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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.

➡️ Get my free weekly newsletter (The Intentional Letter): https://courses.calwalters.me/signup

Follow Jeff's work: https://www.jeffwetzler.com/

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, and fewer surprises, this conversation will give you a playbook.

00:00 The hidden information problem

00:41 Guest intro + what you'll learn

01:37 Chris Argyris + the "left-hand column" tool

08:07 Four reasons people don't tell you the truth

12:06 Why smart/successful leaders struggle to learn

13:55 Jeff's near miss: one question that revealed the truth

15:45 Psychological safety: why curiosity alone isn't enough

21:35 Reactivity: the biggest predictor of future honesty

22:18 Responding well to hard feedback

25:00 The ASK Approach: Choose curiosity

29:48 Curiosity killers + "When you're furious, get curious"

32:29 Busy leaders: "Pay now or pay later"

36:40 Quality questions vs. crummy questions

40:04 Better questions for feedback and performance reviews

44:07 Go-to questions for parties and relationships

47:48 Questions as a gift: helping others gain clarity

49:55 How to handle feedback you won't follow

51:08 Reflect & reconnect: sift it, turn it, and close the loop

53:13 Cal's takeaways and practical challenges

• Replace: "Do you have feedback for me?"

  With: "What's one thing I could do differently that would make your life easier?"

• When you feel defensive, ask one question before making a statement.

• When someone brings hard truth, try:

  "That's hard to hear—and I'm really glad you told me."

➡️ Get my free weekly newsletter (The Intentional Letter): https://courses.calwalters.me/signup

Get Randy's book: https://www.amazon.com/Winning-Begins-Home-Strategy-Leadership/dp/B0CTYGNXCG

Learn about Lead Every Day: https://leadeveryday.com/

In this episode, Cal Walters sits down with executive coach, speaker, and author Randy Gravitt of ⁨@Lead_Every_Day⁩ 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 clichés about work-life balance and gets practical about strategy, systems, presence, and love—and why winning at home actually makes you a better leader at work.

Please visit my website to get more information: https://calwalters.me/

00:00 – Welcome to 2026 & the Intentional Leader community

02:10 – Introducing Randy Gravitt & the tension leaders feel

03:40 – Strategic at work, sporadic at home

06:00 – Why family has quietly been diminished

07:45 – Being home but not really home

08:55 – Proximity does not equal intimacy

10:00 – The servant leadership tension

12:20 – Living in the center of the tension

13:45 – Begin with the end in mind

15:10 – You will never finish all the work

16:50 – Seasons turn into patterns

18:30 – The NFL Super Bowl story

21:00 – Leaving work at work

22:15 – Training presence like a discipline

23:30 – Rituals that help you be present

25:30 – Phone boundaries that actually work

27:40 – Winning the first hour of the day

29:40 – Why home life fuels work performance

32:10 – Choosing priorities on purpose

34:00 – The hidden cost of neglecting home

36:30 – "What kind of family do you want?"

38:40 – Family by design, not by default

41:00 – Marriage after the kids leave

43:00 – Don't go to bed angry

46:30 – Love first

49:50 – See a need, meet a need

54:00 – Final encouragement to leaders

59:00 – Key takeaways & closing challenge