Posted on August 21, 2019

Last year, I, along with over 30 other riders, rode from West Cancer Center in Germantown, TN on a 5-day, 525-mile journey to Rosemary Beach, FL. The Ride to Rosemary supports the WINGS Supportive Care Division of the University of Tennessee/West Institute for Cancer Research.

As we’ve been preparing for this year’s ride, which departs on October 5, I’m reminded of the 5 leadership lessons I observed during last year’s journey. Stay tuned for another round of lessons from this year’s ride.

Lesson 1: Learn To Follow

Our group consisted of primarily Type A alpha leaders who are all successful in their profession and sphere of influence. So, how on earth did this group of 34 manage to ride TOGETHER 525 miles 18 inches apart for 6-8 hours a day for 5 days AND build camaraderie?

By choosing to follow each other – literally and figuratively!

All brought various skills to the team. Some were navigators and some were pacers. Some were strong engines that pulled the group to maintain it’s pace when others were tired. Some kept our bikes in top mechanical shape and some were encouragers and shepherds of souls. Many were a combination of these. Success came through the group’s submission to one another’s strengths and assignments.

EVERYONE had to follow and receive at some point. Even the strongest riders needed to follow in the draft of someone weaker at times in order to recover from a large output of energy. Even the most knowledgeable had to yield to the ideas of others for the sake of unity. This requires humility. Together, we accomplished our goal.

I have experienced times on other rides when the “leader” pulled off the front of the group beyond a point where the others could follow. At this point, the “leader” is no longer a leader because he or she no longer has any followers. He or she has simply become a person out for a bike ride.


Are you a good follower?
Only our pride stands in the way of our ultimate success if we don’t make an effort to follow, submit to and learn from others.

As my mentor, John Maxwell says, if you’re always the smartest person in the room you’re in the wrong room!

Who are you currently following and learning from?

Lesson 2: Love What’s Hard

“The obstacle is the way” – Matt Holiday

Before lunch, on day three of our ride, there were a few optional sprint segments. I decided to try to keep up with some stronger riders. It was fun, but, as they say, I “burned too many matches” with over 50 miles of hot-weather riding left. I was miserable through lunch and for about 2 hours after. I felt DONE but did not want to get in the truck that followed us close behind. Had I not been with the group I would have rationalized quitting. I’m glad I didn’t because even though I thought I’d hit my limit, I hadn’t. After pushing hard for hours with a couple of quick breaks I somehow came fully back to life and felt great for the rest of the day. My last 20 miles were my strongest of the day.

I love that I experienced those dark hours on the ride because it reminds me that when I think I’m done I’ve still got a good 20% left in the tank. The key is to keep peddling until you push through and find it.


Are you facing a challenging task or frustration you wish you could work around, quit on or make disappear?

What if instead of resenting a challenge, you embraced it as an important part of your journey to a much stronger victory?

What if you made the mental decision to love and embrace (not just survive) what’s hard because you know it’s getting you closer to where you want to be?

Lesson 3: Trust The Process

Before 2018, I had never ridden a bike further than 40 miles in a single day. One hundred miles seemed like it would be a significant challenge. I had too many body parts that hurt after being on a bike for only 30 miles! During our ride to the beach, I was able to knock out multiple 100+ mile days with relative ease.

How? Consistent, day after day, week after week preparation and improvement. Four months of training with progressively higher mileage and frequency. I simply had to start and continue the day-by-day process.

It’s easy to push off big, long-term, valuable goals because they seem insurmountable or we feel like we aren’t quite ready to tackle them. Instead of making progress we spend our days getting ready to get ready. The key is to lean into and trust the process because while growth happens daily, it does not happen in one day.

Like dollar-cost averaging and compound interest, daily effort and growth over time turns into something exponentially larger than what it was.


What’s your dream? Personally? Professionally? Within your family?

If you maintain the same habits you are living today will you get to where you want to eventually be?

What’s one thing you could change that would most improve your trajectory? If you can only ride the equivalent of 30 miles today what does it look like to ride 35 tomorrow?

Lesson 4: Prioritize People

Spending 24/7 for 5 days with 33 other people and getting a positive result requires relational intelligence – on everyone’s part.

Did people get frustrated with each other? Sure, but not nearly as much as you might think. When they did, the individuals involved were quick to apologize, grant forgiveness or just move on.

It takes a unique group to get along as well as we did. Each person had proven the type of character that results in positive relationships before the ride was assembled.

This was a great case study on how important it is to be selective in who you ask to join you in the pursuit of large goals that will require interdependence with others. Skill is important, but our group’s cycling ability varied significantly. In the end, it was not the most important factor relative to accomplishing our goal of finishing together and building relationships along the way.

I can envision a situation including athletes far more accomplished than many of us, but with less character, that would have produced a very different outcome. A lot of egos had to be left behind. Many people had to choose to be right relationally over getting to be right. At the same time communication had to be firm and clear. This requires a leader to have a high level of communication skills and emotional and relational intelligence.


Soft skills produce hard results and are frequently the difference maker for leaders who experience greater success than others. It also makes our work more ENJOYABLE since the greatest predictor of happiness is the success of our relationships.

I can’t imagine having to complete the ride alongside a bunch of jerks. Nobody wants to work or live with them either.


Do you sometimes feel frustrated or misunderstood by people?
Consider working on your emotional and relational intelligence skills.

Lesson 5: Autonomy Fuels Responsibility

There were some elite cyclists on our ride. What was a long day’s effort for me would have been boring for them, unless, they had some opportunities to really let loose! The leaders of the ride know this and did a great job building into our day’s sprint opportunities, king of the mountain competitions, back road rambles and more. Yet, they had also set clear expectations, locations and times for when the group needed to reconvene and ride together. this provided an optimal amount of accountability and autonomy.

In my executive coaching practice, I often see leaders err on one of two sides related to the level of autonomy given to their teams. Some like to empower without clarity and follow-up accountability. Others prefer to over-manage. Neither helps the team reach it’s potential.

High-level goals and expectations must be clear (such as finishing a 525-mile ride together), and so should consequences and rewards for achieving success.

Beyond that, high-performers thrive when they have the latitude to run, gun and experiment a little. This is essential to their buy-in, growth, development, and creativity. When an elite cyclist has a clear segment to race the way he or she wants it validates who they are and they don’t at all mind coming back together to help the larger group accomplish its goal. The alternative yields under-cultivated talent and a loss of focus and interest. The result becomes mutual frustration.


On a scale of 1-10, how good are you at balancing the accountability and autonomy you provide for your team?  How about in your parenting?

What’s your next step?


I hope you’re able to apply these practical principles to your current life and leadership circumstances.

I must say, however, that the fuel for all of the above was the purpose behind our ride. It was all about patients, loved ones and friends who have been impacted by cancer and other difficult life circumstances. These people offered continuous support, encouragement and refreshment (physical and metaphorical) along the way! Everything is easier when you have a big enough “WHY!” What’s yours?

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