Leadership and the Art of the Annual Motorcycle Trip

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Leadership and the Art of the Annual Motorcycle TripWhoo! School is back in session and I am so happy to be back at LMU and meet my wonderful new students! I must say however, that September is kicking my butt with busyness. So, I am very lucky that the Chief Development Office of Harris and Associates, Steve Winchester, has agreed to write a guest blog post for me! (full disclosure- he is also my husband!). Do you recall the classic book, Zen and the Art of Motorcycle Maintenance by Robert Pirsig? Well, in this guest blog Steve shares his own version of that book with a look at leadership and the art of motorcycle maintenance on his annual trip with his college buddies . Enjoy!

Leadership and the Art of the Annual Motorcycle Trip
Steve Winchester, Chief Development Officer, Harris & Associates

Each year I take a motorcycle trip with three former college roommates and longtime friends. Our annual sojourn this year began when I joined the group in Columbus, Ohio and included , Canton (Football Hall of Fame), Buffalo, Niagara Falls, Toronto, Ontario, Quebec City, Bar Harbor, Maine, Hanover, NH, (Dartmouth College) Cooperstown, NY (Baseball Hall of Fame), Owego, NY and back to Columbus. My friends actually started and ended in St. Louis, MO, so their trip actually covered close to 4,000 miles in 9 days.

Reflecting after our journey had ended, I realized here were a number of important leadership/business lessons manifest in the trip which I will share in the balance of this piece.

The first lesson has to do with the communication of the vision in sufficient detail that it becomes actionable. While we each had a good understanding of the general route of the trip, only two of the riders actually spent detailed time examining the day’s route, so were intimately familiar with the various exits and highways to be traveled. Unfortunately, we did not do a good job of communicating the specifics of the trip, so when an exit was encountered, not everyone was in the appropriate lane to exit which necessitated a couple of unnecessarily, close calls. If we had taken just a few minutes to go over the details of the day’s route, we would have all been able to prepare for exits appropriately. The business parallel is readily apparent and involves first making sure the vision is communicated thoroughly and completely in sufficient detail to action. Many companies do a great job of developing their vision, but a less good job at breaking it down to actionable bits and communicating up and down the organization.

The second lesson learned involves the path not always being as planned which therefore required us to exercise agility and resilience. We seldom book our hotel rooms ahead of time and when we arrived in Ottawa we could find absolutely no rooms anywhere near. Ultimately we found a room, but had to backtrack some 50 miles. Not to mention there was only one room at the Arnprior Motor Inn (not exactly 5 star accommodation), so we shared a room and two of the group had to sleep on the floor. You’re probably thinking the lesson learned was we should plan ahead….well that wasn’t my takeaway. My takeaway was sometimes you have to move backward in order to move forward. In business, you learn that life is not linear moving forward in a straight-line toward the vision. It is filled with setbacks and sometimes requires you to sleep on the floor! Be prepared for these setbacks and do not be discouraged.

The third lesson came when, on Labor Day, one of our motorcycles had an issue with the linkage and would only proceed in first gear. As you can imagine, on a major holiday in the middle of nowhere, there was no help to be had. However, because of the diversity of skills in our group one was particularly skilled in repairing equipment. This wasn’t his educational background, but believe me this diversity of skill was invaluable. After a trip to a local, small town hardware store to acquire a few tools and parts, in combination with this person’s skill, after just a few hours we were back on the road with a repair that held for the balance of the trip. My leadership takeaway has to do with the diversity of skills and experiences of our teams. You never know when a situation will require someone to dig deep into their bag of tricks to produce a winning result.

The fourth lesson came when one of the members of our group had to cut the trip short after receiving a call in the night that required him to depart early the next morning to head for home. This person was the heart and brain behind our operation and we relied heavily upon him, particularly for developing our daily route and then navigating during the course of the day ensuring we arrived at our location before dusk (when animals are more likely to be on country highways, posing a danger to motorcyclists). When he had to unexpectedly leave the trip, it required the balance of us to take on different roles. One of us had already been working closely with him on the daily routing, so he assumed that role while one of the other of us (with good eyesight!) took on the role of leading the ride. The leadership lesson for me involved succession planning and not just long term succession planning, which is crucial, but also to have a plan in the event of an unexpected departure from the firm.

My final takeaway from the trip is that it was successful only because we had the resolve that at the end of each day we will have reached a certain destination regardless of traffic, weather, mechanical or other issues that could have caused us to deviate from the plan. We were accountable to ourselves and to our group. Again, business parallels in this observation are obvious, always keep focused on where you are headed and don’t let obstacles deter you from achieving your goals.

While at first glance a motorcycle trip has nothing to do with business or leadership, I hope you can see the parallels and will derive some benefit from these observations.

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