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

➡️ 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.