5 Most Challenging Lessons I Learned in Leadership | 10-Year Anniversary Edition

In the last episode, we're moving into a new year. We looked at five ideas that I got wrong about leadership. We're going to go a little bit deeper in this episode. And we're going to talk about five more ideas. But these are challenging lessons that I learned in the last decade. And I want to go straight into the content to value your time. The first thing is this. I used to think, and it was painful to learn this personally, but I used to think that I had to be involved in almost everything organizationally. And that was just naive. I learned, number one, is this very important lesson. You must discern what deserves altitude and what deserves attention. You have to look at your own leadership, your time, your organization, your people, and discern. And the answers may change over time. But what deserves altitude and what deserves attention? And the reason this is painful is because we as leaders want to believe that we're more important than we really are. And the truth is, you are important in your leadership. But you're often important for different reasons than you understand. And so to be really, really clear, whenever you're starting, you're launching an organization, you're in the early season, you want to be involved in the day-to-day details.

You have to be, because without you, things aren't going to work. But as your organization grows and matures, you don't want to just be in the details. In fact, oftentimes, you have to rise above the details, and you actually have to stay out of them. So let's talk about altitude first. For our context, altitude means staying above the noise or staying out of the details, staying above the chaos, the smaller problems that are not missional, that are not mission critical. You're staying out of just the everyday activity. And it's important to maintain altitude often, not all the time. But if you can stay above it, what's going to happen is you're going to get a different perspective on it. And you're going to start to see trends that are forming. You're going to see patterns that are emerging, either positive patterns or negative patterns. You're going to start to see opportunities that are coming. Leaders need to do this. You should be seeing things first and more often than most people. And the only way you do that is to get above it. In the book, it's an old book. If you haven't read it, please do. It's called The E-Myth Revisited by Michael Gerber. One of the many valuable principles, he talks about scaling and systems. He says, in your business or in your nonprofit,

most people just are working in it. But what you have to do is you want to work on it, not just in it. Work on it, not just in it. To work on it, you have to get above it. And it's so important. And this is where I got it wrong. Early and in the maturing season and in the beginning years, I stayed too low for too long. This was a problem. I stayed too low for too long. I was overly involved in details that I should have been delegating and trusting others. Then later on, when I learned, OK, I need to rise above it, then later on, I made the opposite mistake. And I stayed too high or too removed for too long. So early on, it was too involved for too long. Later on, it was too uninvolved for too long. Both created problems. And so as a leader, what you want to do is you have to learn when to rise and when to dive, when to stay above and when to get involved. And it's super important to understand that if you come down too often and you're in the weeds, you're going to lose perspective. If you keep altitude too long, you're going to lose connection. You're not going to know the people. You're not going to know what's going on. And so it's kind of like a dance.

You move back and forth. And so you want to tell yourself the best leaders rise and descend with intention, not emotion. Super important. You're going to be intentional about this because it's tempting when you're emotional to get involved for the wrong reasons. Instead of trusting your team, like, no one does this right. So you get involved because it feels easier. And it may even be easier in the moment, but it's not better in the long run. And you may find yourself like me. Sometimes you're impatient. So you want to fix it now instead of letting your key leaders fix it without you. Or you might even have a big ego. And you want to flex and come in and say, this is the way we do it in our organization. And all that's very counterproductive. So what you want to do is I call it being strategically absent. When you're strategically absent, you're letting your organization mature, develop. You're letting good leaders solve the problems. And that is a very big part of organizational development. Now, when do you keep altitude? Let's talk about it. You want to stay above things. stay out of them at least three different times. One is when you're focused on bigger issues. Occasionally, there's gonna be a big problem,

there's a cultural problem, there's a external problem, there's something, and you gotta be focused on that. So you're gonna stay out of the details and you're focused on bigger issues. Secondly, is when you have a leader that can handle it and you want them to. Don't get in the way of that leader's job. Don't get in the way of their development. And they can often handle it better than you. And if not at this point, maybe later, if you let them grow in their leadership. The third time you wanna stay above it is when you're developing other leaders. You're just intentionally staying out of it. You're looking on, it's kind of like you're teenagers. You send your 16-year-old off to drive and you're going like, I hope they don't hit a tree, and they do hit a curb, and then they ruin somebody. Well, that's part of them learning to drive is getting bumped up a little bit. And so there are times when you're gonna intentionally keep your hands off, stay above it, to let a leader make some mistakes that aren't mission critical, but in order to get better. And the key is that you're staying above on purpose. It's not that you don't care. It's not that you don't know. It's that you're keeping altitude for a reason. And you wanna stay above it when your involvement

would complicate it or slow it or keep someone from growing. Then the question is, when do you get involved? And I'll give you four times you wanna get involved. Very simple, very direct. When culture is drifting, when a key leader is struggling, when there's a decision that'll shape the future, and when something's stuck and needs your authority to move. If culture's drifting, you're in trouble because culture shapes everything. So you gotta get in there immediately and fix it. Culture is a reflection of what you allow, what you expect, and fix it. If a key leader is struggling, that's on you to fix. If there's a big decision that's gonna shape your future, it's kind of mission critical, you better be involved in that all day long. You gotta sit back and trust other people to make one of the top two or three decisions of the year. You wanna be in the room. You may trust and empower them, but you're in the room discussing with them. And then sometimes there's things that just won't move without you. You gotta get involved and say, yeah, I'm needed to break through this barrier to get things moving. So what are you doing? You're managing altitude and attention. And what you're gonna do is you're gonna lead intentionally,

you're gonna rise when you can and dive when you must. Rise as often as possible and then get involved when you have to. Let's talk about the second challenging lesson that I learned. And this was difficult because I didn't see it coming until it was a little bit late and I had to make major adjustments. I used to think that the best leaders always had the best plans. We're gonna have strategic plans, detailed long-term plans. I liked charts, projections. I started with binders and colored tabs and then later on it was stuff on the wall. But here's what I've learned is this. Number two is you wanna plan lightly and prepare thoroughly. Plan lightly and prepare thoroughly. Honestly, this will be different advice than you'll learn in MBA class a lot of times, my opinion. To be clear, planning still matters. You gotta be organized, you gotta know where you're going. Yes, yes, yes, and yes. But I'm gonna tell you right now, it doesn't matter as much as it used to. And the reason is because today, things are changing so fast. Technology's changing. By the time you're through with this podcast, it's gonna be different, right?

The economics swing overnight. We're in a global economy. A crisis could come out of nowhere. Opportunities are appearing because things are changing. And so it's not that long-term thinking is bad, it's just not as realistic as it used to be. It's more impossible to think five years in the future because you can't accurately visualize five years in the future as well as you could a couple of decades ago. And so when we started, we made these five-year plans. And it took me about three rounds, like 15 years to recognize they never worked. The funny thing is they were never even close. So what I did is I thought, I'm not gonna plan as thoroughly, but I'm gonna prepare more deeply. And so yes, you do plan, but do not over-plan. And when you do, I say keep your plans in pencil. Keep them flexible. And so instead of mostly long-term planning, do this. Prepare for future opportunities you can't predict. Prepare for opportunities you can't predict. Yeah, also plan for bad things you can't predict as well. But the truth of the matter is, if you're trying to make a five-year plan, the odds of getting anywhere close are almost one in a million. So if you're going to plan and say, there's gonna be challenges coming

and there's gonna be opportunities coming, and the most. Strategic and important things we do organization are things we did not predict. They were opportunities that we saw and we seized. And so how are you going to be ready for those opportunities? Someone to hire that's available, a piece of property to buy, a product to launch. The way you're going to do it is you're going to create margin. What is margin? Margin is simply this. Margin is the difference between what you have and what you need. That's what it is. It's you need this much, you have this much. This is the margin. It's the difference between what you have and what you need. And most leaders, unfortunately, plan to spend all they have. All their energy, all their effort. That's their plan. And what they do is they plan away margin. We have this much coming in, so we're going to spend this much. It's crazy. As a leader, one of your top goals is to create margin. Now what kind of margin? Not just financial margin. I'll give you several types. Yes, financial margin. You want financial margin so you can act fast when opportunity appears. You can afford it. We can't afford it. You've already planned for it. We planned for something to put our resources toward.

Then you want time margin. And the reason you need time is because you need time to reflect, time to think, time to innovate, time to dream so that you can move fast. You also want emotional margin. Some leaders are leading at such a pace they don't have emotional margin. Something goes wrong and emotionally you fall apart. And so you want emotional margin. So your team, and you want it for your team, you want your team members to have margin so they can say yes without burning out. If you have a great idea and say, hey, let's go attack this, and your team is emotionally on the edge, they're not going to be any good. So you want emotional margin. And then for me as a follower of Jesus, I want spiritual margin. And that's so that I've got time to seek the heart of God and so I can hear God's direction above all the noise. So what I'd say to you is this, planning's good, but planning for opportunities or problems you can't predict is even better. You have to have margin to do it. And so margin isn't accidental, it's a discipline. For example, and a mistake I've seen people make in the church world where I live, sometimes pastors talk about starting, we're going to start 10 new campuses in the next 10 years. And if they're a friend, I'll always say, that's dumb. Don't be dumb. I talk to my friends that way because we're friends, but I don't want to be harsh, but that's really dumb. Because if your plan is to start 10 campuses in the next 10 years, here's what's going to happen is you're probably going to start some you shouldn't start because you're trying to stay on this plan you pulled out of nowhere. Or you'll start some wrong ones because you're trying to stay on track. Or you may actually have been able to do 12 or 13 and you only plan for 10.

And so the best thing to do is we're going to do the right number of campuses in the next 10 years. That's your goal. You don't want to force the future. You want to be prepared to make strategic decisions as it comes. So be ready. Be ready for opportunities that God brings your way. And so I'd say it this way, plan lightly and prepare thoroughly. Because you can't control the future, but you can be ready when God opens a door. The third mistake that I learned was this, is I used to think, hey, if I work harder, we're going to grow faster. Hard work solves everything. And while strong work ethic is ridiculously important, I learned this. I learned that consistency beats intensity every time. So important. Consistency beats intensity every time. Because early in leadership, you might have to rely on intensity because you're just starting out and you really have to go hard. Because you have passion, drive, and hustle. But you have to remember that intensity gets things moving, but consistency keeps things growing. So yes, you bring intensity, but even more importantly for sustainability, you're not focused just on intensity, but you're focused on consistency. And I learned this the hard way because I thought I could always sprint. And what I learned from a mentor is that leadership in ministry or in business, it's a marathon. It's a marathon, not a sprint. And I want you just to stop and think about that. Leadership is a marathon, not a sprint. Yeah, sure, you do sprint. Sure, you do run hard, but you can't run hard all the time.

And you cannot consistently sprint your way into lasting success. And so the principle that I've taught is this, that it's not what you do occasionally that makes the difference, it's what you do consistently. So you can't be intense all the time, but you can be consistent almost all the time. So many leaders will overestimate the power of a few big moments. We're going to take this and crush this, and here's our BHAG, and there's a place for that. But they underestimate the power of the moment. Small, repeated moments. We're appreciating people. We're showing up a little early, we're staying a little bit late, we're dotting the I's, we're crossing the T's, we're working on the systems, we're checking the culture, we're consistently doing the right things over time and consistently doing the right things over time consistently brings the right results over time. It's not a sprint, it's a marathon. So I would say it this way. I've almost said it, but to be really clear, consistency is doing the right things the right way for the right reasons, long enough to see the right results. Think about it, let it sink in. What is it? It's consistency, it's doing the right things the right way for the right reasons, long enough to see the right results. And it may be a little bit boring at first and consistency feels slow at first until it becomes unstoppable.

So yeah, be intense occasionally, but be consistent always. And the team doesn't need bursts of your brilliance. What they need is they need a consistent, steady leader that's predictable and consistent in leadership and that's someone that they can follow. Let's do two more. The fourth thought that I had for years and years is that the best leaders are always certain. The best leaders lead with certainty. But I learned this, especially in the last five years is I learned that you don't need certainty to lead, you need a lot of courage. You just need courage. And early in my leadership, I thought that certainty is a prerequisite. And I used to think like, if I'm not sure, how can I lead? And so what did I do? Sometimes I just honestly pretended to be sure and I acted more confident than I felt. But leadership is more complicated today than it was a couple of decades ago. And what I've learned is that so many times in leadership, you aren't choosing between right and wrong, you're choosing between uncertain and more uncertain. It's not like this is clearly right and this is the wrong thing. It's like, no, I'm not sure about this and I'm even less sure about that. And so if you're waiting to always be sure,

you'll never lead. You have to learn to lead in the gray and the uncertainties. And what's funny as I look back over my leadership is that some of the worst decisions that I ever made were the ones that I was most certain that were right. I thought this is a good decision and it wasn't. And then some of the best decisions that I made were the times where I wasn't sure at all. And what I hope you'll hear is this, is that you will rarely build something great on certainty. You're gonna build something great on a hunch, on an idea, on a vision, on intuition, on a whisper. You build something significant with courage. It takes courage to lead with faith into the unknown. And it takes courage to risk. It takes courage to fail. It takes courage to admit, I don't know, but we're gonna figure it out. And there's a little truth that may help about what your team needs. Your team doesn't need you to be certain. They need you to be honest, steady, and courageous. And you intuitively know this because you'd rather follow a humble leader that's not always sure, that's willing to learn, than you would a prideful leader that's confident and often wrong. You don't have to be certain, you have to have courage. And essentially, there are times when you're gonna say to your team,

I'm really not sure, I don't know, but we're gonna try this. If it doesn't work, we're gonna figure it out. And that's not a bad thing. In fact, if you're not doing that often, you're probably not leading into a place of greatness because greatness isn't a reflection of certainty. Greatness is often a reflection of faith. And so wrap it up with the last one that was challenging to learn and super important is this, is I used to think for years that the worst thing could happen to a leader is that they would fail. We failed and it's embarrassing, but I didn't realize the worst thing that can happen is a leader succeeds without accountability. This is lesson number five, is failure won't ruin you, but success without accountability likely will. Let me say it again. You mess up, you fail, you fall short, you try something that doesn't work, that's not gonna kill you. But if you're successful and you don't have accountability and strength around you, you will likely self-destruct. And that doesn't sound like a great place to end a New Year's podcast, but it's ridiculously important. And for me, when I was younger, I was afraid of failure.

I was afraid of letting people down or making the wrong call but I actually learned that failing is many times easier than managing success. Because if you're not careful, success does something to you. Yes, you grow in your confidence, but there's also something subtle and dangerous that... If left unchecked, success isolates and insulates. And this is horrible. If you're not careful, the more successful you become, the more isolated you are and the more lonely you are, and you have to intentionally work against that. Because without the right people around you, without people that have the authority to speak into your life and leadership, you are more vulnerable than you can imagine. I'll give you three reasons that are super important. One is the more successful you become, the less likely people are to challenge you. They just kind of let you go off and do dumb things. The second reason is the more gifted you appear, the more blind spots you can ignore. You're gifted, so you're getting things done, and so if you've got a blind spot, nobody even, you don't notice, they don't notice, and you think everything's fine, but it's not. You get a real vulnerability. The third thing is the more success you experience, the more entitled you're tempted to feel. And this is dangerous beyond measure.

I think, well, I earned it, and I deserve it, and the truth of the matter is we don't deserve anything. So you need accountability. The more successful you become, the more accountability you need. And some people say, but that's restricting. And what I want you to do is see it not as restricting, but see it as protecting. What does accountability look like? It could be a board, it could be a boss, it could be your friends, it could be overseers, but you're gonna want friends, systems, and a team. Systems that hold you accountable, systems that hold you accountable, and a team that holds you accountable. Friends that aren't impressed with you or intimidated by you, that can get in your face and say, and I've got several. Just yesterday, Bobby came in and sat down with me, he goes, hey, we're in one of those months right now where it's intense and you need to know that you're a little bit uptight, and just kind of got in my face and gave me some perspective. Friends that are not impressed or intimidated by you. You need systems that can keep you honest. And when leadership is usually with money, power, and pace. You've gotta make wise financial decisions. You can't let power go to your head and be abusive with it. And with pace, someone who can slow you down.

Systems, and I've got systems in place that are checks and balances for me. And then you need a team of people that can be honest with you and tell you what you need to hear, not what you wanna hear. The higher you rise, the harder it is to hear the truth from people, and you have to create a culture where people freely can speak into you. And so, where do you need accountability most? Super important. And I'll answer that question, where do you need it most? Probably here, where you resist it the hardest is likely where you need it the most. Wherever you resist accountability and say, I don't want anybody knowing that. I don't want people to know where I am all the time. I don't want people to know what I spend my money on. I don't want them to see what I look at online. The place you resist it the hardest is likely the place that you need it the most. And so, I tell leaders all the time, and I tell myself, you're only as strong as you are honest. If you're not honest, the likelihood of your long-term success drops like a rock. And so, I know some places that I'm vulnerable, and so I put systems in place to protect me. I've told the people around me.

I have friends that hold me accountable because as my friend and counselor, Dr. Chappelle says, no one becomes their best version of themselves by themselves. You need other people in your life. And the bottom line is this. I hope you succeed. I pray you do. But success will grow your platform. Accountability helps guard your character. In the long run, character always wins. So, new year, you want to be your best. Let me give you application questions on the things that we've talked about. First question is this. What are you doing that someone else should be doing? And what are you avoiding that only you should be doing? We're talking about altitude and attention. What are you doing, you're two in the weeds, that someone else should be doing? Or where do you have too much altitude? What are you avoiding that you should be doing? You need to come down and get involved. Second question. What margin do you need to create so you're ready for opportunities you can't predict? You're not just making five-year plans. Yes, you're organized, but you're actually aware that the world could change really quickly,

so I need to be prepared for a downside or an opportunity. What margin, emotional, relational, time, spiritual, team, financial, what margin do you need to create so you're ready for opportunities you can't predict? Next question. What small, consistent actions done daily would make the biggest long-term impact? You're not just sprinting, you're on a marathon. So what are the small, consistent disciplines that you can do for long-term organizational impact? Question four. Where are you waiting for clarity when what you really need is courage? This is a big one for some of you right now. You're afraid of failure, and your fear of failure is gonna keep you from actually succeeding. You have to, you're not gonna know it all. You have to have faith and step into it with courage. And then finally, where are you resisting accountability the most, and what are you gonna do about it? If there's some area of vulnerability, you gotta be honest about it and address it now. The good news is, it's a new year, and there are new opportunities. And I wanna tell you right now that God is not done with you yet. And I believe as you step into a new year, that you have everything you need to do everything that God wants you to do.

And so if you'll hear it from me as someone that cares, you're gifted, you're called, you have talent. If you're a follower of Jesus, you have the same spirit that raised Christ from the dead dwelling within you. You have faith, you have great people in your life that you can grow with and help them grow. And when you lead with humility, you lead with intentionality. You have a plan, but you're flexible. You're being directed by the spirit of God. You can make a tremendous difference. I pray that this year is your most productive year of leadership ever, but not just productive to make a difference in the lives of others, but deeper than that, that is God glorifying, God honoring as God works in you and through you. So open up your heart to him, hear what he has to say, do what he leaves you to do and make a difference for him. The good news is, guess what? You got better today. That's really good news because everyone wins when the leader gets better.