasiya

91

115: "Is Your Once-Greatest Strength Now Holding You Back?" ft. Alli Murphy

92

114: "Are You Managing Your Strengths Like a Portfolio?" (lessons from David Nickelson)

93

113: "Knowing Your Limitations Is a Great Leadership Asset" ft. David Nickelson

94

112: "How Should Leaders Manage in Moments of Uncertainty?" ft. Alli Murphy

95

111: "Are You Taking Your Infrastructure For Granted?" (lessons from Victor Almeida)

96

110: "Is Survival Mode Your Greatest Startup Asset?" ft. Victor Almeida

97

109: "How Playing the 'Chief Everything Officer' Role Leads to Burnout" ft. Alli Murphy

98

108: Are You Solving the Wrong Problem Really Well?" (lessons from Bruce Vojak)

99

107: "Is a New Question More Valuable Than a New Solution When Innovating? ft. Bruce Vojak

100

106: "SMART Goals vs. Vector Goals: Which One Belongs in 2026?" ft. Alli Murphy

101

105: "Do You Know What Kind of Puzzle Piece You’re Actually Looking For?" (lessons from Brett Jesson)

102

104: "How Do You Build Culture That Isn’t Just a Slide Deck?" ft. Brett Jesson

103

103: “How to Support a Team Member's Growth Without Undermining It” ft. Alli Murphy

104

102: "Is Building Leaders Better Than Hiring Them?" (lessons from Jeremy Brady)

105

101: "What Happens When You Start Hiring for Alignment, Not Just Experience?" ft. Jeremy Brady

106

100: "How To Prevent AI from Atrophying Our Brain?" ft. Alli Murphy

107

099: "Balancing Intuition and Iteration" (lessons from Chase Damiano)

108

098: "Knowing When to Delegate Vs. When to Develop a Skill" ft. Chase Damiano

109

097: "Why Saying 'I Messed Up' is Actually a Superpower" ft. Alli Murphy

110

096: "The Power Behind Zigging When Others Zag" (lessons from Monique Lecomte)

111

095: "Letting Go Of Your Fixer Instinct" ft. Monique Lecomte

112

094: "How Can Leaders Manage Ghost Growth Effectively?" ft. Alli Murphy

113

093: "Coaching Is More About Revealing Than Perspective" (lessons from Ann Rivera)

114

092: "How Does the Transition From Performer to Leader Look Like?" ft. Ann Rivera

115

091: "How Can I Be Diplomatic Without Sugar-Coating?" ft. Alli Murphy

116

090: "Scalability Breaks When Dismissing the Impact of Small Inefficiencies" (lessons from Craig Dunaway)

117

089: "What Most People Get Wrong About Franchising" ft. Craig Dunaway

118

088: "Are We Confusing Leadership With Responsiveness?" ft. Alli Murphy

119

087: "The Hack of Seeing Things as Signals Instead of Symptoms" (lessons from Eric Collett)

120

086: "Is Your Brain Functioning Normally—Or Optimally?" ft. Eric Collet

121

085: "What If Finishing The Year Strong Meant Doing Less?" ft. Alli Murphy

122

084: "The Best Salespeople Aren’t Smooth Talkers—They’re Process Machines" (lessons from Gene McNoughton)

123

083: "Is Your Sales Process Making You Scale—Or Survive?" ft. Gene McNaughton

124

082: "What If Leadership Looked Like a Hammock and a Hoodie?" ft. Alli Murphy

125

081: "Support Isn't Weakness, Both for Leadership & Parenting" (lessons from Cassandra Asleson)

126

080: "Should You Treat Your Team Like a Family (and Vice‑versa)?" ft. Cassandra Asleson

127

079: "Do You Really Need to Be This Busy?" ft. Alli Murphy

128

078: "The Quiet Toll of Being the Go-To Person" (lessons from Michael Bostarr)

129

077: "Performing and Leading Are Entirely Different Sports" ft. Michael Bostarr

130

076: What Actually Builds Trust in a Team? (It’s Not What You Think)

131

075: "What Does It Mean to Truly Empower a Team?" (lessons from Chris Dyer)

132

074: "The Future CEO Will Be a Chief Executive Orchestrator" ft. Chris Dyer

133

073: Which Leadership Phase Are You In (Really)?

134

072: "Must Capitalism Be Realigned Toward More Desired Outcomes?" (lessons from Dr. Helmut Love)

135

071: "Is It Possible to Restructure Capitalism Without Losing its Drive for Innovation? (ft. Dr. Helmut Love)

136

070: Are You Too Nice to Be a Good Leader?

137

069: "How Parental Presence Intersect Across Sports And Leadership" (lessons from Sandy Cohan)

138

068: "The Dangerous Difference Between Expectations And Standards" ft. Sandy Cohan

139

067: How to Build Rock Star Teams (Even If You Didn't Hire One)

140

066: "Is Loyalty Enough to Keep Someone From Leaving?" (lessons from Alan Bell)

141

065: "What Happens When a Whole Team Quits Together?" ft. Alan Bell

142

064: What’s the Real Cost of Winging It?

143

063: "Is Your Company Ready for AI, or Just Excited by the Hype?" (lessons from Tulio Siragusa)

144

062: "Why Most Leaders Aren’t Self-Aware (and How to Change That)" ft. Tullio SIragusa

145

061: What’s the Best Way to Change Your Culture (Without Faking It)?

146

060: "Are You Coaching Your Team or Just Saving the Deal?" (lessons from Kim Willis)

147

059: "Can Storytelling Be Your Most Underrated Leadership Skill?" ft. Kim Willis

148

058: How To Deal With The Looming Talent Glut

149

057: "Are We Training People to Know—or to Do?" (lessons from Cortney Harding)

150

056: "Will VR Reshape The Future Of Corporate Learning & Training?" ft. Cortney Harding

151

055: Why Do We Struggle to Have Meaningful 1:1 Conversations?

152

054: "The Power of Saying 'I’m Happy Today'" (lessons from Andrew Anderson)

153

053: "Why Does Vulnerability Build More Trust Than Success?" ft. Andrew Anderson

154

052: What Should You Be Saying 'No' To?

155

051: "Authenticity as a System of Living—Not Just a Buzzword" (lessons from Rose Archer)

156

050: "Authenticity Scales When It's Felt" ft. Rose Archer

157

049: What If Every Excuse You’ve Ever Heard Was Just One of Four?

158

048: "Seeing Gen Z as Problem Solvers, Not Problems" (lessons from Logyn Coats)

159

047: "Can Gen Z’s Drive Reframe the Way We Lead Today?" ft. Logyn Coats

160

046: Stop Hiding Behind The 'I Lead By Example' Phrase

161

045: "Why Asking for Help Builds More Trust Than Giving Answers" (lessons from Jake Stahl)

162

044: "My Only Competitor Is Me From Yesterday" ft. Jake Stahl

163

043: How to Give Feedback People Actually Hear (And Act On)

164

042: “Can You Build Systems for Emotional Resilience?” (lessons from Troy Karnes)

165

041: “How Do You Lead When You’re Still Healing?” ft. Troy Karnes

166

040: What Do You Do When Your Team Thinks You Don’t Deserve the Job?

167

039: Why Your A-Players Leave (And How to Prevent It)

168

038: The Leadership Hack That Eliminates 80% of Check-Ins

169

037: How to Make More Time by Choosing What Not to Do

170

036: "Are You Creating Space for Others to Shine?" (lessons from Sam Bennet)

171

035: "What If You Led Like You Liked People?" ft. Sam Bennet

172

034: Does Asking The Right Question Beat Giving The Right Answer?

173

033: "Are You Chasing Success Without Knowing Why?" (lessons from Peter Awad)

174

032: "Why Do We Coast Into a Life We Don’t Even Want?" (Ft. Peter Awad)

175

031: The Secret to Make Hard Conversations EASY

176

030: “What’s Worth Being Relentless About?” (lessons from Chris Jones)

177

029: “Can You Learn to Be Relentless?” ft. Chris Jones

178

028: What If the Rock Star Team You Want… Isn’t the One You Hired?

179

027: “What If Great Leadership Starts with Being Wrong First?” (lessons from Ian Beaty)

180

026: “Why Is It So Damn Easy to Be a Bad Leader?” ft. Dr. Ian Beaty

181

024: “Can You Charge More, And Sell More?” (lessons from Amanda Bedell)

182

023: “What does it take to build a profitable business?” ft. Amanda Bedell

183

022: What If Reviews Could Actually Make You a Better Leader?

184

021: “Will You Adapt Before You’re Forced To?” (lessons from Justin Coats)

185

020: “Can You Build a Culture Around Systems?” ft. Justin Coats

186

018: “Can You Lead Without Knowing Where You’re Going?” (lessons from Brendan Burns)

187

017: “Is There a Difference Between Success and Satisfaction?” ft. Brendan Burns

188

015: “What Happens When You Finally Ask the Real Questions?” (lessons from Kyle Nelson & Eli Libby)

189

014: “What Does It Take to Realign Your Life and Business?” ft. Kyle Nelson & Eli Libby

190

013: What If Motivation Isn’t the Problem?

191

012: “Are You Settling for ‘Good Enough’ on Your Team?” (lessons from Alex Kudelka)

192

011: “Can You Scale a Business Without Diluting Your Magic?” ft. Alex Kudelka

193

010: Are You Ready to Lead an AI-Empowered Team?

194

009: “Are You Committed to the Process or Just the Result?” (lessons from Alex Boyd)

195

008: “What’s the Secret to Sales That Don’t Suck?” ft. Alex Boyd

196

007: Are You Leading the Person or Fighting the Generation?

197

006: What The F Is Accountability?

198

005: "What If You’re One Swing Away from Breakthrough?” ft. Brian Lofrumento

199

004: How Do People Get Better at Things?

200

003: “Are You Asking Too Much of Your Team… Without Realizing It?” (lessons from Tim Whitmire)

201

002: “Can a Free Workout Teach You How to Be a Better Man?” ft. Tim Whitmire

202

001: What Does It Mean to Be a Leader?

203

000: Welcome to “I Have Some Questions…”