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

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)

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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.

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