Episode Overview
In this episode of Mastering the Art of Success, Debbi DiMaggio sits down with Crispin Thompson, leadership coach, speaker, and founder of The Leadership Studio, to unpack what truly separates good managers from impactful leaders.
After more than 25 years in senior leadership roles at companies like Hewlett Packard Enterprise, TaskUs, and QSC, Crispin noticed a recurring challenge: talented managers were being promoted without the confidence, presence, or leadership identity needed to succeed at the next level.
Today, Crispin helps leaders close the gap between how they see themselves and how others experience them—focusing on real-world leadership moments that matter most.
This conversation explores leadership confidence, perfectionism, imposter syndrome, and how AI-powered coaching tools are reshaping leadership development.
👤 About Crispin Thompson
Crispin Thompson is a leadership coach, speaker, and the founder of The Leadership Studio. He specializes in helping leaders show up with clarity, calm, and confidence—especially in high-pressure environments.
Drawing from personal missteps, vivid storytelling, and global leadership experience across the U.S., India, Mexico, and Europe, Crispin makes leadership development practical, human, and actionable.
He also builds AI-powered leadership tools that support reflection, assessments, and growth between coaching sessions—extending leadership development beyond the room and into daily practice.
⏱ Episode Chapters & Highlights
🔹 How AI Powers Leadership Coaching: Tools for Resume Analysis & Self-Assessment
⏱ 11:25 – 20:22 (8 min 58 sec)
How AI is being used to support leadership reflection, resume analysis, and self-assessment—helping leaders gain clarity between coaching sessions.
🔹 Mastering Leadership: Overcoming Perfectionism & Imposter Syndrome
⏱ 21:45 – 26:50 (5 min 5 sec)
Why perfectionism holds leaders back, how imposter syndrome shows up at higher levels, and what it takes to lead with confidence—even without perfect information.
🔹 Why Good Managers Fail as Leaders: The Hidden Trap of Underfunded Development
⏱ 29:12 – 37:56 (8 min 45 sec)
A powerful look at why organizations underinvest in leadership development—and how that gap causes capable managers to struggle in senior roles.
🔹 The Five Essential Traits of Effective Leaders in the Age of AI
⏱ 38:59 – 44:39 (5 min 41 sec)
Crispin breaks down the five leadership traits that matter most today—especially as AI changes how leaders communicate, decide, and show up.
📘 Learn More & Book Crispin Thompson
🌐 Website: https://leadership-studio.com
🎧 About the Podcast
Welcome to Mastering the Art of Success: Where Mindset Meets Momentum—the go-to podcast for entrepreneurs, business leaders, real estate professionals, and ambitious dreamers ready to achieve their goals and design a life they love.
Hosted by Debbi DiMaggio—top 1.5% Realtor nationwide, author, coach, and mindset strategist—each weekly episode features in-depth conversations with inspiring entrepreneurs, industry innovators, bestselling authors, and thought leaders.
We explore their success stories, winning strategies, and the mindset shifts that helped them turn challenges into opportunities.
You’ll walk away with practical tools, proven strategies, and actionable insights you can apply immediately.
🎯 Perfect For:
Entrepreneurs & Small Business Owners
Real Estate Advisors & Sales Professionals
Coaches, Consultants & Creatives
Anyone ready to level up their success mindset
📩 Connect with Us
Interested in being a guest or collaborating?
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