Episodes

  • #61 Leadership Insights from my Conversation with Jon Dario

    #61 Leadership Insights from my Conversation with Jon Dario
    Jun 29 2026

    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 episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.


    Contact Mark at: mark@markjcundiff.com
    Show More Show Less
    9 mins
  • #60 Execution Beats Intention: How Great Leaders Turn Plans into Results with Jon Dario

    #60 Execution Beats Intention: How Great Leaders Turn Plans into Results with Jon Dario
    Jun 27 2026
    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 experience from major retail and service organizations, including Macy’s, Gap, Bank of America, and Travelex, and currently leads a real estate management company in the New York-New Jersey market. Episode SummaryWhat separates leaders who make plans from leaders who actually get results?That question sits at the center of this conversation with Jon Dario. Jon shares how his leadership journey began in retail management and how one honest conversation with an employee changed the way he saw leadership forever.Early in his career, Jon told a team member he did not have to work the same long hours Jon worked. The employee’s response was direct: “You can tell me that all day long, but your actions are what drives my behavior.”That moment helped Jon realize leadership is not just what you say. It is what you model.Throughout the conversation, Jon and Mark discuss the difference between management and leadership, why consistency builds credibility, why execution is often undervalued, and how leaders can use follow-up, feedback, and focused action to create more reliable results.This episode is a practical conversation for leaders who are tired of strategy sitting in binders, action items dying in meetings, and teams struggling with unclear priorities.About Jon DarioJon Dario is an author, speaker, management skills trainer, and the creator of AIM, which stands for Action Item Management.His leadership background includes roles with some of the world’s most recognizable retail and service organizations, including: Macy’s Gap Bank of America Travelex Jon’s AIM system helps managers and organizations improve execution by clarifying actions, external influences, and desired results.His work focuses on helping leaders build systems, routines, follow-up rhythms, and cultures of accountability that produce consistent results over time.Key Ideas Discussed1. Leadership Is Influence, Not Just Authority2. Your Actions Drive Your Team’s Behavior3. Follow-Up Is Foundational to Execution4. Consistency Builds Credibility5. The AIM Framework: Actions + External Influences = Results6. When the Plan Gets Punched in the Face7. Deciding Is Not the Same as Doing8. High-Performing Teams Use the Same Language9. Behaviors Fall Into Three Buckets10. Accountability Is a Shared Obligation📚 Resources MentionedAIM (Action Item Management) — Jon DarioThe Slight Edge — Jeff OlsonAtomic Habits — James ClearGood to Great — Jim CollinsThe Contrarian’s Guide to Leadership — Dr. Steven SampleTiny Experiments - B. J. Fogg🎯 Connect with Jon DarioLinkedInWebsiteEmail: jon@jondario.comFree Learning To Lead ResourcesFree Book: The Trust GapThe Learning To Lead NewsletterLeaderNotes🔎 About LeaderNotesLeaderNotes 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 episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.Contact Mark at: mark@markjcundiff.com
    Show More Show Less
    47 mins
  • #59 Leadership Insights from my Conversation with Jonathan Milligan

    #59 Leadership Insights from my Conversation with Jonathan Milligan
    Jun 22 2026

    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 before becoming a successful entrepreneur, he was a school teacher searching for a greater outlet for his gifts and talents.

    In this episode, Mark unpacks five powerful leadership lessons from their conversation—lessons on confidence, clarity, consistency, community, and taking action before you have all the answers.

    If you're a growth-minded leader looking to increase your influence, build momentum, and lead with greater confidence, this episode is packed with practical wisdom you can apply immediately.

    Five Leadership Takeaways

    1. You Don't Need Certainty—You Need the Next Step

    2. Clarity Is Kindness

    3. Confidence Is Built Through Action

    4. Consistency Beats Talent

    5. Success Happens in Community

    Memorable Quotes from the Episode

    "Progress creates clarity."

    "Clarity is kindness."

    "Fear thrives in big-picture thinking. Fear dies in small-step action."

    "Consistency beats talent every single time."

    "People trust leaders they can depend on."

    "Community doesn't just support growth—it multiplies it."


    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 episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.


    Contact Mark at: mark@markjcundiff.com
    Show More Show Less
    9 mins
  • #58 "Consistency Beats Talent: The Secret Hiding in Plain Sight" Leadership Lessons with Jonathan Milligan

    #58 "Consistency Beats Talent: The Secret Hiding in Plain Sight" Leadership Lessons with Jonathan Milligan
    Jun 18 2026
    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 into a business they love. We talk about his winding journey from teaching to flipping houses to recruiting and finally into coaching, the hardest leadership decision he ever made (cutting his team from 15 people down to two), and why he believes consistency — not talent — is the real secret to lasting influence.If you've ever struggled with self-doubt, shiny object syndrome, or wondering whether your story is even worth telling, this conversation is for you.About Jonathan MilliganJonathan Milligan is an author, blogger, speaker, and online business coach who has spent the last decade guiding creative professionals toward meaningful work. Since 2009, he's run his own portable lifestyle business online, and he's the author of 17 books (with another on the way). His book, Your Message Matters, has inspired thousands of people to get their story out into the world — whether through writing, speaking, or teaching. I've had the privilege of being coached by Jonathan for over a decade; he's the one who first taught me how to blog, and most recently, how to launch this very podcast.Key Topics DiscussedJonathan's leadership origin story growing up as a coach's son in IndianaWhy he left teaching and what he learned bouncing between house flipping, recruiting, and entrepreneurshipThe hardest leadership decision of his career: shrinking his team from 15 to 2How his definition of leadership has evolved from "having the answers" to providing clarityThe story behind his book Your Message Matters and why it starts with self-development, not strategyWhy "broken focus" is the number one enemy of growth-minded leadersPractical steps for working through fear and self-doubtHis "Five Ones" filter for cutting out distractions and noiseWhy consistency is the "secret hiding in plain sight" of long-term influenceHow to rebuild confidence after a setback — one rep at a timeThe lies leaders tell themselves that quietly hold them backLeadership lessons he learned from his father, a longtime basketball coachHis daily and weekly habits, reading rhythms, and why he believes in always having a coachMemorable QuotesConsistency does not require talent. It just requires showing up.You don't need certainty. You just need clarity on what the next step is, and then you take that step.A confused leader creates confused followers, so clarity is essential... clarity is kindness.Confidence isn't the absence of doubt. It's the decision to move forward while the doubt is still talking.Your story's unique. Your combination of experience, pain, and perspective is unrepeatable, so focus on that."Connect with Jonathan:Get a free copy of Your Message Matters: yourmessagemattersbook.comConnect with Jonathan's coaching community: marketyourmessage.comYouTube: Jonathan MilliganLinkedIn📚 Resources MentionedYour Message Matters — Jonathan MilliganThe One Thing — Gary KellerThinking for a Change — John MaxwellBuilding a StoryBrand 2.0 — Donald MillerThe Bible — referenced as "the ultimate leadership manual"Action Items for This WeekRun your next decision through a filter. Borrow Jonathan's "Five Ones" approach — ask whether a new idea or opportunity serves your one person, one product, one path, and one platform right now. If not, let it go.Shrink the window. If fear or doubt is loud this week, don't think about the whole year. Identify just the next small step you can take today.Protect one block of deep work. Block off a recurring window (mornings, if you can) where you create before the rest of the day's demands pull you away.Start wrestling your message onto paper. Journal, dictate your thoughts, or start outlining — even rough writing builds the clarity Jonathan talks aboutFree Learning To Lead ResourcesFree Book: The Trust GapThe Learning To Lead NewsletterLeaderNotes🔎 About LeaderNotesLeaderNotes 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 episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.Contact Mark at: mark@markjcundiff.com
    Show More Show Less
    54 mins
  • #57 Leadership Insights from my Conversation with Preston Zeller

    #57 Leadership Insights from my Conversation with Preston Zeller
    Jun 11 2026

    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’s journey after losing his brother and creating a daily painting for 365 days that became the documentary The Art of Grieving.

    Cundiff emphasizes that people need leaders who listen and care, then shares five takeaways: empathy as a leadership superpower; small daily actions compounding into big results; using stories to inspire beyond facts; building trust through alignment between intentions and the employee experience; and recognizing that many growth problems are operational issues. He encourages listeners to watch the documentary, download leader notes, subscribe, and leave a rating.

    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 episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.


    Contact Mark at: mark@markjcundiff.com
    Show More Show Less
    7 mins
  • #56 The Art of Empathy in Leadership with Preston Zeller

    #56 The Art of Empathy in Leadership with Preston Zeller
    Jun 3 2026

    Grief, Growth, Storytelling, Operations, and the Future of AI

    What happens when personal tragedy forces you to slow down, reflect, and rebuild?

    In this episode of The Learning to Lead Show, Mark Cundiff sits down with entrepreneur, consultant, filmmaker, and storyteller Preston Zeller to explore how one of the most painful seasons of his life transformed the way he leads, serves others, and helps organizations grow.

    After the loss of his brother, Preston embarked on an extraordinary journey—creating a painting every day for 365 days as a way to process grief. That experience eventually became the documentary The Art of Grieving and fundamentally changed his perspective on empathy, leadership, and human connection.

    The conversation also explores storytelling as a leadership skill, building trust inside organizations, operational excellence, AI adoption, and the habits that fuel long-term growth.

    Whether you're leading a team, growing a business, or navigating a difficult season of life, this episode offers practical wisdom and powerful reminders about what matters most.

    Listen now and discover how great leaders combine empathy, vision, trust, and execution to create lasting impact.

    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 episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.


    Contact Mark at: mark@markjcundiff.com
    Show More Show Less
    40 mins
  • #55 Leadership Insights from my Conversation with M. K. Palmore

    #55 Leadership Insights from my Conversation with M. K. Palmore
    May 29 2026



    What separates good leaders from truly great leaders?

    According to M.K. Palmore, it's not strategy, authority, or expertise.

    It's people.

    In this episode of The Learning to Lead Show, Mark Cundiff shares key leadership insights gained from his conversation with M.K. Palmore, Founder and CEO of Apogee Global RMS, former FBI executive, U.S. Marine Corps officer, U.S. Naval Academy graduate, and cybersecurity leader with Google Cloud and Palo Alto Networks.

    Drawing from more than three decades of leadership experience across the military, federal law enforcement, and corporate America, M.K. shares powerful lessons on trust, integrity, accountability, resilience, mentorship, and why leadership is ultimately about investing in people.

    M.K. explains why risk is fundamentally a leadership challenge, how great leaders build cultures of trust, and why the small moments of encouragement and mentorship often have the greatest impact.

    Whether you're leading a team of two or an organization of thousands, this conversation will challenge you to think differently about leadership and the lasting legacy you leave behind.

    In This Episode, You'll Learn:

    • Why do the best leaders focus on people before mission
    • The leadership lessons M.K. learned at the U.S. Naval Academy, the Marine Corps, the FBI, and Silicon Valley
    • How mentors helped him beat the odds and build an extraordinary career
    • Why trust is built through integrity, transparency, and accountability
    • The hidden ways leaders unintentionally damage trust
    • How to rebuild trust after it's been broken
    • Why high-performing teams practice before pressure arrives
    • The role of reflection and self-awareness in leadership growth
    • How leaders can create cultures of psychological safety
    • Why every leader has a responsibility to develop future leaders

    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 episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.


    Contact Mark at: mark@markjcundiff.com
    Show More Show Less
    11 mins
  • #54 "Never Tell Me the Odds" Leadership Lessons from the Naval Academy, Marine Corps, FBI, and Silicon Valley with M. K. Palmore

    #54 "Never Tell Me the Odds" Leadership Lessons from the Naval Academy, Marine Corps, FBI, and Silicon Valley with M. K. Palmore
    May 24 2026

    What separates good leaders from truly great leaders?

    According to M.K. Palmore, it's not strategy, authority, or expertise.

    It's people.

    In this episode of The Learning to Lead Show, Mark Cundiff sits down with M.K. Palmore, Founder and CEO of Apogee Global RMS, former FBI executive, U.S. Marine Corps officer, U.S. Naval Academy graduate, and cybersecurity leader with Google Cloud and Palo Alto Networks.

    Drawing from more than three decades of leadership experience across the military, federal law enforcement, and corporate America, M.K. shares powerful lessons on trust, integrity, accountability, resilience, mentorship, and why leadership is ultimately about investing in people.

    M.K. explains why risk is fundamentally a leadership challenge, how great leaders build cultures of trust, and why the small moments of encouragement and mentorship often have the greatest impact.

    Whether you're leading a team of two or an organization of thousands, this conversation will challenge you to think differently about leadership and the lasting legacy you leave behind.

    In This Episode, You'll Learn:

    • Why do the best leaders focus on people before mission
    • The leadership lessons M.K. learned at the U.S. Naval Academy, the Marine Corps, the FBI, and Silicon Valley
    • How mentors helped him beat the odds and build an extraordinary career
    • Why trust is built through integrity, transparency, and accountability
    • The hidden ways leaders unintentionally damage trust
    • How to rebuild trust after it's been broken
    • Why high-performing teams practice before pressure arrives
    • The role of reflection and self-awareness in leadership growth
    • How leaders can create cultures of psychological safety
    • Why every leader has a responsibility to develop future leaders


    📚Books Mentioned

    • Good to Great — Jim Collins
    • 21 Irrefutable Laws of Leaders - John Maxwell
    • Steve Jobs — Walter Isaacson
    • It Worked for Me - Colin Powell Autobiography
    • Long Walk To Freedom - Nelson Mandela

    Connect with M.K. Palmore

    • Website
    • Apogee Global RMS
    • LinkedIn

    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 episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.


    Contact Mark at: mark@markjcundiff.com
    Show More Show Less
    45 mins