Lead to Win with Jeff Little

Lead to Win
  • 4.9 (48)
  • Christianity
  • Updated Weekly

The Lead to Win podcast with Jeff Little isn’t just leadership principles—it’s a game-changer for everyday life. In each episode, we dive into meaningful conversations about what it truly means to lead and succeed in a world obsessed with the wrong scoreboards. Because the greatest loss in life isn’t falling short; it’s winning big at something that doesn’t matter.

  1. Todd & Julie Mullins | How to Build a Team People Want to Be On

    Jun 23

    Todd & Julie Mullins | How to Build a Team People Want to Be On

    In this episode of Lead to Win, Pastor Jeff Little sits down with Todd and Julie Mullins of Christ Fellowship for a practical conversation on building healthy teams and shaping culture with intention. Todd and Julie share why culture cannot just be caught — it has to be taught. From clarifying expectations to communicating values often, they unpack how leaders can build teams people want to be part of and create a culture that is life-giving, healthy, and clear. TIMESTAMPS 0:00 - Culture As Soil For Vision 3:30 - The Team Question Everyone Asks 8:50 - The Origin Story Behind The Church 15:10 - Succession And Scaling To Multisite 21:30 - Culture By Design Not Default 27:55 - Turning DNA Into Leader Values 35:40 - Communicate Often And Celebrate It 42:10 - Accountability When Culture Slips 49:10 - Hiring On Purpose And Onboarding Fast 56:05 - Clear Expectations And The 30 60 90 1:01:55 - Lead People Holistically And Close LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/ MB01KTGA8DJ2NXM MB01UVECBC9UVOL

    1h 4m
  2. Rich Wilkerson Jr. | Success Isn’t the Goal. Lasting Is.

    Jun 9

    Rich Wilkerson Jr. | Success Isn’t the Goal. Lasting Is.

    In this episode of Lead to Win, Pastor Jeff Little sits down with Rich Wilkerson Jr. for a conversation on calling, resilience, and playing the long game in leadership. Rich shares why success isn’t the ultimate goal — lasting is. From processing pain to guarding your heart, this episode will help leaders reframe the story they’re telling themselves and stay faithful to what God has called them to do. TIMESTAMPS 0:00 - Wanting To Last 3:20 - Playing The Wrong Game 6:05 - Esau Spirit And Outdoor Identity 10:20 - Skee Ball Church And Hidden Talent 14:55 - Growing Up In A Ministry Family 21:10 - Pain Trials And Forgiveness 27:45 - Reframing Stories And Trust 33:10 - Discernment And Almost Right 37:40 - Success Redefined As Faithfulness 41:55 - Calling Chose You 45:50 - Exegeting Miami And Loving The Crowd 49:45 - Habits Resilience And Leadership Landmines 58:45 - Final Thanks And Subscribe LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/ Musicbed Sync ID: MB01EIB335NJCWV

    1 hr
  3. The Secret to Leading Young People Well

    May 26

    The Secret to Leading Young People Well

    In this episode of Lead to Win, Pastor Jeff Little sits down with Tyron Caswell to talk about reaching the next generation, building a lasting student ministry, and creating environments where young people can encounter Jesus. Pastor Tyron shares pieces of his own story, the early days of Milestone Church, and practical wisdom for pastors and leaders who want to lead with vision, authenticity, and consistency. LEARN MORE ABOUT MILESTONE COLLEGE https://milestonecollege.org/ APPLY FOR RESIDENCY https://milestonechurch.com/ministries/residency/ TIMESTAMPS 0:00 - Finding Your Strength And Staying Consistent 2:10 - A Crisis Moment And Meeting Jesus 6:30 - From Secular Jobs To Church Planting 18:00 - How To Build A Student Ministry 24:00 - Creating Environments For Encounter And Growth 32:30 - Milestone College And Hands On Leadership 39:00 - Developing Leaders And Next Steps LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/

    42 min
  4. Why Great Leaders Raise Up Generations | Russell Evans

    May 12

    Why Great Leaders Raise Up Generations | Russell Evans

    In this episode of Lead to Win, Pastor Jeff Little sits down with Russell Evans, founder and global senior pastor of Planetshakers, for a powerful conversation on culture, honor, and raising up the next generation. Russell shares how great leaders build beyond themselves by creating a culture that releases people, honors every generation, and develops sons and daughters who carry the vision forward. From leading a global church movement to empowering young leaders, this conversation unpacks why lasting leadership is not built on celebrity or personality — it’s built on family, honor, obedience, and a heart to see others go further. If you’re a pastor, leader, parent, or anyone passionate about developing people, this episode will challenge you to think differently about legacy, culture, and what it really means to build for generations. TIMESTAMPS 0:48 - A Back Row Story On Humility 3:50 - Russell Evans Origin Story 11:43 - Culture Takes Time And Heart Work 25:40 - Honor As The Key To Family 34:02 - Sound That Shapes Atmosphere And Faith 42:12 - Skill Without Shortcuts DNA Process 52:22 - The Struggle That Forms Leaders 57:38 - Raise Sons And Daughters Not Celebrities LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/

    1h 6m
  5. It's Not About the Platform | Betsy Caswell

    Apr 28

    It's Not About the Platform | Betsy Caswell

    In this episode of Lead to Win, Pastor Jeff Little sits down with worship leader Betsy Caswell for a practical and honest conversation about worship, platform, character, and serving the local church. Together, they unpack why worship leadership is about more than talent, songs, or stage presence. It’s about purity of heart, alignment with vision, serving people well, and keeping Jesus at the center. Betsy shares wisdom from years of leading worship, developing teams, and building a culture where the platform is never the goal — it’s simply a place to serve. TIMESTAMPS 0:00 - What A Worship Win Looks Like 0:36 - Why Worship Shapes Church Theology 6:35 - Betsy’s Story From Music To Jesus 13:38 - Discipleship Before Platform Opportunity 18:31 - Training Worship Leaders With Dev Night 23:44 - Lead To Jesus With Eyes Open 30:34 - Serve Local Church Over Comparison 37:13 - Alignment With Pastor And Team Culture 42:57 - Heart Integrity Beats Production Value 51:55 - Final Thanks And Subscribe Request LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/

    53 min
  6. What You Actually Want For Your Kids

    Apr 14

    What You Actually Want For Your Kids

    In this episode, Pastor Jeff, Brandy, Caleb, and Hannah unpack one of the most important questions a parent must ask: Are you shaping their behavior… or their heart? Learn how to look beyond outward actions and understand what’s really going on beneath the surface. When you focus on the heart, you’re not just managing moments but shaping who your child becomes over time. TIMESTAMPS 0:00 - The RV Vacation From Hell 4:20 - Why We Teach On Family 10:20 - What Parenting The Heart Means 19:00 - Finding The Heart Under Pressure 20:05 - Moving From Cop To Coach 28:50 - Parenting The Heart With Technology 33:30 - Repairing Connection With Adult Kids 39:15 - Hope, Next Steps, And Closing THE RELUCTANT LEADER EPISODE https://www.youtube.com/watch?v=wisaGThTjKk&t=1s LET'S TALK FAMILY SERMONS https://www.youtube.com/watch?v=ZUcmyRGfTvk LEAD TO WIN RESOURCES: More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/

    40 min
  7. The Reluctant Leader: Called Into Something You Didn’t Choose

    Mar 31

    The Reluctant Leader: Called Into Something You Didn’t Choose

    The hardest room to lead is often your own home. In this conversation, we sit down with Pastor Jeff to share the tension every communicator feels when teaching on family: staying honest without dishonoring your story, offering hope without pretending you have a perfect formula, and resisting the pressure to turn principles into rigid methods people can copy and compare. TIMESTAMPS 0:00 - Welcome And How It Began 3:05 - Why Family Topics Draw Leaders 10:15 - Defining The Reluctant Leader 18:55 - Why Family Feels So Painful 28:55 - Prodigals And The Need For Hope 33:10 - When Kids Become A Bigger Idol 38:20 - Home Stability Expands Leadership Capacity 41:50 - Parenting Principles Beat Parenting Formulas 49:40 - Marking Moments That Make Love Felt LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/

    51 min
  8. The Legacy Question Every Leader Must Answer | Coach Tom Mullins

    Mar 17

    The Legacy Question Every Leader Must Answer | Coach Tom Mullins

    In this powerful episode of Lead to Win, Pastor Jeff Little sits down with leadership coach and pastor Coach Tom Mullins for a conversation on the one thing every leader must protect—integrity. Drawing from decades of experience developing leaders, Coach Tom shares the lessons that shape a lifetime of influence. From defining your legacy to calling out the champion in others, this episode is packed with practical wisdom for leaders who want to finish well, not just start strong. You’ll discover why integrity is the foundation of lasting leadership, how to build a life that outlives you, and what it really means to lead with honor in every season. If you’re serious about becoming the leader God has called you to be, this conversation will challenge and strengthen you. TIMESTAMPS 0:00 - Legacy Starts With Integrity 0:25 - Fishing Trips And McDonalds Laughs 5:00 - Why Coaching Principles Transfer Everywhere 8:05 - Coach Not Boss Leadership Model 12:35 - Building A Coachable Curious Culture 17:45 - Recruiting Team Depth And Developing Leaders 23:40 - Keeping Score And Staying In Growth 24:05 - Integrity Under Pressure In Public Life 30:32 - Crisis Preparation And The Four As 37:01 - Final Charge Call Out Champions LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/

    40 min
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Trailer

4.9
out of 5
48 Ratings

About

The Lead to Win podcast with Jeff Little isn’t just leadership principles—it’s a game-changer for everyday life. In each episode, we dive into meaningful conversations about what it truly means to lead and succeed in a world obsessed with the wrong scoreboards. Because the greatest loss in life isn’t falling short; it’s winning big at something that doesn’t matter.

Information

  • Creator
    Lead to Win
  • Years Active
    2025 - 2026
  • Episodes
    37
  • Rating
    Clean
  • Copyright
    © 2026 Lead to Win with Jeff Little
  • Show Website
    Lead to Win with Jeff Little

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