Key Takeaways

• Coaching ≠ outperforming. Performance expertise and coaching expertise are different muscles.
• Discomfort is data. If growth feels easy, you’re probably not growing.
• Trust follows vulnerability. Coaching conversations require safety, time, and honesty.
• Aim feedback at the work. Focus on the task/approach, not the person.
• Decide your mode. Coach, teach, or direct based on the question, urgency, and learning goal.
• Beat imposter syndrome with action. If the finish line is fuzzy, take the next step and practice.

• Jamie and Matt discuss the idea of “experiencing wellness” through hormone therapy and health practices.
• Matt reflects on some of his favorite bosses and what they had in common.
• The conversation shifts into how great leaders act like coaches—seeing potential and helping others develop it.
• Matt explains how coaching differs from supervising or managing, with curiosity as a key factor.
• The role of different learning styles and how coaching adapts to each.
• How coaching shapes workplace culture, using examples from Your Health and its leadership approach.
• Teaser for part two, where they continue exploring the role of coaching in leadership.

• Jamie’s story of regret: the trapeze he didn’t swing on in El Salvador.
• How regret often comes not from what we did, but what we avoided.
• Fear’s purpose: when it protects us and when it holds us back.
• Biblical and historical reminders that “do not fear” is a universal human need.
• The role of encouragement from spouses, friends, and colleagues in building courage.
• How fear of failure causes inaction — and why inaction is often worse than failure.
• Practical steps for leaders to cultivate courage and embrace discomfort.