136: Jordan Montgomery — Why Even High Performers Need Encouragement (and How to Lead with It)

136: Jordan Montgomery — Why Even High Performers Need Encouragement (and How to Lead with It)

April 23, 2026 · 29 min

About this episode

In this episode, Cal Walters discusses the importance of encouragement for high performers with guest Jordan Montgomery.

➡️ 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…

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