What if the biggest obstacle in your business isn't the problem you're trying to solve—but the question you haven't been willing to ask? In this episode of The Story Engine Podcast, I sit down with executive coach and Vistage chair Ken Proctor to explore the power of asking better, tougher questions. Ken shares how his own failures taught him that leaders don't necessarily need more answers—they need someone willing to challenge them, uncover their blind spots, and help them see what's really driving their decisions.
We dive into the "ghosts" that can quietly shape the way leaders operate, from fear and insecurity to old stories carried from childhood into business. Ken explains why asking uncomfortable questions can create more respect than simply trying to be liked, while I explore my own experience of discovering how a single comment from my father influenced years of decisions in my career. This conversation is ultimately about using honest questions to break out of familiar patterns, create greater self-awareness, and move toward more alignment and integrity as a leader.
Highlights
(01:03) – How Ken's failures turned into the foundation for his "Art of the Question" methodology
(01:25) – The question that uncovered a CEO's deepest fear—and revealed the connection to his micromanagement
(02:29) – Why challenging leaders with questions can create movement when advice and answers fall short
(03:29) – The difference between asking questions to be liked and asking questions that earn respect
(03:45) – A powerful CEO question: If you fired yourself, what qualities would you want in your replacement that you don't possess?
(05:00) – How tough questions can uncover hidden constraints affecting executives, sales teams, and company culture
(06:30) – Why the "sting" of an honest question can be the thing that finally wakes someone up
(08:10) – The hidden cost of avoiding uncomfortable truths inside a company
(09:50) – How an old comment from a parent can become a "ghost" that silently drives years of business decisions
(11:00) – Recognizing the moment when a familiar pattern repeats—and realizing the ghost may still be running the show
(12:50) – Turning painful business experiences into greater self-awareness, significance, and alignment
(13:20) – Why leaders need to be willing to ask themselves the same tough questions they ask everyone else
(14:00) – Moving from constantly circling the problem to finally confronting what's driving it
