I returned about a month ago from a trip to Iceland, a week-long motorcycle tour with my spouse and two good friends. The motorcycle trip is an annual event, with a new route and different destinations each time, and we have been all over the United States and abroad. When I reflect on our adventures over the last ten years that we’ve been traveling together, I see analogies between our motorcycle experiences and advice for leaders. Here are the leadership lessons from our journeys:

Be prepared, but expect the unexpected. Leaders set goals for their organizations and teams and plan ahead of time the best way to accomplish them. But it is almost certain that we will run into unforeseen snags, issues, and challenges. On every trip, I take many layers of clothing, to accommodate cool through hot weather, and I also take waterproof rain gear. This usually gets me through most conditions. Some of the things that me and my crew did not anticipate over the years were: running out of gas in the Arizona desert, losing a custom-fit oil cap in a remote part of southern Virginia, and getting multiple flat tires while riding off-road in Iceland. When there is no cell phone service, and no one else around for many miles, it’s up to you and your team to figure out Plan B. And no one is going anywhere on a flat tire or without an oil cap. One of your jobs as a leader is to help your team solve problems and continue toward your destination.

Meaningful goals come with discomfort. You may set “stretch goals” for your team, which means that all of you will be pushed past the bounds of what you thought was reasonable or possible. However, in setting such goals, it also means that when you achieve them, you have the satisfaction and pride of accomplishing something new and challenging. On every motorcycle trip that I have been on, I do at least one thing that pushes me out of my comfort zone. But I do it because I know that the payoff is worth it. I have willingly ridden through 45mph crosswinds in Utah to see the incredible Dinosaur National Monument Wall of Bones, hail on Independence Pass in Colorado for the view at 12,000 feet, and rocky unpaved roads in Iceland to see amazing landscapes with glaciers, natural hot springs, and waterfalls. And the nice side effect is that I have more confidence that I can attempt and accomplish more than I ever have. If you set high expectations for your team, make sure that they understand ahead of time what you are asking of them, and give them the support they need to meet the challenges.

Pick the right team. Even the best leader cannot make the journey without a strong supporting cast. There is so much that you can’t control, but what you can control is whom you travel with. And this in turn means choosing a team with certain attributes – complementary skillsets, different perspectives, the ability to collaboratively problem-solve, mutual respect, and an ability to maintain a positive outlook and calm demeanor even when dealing with adversity. Challenges should bring your team closer together not push your team apart. Our bumps in the road (pun intended) over the years have turned into great stories than we continue to tell over and over. And we continue to look forward to next year’s trip, knowing that it will likely come with some combination of getting lost, wild weather conditions, more flat tires, and who knows what else. I can’t wait.

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