These are the 5 lessons that cycling taught me about building a team

Over my 40-year career leading organizations in business, government, and now nonprofit, I’ve often looked to other experiences in life to learn and develop as a leader. One constant throughout that time has been my love for cycling and the many opportunities it has afforded to draw parallels between life in the saddle and life in the C-suite.

The list of lessons is long, but below are ones I’ve found to be the most relevant to leading an organization.

1. A strong, coordinated team wins the day

I marvel at the precision dynamics of the teams in cycling races. Riders are just inches off each other’s wheels, and move in lockstep and communicate seamlessly. Each element contributes to the pace and success of the team.

High-functioning organizations need their people to work together, trust each other, and constantly communicate. The more complex the issues and the more aggressive the goals, the more essential it is for the team to be in sync. I can think of more than one major initiative (as painful as it is to do so) where months of effort and millions in investments were derailed because leaders didn’t coordinate or communicate well and didn’t make informed decisions. But when the team is truly in sync, amazing things happen.

I’ve also learned that bigger riders generate a more powerful draft for their leader. As a CEO, I draft off of power riders every day—competent, confident leaders who think out of the box and can lead major initiatives, communicate their ideas, and inspire their teams. I can ride the fastest when I surround myself with high performers who excel and challenge me every day.

2. Smart, disciplined training builds a healthy, winning rider

When it came to physical pursuits, I was never very balanced in my training. I was the guy who trained at one speed—all out, all the time. Then a few years ago, I started working with a personal trainer, because I was experiencing too many injuries and wanted to build more all-around strength. When summer arrived, my Strava PRs (personal records) started adding up. Then, I began reading more about the value of a more diversified training plan to improve performance—long light rides, focused intervals, strength training as well as nutrition, recovery time, and sleep.

Leading a high-functioning organization is similar. There is a place for riding “all out” on race day, whether that be getting a major project over the line, negotiating a large transaction, or rolling out a new product. But every day is not race day, and the organization needs healthy foundations to perform when the pressure is on.

Organizations need time to refuel, to celebrate their wins, and to know the value every person, at every level, brings to its mission. They also need to develop their people and create a culture that encourages collaboration and growth. That way, when the next “race day” comes around, everyone can be at their best and not burn out.

3. It’s important to keep your eyes further down on the road and be agile along the way

I had a friend named Phil who was a lifelong mountain biker and had been a competitive skier in college. I learned early from Phil that when heading into a tough section, look ahead down the trail, pick your line, and ride over the boulders and obstacles with confidence. If you don’t, fear sets in, confidence wanes, and you’re much more likely to wipe out.

This balance of confidently committing to executing a strategy, through all obstacles, while being agile enough to course correct can be tricky. The same thing applies to business.

Business strategies supported by solid execution plans are great for giving us a thoughtful, informed path to pursue. They help us keep our eyes on the goal and manage through the challenges that come our way. However, much like in mountain biking, you need to be agile when new information comes along. That might require you to loosen your grip, or pivot to a better opportunity.

4. You need to love the climb to see the beauty along the way

In 2005, I spent 10 days in the Pyrenees with a group riding the peaks just ahead of the Tour de France. It was really hard and really wonderful. Along the way, there were centuries-old villages to savor, unexpected vistas, and fellow riders to share pain, amazement, and encouragement. At the end of the long climb, we literally shared a mountaintop experience with stunning vistas and shared joy in our joint accomplishment.

We typically look ahead in life and in our work. We have missions to accomplish, initiatives to be completed, crises to overcome, and organizations to build. But it’s the time we spend on those journeys where we build relationships, grow as leaders, and watch our teams flourish. And of course, when we get to the top of whatever mountain we are climbing, it all culminates into something remarkable.

5. Being strong is important, but you also need to have heart to succeed

We all wait for it when we are watching a world-class race. The peloton is riding along. You may have a group that goes ahead for a while, but others catch up. Then the magic happens. Someone or a small group taps into something greater to break away. And as they near the finish line, something supernatural propels a winner across the line.

I spent many years of my career as an investment banker and then a CFO. I understood the complexities of the financial world well and how to deliver results with confidence. But as I began to consider opportunities to step into the top job, I didn’t have the same confidence and felt like I was missing something.

In a meeting with an executive coach, he said to me, “Steve, you are operating as if the strongest arrow in your leadership quiver is your brain, but it’s not. It’s your heart. And if you don’t tap into that, you’ll never reach your potential as a leader.”

Not long after that, I was appointed as the head of a federal agency in the midst of a major disaster. I needed to draw on all of the financial and operational skills I had developed over many years, but it became clear to me that I needed to tap into the heart while doing so.

That perspective elevated my personal engagement and drove a higher level of creativity, compassion and drive that I had never experienced. And that taught me what is possibly the most important lesson of all—the best I had to give came out of me, because it came from the heart.