Pretender or Contender?: A Leadership Case Study


I have good news. You need far less than you think in order make a fundamental change: personally, professionally, or organizationally.


The tough news is that making a firm decision to actually change is hard. In fact, it’s the hardest part of any transformation process.


Very few leaders have had the life-experience or the deliberate mentorship to learn how to do this strategically, deliberately, and on demand when circumstances require it. Most of us do not confidently sail into the future - at least in all areas of life. We are dragged into it. If you're like me, often kicking and screaming.


And yet, this is one of the key factors that separates a good-enough leader from a great one.


You can’t buy resolve from a consultant. There’s no packaged program of defined steps that will download determination into your psyche. When it’s time to change, you either will or you won’t. It’s entirely in your hands.

As my favorite little green mentor said, “Do or do not. There is no try.”


What the master from Dagoba meant with the above advice is that you must decisively put yourself into a position where you will either definitively succeed in making the change or fail boldly.


To “try” is to hedge your bets, or rather, your ego. To “try" is to leave yourself an out. It’s an attempt to bet on yourself, while wagering as little as possible. It's the mental equivalent of hoisting the sail, casting off your mooring ropes, putting one foot on the boat, and leaving one foot on the dock. You won't be going anywhere except into the water.


In Lead from the Future: Leading Conflict Principle 9, I discussed how to lead change in an organization by behaving “…as if the thing you want to be true has already happened. Then work backward to fill in the relational or cultural architecture that will cement that reality into place.”

The central fallacy around which many organizational culture-change programs and leadership consultants build their product is that the order of change activities looks something like this:


Present --> New Skill/Process/Program Acquisition --> Change to Desired Future


In reality though, the psychology of change looks more like this:


Present --> Change to Desired Future --> New Skill/Process/Program Acquisition


This means that there’s a definitive, though often overlooked step that comes long before the acquisition of new skills and abilities.


This is the step where a leader must make a definitive decision to step into the future before it is fully formed. This is not simply a trick of “mindset”. It is the tangible and concrete ability to selectively and usually prudently say, “This is happening. Come what may.” Then, back it up with action.


This is hard to teach, which is why most mentors don't sell it. It's the part that most clients want to avoid, often in the vain hope that they can outsource the risk, fear, and doubt related to change.


However, proficiency in this stage of change can be taught or learned from experience. The first step is that leaders and organizations must face what makes this stage hard, namely:



The more you practice those four fundamental principles, the more ready you'll be to make a move and lead from the future (Principle 9) when needed.


If this early step is skipped, no new practice or program will stick. In fact, if this stage of change is neglected, the organization will likely attempt to import change from the outside. This might be framed as needed expertise, insight, or technical support.


In reality, the use of outside resources will simply be an attempt, consciously or unconsciously, to offset uncertainty and the possibility of failure. In other words, the organization will blame the program or experts they hired, and not the real problem, their own leadership proficiencies and internal culture.


No external expert can do the one thing that is the organization’s, and ultimately the leader’s job alone: decide what’s next.

Here’s a short case study.


Much too long ago, I attended a very small rural high school. In addition to our wonderful language programs, top-shelf quiz bowl team, and excellent theater program, we were also known for having perhaps the losing-est football team in the state.


Since they first hit the field in the early 1970’s, this team had precisely zero winning seasons by the time I joined. If memory serves, they often went several years without winning a single league game.


There were lots of excuses bandied about for this spectacularly consistent under-performance. The school was small. Soccer was a winning program that drew some of the best natural athletes away from gridiron greatness. Funding was limited. Etc., etc., etc.


However, it’s one thing to be a mediocre sports program. It’s quite another to be this consistently awful through multiple generations of players and coaches. Then, just around the time I moved into the school district, a new team of coaches correctly assessed what the real problem was. This history of failure had nothing inherently to do with the people in the program or funding. The problem was the culture.


One coach in particular is remembered by all. He was a tough-as-nails combat veteran who had done multiple tours as a Marine in Vietnam. He had, as they say, “command presence.” When he talked, you listened. He didn’t need to yell. He just needed to look you in the eye.


At the time, we were the most scraggly bunch of unlikely candidates for transformation that you could imagine. We were (in order of generational pop-culture) the Dirty Dozen, the Bad News Bears, or dare I say, the Mighty Ducks.


Instead of practice one Monday afternoon, this coach called a team meeting. As usual, we had lost badly the previous Saturday. As we sat around goofing-off and talking about everything except football, the coach walked in and simply stood at the front of the room staring at us. We quieted down, but he didn’t speak. He just stared, and stared, and stared.


Eventually, he said with a strange mix of sadness and intensity, “You didn’t just lose. Hard as losing is, that’s something we can work on. No, you gave up. I saw it. You saw it. You gave up last Saturday and you’ve been giving up all year. This isn’t just about football. It’s about who you are and who you want to be in life." His eyes began to water. We had never seen him like this.


He said, "I can teach you everything you need to know about football, but I can’t give you self-respect. That's something you have to give to yourself.”


You could have heard a pin drop. Now, a few guys were also quietly tearing up. Coach continued with something I’ll never forget:


“You need to decide if you’re a pretender or a contender. If you’re only here to pretend, to wear a jersey around school and date cheerleaders, we don’t need you. I’ll field a team of freshman who want win before I’ll field a team of pretenders.”


He told us plainly, “Pretenders will never win. They don’t deserve to win.”


Heads hung low.


“Or, are you contenders? Being a contender doesn’t mean that you’ll win every game. It does mean that you’ll train to win. You’ll run every play to win. You’ll leave everything on the field at every game, every weekend. It means you’ll start doing the one thing I can’t make you do, believe in yourselves.”

He ended by saying, “There’s no practice today. If you’re not 100% committed, if you’re just a pretender, leave your jersey in the room before you leave. We don’t need you. I only want contenders at practice tomorrow, because we’re going to start training like young men who intend to win.”


Then, he left us in the room not knowing what to do next. What followed was a lot of soul searching. New leaders spoke up. Promises were made. To a sixteen-year-old kid, it felt like this.


It was the beginning of something new.


Those of us who showed up the next day should have also been told to “prepare for hell”, as the coaches made good on their promise that a new day had dawned. The intensity of practice, shall we say, increased dramatically.


Over the next year, we starting doing all of the things that winning teams do. We started a yearlong training cycle, three-a-day practices in the summer, powerlifting programs, sprinting coaches, etc. We also showed up on time for practice. We stopped partying before games.


All of those things helped, but none of them alone or together were the reason for what became a miraculous turn-around.


We started acting like a winning team. Many people mocked the change in behavior, and deservedly so based on our past performance. This upped the psychological ante and meant we had to make it real – every single Saturday. We desperately wanted to earn the new identity we were now practicing. We weren’t pretending anymore.

Then, we beat the previous year’s league champs.


“Aww, just a fluke..,” many said.


Then we beat the second-ranked team. With our newfound determination we racked up a couple more wins before the end of year, but still ended with a losing record.


The next year, we had the first homecoming game win in school history (yeah, really…). We ended the season 6-5, decided by the final play of the final game, against the local rival. Pretty sweet.


Admittedly, “first winning season in school history” is not the most glorious of distinctions. You don't get a trophy for that.


Yet, it would have been impossible if we didn’t decide we were going to be contenders. And compared to the past, we felt like champs. No one gave it to us or made it easy.


There was nothing mystical about it. We started winning when we decided to behave like we deserved to win. Then, we did the hard work to make it happen – not the other way around.

That’s why “leading from the future” works. Our coach realized that there was no path to success within the prevailing cultural reality. He, like us, was enmeshed in a story (in this case about a football team) that would always be about losing, failure, and quitting.


We were all playing parts handed down to us. The faces were different, but the story was always the same. Depressing as it was, that story was strong and durable.


So, coach didn’t just change the story, he started a new one.

At first, he was the only person in that story. As he said, he was only going to coach contenders. He made good on that promise. Some seniors and juniors with bad attitudes were benched or sent packing. He put fired-up freshmen and sophomores in the starting line-up when needed. Gradually, he and the rest of the coaches built a new future from scratch, brick by brick, person by person.


He taught me one of the greatest leadership lessons of my life. If you want to change the story of an organization, you lead by being the first person to go all-in on the future. Coach was willing risk failing miserably, and potentially look like a fool in the process, in order to create a different future.

The other day, I drove past my old high school. In my day, the football field was a pot-holed mud puddle. The stands were tiny and usually quite empty – even when we started winning. We had no lights, so games were always on Saturday mornings.


As I drove by, I realized it was Friday night. Huge stadium lights glowed far into sky and lit up the new professional-grade turf field. Hundreds of fans were packed into a new and expanded stadium paid for many years ago with donations from the community. They'd been a winning team for many years now, and they had a stadium to match.


The guys on the field and people in stands were living in a new story – one that started decades ago. It started when a coach walked into a musty room and looked a doubtful group of young men in the eye and said:


The future is here. Who’s coming?


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