The Learning To Lead Show with Mark J. Cundiff

What if the biggest thing holding your organization back isn't the market, the competition, or your team, but you? In this episode, Mark Cundiff shares his top leadership takeaways from Episode 80 with business coach and author Gary Mitchell. Together they tackled one of the hardest truths in leadership: most of the time, the biggest obstacle to an organization's growth is the leader at...

Episode Summary What if the biggest obstacle to your organization's growth is you? In this episode, I sit down with Gary Mitchell, a business coach ranked among the top ten law firm coaches by two independent organizations and author of The AND Approach: How to Grow Your Law Firm AND Gain More Freedom.  Gary has spent 20 years coaching lawyers, some of the most intelligent, disciplined, and s...

  Never Quit on Your Hard Day: 5 Lessons on Self-Leadership, Grace, and Becoming Who You Were Created to Be What if the true measure of your leadership isn't how you perform on your best days, but how you show up on your hardest ones? In this episode, Mark revisits his powerful conversation with Chris Avery from Episode 78 and breaks it down into five practical takeaways you can put to work r...

"Never quit on your hard day. Only quit on your best day." - Chris Avery What would it take for you to keep showing up every day, even on the days when everything in you wants to quit? In this episode, I sit down with Chris Avery, a coach, speaker, and endurance runner whose life proves leadership starts from the inside out. Chris spent years unable to lead himself as he battled drugs an...

Just because you have an AI tool doesn't mean you have an AI strategy.  That's the truth sitting at the center of this episode. Following up on Episode 76 — Why 95% of AI Implementations Fail and How to Be the Exception — I'm breaking down my key leadership takeaways from my conversation with Ben Tasker, an AI capability and workforce transformation expert leading a data and AI acad...

Episode Summary What if the biggest obstacle to AI adoption isn't the technology at all — it's the humans who have to trust it, learn it, and choose to use it? In this episode, Mark sits down with Ben Tasker, an AI capability and workforce transformation expert, to unpack why AI success has almost nothing to do with the algorithm and everything to do with people. Ben shares his journey f...

Leadership Insights from My Conversation with Katie Neal   If you don't tell your story, someone else will.   Let that sink in for a second. If you don't tell your story, someone else will tell it for you. That single truth is the heartbeat of this episode, and it's why I wanted to sit back down with you—just the two of us—to unpack the leadership gold from my conversation with Kati...

Episode #74: Own Your Story — Communication, Confidence, and the Courage to Pivot with Katie Neal   Episode Overview If you don't tell your story, someone else will tell it for you. That's the thread running through my entire conversation with Katie Neal — communications leader, certified executive coach, and my first-ever Demon Deacon guest. Katie has built a career on helping people an...

What does it cost you to keep chasing success once it stops feeling like enough?   That's the question sitting at the center of this episode. Last week, Adam Roach joined the show for a candid, story-filled conversation in Episode #72, From Success to Significance: The Beach Chair Moment.   Adam is the founder of the I Love Coaching community, where he helps established coaches build business...

#72 From Success to Significance: The Beach Chair Moment with Adam Roach You can check every box success is supposed to give you — the businesses, the income, the lifestyle — and still feel like something's missing. That's exactly where my guest today found himself. Adam Roach built three real estate franchises, a SaaS technology company, and ran a Beverly Hills tennis club in his twenti...

Episode 71: Leadership Insights from My Conversation with Greg Gerber The Question Behind This Episode What happens when the career that once defined you disappears? That's the question at the heart of this episode. It's my follow-up reflection on Episode 70, Stories of Reinvention, Forward from 50: How to Rediscover Purpose, Passion, and Possibility with Greg Gerber — and I wanted to si...

#70 Stories of Reinvention, Forward from 50: How to Rediscover Purpose, Passion, and Possibility with Greg Gerber   What happens when the career that defined you for 20 years disappears, not slowly, but all at once?  That's exactly what happened to my guest today, Greg Gerber. For nearly two decades, Greg was the voice of the RV industry, building a daily publication that reached 16,000 subsc...

Episode #69: Leadership Insights from My Conversation with Hanna Bauer   What if the crisis you're dreading isn't actually your biggest problem? What if it's simply the spotlight that finally shows everyone what was already there?   That's the question I couldn't stop thinking about after my conversation with Hanna Bauer in Episode #68, "The Great Recession of Trust:...

#68 The Great Recession of Trust: How Leaders Can Rebuild What's Been Lost with Hanna Bauer Episode Summary   What do you do when the very system you built to create clarity ends up costing you the heart of your organization? That's the question Hanna Bauer had to face — and it's the question we're wrestling with together in this episode.   Hanna's story starts long before...

#67 Leadership Insights from my Conversation with Neill Marshall and Kurt Mosley Guests: Neil Marshall & Kurt Mosley, HealthSearch Partners Episode Overview What if the most important leadership decisions you'll ever make happen before you've even earned the right to lead? In this episode, I sit down with Neil Marshall and Kurt Mosley of HealthSearch Partners — an executive search fi...

Guests: Neill Marshall (Board Chair) & Kurt Mosley (Associations Practice Leader), HealthSearch Partners Host: Mark J. Cundiff — The Learning to Lead Show Episode Summary What if the first 90 days in a new role mattered more than your strategy, your resume, or even your title? That's the question at the heart of this episode. Neill Marshall and Kurt Mosley have been part of more than 700...

Free Learning To Lead Resources Free Book: The Trust Gap The Learning To Lead Newsletter LeaderNotes 🔎 About LeaderNotes LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show . In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the...

Have you ever noticed that some of the most successful people you know have it all figured out in one area of life... and are quietly falling apart in another? The CEO who can close a nine-figure deal but can't stick to a diet for two weeks. The entrepreneur who built an empire from nothing but hasn't had a real conversation with his own kid in months. We've all seen it. Maybe you&a...

Free Learning To Lead Resources Free Book: The Trust Gap The Learning To Lead Newsletter LeaderNotes 🔎 About LeaderNotes LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show . In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the...

What if the biggest obstacle to your leadership isn't your experience—but the story you're telling yourself? In this episode of The Learning to Lead Show , Mark Cundiff sits down with Jennifer Doty , former Fortune 100 executive, speaker, author, and leadership coach, to explore how leaders can overcome self-doubt, embrace uncertainty, and create meaningful career and life pivots. Jennif...

Free Learning To Lead Resources Free Book: The Trust Gap The Learning To Lead Newsletter LeaderNotes 🔎 About LeaderNotes LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show . In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the...

Execution is not about having better intentions. It is about building better systems, stronger follow-up, clearer behaviors, and a culture where accountability helps people win. In this episode of The Learning to Lead Show , Mark Cundiff sits down with Jon Dario , author, speaker, management skills trainer, and creator of the AIM Framework: Action Item Management . Jon brings decades of leadership...

In this Leadership Insights episode, Mark Cundiff reflects on his conversation with entrepreneur, author, speaker, and coach Jonathan Milligan from Episode #58, Consistency Beats Talent: The Secret Hiding in Plain Sight. Jonathan has spent more than a decade helping experts, coaches, and entrepreneurs clarify their message, build businesses around their expertise, and create meaningful impact. But...

What happens when a burned-out school teacher decides to bet on himself? In this episode, I sit down with my longtime mentor and friend, Jonathan Milligan — author, online business coach, and the very person who taught me how to build the blog and podcast you're listening to right now. Jonathan has spent over a decade helping creative professionals turn their story, message, and expertise int...

5 Leadership Takeaways from Preston Zeller: Empathy, Trust, Storytelling, and Sustainable Growth Host Mark Cundiff welcomes listeners to Learning to Lead episode 57, reflecting on his prior conversation with Preston Zeller from episode 56, “The Art of Empathy in Leadership.” He highlights themes of empathy, resilience, grief, storytelling, trust, leadership, and business growth, including Preston’...