Lead to Win with Jeff Little

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.TIMESTAMPS0:00 - What A Worship Win Looks Like0:36 - Why Worship Shapes Church Theology6:35 - Betsy’s Story From Music To Jesus13:38 - Discipleship Before Platform Opportunity18:31 - Training Worship Leaders With Dev Night23:44 - Lead To Jesus With Eyes Open30:34 - Serve Local Church Over Comparison37:13 - Alignment With Pastor And Team Culture42:57 - Heart Integrity Beats Production Value51:55 - Final Thanks And Subscribe RequestLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

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.TIMESTAMPS0:00 - The RV Vacation From Hell4:20 - Why We Teach On Family10:20 - What Parenting The Heart Means19:00 - Finding The Heart Under Pressure20:05 - Moving From Cop To Coach28:50 - Parenting The Heart With Technology33:30 - Repairing Connection With Adult Kids39:15 - Hope, Next Steps, And ClosingTHE RELUCTANT LEADER EPISODEhttps://www.youtube.com/watch?v=wisaGThTjKk&t=1sLET'S TALK FAMILY SERMONShttps://www.youtube.com/watch?v=ZUcmyRGfTvkLEAD 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

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.TIMESTAMPS0:00 - Welcome And How It Began3:05 - Why Family Topics Draw Leaders10:15 - Defining The Reluctant Leader18:55 - Why Family Feels So Painful28:55 - Prodigals And The Need For Hope33:10 - When Kids Become A Bigger Idol38:20 - Home Stability Expands Leadership Capacity41:50 - Parenting Principles Beat Parenting Formulas49:40 - Marking Moments That Make Love FeltLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

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.TIMESTAMPS0:00 - Legacy Starts With Integrity0:25 - Fishing Trips And McDonalds Laughs5:00 - Why Coaching Principles Transfer Everywhere8:05 - Coach Not Boss Leadership Model12:35 - Building A Coachable Curious Culture17:45 - Recruiting Team Depth And Developing Leaders23:40 - Keeping Score And Staying In Growth24:05 - Integrity Under Pressure In Public Life30:32 - Crisis Preparation And The Four As37:01 - Final Charge Call Out ChampionsLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

In this episode of the Lead to Win podcast, Jabin Chavez joins Pastor Jeff to talk about the real cost of leadership at the next level. From public success and private pressure to unmet expectations and pushback, this conversation gets honest about what happens when expansion exposes your internal health.New levels bring new devils.New influence brings new responsibility.And if you’re not healthy, growth will reveal it.Jabin shares practical wisdom on leading through criticism, building the right team, embracing spiritual maturity, and staying grounded when momentum increases. If you’re building something meaningful — in ministry, business, or leadership — this episode will challenge you to focus not just on growth, but on depth.Because the question isn’t how big you can grow.It’s how healthy you are when you get there.TIMESTAMPS0:00 - Public Success, Private Strain1:45 - Vegas Church Plant And Building Miracle5:55 - From Youth Pastor To Senior Leader9:50 - Discernment, Timing, And Wise Counsel14:35 - COVID Shock: Becoming A Leader18:30 - Casting Vision And Inviting People In23:20 - Growth Surges And Unmet Expectations28:40 - Clarity Of Vision Over Crowd Noise33:10 - Designing Spaces For Connection36:50 - Filtering Feedback And Inputs41:20 - Tribe, Comparison, And Security45:10 - Rhythm Over Balance For Sustainability49:20 - Managing Time, Systems, And SermonsLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

What if the key to leading with clarity isn’t found in a strategy—but in stillness?In this powerful episode of Lead to Win, Pastor Jeff sits down with Pastor Jim Lafoon to unpack one of the most important disciplines for any leader: learning to hear the voice of God. From real-life crisis moments to daily decisions, Jim shares how practicing quietness before the pressure comes prepares you to stand strong when it does.You’ll hear practical wisdom on discerning God’s voice, building a reflex of prayer, cultivating a culture of intercession around your leadership, and why “dialogue is your birthright.” Whether you’re a pastor, business leader, parent, or team builder, this conversation will challenge you to pause, quiet your soul, and give God space to lead you.If you want to win at what matters most, it starts by learning to listen.TIMESTAMPS6:21 - From Monologue To Dialogue With God11:41 - Sense God Before You Hear God18:22 - Training To Hear Under Pressure26:04 - Signs Of A Spreading Revival27:06 - Posture: Repentance, Holiness, PrayerLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

What if the thing holding your leadership back isn’t strategy… but your soul?In this episode, Pastor Jeff sits down with Pastor Steve Robinson to unpack Soul Leadership—how trauma and chronic stress reshape the brain, why leaders get triggered, and how healthy leaders build healthy teams. You’ll learn the difference between self-leadership and soul leadership, why unprocessed pain turns into unhealthy patterns, and how God can bring you from fragmentation to wholeness.If you’re a pastor, leader, or team builder trying to finish well, this conversation will give you language, tools, and hope.TIMESTAMPS:0:00 - Why Soul Leadership Matters4:25 - The Book’s Big Idea And Audience8:40 - Katrina, Burnout, And Hitting The Wall11:30 - The Soul Leadership Cycle14:20 - Self Leadership vs Soul Leadership20:00 - Saul’s Wounds, Shame, And Control29:20 - Moses Triggered: Accusation And Delay34:20 - Building Resilience Before Crisis41:00 - You Can’t Pray Trauma AwayLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

Honor isn’t outdated—it’s essential. In this episode of Lead to Win, Pastor Jeff Little sits down with Earl McClellan to explore why honor is one of the most overlooked—and most powerful—forces in leadership today.They unpack how honor shapes culture, strengthens trust, and determines whether teams thrive or fracture under pressure. You’ll hear practical insights on leading with humility, honoring people even when it’s difficult, and building environments where respect fuels growth.This conversation will challenge the way you lead—and remind you why honor always matters.TIMESTAMPS0:00 - Cold Open And Defining Friendship2:56 - The Box Lunch Revival Story5:10 - Laughter, Men’s Event, And Influence9:20 - Parenting Wisdom And Roles At Home13:15 - Culture Over Strategy And Tone19:30 - Receiving Honor Without Pride25:05 - Laying Down Crowns And Guardrails30:40 - Jesus-Centered Leadership And Discipleship36:20 - Seeds Of Honor From A Single-Mom Story42:10 - Formative Years As An Executive Pastor48:05 - Timing, Submission, And Leaving Well54:40 - The Real Test: Character Over Platform1:01:20 - Biggest Surprise Of Senior Leadership1:07:10 - Growth, Grit, And Eternal Stakes1:14:00 - Humor, Style, And Closing CommitmentsLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

What an honor it was to sit down with Brooke Ligertwood at this year's Leaders Gathering.  In this conversation, she shares her personal story of encountering God through worship, why she believes worship is first and foremost for God’s glory, and how a life rooted in Scripture and prayer shapes everything we offer publicly. Together, Pastor Jeff & Brooke explore the partnership between pastors and worship leaders, the importance of stewarding people well, and how cultivating a strong inner life sustains long-term leadership.This episode is powerful, we promise you aren't going to want to miss it! Whether you’re a pastor, worship leader, or ministry leader, this conversation will encourage you to lead with depth, humility, and devotion to Jesus.TIMESTAMPS0:00 - From Conference To Conversation0:54 - Worship’s Purpose And Brooke’s Conversion3:37 - Songs That Carry Theology6:16 - Writing From Scripture And Warfare8:16 - A Generational Vision For Worship10:23 - Pastoring Worship Teams Well12:25 - Teaching The Hidden Life15:31 - Guarding The Stage And Hearts16:20 - Closing Thanks And Subscriber AskLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

In this episode, Pastor Jeff Little and Pastor Mark Francey dive deep into the process behind every leader’s breakthrough—from the decades of formation you don’t see to the moments of obedience that unlock supernatural authority. Pastor Mark reveals why being sent is different than simply going, how leaders can minister to high-capacity people, and why rushing your calling can do more harm than good.If you’ve ever wondered when to move, how to wait, or what spiritual authority really looks like, this conversation will bring clarity, courage, and faith for your next step.TIMESTAMPS0:00 - Redefining Riches And Pastoral Value8:20 - Calling To Pastor The “Up And Out”15:20 - Oceans Church Origin Story27:00 - Vision, Dream, And Statewide Baptisms37:00 - Timing, Process, And Being SentLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

What does it really mean to win? Pastor Jeff sits down with Pastor Jacob Aranza to talk about hidden character, spiritual fathers, breaking generational patterns, walking through the loss of a child, and why true success means winning in faith, family, and legacy—not just on a financial or ministry scoreboard.TIMESTAMPS4:50 - Redefining True Success9:50 - The Five Containers Of Life14:50 - From National Speaker To Local Pastor17:40 - Jacob’s Origin Story22:30 - Saved By Jesus, Shaped By Church28:40 - Honoring Spiritual Fathers33:20 - Breaking Generational Patterns38:20 - Foundations That Survive Storms43:20 - Winning At Home48:00 - Daily Practices That Anchor Family52:30 - Name, Claim, And Bless Your ChildrenLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

Every young person is searching for identity, belonging, and purpose—but they can’t find it alone. In this episode, Pastor Jeff Little sits down with Next Gen pastor Drew Nguyen to unpack what today’s students really need from the leaders who guide them. TIMESTAMPS0:00 - Present, Not Perfect Parenting3:28 - Setting The Next Gen Focus4:41 - Scale With Heart: Youth Numbers5:37 - A Youth Pastor’s Origin Story9:15 - Finding Family In The Church12:27 - From Brokenness To Belonging14:16 - Programs Don’t Raise Sons And Daughters17:02 - Multi‑Generational Discipleship In Action19:06 - Five Core Values For Kids22:08 - Don’t Wait To Be Great24:08 - Pressures, Options, And Anxiety26:17 - A Hunger For God Among Students28:21 - Templates: Retreats, Camps, Super Series32:16 - Identity, Purity, And Affirmation35:02 - Evangelism That Mobilizes Students38:24 - Parent The Heart, Not Performance42:04 - Be Emotionally PresentLEAD TO WIN RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

In this powerful episode of Lead to Win, Pastor Jeff Little sits down with leadership legend Dr. Sam Chand for an honest and deeply practical conversation about what real growth requires—and why so many leaders stall before they reach their potential.TIMESTAMPS2:16 - Leadership is Who You Are4:34 - Systems, Scale, and Honest Self-Assessment8:46 - Hunger, Curiosity, and Capacity11:55 - Imagination as a Leadership Muscle16:40 - When-and-Then Thinking Stifles Vision19:40 - Wins You’ll Never See22:30 - Growth Equals Pain Framework27:40 - Playing to Win vs. Not to Lose31:40 - Control the Uncontrollables: Grow Yourself35:20 - Questions that Unlock Imagination39:10 - Comfort vs. Growth: Choosing ForwardRESOURCES FROM DR. SAM CHANDSam Chand Leadership Institute: https://setyourowntuition.com/https://Availbox.com/LEAD TO WIN RESOURCESMore Resources: https://leadtowin.com/Servolution: https://www.servolution.org/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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

Jeff Little and Dino Rizzo reveal how a serving posture fuels real growth. Learn to start with what you have, partner wisely, “see the one,” and build a culture where compassion multiplies. It’s not about bigger buildings—it’s about a bigger heart. Use these practical plays with your team now!TIMESTAMPS2:20 - Humble Beginnings and Early Ministry Stories3:20 - A Burden for Single Moms Takes Shape5:05 - From One Act of Kindness to Scalable Service7:05 - Bigger Buildings of Bigger Love?10:15 - Designing a Gathering to Build Leaders12:25 - Serve Day Impact & Community Partners15:05 - Outreach Starts with What You Have18:05 - Understanding Your City's Needs25:00 - Is The Church Healthy Right now?28:00 - Global Signs of Renewal and Hope31:00 - Lift Up Your Eyes: Regaining PerspectiveADDITIONAL RESOURCESMore Resources: https://leadtowin.com/Servolution: https://www.servolution.org/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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

Every leader wants a winning team—but few know how to build one. In this conversation, Jon Gordon and Jeff Little share the real ingredients behind high-trust, high-performing teams: consistency, clarity, and commitment. Discover why culture beats strategy, how to move from “goals” to “commitments,” and why helping others grow is the greatest growth strategy of all.TIMESTAMPS3:02 - Why Teams Beat Solo Leaders7:46 - Principles & Practices of Leadership9:50 - Culture, Values, and Cascading Leadership15:40 - Consistency, Trust, And Positive Energy19:15 - Engagement Over Dictation In Modern Leadership23:40 - Accessibility, Listening, & Learning28:10 - Bridging Pastors & Marketplace Leaders33:20 - The Power of Valuing People36:20 - Commit to the Person, Moment, Team40:30 - Culture Fit, Letting People Find The Right Team44:05 - Clarity Of Vision, Roles, And Buy-InADDITIONAL RESOURCESMore Resources: https://leadtowin.com/Jon Gordon's Resources: https://jongordon.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.comGET IN TOUCH: Contact us at [email protected] PASTOR JEFFInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittleFOLLOW LEAD TO WINInstagram: https://www.instagram.com/leadto.win/

What does it take to build a championship team—on the field and in the church?Pastor Jeff sits down with Coach Tom Mullins to talk about the plays that never stop working: servant leadership, character, and culture.From football locker rooms to a thriving church of 30,000, Coach Tom shares the habits, values, and mindset that help leaders win where they’re at. You’ll walk away challenged to serve deeper, lead stronger, and celebrate the people around you.TIMESTAMPS0:00 - Servant Heart and Humble Beginnings3:10 - Coaching to Church: The Call and Launch7:45 - Defining Leadership and Winning12:20 - Preparation, Evaluation, and Growth Mindset17:35 - What Great Team Members Do23:45 - Bloom Where You’re Planted - Character First28:50 - Trust, Excellence, and the Zone Above Expectation35:10 - Lifting Others: “Run With Me” Culture41:00 - Staff Values: People Lean InADDITIONAL RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

You can’t parent a teenager the same way you parent a toddler. Yet many parents never change gears — and they pay for it later. In this episode, Pastor Jeff and his two oldest kids talk about recognizing the signs, making the shift, and leading your kids with influence instead of control. You don't want to miss this honest and real conversation!TIMESTAMPS0:00 - Grounded Parents Over Trends2:19 - Kids, Boundaries, and Security7:52 - Discipline, Integrity, and Respect17:36 - Settled Homes Reduce Anxiety19:07 - Shaping A Biblical Worldview31:44 - Pressing in During the Teen Years40:46 - Becoming the ConsultantADDITIONAL RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

30 years. 4 kids. Countless seasons. Through it all, Jeff and Brandy have discovered the plays that keep a marriage strong. From early church-planting days to parenting and now grandkids, they open up about the wins, struggles, and values that have carried them through.TIMESTAMPS0:00 - What God Blesses & Why5:43 - Marriage is Your First Ministry11:21 - Navigating Different Family Seasons17:41 - The Unity Principle22:54 - Meeting Your Kids Where They Are31:19 - Dating and Marriage WisdomADDITIONAL RESOURCESMore 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.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

In this episode of Lead to Win, Priscilla Shirer joins us to share the single habit that drives lasting success in leadership, family, and life. Far from complicated formulas or quick fixes, Priscilla breaks down practical ways to anchor yourself in what matters most—even when time is short and life feels chaotic. Whether you’re leading a team, raising kids, or chasing your next big goal, you’ll walk away with timeless insight and a fresh sense of focus.TIMESTAMPS0:00 - Positioning Yourself for Success3:45 - Why the Word Matters as an Anchor8:10 - Making Bible Reading Less Intimidating12:15 - Practical Ways to Engage Scripture17:35 - Preaching vs Personal Study Balance24:25 - Advice to Your 20 Year-Old SelfADDITIONAL RESOURCESMore resources: https://leadtowin.com/Win With People: https://leadtowin.com/pages/win-with-peopleRegister for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/Going Beyond Ministries: https://www.goingbeyond.com/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

What if the real barrier to your growth isn’t your situation—but your standards, character, or clarity? In this honest and practical episode, Jeff and Dharius talk about the internal adjustments leaders must make to truly win. From redefining success, to building competencies, to setting high standards and stewarding self-leadership, this episode is packed with the kind of wisdom that can shift your trajectory. If you’re feeling stuck despite outward success, this one will help you realign what matters most.TIMESTAMPS10:52 - Coaching: An Underrated Leadership Competency17:45 - Four Reasons People Get Stuck25:05 - Standards: The Floor, Not The Ceiling34:25 - The Power of Self-Leadership50:28 - Choosing Your Influences WiselyADDITIONAL RESOURCESMore resources: https://leadtowin.com/Win With People: https://leadtowin.com/pages/win-with-peopleRegister for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

When it comes to building a team, the people you choose determine more than just productivity—they shape the culture, carry the vision, and impact everyone around them. In this episode, Pastor Jeff and Pastor Jed talk about the kind of teammates they value most: people who are humble, trustworthy, aligned with the mission, and committed to growing. You’ll hear real insights on what makes someone not just a good hire, but the kind of person you’d want in your corner through every season. Whether you’re building a new team or reevaluating your current one, this conversation will help you clarify what really matters.TIMESTAMPS5:38 - Team Building vs. Being a Superstar10:45 - Teaching Team Principles Early17:15 - Character: The Foundation of Great Teams22:10 - Competency: What can You Actually Do?25:32 - Curiosity: The Drive to Keep Growing31:06 - Chemistry: Why Team Flow MattersADDITIONAL RESOURCESMore resources: https://leadtowin.com/Win With People: https://leadtowin.com/pages/win-with-peopleRegister for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

Every leader wants a thriving, healthy culture—but too often, we forget that culture isn’t something you create once and walk away from. It’s something your team carries every single day. In this episode, Jeff and Jed talk about how the wrong team members can quietly undermine your values, and how the right ones can bring them to life. You’ll learn what to look for when hiring or promoting, why smart leaders prioritize team fit over short-term fixes, and how to build a culture that actually reflects your heart and vision.TIMESTAMPS1:15 - Shepherds: Biblical Leaders Who Care3:56 - The Value of Sheep in Biblical Context6:10 - Jesus as the Good Shepherd9:54 - Building Teams That Last16:00 - Hired Hands: Leaders Who Don't Stay24:23 - Building Culture, Not Just Results29:50 - The Dangers of Self-Promotion33:16 - Respect Comes From Dealing With ProblemsADDITIONAL RESOURCESMore resources: https://leadtowin.com/Win With People: https://leadtowin.com/pages/win-with-peopleRegister for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

What if the strongest thing you could do as a leader is go first? First to show up. First to celebrate someone else. First to risk being vulnerable. In this powerful episode, Jeff and Steve talk about how secure leaders create space for others to thrive—not by posturing, but by being present. You’ll hear how the willingness to risk rejection opens the door to deeper relationships, stronger teams, and lasting impact. If you’ve ever struggled with isolation or insecurity in leadership, this episode is for you.TIMESTAMPS9:36 - Breaking the Cycle of Leadership Loneliness17:13 - How to Build Meaningful Relationships25:54 - Celebrating Others' Successes34:47 - The Gift of Pastoral Leadership41:14 - Resources for Growth and HealingADDITIONAL RESOURCESSteve Robinson's Resources: https://steverobinson.com/More resources: https://leadtowin.com/Win With People: https://leadtowin.com/pages/win-with-peopleRegister for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

It’s one thing to put “authenticity” on your website—it’s another for people to actually feel seen and known. Pastor Jeff shares insights on what it takes to build a culture that’s not just well-branded, but genuinely life-giving. This episode will help you define, assess, and adjust the culture of your team so it reflects your true heart and purpose.TIMESTAMPS3:20 - What People Experience is Your Real Culture8:15 - Being a Culture Carrier with Integrity11:30 - Family and Function: Two Cultural Pillars16:45 - Balancing Relationships and Results22:20 - Evaluating and Shifting Your CultureADDITIONAL RESOURCESMore resources: https://leadtowin.com/Win With People: https://leadtowin.com/pages/win-with-peopleRegister for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

Pastor Jeff sits down with his longtime friend and leadership mentor, Chris Hodges (founding pastor of Church of the Highlands and founder of Highlands College). Together, they dive deep into what it really means to win—not just in ministry, but in life. Chris shares his journey of planting Church of the Highlands, passing the leadership torch, and the powerful vision behind Highlands College. They discuss the critical need for mentorship, the importance of identifying the right models, and the urgency of raising up more leaders for the future of the church. The conversation also tackles the essential balance between spiritual passion, practical systems, and structural integrity in building a thriving church. Chris shares personal insights on mentorship—how to seek out great mentors, why you need to bring value to the relationship, and the transformative power of being coachable.TIMESTAMPS:6:22 - Transitioning Leadership Roles10:18 - Highlands College: Transforming Ministry Education17:10 - Grow Leader24:03 - The Power of Models & Mentors32:10 - Pursuing Mentorship Relationships36:25 - Being Coachable: Embracing Outside Perspective42:40 - Defining Winning in MinistryADDITIONAL RESOURCES:More resources: https://leadtowin.com/Register for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/Milestone College: https://milestonecollege.org/ Grow Leader: https://www.growleader.com/Highlands College: https://www.highlandscollege.edu/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

Ever wonder why your team feels stagnant or why progress seems slow? In this episode, Pastor Jeff unpacks the hidden obstacle that holds many teams back: a lack of clear, compelling vision. We’ll discuss why it’s not enough to assume everyone knows where you’re headed, and why the leader’s job is to make the vision tangible and personal. Learn how to identify vision leaks, align your team around a shared purpose, and inspire them to move forward with passion and unity. If you’re ready to take your team from stuck to unstoppable, this is the episode for you.TIMESTAMPS5:45 - Why Vision Requires Regular Clarity12:09 - Vision Produces Your Why17:22 - Clarity Before Frustration22:15 - Helping People See Their Contribution24:49 - Taking People Where They Need to GoADDITIONAL RESOURCESMore resources: https://leadtowin.com/Register for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

In a world where performance and platform can easily overshadow purpose, Natalie Grant shares a refreshing perspective on what it means to lead authentically. She discusses the difference between hype and heart, challenging leaders to shift their focus from impressing people to serving God with a pure heart. With stories from her own journey and practical wisdom for teams and leaders, Natalie helps us rediscover the essence of worship: giving God the glory He deserves while leading people to encounter Him genuinely.TIMESTAMPS3:18 - Modern Worship vs. Traditional Hymns8:25 - Pastor & Worship Leader Relationships14:17 - Building Church Culture Through Relationship19:21 - Servant Leadership in Ministry24:12 - Redefining Winning in Ministry30:22 - Success Takes Grit and Faithfulness32:09 - Return to Jesus-Centered MinistryADDITIONAL RESOURCESMore resources: https://leadtowin.com/Register for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

Leadership isn’t about who crosses the finish line first—it’s about who crosses with you. In this episode, Pastor Jeff unpacks why true success means celebrating the people who help you get there. Drawing from real-world examples and personal stories, he explains how investing in others not only strengthens your team but also multiplies your impact. If you want to build a legacy that lasts, start by focusing on who’s with you in the race.ADDITIONAL RESOURCES (links to anything mentioned in the episode)Win with People Book: https://leadtowin.com/pages/win-with-people  More resources: https://leadtowin.com/Register for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AT: https://leadtowin.comGET IN TOUCH: Contact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

What do joy, calling, and legacy really look like in everyday leadership? In this episode, Tauren Wells joins Pastor Jeff Little to talk about his journey from celebrated recording artist to local church planter. Tauren reflects on the unseen moments that shaped him, the role of spiritual fathers, and why a life built on conviction is stronger than one built on convenience. If you’re navigating change, growth, or wondering what “winning” really means, this episode will refresh your vision—and challenge you to live with deeper purpose.TIMESTAMPS5:10 Finding Value in Feedback and Coaching13:34 The Generational Gap in Spiritual Fatherhood22:51 Tauren’s Journey from Music to Ministry34:13 The Surprising Challenge of Pastoral Leadership45:25 Creating Space to Process Your Pain1:09:02 The Joy Bomb: Finding True HappinessADDITIONAL RESOURCESJoy Bomb book: https://www.amazon.com/Joy-Bomb-Unleash-Explosive-Extraordinary/dp/0310368901More resources: https://leadtowin.com/Register for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AThttps://www.leadtowin.comGET IN TOUCHContact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

Shepherds take care of sheep. Pastors take care of people. Our first job is to create the culture that people experience when they come into our environments. Good shepherds facilitate growth and health. Discover why the culture you carry matters more than the platform you build. Pastor Jeff shares how a healthy team and a heart for people will always outlast trends, hype, or systems.TIMESTAMPS0:00 Intro5:32 Pastor Jeff's Ministry Journey12:48 Learning from Early Failures17:06 Building Milestone Church20:26 Shepherds vs. Ranchers Explained28:25 Hired Hands vs. Sons & DaughtersADDITIONAL RESOURCESWin with People Book: https://leadtowin.com/pages/win-with-peopleARC Conference Message: https://youtu.be/rq04A4hk-dURegister for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AThttps://www.leadtowin.comGET IN TOUCHContact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

In this episode, Pastor Jeff Little sits down with Dr. John Maxwell for a raw and inspiring conversation on legacy, growth, and what it really means to win. Recorded live at Leaders Gathering, they talk about defining true success, the eternal scoreboard that matters most, and why failure is often our greatest teacher. John shares personal stories—from mentoring to reaching millions people with the gospel—and challenges every leader to stay focused on their God-given assignment. Whether you're in ministry, business, or just hungry to grow, this is one you don't want to miss.TIMESTAMPS0:00 Intro7:42 Winning Through Sharing Faith16:26 What Is True Success?24:07 Getting a Return on Failure32:46 Growing vs. Taking Shortcuts36:57 The Two Percent FactorADDITIONAL RESOURCESEQUIP Leadership: https://www.iequip.org/The Way to Win book: https://leadtowin.com/products/the-way-to-winWin with People Book: https://leadtowin.com/pages/win-with-peopleMore resources: https://leadtowin.com/Register for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AThttps://www.leadtowin.comGET IN TOUCHContact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle

Pastor Jeff introduces his new podcast "Lead to Win with Jeff Little".

Welcome to the very first episode of Lead to Win with Jeff Little. In this foundational conversation, Pastor Jeff Little lays out the “why” behind the podcast—and the heartbeat of the leadership journey he’s lived for decades. Whether you're a pastor, a business leader, a parent, or someone simply trying to make a difference in your sphere of influence, this episode invites you to rethink how you define success. Learn why stewardship is the true scoreboard, how to build a healthy culture, and why the real win isn’t found in comparison but in becoming who God has called you to be.TIMESTAMPS0:00 Intro4:45 Defining Winning: The Right Scoreboard9:57 Biblical Perspective on Winning16:14 Building a Winning Culture25:13 Stewarding What Matters Most28:25 Hired Hands vs. Sons & Daughters29:47 Don't Quit and Keep GoingADDITIONAL RESOURCESThe Way to Win book: https://leadtowin.com/products/the-way-to-winWin with People Book: https://leadtowin.com/pages/win-with-peopleMore resources: https://leadtowin.com/Register for Leaders Gathering: https://leadersgathering.leadtowin.com/Information on Milestone Church: https://milestonechurch.com/FIND US AThttps://www.leadtowin.comGET IN TOUCHContact us at [email protected] US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle