Lead to Win with Jeff Little

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 info@leadtowin.comFOLLOW 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 info@leadtowin.comFOLLOW 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 info@leadtowin.comFOLLOW 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 info@leadtowin.comFOLLOW 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 info@leadtowin.comFOLLOW 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 info@leadtowin.comFOLLOW 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 info@leadtowin.comFOLLOW 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 info@leadtowin.comFOLLOW 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 info@leadtowin.comFOLLOW 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 info@leadtowin.comFOLLOW US ON SOCIALInstagram: https://www.instagram.com/jefflittle/Facebook: https://www.facebook.com/pastorjefflittle