5 Times I Was Wrong and What It Taught Me | 10-Year Anniversary Edition

As I look back over the last decade, we know so many things have changed. COVID hit. There's new values and work rhythms. Attention span is decreasing. Trust in organizations is collapsing. A whole new generation of people are entering the workforce with different values and expectations. You've had AI and many other things. And so when it comes to leading, if you're not changing, you're probably not growing. And as one who's led now for over three decades, when I look back at my own leadership, while my values haven't changed, my views on leadership, they're continually evolving and changing, and many times in big ways. And so what I want to do in the next couple of episodes is I want to dig into some of those changes, some of the things that I got wrong. And in this episode, I'm going to talk about five times I was wrong and what it taught me. In the next episode, we're going to deal with some other more specifics that I believe can help you grow in your leadership. So first of all, when I started three decades ago in leadership, I used to believe some things. I'm going to tell you what I used to believe, and I'm going to tell you what I believe now. These are some of the things that I got wrong.

I used to believe that great leaders needed to be confident and right. We needed to stand up and be right. But I learned, number one, that a key to growth is a willingness to be wrong often. And I want to highlight the part often, that if you really want to be growing as a leader, you have to be wrong, be willing to be wrong, and not just occasionally, but you have to actually be good at being wrong so that you grow. And I'll unpack this, because whenever you start leading, and some of you are younger or newer in your leadership, you'll see that you start with this very pure passion. And that's a good thing. You're almost naive in a good way. But the problem is you have limited perspective. You just haven't seen a lot yet. And this was me early on. And since your passion is high and your experience is low, you'll often speak in absolutes. You see this, especially with younger leaders, and this was me for sure. I would say early on, hey, at our church, we're going to always do this. Or I would say with confidence, we will never, ever do this. And these promises come from deep values and sincere motivation and really a desire to do things maybe better than where you came from or do them different or whatever. But what you'll learn if you lead long enough

is that the promises you make early can become the limitations you live under later. Let me say it again, that the promises that are made from a sincere place that you make early, those definitive declarations, they can become the limitations that you live under later. And if you think about it for a while, it makes sense because the world changes. Your team changes. The challenges that you face, they're new and they're different. The opportunities emerge out of nowhere. They're different. And most importantly, you change. If you're growing, you're becoming different. And so 5, 6, 7, 8, 10 years into it, hopefully you are different in your leadership. And so sometimes when you're growing, you actually have to admit that you were wrong. And when you admit that you were wrong, it doesn't mean that you lack integrity. It means that you lacked information. In other words, you didn't know what you didn't know. Or you might have even been right then, but the world changed. And so you needed to adapt some of the stuff that you believed then. Here are a few things, for example, that you might want to grow in order to have a bigger or a broader impact.

You can write these down if you want. You want to get good at being wrong. If you want to grow fast, you have to change often. Let me say it again. Get good at being wrong. If you want to grow fast, you have to change often. I'll say this. Be wrong fast. The longer you wait, the higher the cost. When you're wrong, admit it and move on. And this is super important. The place that you're most confident that you're right is often the place that you're most vulnerable to being wrong. I want to sit there for a moment. Wherever you say, oh, I'm sure about this, and they're all wrong, and they're a bunch of idiots, wherever you are that you dig your feet in the deepest may reveal the place where you lack perspective. Not always, but often. And so your goal as a leader, honestly, is not to be right, but your goal is to be better. And to be better, sometimes you have to be wrong. So the first lesson I learned is I don't need to be right. I actually need to be wrong often. And that's a mark of growing. The second thing that I used to believe is that the organization should always reflect the leader. If the organization is going to be strong, it's going to reflect a strong leader.

And it's true in one sense, but it's incredibly limiting in another. And what I learned, the second thing that I was wrong about is this. I learned that leaders shouldn't lead by preferences, but by purpose. Super important. As a leader, you're going to have a lot of strong opinions. And those opinions can be good until they're not. You don't want to lead by what you prefer and what you like only. But you want to lead very purposefully. For example, in the early years, I always had a strong bias that things should be the way I wanted them. And I honestly believe that the best leaders shape almost everything to what they like and what they want. I wanted people to think like me. I wanted them to work like me. I wanted them to make decisions like me. And it sounds kind of wise, but it's really wrong. It's limiting. And I'd say it this way. Honestly, it's occasionally dangerous. Why? You can jot this down, or I will repeat it. If everything has to match your preference, nothing will ever outgrow your leadership. Let me say it again. If everything has to match what you like,

then nothing is ever going to outgrow you or your preferences. And that's why to really grow, to really increase your impact, to really broaden your reach, you must increase your tolerance for many things that are outside your preference. Let me say it again. You want to reach more people. You want to have a bigger team. You're going to have to get used to tolerating some things in your organization that you don't love or you don't prefer. And I'll just be real honest with you. Some of my team members that are in here behind the scenes, they will vouch for this. Some of the most effective things that we do organizationally and for our people, I would not choose them. And I could give you a list, but honestly, the list is pretty long. And so I'll just kind of keep it broad and tell you this. There are some styles that I wouldn't choose, which is probably a good thing. Because in case you haven't noticed, I'm a 58-year-old grandpa, right? And so if I love everything about the look and the sound and music, the lights and the decoration and the branding, then we're probably in trouble because I'm not the typical person we're just trying to reach. I'll tell you this.

There are different workflows of how people are most effective. I am incredibly biased toward early. But why aren't you here early like me? Some people are actually better working and more productive at other times of the day. There are different meeting rhythms. I prefer short, limited meetings, whereas other people really need to process things in different meetings. There are different leadership styles. I like to be direct, I like to be quick, but sometimes being much more patient, much more empathetic, much more intuitive in leadership can be so much better. So I'll say this. To have a broader impact, you need to have a broader perspective. If everyone thinks like you, works like you, then you actually hire a lot of unnecessary people. I don't want that to sound harsh. It's just true. What is your assignment? I'll be very specific. One of your assignments would be this. Get good at letting great people do things their way and not your way. Get good at letting them go, I wouldn't do it that way. But actually, your way may be better. And again, I'm not talking about direction or mission or values, but I'm talking about non-essentials, style

and approach and methods. And the hard truth that you have to face is this, if you limit strong leaders, you'll lose strong leaders. If everything has to be your way, they're not going to stay forever. So when you're leading, you want to think purpose over preferences. It doesn't have to be your way. If nothing rubs you the wrong way, if every decision feels safe and comfortable in something you like, here's your problem. You're building what you like. And I promise you, what you like will limit the impact. Get good at letting great people do things their way, and you will have an organization that reaches more people or does more good. I'm not always right. You won't be either. Discover it, admit it quickly. I'll give you a third thing. Whenever I first started leading, I thought that everyone should perform at the level I expect of myself. Like, these are my standards, and you better hit those standards as well. But I learned that I was actually wrong. Number three thing I learned was this, that my standards can be high, but my expectations must be fair.

You can hold yourself to the highest level of standards and expectations, but when it comes to leading people that are not like you, not in the same stage of life you are, you have to be fair in what you expect of others. And I'll be honest with you and tell you, this one took me a little bit of time. to learn because I always push hard and so I thought to myself like hey if I push with intensity then everybody else should push as hard as I'm pushing and that sounds kind of noble and fair at first but it's really not fair and it's not possible for a lot of people because the truth is that even the best team member they they can care a lot I mean they can care about their area but they will never carry the same weight that you carry they won't they won't by nature because they don't know what you know they don't see what you see and if they don't know what you know and don't see what you see then how can they think about what you think about how can they care like you they simply can't just by design and so we have a team of amazing people with really strong at work ethics that really do care a lot and they're gonna push hard and I'm grateful for all that they do but it's not fair to expect them to run at the same pace that I run at it's simply not fair for one thing I've got support that they don't have like I've got a whole team of people that do things for me that give me the margin to push exceptionally hard and you can have great people around you but they don't have the support that you have or you may have really capable of people around you but they don't have the same capacity that you have where you are is different than where you were five years ago so you you may have grown into a place of being able to focus better or work longer and they haven't grown to that place yet or they might be able to carry the same emotional load that you can but they're in an entirely different season of life and so you think about it like I'm my kids are grown and I'm an empty nester and so of course I could work hard and so you had different people at different

stages in life and you have to recognize that you can have really high standards for yourself but be fair to them you might have a Gen Z rookie worker first real job and so they've got more time maybe to devote but perhaps less resilience you get someone else who's a single parent and they got a lot of resilience but man they don't have any time they're raising kids and maybe working two jobs and so you don't want to try to get people to be like you what you want to do is you want to help them become their best in the season that they're in so important because you're gonna care and you're gonna push yourself but don't push them to your standards keep your standards high for yourself but but be fair and what I've learned is it's possible to have really world-class standards for yourself and to still be fair with what you expect from the team that you love and here's the truth is you are not lowering the bar we're not excusing late laziness we're simply being fair about what's reasonable for the people that we love and lead so keep your standards really really high and keep your expectations fair ironically and this is really fun and important when you're kind and you're compassionate and you're clear and you're fair great people will often exceed your expectations and it's not because you pressured them to but because they were a valued enough to thrive and so it's great you push hard you be fair and watch great people growing their leadership and together you learn to win and do great things I've learned a lot over the last decade I'll give you another one that I used to think and this is one that many leaders are very vulnerable to I used to think that more options meant more opportunities the more successful we are the more we can do the more opportunities we have the better it's going to be and I've learned number four is this that success creates options options create distractions and distractions diminish success let me say it again I want to hear this and feel it success it creates options or opportunities options or opportunities create distractions away from what was creating the success and distractions diminish and even can kill success and this is one of the most important lessons that I think a lot of leaders

miss because what happens is when you stay focused on your mission yeah you start to move the mission forward and you move the mission forward so you get more resources and then when you have more resources you have more choices you have more freedom but when you have more freedom and more resources it actually gets more challenging to stay focused you you do the big things that matter you get some resources you get some flexibility you start doing some other things and then you start losing the focus on the things that made you successful in the first place so what I want to do is I want you to listen to this as you're moving into a new year you're training your mind to think on things they're gonna help you be more successful this year I want to beg you to watch for this because it sneaks up on the best leaders Success, it gives you the ability to do more things. So important. More things is usually the beginning of losing the main thing. I want to say it again. Success, it gives you options. It gives you the ability to do more things, but doing more things is usually the beginning of losing the main thing. You have to fight for it, fight for focus, fight for simplicity. Tell yourself over and over again, and I tell myself this and then I end up blowing it and going and doing too much. Tell yourself over and over and over again, just because we could doesn't mean we should. Just because we could doesn't mean we should. The best don't do too many things. The best always focus on doing the main thing.

And think about it. We could add more staff. We could add more programs. We can say yes to this. It's easy to add staff. It's hard to reduce. So you want to fight to stay lean so that you don't become big and slow. It's easy to add a program. We can do this and this and this. Well, it's hard to sustain them, or it's hard to remove them later on. So if I'm going to make a mistake, it's easy to say yes, but it takes discipline to say no. In order to focus on growing more, I want to work on saying no to things we could do that are not strategic and don't help the main thing become better. And it sounds dramatic, but it's true. And I want to say this. I want you to hear it. I want you to feel it. Every time you say yes. Sure, we can do it. Yes, I can go there. Yeah, we can hire it. Yeah, we can add that. Oh, that sounds like a good idea. Yeah, we'll do another meeting. Every yes costs you something.

Too many yeses cost you everything. Slow it down. I know I'm being repetitive, but I need to do this. You need to hear this. It's so easy to say yes. Sure, let's do it. Let's add it. Let's do it. Every single time you say yes, it removes something. Time, energy, cost, whatever. Every yes costs you something. Too many will cost you everything. Some of the best are no longer the best because I said yes too many times. What do we know? Success creates options. Options create distractions, and distractions diminish success. So I'll just be direct. Guard your focus like your future depends on it. Why? Because it does. Fifth thing, over the last decade, I've learned a lot of things. I used to think that over time that leadership would get easier. I'm gonna get better. We're gonna have more resources, and it's gonna be easier to be a leader. What I've learned is this, number five,

is that as a leader, you must become comfortable being uncomfortable. In other words, it really doesn't ever get any easier. In fact, with more success comes more complications. To be really effective over a decade, two decades, three decades, honestly, you gotta be really comfortable hurting. You gotta be really comfortable being uncomfortable. I just kind of assumed that as I grew in leadership and maturity over time, I'd become more comfortable and confident in it. I was dead wrong that the more you grow, the more impact you have, the more you have to live in kind of what I call a constant state of discomfort. In the church world, we have these little sayings. I'm a pastor, and so pastors have these little sayings. They're little saying, people will say, when you reach a new level, you face a new devil. And everybody says, amen. New level brings new devils. I say it this way. When you have more impact, you'll have more opposition. In business, we could say it this way. New levels create new pressures. And many of you know that. Or new opportunities actually expose new insecurities. We got an opportunity now, I'm more insecure. And so you wanna get good at being uncomfortable. And when you're uncomfortable, it doesn't feel good,

but it actually is a good thing. And the reason is because growth and comfort never coexist. You never get better when you're not doing anything difficult and you think about it. If you're comfortable, you're not growing. It's true in the gym. You go to the gym and everything's easy. You're not building muscles unless you have resistance. The same is true in your leadership. It's the resistance, it's the opposition, it's the hard times that force you to look at what you're doing and go, okay, I wasn't right about that. I need to change. I need to grow. I need to increase my resilience. I need for my faith to grow. I need to have more people around me. It's the challenging times that make you better. So I'd say this because some of you right now are going, oh, I'm uncomfortable, Craig. I get it. I am too all the time. And I'll tell you, don't worry when you're uncomfortable. Worry when you're not. So step into it. Step into the things that make you uncomfortable. It's a new year. And to really be effective this year, you're gonna have to face some uncomfortable things. Have the uncomfortable.

uncomfortable and difficult conversation. You need to develop somebody. They are not going to get better without development. Try the thing that makes you nervous. Push yourself a little bit. Try something and actually fail. One of the biggest blessings to me is when I fail at something, I go, oh, it wasn't that big a deal. It didn't kill me. And then it gives you permission to push yourself in faith in other ways. And I'll say to some of you right now, as you're moving into a new year, if you want to max out and honor God and be your best, you're going to, I promise you, you have to be uncomfortable. And I'll say this, the difference for some of you between where you are and where you could be is the discomfort that you're unwilling to endure. You have to face it, step into it. So we've covered a lot of ground and it's been 10 years. We celebrate what God has done in 10 years. I'm going to give you some reflection questions. I want you to go over these with your team, if you have a team. And if this is helpful to you, please share it on social media, invite others to be a part. This content will be in the leader guide. If you don't have the leader guide, go to cglp.com and you can get the leader guide there. These questions are there.

These are the five questions that you want to ask yourself and apply or ask with your team. Question number one, what is a leadership belief that you need to admit is wrong? Name it, change it, adjust it, be quick at being wrong. Number two, what preferences are limiting the people you lead or the impact you could make? Think about it. Where is it that what you like, what you prefer is getting in the way of missional progress. You're not going to lead with preferences, but with purpose. Number three, where are you expecting something from others that isn't reasonable for their role, season, or capacity? You have high expectations for yourself, but you're expecting something from someone else that isn't fair for where they are right now. Number four, what good thing is distracting you from the main thing? What good thing, what good opportunity is distracting you from the main thing? Have the courage to say no, to stay focused. And number five, what discomfort are you avoiding that you need to endure and embrace? Super important. What is that thing that you're called to do that you need to do that you should do that you're not doing? What discomfort are you avoiding that you need to endure and embrace?

In the next episode, we're going to go a level deeper and we're going to talk about five other issues that you're going to want to adjust to grow in your leadership. Before we wrap up today, I want to just share with you from my heart and tell you sincerely, like, thank you, thank you, thank you for trusting me to invest in your leadership. You've given me the honor of sharing things with you that could help make you better. And I want you to hear it again. I told you earlier, but you're the reason I do this. It's not the numbers, not the reach, not the money because we don't monetize it, we don't sell anything. We just work really, really hard to help you grow in your leadership because when you lead well, when you lead with integrity, when you do it for the glory of God, you can make a difference in the lives of people. So I'm doing this for you and I'm going to keep doing this for you. Who are you? Who are you becoming? You're going to become the leader that refuses to quit and keep showing up when no one else even sees and making the sacrifices. You're the leader who cares enough to grow so that other people can win and make a difference. And so as you step into a new year, my prayer for you is simple and it's sincere.

And I pray, may God strengthen you with courage. May He deepen your character. May He expand your influence far beyond what you believe is possible and not for your glory, but for His. And after 10 years of doing this, I am absolutely completely more convinced than ever that your leadership matters. It matters more than you know because everyone wins when the leader gets better.