June 9, 2025
The People-First Playbook: Leadership for the Long Game
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.com
GET IN TOUCH: Contact us at info@leadtowin.com
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Instagram: https://www.instagram.com/jefflittle/
00:00 - When We Care About Others
08:24 - What Makes This Podcast Different?
14:43 - Connecting with People First
21:43 - Redefining What Winning Means
25:55 - The Leader as Shepherd
30:00 - Your Team Promotes You
WEBVTT
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When we care about others, winning everything for us begins to take care of itself, and if I had to say the number one culprit to team is, my main desire is to get there.
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Whatever there is, that's my main desire More money, more fame, more notoriety.
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And so what happens is there, takes precedent and focus to such a degree that you leave the people around you behind.
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I want to welcome you to the Lead to Win podcast, where we help you win in the areas that matter most.
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We're joined again by Pastor Jeff, so glad to have you here with us.
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I wanted this week, to jump into this idea of leadership podcasts.
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It's a crowded space.
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Like you and I both have advanced degrees in leadership, there's a lot of places that you can go to get leadership content, so I thought it would be helpful because I know you.
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We've been friends for a long time.
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I even asked you to do a podcast years ago.
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You're like Jed, we've got plenty of things to do.
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We don't really need to do that and we were talking about it.
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So help us understand.
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This space is crowded.
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Why would someone, maybe unless they knew you or they were a pastor why would a business leader or somebody who we think could really benefit from engaging with this podcast?
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Why would they listen to you and what makes us different in this podcast?
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space.
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I think it's a good question.
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I mean, I remember several years ago, you and the team asking, because we're always having conversations of growth.
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Like how do you grow?
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I mean we talk a lot about having a growth mindset right Not a fixed mindset and wanting to grow.
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So we're all the time, as a team, continuing in this conversation.
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It's one of my favorite things about you.
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It's really one of the reasons why I'm on the team is because, from the very beginning of our relationship, one of the things about you that you wouldn't say about yourself that sets you apart is you're naturally curious.
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You're always trying to get better.
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You're always thinking about you.
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That you wouldn't say about yourself.
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That sets you apart is you're naturally curious.
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You're always trying to get better.
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You're always thinking how can the team get better?
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So we were coming to you to go with that, and you're like I don't think it's time yet, but, like you said, we're having these conversations.
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Yeah, and I like podcasts and I receive a lot from you know podcasts in multiple spaces.
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I mean, I love to fish, so I listen to an inordinate amount of fishing podcasts, your algorithm's filled with it.
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It's filled with it.
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Yeah, but I did win my local tournament last night.
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Of course, we would expect nothing less, right.
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So I mean you have interest that you listen to or whatever, and I also love growing.
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So I follow some of that and I want to.
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I want to be very clear.
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I am not in any way putting any of that down.
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I think all all of those things are good, but for me I wouldn't think it would be a value to enter a space where, in a lot of ways, I believe, there's people better than me in many of those areas.
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And so what I believe for us that this podcast, and why did I agree to it Part of it is the function of I believe when you get to be my age and station in life, there's a responsibility to give back, and so I love developing people.
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I love pouring into young leaders.
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It's one of my favorite things and, I'll be honest, I had a lot of investment in me.
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I've had some amazing people pour into my life.
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There's just no way I would be where I'm at without the investment, and so this is just a great way to leverage technology to.
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Maybe there's a young Jeff Little out there back in the day where I used to get cassette tapes John Maxwell now, or other names I could mention.
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I used to get their cassette tapes and I remember being a young leader and those the things being talked about on those old cassettes.
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They were impacting me.
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You know, I'm going to be a leader who doesn't lead to position.
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I'm going to all these different things and so I I I began to see, okay, there's that, but, but.
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But what about the content?
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Cause that's what you're really hitting on.
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What are we going to talk about?
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And I think that when you say the word pastor, people have a perception.
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You know that, you know, even Pastor Jeff or he's a pastor 30 years he's been a pastor.
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I think it's a perception, maybe, of what that word means.
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Obviously, the biblical concept is this shepherd who takes care of sheep.
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Then that's a problem, because people are like I don't want to be a sheep and most pastors don't want to be a shepherd, it's true, but God's okay with it he is.
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He calls himself our shepherd, and Jesus said you know, like he is, he's the good shepherd.
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But he also identified as the lamb of God who takes away the sin of the world.
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But I think, you know, there could be someone who's like I'm not the pastor, the senior pastor.
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Now what does that mean for me?
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Right, or I'm not a pastor, I'm on the team at a church, I'm, I'm executing some other part of the vision, or maybe I'm not a part of church at all.
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Maybe I'm just over here, maybe I'm a parent, maybe maybe I'm in a business role.
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And here's what I really believe that that, for me, want to hone in in this podcast is the heart for people, like helping others win, caring about people.
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It's sincerely not being about you, and so I think when we care about others, winning, everything for us begins to take care of itself.
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And that's such a true statement.
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It's really big, it's really big.
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You're talking about content, and content's valuable Content are principles and ideas that kind of generally apply.
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But what I hear you saying I know you enough to know you're talking about connecting with people.
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But you're also talking about context, because what you're saying is if I'm a pastor, it works like this.
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If I'm in my boardroom, it works like this.
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If I'm a dad, it works like this.
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If I'm a coach, it works like this.
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So you're seeing a gap, really identifying a gap between general content and theory and the actual application, in a way that not the person who's leading, but the actual person who's being taken care of, who's being led, goes.
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I feel like they care about me because they want the extra step to just take concepts and to make it real to me.
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And I don't mind talking about the principles or the concepts, but I'm actually, I think, in our dialogues here and I want to be very clear, this is not either, just me saying let me get all these important people to come on here and talk with us, and I have a lot of amazing friends and amazing guests that I think that the people listening will benefit from, but it's much more than even the personalities or the people.
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When I have those people, I want to draw out of them what, what have you learned about the people you're serving that has has your?
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What you're learning about those people you're serving and your ability to connect with them and to serve them and love them?
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What, what, what have, what, what?
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What can I draw out of you that we could learn?
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from.
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It's that phrase you intuitively go to.
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That we've said to many of the guests on the podcast is you don't just want what successful people have, you want to know how they think.
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You're always trying to bring us and I appreciate that about you.
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You're always trying to bring us into an understanding of think like they, think, think like they think and think like they think, and I think that successful people either were born with some natural, supernatural whatever way gifting that they're better at connecting and motivating people naturally, or their gift is so big it just draws people.
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It draws people.
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It draws people, it draws people.
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But one of the things for me that I want to really help maybe even some younger leaders or people out there is you can really quickly, as you grow, lose self-awareness, right.
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You can quickly lose sight of even some of the closest relationships.
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You can take your wife for granted, for that matter, or your spouse or your kids, and you can lose sight of the people around you.
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Matter or your spouse or your kids, and you can lose sight of the people around you.
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And I think that there is a trap that you end up in this place and you think one thing, but everybody else around you think something totally different.
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That's so important.
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Let me just jump in right there, because this is something that you say.
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That's really getting to the heart of what you're talking about there, because what you're saying is there's a gap between the leader who's leading how it feels to them, and the person who's out there being led, like I was saying a minute ago.
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But you're always asking this question how does it feel to be that person?
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It's one of the things I appreciate about your leadership style.
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You're not just charging ahead.
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You have no shortage of vision.
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You have no shortage of let's make it happen, but you're always thinking through this lens of how does it feel to be the person.
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Are we going too fast?
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Do they understand what we're trying to do?
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Why is that hard for leaders?
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Why do they miss that?
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It seems obvious and I know you're not trying to say that it's easy for you, and I'm going back to this podcast.
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What I want to draw out is I don't want you to end up at the next step and then think, oh, I've arrived, when really you haven't brought the people with you.
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Again, there's so many books on it's lonely at the top.
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Well, there's an element of being a leader means you have to be in front, yes, but there's also, I believe, a way in terms of leadership that I want to talk about in this that you bring people with you, because the real celebration is not you in the end zone by yourself, but the real celebration is when the whole teams are celebrating together.
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So true, and so there's there I am always this proponent of there's the possibility for it to not be as lonely.
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Wow, if you were to actually care about bringing everybody with you.
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Well, we both love sports.
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It's one of the things both love sports.
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It's one of the things that we share and one of the things that I'm always impacted by.
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When you listen to a great athlete, when you listen to a tom brady, when you listen to a jordan, those guys, when you ask them, what do you miss so much of the time they don't just talk about playing in the big game.
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They never say they miss practice.
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What they always say they miss are those moments with their teammates working hard towards a great cause.
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It's amazing how, again, we miss that.
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I think that scales to every situation, whether you're a pastor or a business leader in your home.
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So much of the joy of leadership is who you're doing it with.
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So back to your original question there, in this idea of why do we miss it?
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Because if you have responsibility for people or you have responsibility in general, it's easy to become task oriented because there is a checklist of tasks that you are responsible for and there's only so much time in the day, and so we talk about time management a lot and we talk about scheduling and planning, and so you do have these tasks ahead of you.
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I think that we can become task oriented.
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I think we also have a misperception that we can get there without the need of other people, and if I had to say the number one culprit to team is, my main desire is to get there, whatever there is.
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That's my main desire More money, more fame, more notoriety, more accolades, a new position, a new title, whatever there is.
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My main goal is if I can just get there, and so what happens is there takes precedent and focus to such a degree that you leave the people around you behind and what you realize is you might get to that temporary there, but you don't get to the ultimate there without the team and you don't get to stay there.
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Yeah, and so the cliche line, which I really love, you know if you, if you want to go fast, go alone, but if you want to go far, you got to go with everybody else.
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Good, so I'm a proponent of the long game.
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Right, I'm a, I'm a, let's play the long game.
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I'm saying it's my, my book that I wrote about um, our vision at Milestone Church is called it's Worth it.
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Right, it's based on this treasure.
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That's the parable, that there's this hidden treasure, that a guy finds it in the field and sells everything by the whole field just to get the treasure.
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And obviously the treasure is the kingdom of God, it's Jesus, all of that.
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But the principle there is still true in what we're talking about, like, the treasure of God's kingdom is himself, but he himself is expressed through the relationships with people.
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So my point is that I'm always a proponent of what, what really is winning.
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Like, leadership principles are good, but if they don't apply to the people and you don't know how to connect with people, all the principles in the world are not going to help you win.
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That's really true.
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It's like preaching.
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Now I preach, so people listening may give presentations.
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I had a young leader this week ask me this he's starting to get more and more responsibility for speaking, you know, and so he's just asking me like I want to be better at it.
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It's one of the top fears that people have, and so I want to be better.
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There may be people listening that are like I want to speak better.
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Well, what I would say is is that a lot of people who speak are so bad with people, even some that are good at speaking, that the people say we prefer you stay up there because every time you get down you're terrible.
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We've all met that person who looked great in the lights, but then we got close to them and was like I'm very not impressed.
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Well, you said cliche.
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How about the cliche of never meet your heroes?
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And the reason is because of that.
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You see them from a distance and they look amazing.
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You meet them and you're like wow, I thought they would be better than that, Exactly.
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So what I would actually say is connecting with people and being better with your self-awareness, and being about serving people actually makes you communicate better, because it's the same principle You're connecting with them, even though it may be a larger room.
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Your desire is to connect and help and serve them.
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I would say, even speaking or this podcast, what's my?
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What's my goal with this podcast?
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To introduce concepts, thoughts and help from a pastor's perspective that I and we can, we can talk about that.
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I believe there's not a big gap, even from a pastor to business or coaching or any other thing as well.
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But what's my desire?
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My desire is that what we're talking about actually impacts and helps you.
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I love that.
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So that's the goal.
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Yeah, we talked about it's lead to win, and so we've talked some about leading.
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Now you're giving us an insight.
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Let's go a little deeper on this concept of winning and you're giving us some here, because I think sometimes when people hear win, they think do what it takes to be the top step on everybody else on your way up.
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You're really redefining what you mean, and we know when the Bible talks about winning, nobody else has to lose for you to win.
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You've got a race that's set before you.
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It's a stewardship.
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Help us understand a little bit more about this winning aspect of what we're talking about.
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Winning doesn't mean that you never have a loss, right.
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So it doesn't mean that you don't have some setbacks.
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It doesn't mean someone else has to lose, but, again, I believe winning is holistic.
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So for me, it's not a win if I get to said mountaintop and there's just a row of bodies, and that's not a win.
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Right, I want to bring as many people with, and there may be people who superimpose on me the responsibility to make them a winner.
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I can do my best, but you have to make personal choices and own your own responsibility.
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Yes, that's really good.
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So I'm not talking about, I'm going to carry everybody up the mountain which I've done my fair share of carrying.
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But what I am saying is I do care, I do care, I do care if you can make it to where God's trying to get you.
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So it's not just about my there, it's about your there and then it's about our there wherever we're going.
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And again, teams win championships.
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It's like what is winning actually?
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There's a version of winning in our culture that says promote yourself, build yourself.
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We have never been in a more me-centered culture in the history of the world.
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Yes, it's so true, there's never been a more me-centered.
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It's so true build yourself, promote yourself.
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You know, step on everybody and just get to wherever it is you're going there's all kinds of consequences.
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we're also the most lonely group ever.
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We're also the most lonely group ever.
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We're also the most anxious group ever.
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And so when you understand, this approach is creating all these unintended consequences, because this idea of I, you know, in a marriage you didn't make me happy, so now I've got to go find someone else, as if it's the other person's responsibility.
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So we've got to shift from that of like everybody else exists to help me win to what I hear you saying is that great leaders and great teams and the culture of a healthy team is we win, we win.
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We win.
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That's what really winning is Right.
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You know and I think I think again, I hear a lot of people talk about you know, here we are in a podcast space or you have a YouTube or social media.
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I hear this a lot is just people's kind of their surprise at the dysfunction expressed and the criticism and the you know.
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It's like really did they really say all that?
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You know?
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The sad thing is social media did not create that.
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It's just revealing where people are at.
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It's like during COVID, everybody used to say, well, if I had more time with my family, my marriage and my relationships would be better, only to find, when we were actually cooped up together, we all ended up in a major challenge because of isolation and the dysfunction.
00:18:30.993 --> 00:18:43.632
So what I'm saying is that winning is me helping your relational world get better, like helping you in those, helping you your marriage.
00:18:43.632 --> 00:18:47.804
Like if you get better there, you walk out into the world and if you're stronger there.
00:18:47.864 --> 00:19:04.906
I want to talk about some of that the leader in marriage, the leader, the leader in friendships A lot, of, a lot of quote unquote leaders are pretty bad friends, or they don't have a lot of friends and they think that almost that's the goal Right as if somehow, if you're that great of a leader, you live this isolated life.
00:19:04.906 --> 00:19:06.090
We don't see that as winning.
00:19:06.240 --> 00:19:07.404
I don't see that as winning Like.
00:19:07.404 --> 00:19:07.866
I think.
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I think leaders need to and I'm actually working on content in that area.
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So when I talk about lead to win or I talk about this pastor, heart or connect I mean I'm talking about young parents are asking we need help teaching our kids how to make friends.
00:19:24.040 --> 00:19:24.603
It's a huge problem.
00:19:24.603 --> 00:19:26.368
It's a major problem In our student ministry.
00:19:26.368 --> 00:19:31.762
One of the biggest problems is your student ministry is big, which we're excited about it because it means God's doing things.
00:19:31.762 --> 00:19:35.648
The biggest fear in our student ministry is my kid can't make a friend.
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My kid can't make a friend, so we've got to have an environment to where we begin to unpack.
00:19:42.278 --> 00:19:43.462
Why is that?
00:19:43.462 --> 00:19:44.105
Why is that?
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What is our targets?
00:19:46.346 --> 00:19:48.146
What is how we're doing life?
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What are the things about how we're doing life that is impacting that result?
00:19:53.720 --> 00:20:09.224
I want to talk about another area and that is, if I'm listening to this and I primarily work in business, maybe I own my own business, maybe I work in said job so what is a pastor Like?
00:20:09.727 --> 00:20:17.798
And I'm I've I've constantly found myself sharing to say, hey, there's not as big a gap as you think.
00:20:17.798 --> 00:20:39.153
Right, like I, I believe that actually, like church volunteer teams, I've seen the leaders in our church serving, helping or even some of the things I'm talking about, I believe do primarily and can apply to ministry.
00:20:39.153 --> 00:20:43.003
You know leadership, but I still think it's it's it's people, are people.
00:20:43.003 --> 00:21:18.314
So, asking yourself about how you interact with your customers, asking yourself about do you, do you believe what it is that you offer is is going to actually be of value to your customer and you will go to great lengths to make sure you get to them what will add value to them, what will add value to them, do you, do you, do you truly say I believe my employees, if I'm the boss, or or my team or or, or my intern or whatever they're going to be better.
00:21:18.700 --> 00:21:26.057
Well, see that you just you just touched on something, and it may not seem natural to think why a business leader would want to listen to this podcast, but the data backs it up.
00:21:26.057 --> 00:21:28.008
We know the reason why people leave their job.
00:21:28.008 --> 00:21:32.905
Number one reason is they feel like no one's acknowledging their contribution, so they don't feel fulfilled.
00:21:33.205 --> 00:21:51.971
But you just described it right or their manager, which is really both of those things the direct report Right and we know one of the books that's been disruptive in that space the Unreasonable Hospitality and they really revolutionized the restaurant space by thinking about it's less about the food, it's about the experience that you create for people.
00:21:51.971 --> 00:22:03.560
And they said everything shifted when, in their kitchens and in their restaurants, they started putting the needs of the team first, even ahead of the diner and the customer, and it radically changed.
00:22:03.560 --> 00:22:05.925
That's a totally different way to think about business.
00:22:05.925 --> 00:22:14.669
But from your situation, what you're talking about, you're saying, guys, if you would pay more attention to the experience of the environment and not just the bottom line.
00:22:14.669 --> 00:22:16.922
How does it feel to be on the team, your teams?
00:22:16.942 --> 00:22:17.483
would be better.
00:22:17.483 --> 00:22:18.766
Yep, so true.
00:22:18.766 --> 00:22:27.188
Well, we say it in church, we say, or I say to pastors how you treat your staff, it's a big deal, it's how they'll treat the people.
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So the problem's always with the people closest to you, right?
00:22:31.255 --> 00:22:37.085
And so it's really about learning how to lead.
00:22:37.085 --> 00:22:52.701
Yes, like you have to provide direction and leadership, but also care, shepherd, also instruct, coach, and so, yeah, there's a dynamic here that can be somewhat complicated to us.
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How do we unpack that?
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What does it mean?
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And I guess, for me, what am I saying?
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