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.

TIMESTAMPS
0:00 - What God Blesses & Why
5:43 - Marriage is Your First Ministry
11:21 - Navigating Different Family Seasons
17:41 - The Unity Principle
22:54 - Meeting Your Kids Where They Are
31:19 - Dating and Marriage Wisdom

ADDITIONAL 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 [email protected]

FOLLOW US ON SOCIAL
Instagram: 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.

TIMESTAMPS
0:00 - Positioning Yourself for Success
3:45 - Why the Word Matters as an Anchor
8:10 - Making Bible Reading Less Intimidating
12:15 - Practical Ways to Engage Scripture
17:35 - Preaching vs Personal Study Balance
24:25 - Advice to Your 20 Year-Old Self

ADDITIONAL RESOURCES
More resources: https://leadtowin.com/
Win With People: https://leadtowin.com/pages/win-with-people
Register 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.com

GET IN TOUCH: Contact us at [email protected]

FOLLOW US ON SOCIAL
Instagram: https://www.instagram.com/jefflittle/
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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.

TIMESTAMPS
10:52 - Coaching: An Underrated Leadership Competency
17:45 - Four Reasons People Get Stuck
25:05 - Standards: The Floor, Not The Ceiling
34:25 - The Power of Self-Leadership
50:28 - Choosing Your Influences Wisely

ADDITIONAL RESOURCES
More resources: https://leadtowin.com/
Win With People: https://leadtowin.com/pages/win-with-people
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 [email protected]

FOLLOW US ON SOCIAL
Instagram: 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.

TIMESTAMPS
5:38 - Team Building vs. Being a Superstar
10:45 - Teaching Team Principles Early
17:15 - Character: The Foundation of Great Teams
22:10 - Competency: What can You Actually Do?
25:32 - Curiosity: The Drive to Keep Growing
31:06 - Chemistry: Why Team Flow Matters

ADDITIONAL RESOURCES
More resources: https://leadtowin.com/
Win With People: https://leadtowin.com/pages/win-with-people
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 [email protected]

FOLLOW US ON SOCIAL
Instagram: 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.

TIMESTAMPS
1:15 - Shepherds: Biblical Leaders Who Care
3:56 - The Value of Sheep in Biblical Context
6:10 - Jesus as the Good Shepherd
9:54 - Building Teams That Last
16:00 - Hired Hands: Leaders Who Don't Stay
24:23 - Building Culture, Not Just Results
29:50 - The Dangers of Self-Promotion
33:16 - Respect Comes From Dealing With Problems

ADDITIONAL RESOURCES
More resources: https://leadtowin.com/
Win With People: https://leadtowin.com/pages/win-with-people
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 [email protected]

FOLLOW US ON SOCIAL
Instagram: 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.

TIMESTAMPS
9:36 - Breaking the Cycle of Leadership Loneliness
17:13 - How to Build Meaningful Relationships
25:54 - Celebrating Others' Successes
34:47 - The Gift of Pastoral Leadership
41:14 - Resources for Growth and Healing

ADDITIONAL RESOURCES
Steve Robinson's Resources: https://steverobinson.com/
More resources: https://leadtowin.com/
Win With People: https://leadtowin.com/pages/win-with-people
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 [email protected]

FOLLOW US ON SOCIAL
Instagram: 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.

TIMESTAMPS
3:20 - What People Experience is Your Real Culture
8:15 - Being a Culture Carrier with Integrity
11:30 - Family and Function: Two Cultural Pillars
16:45 - Balancing Relationships and Results
22:20 - Evaluating and Shifting Your Culture

ADDITIONAL RESOURCES
More resources: https://leadtowin.com/
Win With People: https://leadtowin.com/pages/win-with-people
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 [email protected]

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Instagram: 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 Roles
10:18 - Highlands College: Transforming Ministry Education
17:10 - Grow Leader
24:03 - The Power of Models & Mentors
32:10 - Pursuing Mentorship Relationships
36:25 - Being Coachable: Embracing Outside Perspective
42:40 - Defining Winning in Ministry

ADDITIONAL 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.com

GET IN TOUCH: Contact us at [email protected]

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Instagram: https://www.instagram.com/jefflittle/
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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.

TIMESTAMPS
5:45 - Why Vision Requires Regular Clarity
12:09 - Vision Produces Your Why
17:22 - Clarity Before Frustration
22:15 - Helping People See Their Contribution
24:49 - Taking People Where They Need to Go

ADDITIONAL RESOURCES
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.com

GET IN TOUCH: Contact us at [email protected]

FOLLOW US ON SOCIAL
Instagram: https://www.instagram.com/jefflittle/
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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.

TIMESTAMPS
3:18 - Modern Worship vs. Traditional Hymns
8:25 - Pastor & Worship Leader Relationships
14:17 - Building Church Culture Through Relationship
19:21 - Servant Leadership in Ministry
24:12 - Redefining Winning in Ministry
30:22 - Success Takes Grit and Faithfulness
32:09 - Return to Jesus-Centered Ministry

ADDITIONAL RESOURCES
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.com

GET IN TOUCH: Contact us at [email protected]

FOLLOW US ON SOCIAL
Instagram: https://www.instagram.com/jefflittle/
Facebook: https://www.facebook.com/pastorjefflittle