Lead to Win with Jeff Little

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/

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/

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/

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/

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/