136: Jordan Montgomery — Why Even High Performers Need Encouragement (and How to Lead with It)
Intentional Leader with Cal Walters
Release Date: 04/24/2026
136: Jordan Montgomery — Why Even High Performers Need Encouragement (and How to Lead with It)
Intentional Leader with Cal Walters
➡️ Get my free weekly newsletter (The Intentional Letter): Check out Jordan's work: 00:00 Intro + Why Encouragement Matters (Even for High Performers) 01:09 Why Everyone Needs Encouragement (No Matter Their Success) 02:35 What Elite Performers Have in Common (They All Have Coaches) 04:16 The Paradox of Growth: The More You Learn, The More You Need Help 06:25 How Jordan Coaches Leaders (2 Powerful Questions) 07:44 “What Do You Want?” + “Who Are You Really?” 10:01 Why Most Leaders Struggle with Self-Awareness 11:47 Identity, Calling, and Becoming an Encourager 13:27 Jordan’s...
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135: Dr. Jeff Wetzler — Why People Don’t Tell You the Truth (and the Questions That Change Everything)
Intentional Leader with Cal Walters
➡️ Get my free weekly newsletter (The Intentional Letter): Follow Jeff's work: Dr. Jeff Wetzler, author of Ask, joins Cal Walters to unpack a leadership blind spot: the crucial information your team has… but isn’t telling you. Jeff explains the “left-hand column” (what people think and feel but don’t say), the four reasons honesty gets filtered, and the ASK Approach—a practical framework for choosing curiosity, building psychological safety, asking better questions, and closing the loop when feedback is hard to act on. If you want better decisions, healthier relationships,...
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134: Randy Gravitt — Winning at Home Without Losing at Work, Leading With Presence, and Why Hope Is Not a Strategy
Intentional Leader with Cal Walters
➡️ Get my free weekly newsletter (The Intentional Letter): Get Randy's book: Learn about Lead Every Day: In this episode, Cal Walters sits down with executive coach, speaker, and author Randy Gravitt of to explore one of the most important leadership questions of our time: How do you pursue excellence at work without sacrificing what matters most at home? Randy shares powerful insights from decades of coaching leaders across Fortune 100 companies, professional sports teams, and nonprofits—along with lessons from his book Winning Begins at Home. This conversation goes beyond...
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133: LTG(R) Milford Beagle "Beags" — A Three-Star General on True North, Resilience, Feedback, and How to Lead With Confidence Without Becoming Overconfident
Intentional Leader with Cal Walters
➡️ Get my free weekly newsletter (The Intentional Letter): 📚 Get LTG (Ret.) Beagle's new book, When the Map Runs Out: As leaders rise, they often hear less and less truth. LTG (Ret.) Milford Beagle calls this the cone of silence—and he warns that it’s one of the quietest ways leaders lose their true north. In this episode, we explore how to lead when your “map” falls apart. General Beagle shares his journey from a stunned new platoon leader at Fort Polk to commanding the U.S. Army Combined Arms Center, and what he’s learned about staying grounded, humble, and effective...
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132: Joe McCormack — Special Operations Communication Expert Shares How to Say Less, Communicate With Clarity, and Lead With Quiet Confidence
Intentional Leader with Cal Walters
Connect with Joe: Learn more about The Brief Lab: How do you become the kind of leader who cuts through noise, communicates with clarity, and actually moves people to action? In this episode of the Intentional Leader Podcast, Cal talks with Joe McCormack—founder of The Brief Lab and author of Brief, Noise, and Quiet Works. Joe has trained elite military units and Fortune 500 executives to be clear, concise, and intentional communicators, and to rediscover the quiet that makes powerful communication possible. They explore: Why noise is the real villain in your leadership story The...
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131: Dr. Liz Werly — What an Army Psychologist for Special Ops Teaches About High Performance and Emotional Intelligence
Intentional Leader with Cal Walters
How do the best military leaders go from operating at an already elite level… to an even higher level under pressure? In this episode, Army psychologist Dr. Liz Werly (who works directly with some of the U.S. military’s most elite units) breaks down the exact framework she uses to help high performers: build accurate self-awareness using gold-standard assessments, “engineer” their personality to fit the context (calm under fire and present at home), develop emotional intelligence as the differentiator once IQ and talent are in place, and translate values into visible daily...
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130: Dr. Zach Mercurio — The Hidden Engine of High-Performing Teams: Mattering, Trust, and Purpose-Driven Leadership
Intentional Leader with Cal Walters
Apply to work with me 1-1: Join the Intentional Leader Lab waitlist: Learn more about Zach: In this conversation, Dr. Zach Mercurio discusses the importance of creating a sense of purpose and mattering within teams. He emphasizes that feeling valued is a basic human instinct and that leaders play a crucial role in fostering an environment where everyone feels significant. The discussion covers the psychological impacts of not feeling like one matters, the barriers leaders face in demonstrating care, and practical strategies for enhancing team dynamics through small, intentional...
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129: Dr. Ryan Gottfredson — The Groundbreaking Science of Personal Transformation, Mindsets, Emotional Intelligence, and Becoming Better
Intentional Leader with Cal Walters
Update: Now only 6 spots left in the Intentional Leader Lab! ➡️ Learn about the Intentional Leader Lab: Book a call: Apply today: Please visit my website to get more information: In this episode, Dr. Ryan Gottfredson returns to discuss the concepts of trauma, vertical development, and the distinction between 'being' and 'doing' in leadership. He emphasizes the importance of self-awareness and healing one's internal operating system to achieve true personal transformation. The conversation explores how mindsets shape our experiences and the role of emotional...
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128: Accomplish Anything as a Leader with the 3 Levels of Clarity and the Intentional Leader Lab
Intentional Leader with Cal Walters
➡️ Learn about the Intentional Leader Lab: Book a call: Apply today: The Intentional Leader Lab: A Mastermind for Successful Leaders Who Refuse to Plateau Even the best leaders can drift, but this carefully curated leadership community and Cal's Narrow Path™ Framework give you the tools, accountability, and systems to accelerate your growth. Only 11 spots left.
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127: Dr. Travis Bradberry — Emotional Intelligence Expert Gives Practical Advice to Increase Your EQ, Increase Your Self-Awareness, and Change Your Thinking
Intentional Leader with Cal Walters
➡️ Apply to the Intentional Leader Lab (only 12 slots available): In this conversation, Cal introduces the Intentional Leader Lab, a coaching program aimed at enhancing leadership skills through emotional intelligence. Dr. Travis Bradberry, an expert in emotional intelligence, discusses its significance in leadership, differentiating it from IQ, and the importance of self-awareness, self-management, and social awareness. The conversation emphasizes practical strategies for developing emotional intelligence and the impact it has on personal and professional relationships. Dr. Travis...
info_outline➡️ Get my free weekly newsletter (The Intentional Letter): https://courses.calwalters.me/signup
Check out Jordan's work: https://www.montgomerycompanies.com/
00:00 Intro + Why Encouragement Matters (Even for High Performers)
01:09 Why Everyone Needs Encouragement (No Matter Their Success)
02:35 What Elite Performers Have in Common (They All Have Coaches)
04:16 The Paradox of Growth: The More You Learn, The More You Need Help
06:25 How Jordan Coaches Leaders (2 Powerful Questions)
07:44 “What Do You Want?” + “Who Are You Really?”
10:01 Why Most Leaders Struggle with Self-Awareness
11:47 Identity, Calling, and Becoming an Encourager
13:27 Jordan’s Failure Story (Losing His Career at 27)
15:53 “You’re Not Buried, You’re Planted” (Valley Season Lessons)
17:01 The Power of Self-Encouragement
19:32 How to Rewire Your Thinking (Speak vs. Listen to Yourself)
21:32 Practical Self-Talk (What It Actually Looks Like Daily)
23:27 The Art of Authentic Encouragement
23:56 Why Specific Encouragement Is More Powerful
26:59 Final Takeaways + How to Encourage Others Better
27:42 Practical Leadership Application (Cal’s Closing Thoughts)
What if encouragement isn’t just “nice”… but essential for leadership?
In this episode of the Intentional Leader Podcast, I sit down with Jordan Montgomery, bestselling author of The Art of Encouragement, to unpack:
- Why even elite performers need encouragement
- The surprising link between success and coaching
- How to lead yourself when your mindset is off
- Why most encouragement feels fake—and how to fix it
- A simple framework to become a better encourager today
This conversation is short—but packed with practical wisdom you can apply immediately in your leadership, your family, and your team.