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John Mattone Global
Mainline Executive Coaching ACT Podcast
Episode 341June 22, 2025

341: The Questions Only Great Leaders Dare To Ask

Rich BaronMaikel Bailey
Rich Baron & Maikel Bailey

Episode Notes

What sets great leaders apart from the mediocre? It’s not the title—they often hold the same one. The real difference lies in how they show up when it matters most: in moments of discomfort, uncertainty, and challenge.

Great leaders dare to ask the questions others won’t. They lean into the bold, uncomfortable conversations that disrupt the status quo, expose blind spots, and spark real transformation. Because leadership isn’t about always having the answers—it’s about having the courage to ask the questions that truly matter.

Join Rich and Maikel on this episode of Mainline Executive Coaching ACT as we explore what it means to lead with boldness, trust, and the courage to go deep.

Leaders, Lead Well!

Thank you to all of our listeners in over 90 countries and now, 1,000 cities worldwide, we greatly appreciate your support! We truly hope that what we bring to our listeners will improve your ability as leaders.

Mainline Executive Coaching ACT has been recognized by FeedSpot as one of the top Executive Coaching Podcast in the world based on thousands of podcasts on the web and ranked by traffic, social media, followers & freshness.

John Mattone Global: https://johnmattone.com/

About the Hosts

Rich Baron

Rich Baron

Chief Operating Officer & Master Certified IL Coach

Master Certified IL Executive Coach, Lean Six Sigma, 100% Customer Retention (2006-2019)

As JMG's Chief Operating Officer and a Master Certified Intelligent Leadership Executive Coach, Rich brings diverse expertise in cultural transformation, operational leadership, and coaching leaders from emerging talent to CEOs.

Maikel Bailey

Maikel Bailey

Master Certified IL Executive Coach

Master Certified IL Executive Coach

Maikel Bailey is a Master Certified Intelligent Leadership Executive Coach with extensive experience in executive leadership, cultural transformation, and emerging leader development.

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