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Leadership Pilgrimage

| August 16, 2022

by Bill Wrobleski

[Today’s Tuesday Reading is from Bill Wrobleski. Bill is currently on a trail somewhere in rural France. Need to find him? Check or email him at [email protected].]
Tomorrow, I head out on a 1,000-mile pilgrimage across France and Spain. For over seventy-days, I’ll be walking the Camino de Santiago, a series of well-worn trails used by pilgrims for the last 1,000 years. The trails come from all parts of Europe and lead to Santiago de Compostela, Spain, the legendary site of the bones of St. James the Apostle.
In preparation for this journey, I have immersed myself in materials about the Camino. Books. Podcasts. Movies. Videos. I’ve consumed them all, and, although I take my first steps on the Camino as you read this article, I feel like I have learned so much from the pilgrims that have proceeded me. Many of these lessons are not only important with regards to taking on this hike, but they are valuable insights on relationships, leadership and personal priorities.

You win some, you lose some.
Each evening after a hard day of hiking, the pilgrim checks into a hostel or other lodging for an evening of rest and nourishment. Author Beth Justino quickly learned that some of these lodgings were wonderful, and some were not. All day long she would look forward to her next stop, and she would become discouraged when that night’s stay was dirty, cramped or uncomfortable. Everything changed for her when she adopted the motto: “you win some, you lose some.” It was her way of recognizing that today’s experience may be bad, but it’s only temporary, and great experiences still lie ahead.
This lesson is so simple and obvious, but so easy to ignore. Often a challenging or negative situation overwhelms us and dominates our perspective. When this happens, it’s helpful to remind ourselves, that we lost this one, but there are plenty of wins ahead. Optimism can be contagious in an organization, and is especially powerful when a leader is able to maintain an optimistic perspective when her/his organization is facing a particularly difficult obstacle.

Is your organization more or less optimistic because of the attitude you demonstrate?
Say “yes” more often.
On her Camino, author Kate Soper remembers clearly the day she walked by an Italian woman sitting by the side of the trail. The woman smiled, and asked Kate to sit down and offered her a piece of chocolate. Focused on her goal of reaching the next village, and not wanting to be a burden, Kate smiled and graciously declined, then she continued walking.
For hours Kate was haunted by this exchange. A kind person had offered her a gift and companionship, and Kate had turned her down without a thought. What experience had Kate missed? What stories might she have heard? What lessons might she have learned? Was a new potential friend lost forever? Until then, Kate hadn’t realized that her default response had become “no,” and as a result, she was missing out on so much.
Over our careers, it’s hard not to grow increasingly cynical. We’ve seen so much that nothing seems new. Ideas offered by others often look similar to things we’ve tried in the past with no success. As a result, slowly over time, “no” has become our default. Kate’s lesson is a valuable one for us all to consider. Innovation, learning and valuable experiences all start when we say “yes.”
Does your organization see you as someone who seeks “yes” or defaults to “no?”
Listen and hear.
Perhaps the strangest, and most wonderful thing about the Camino, is that although the pilgrims on the trail have never met before, they quickly open up and share details of their lives with each other that they would find difficult to share with their friends and families back at home. This means that as a pilgrim, a unique door into someone else’s life will be opened to you, and you don’t want to miss this precious opportunity.
The same is true for leaders. We have the chance to walk alongside so many people during our careers. Sometimes as subordinates. Sometimes as coaches. Sometimes as friends. In each of these roles our ability to not only listen, but to put what we hear into practice, is critical to our journey.
Podcaster and musician Dan Mullins put it this way to me in a recent email: “You don’t want to just listen – you need to hear.” Listening shouldn’t be passive. You have to be attentive and focused on learning. Simply put, good leaders listen, great leaders hear.

Despite your busy schedule and many responsibilities, do you still take the time to truly hear people?
Keep it simple, stupid.
Camino life is the ultimate form of simplicity. Each day is exactly the same. You wake. You eat. You walk. You sleep. This pattern repeats itself for weeks on end. The complexities of deadlines, strategies, budgets, and the other aspects of professional life are forgotten. There is time to breath and to think.

Simplicity is reinforced by the very few possessions pilgrims carry with them. Every pound carried adds stress on the body and increases the risk of fatigue and injury. It’s common for pilgrims to jettison items along the trail that they once thought were necessities. Author Russ Eanes put it this way: “On the Camino people brag about how little they have rather than how much they have.”
All this leads to a transformative experience for pilgrims. They find that the complexities and abundance of their normal lives start to look shallow and unsatisfying. Their busy lives and full closets aren’t quite as important after they realize how little they truly need to be happy.
I’m not suggesting we all quit our jobs and live on the trail, but we should learn from these pilgrims. We need to find ways to bring simplicity into our individual lives, and into the cultures of our organizations. If the leader of an organization lives life at a healthy sustainable pace, that can trickle down through the organization and have great benefits for our employees and our institutions.
Is your lifestyle/workstyle demonstrating to your team the importance of healthy balanced lives?
Plan B is Plan A.
People outside of our industry think IT is about computers, but those of us inside the industry know that IT is about planning. We seem to spend all of our time developing strategies, planning projects, and overseeing roll-outs. All this planning is for one purpose, to have control. We want things to be predictable.

If the Camino is one thing, it’s unpredictable. The weather can change. Lodging plans may fall through. You may get sick or hurt. You may get lost. Beth Justino shared this conclusion with me about the unpredictability of her Camino: “It all led to a reminder that there’s a lot in the world that’s not in my control.”
While control is illusive, adaptability is not. Problems that arise frustrate everyone, but an adaptable pilgrim doesn’t let the problem ruin the journey.  Instead, the pilgrim recognizes overcoming challenges is an important part of the pilgrimage. A pilgrimage with no challenges is just a walk. Similarly, an adaptable leader isn’t wed to a plan, but rather to accomplishing a goal. The leader recognizes that the team’s success often depends on how smoothly one can react to problems and move the team from Plan A to Plan B.
Do you help or hinder your organization’s ability to react positively to problems, and to adjust plans in a timely manner?
Leadership pilgrimage.
“A pilgrimage is a journey, often into an unknown or foreign place, where a person goes in search of new or expanded meaning about the self, others, nature, or a higher good, through the experience.” (Wikipedia, 2022)
In the MOR IT Leadership Program, we often talk of our “leadership journey.” In fact, one of the critical aspects of the program is when participants document their own journeys and present them to their cohort.
I wonder though, if the term “leadership pilgrimage” may be more appropriate for this exercise. We aren’t just on some random trip that is beyond our control, we’re on a journey to somewhere special. We’re on a pilgrimage. A pilgrimage where we intentionally seek to learn who we are, how we can positively influence others, and how together we can achieve great things.
Are you intentional about the direction you are headed in your leadership pilgrimage and how that benefits both you and your organization?

This Week’s Survey

Which topic do you find most captivating to further explore?  How your organization is impacted by your…


From Last Week
Last week, we asked: Which part of executing on strategy resonated most with you?

  • 30% said setting the vision and its targets.
  • 24% said gathering input.
  • 18% said removing obstacles.
  • 17% said convening and encouraging.
  • 10% said free celebratory beer.

It’s not surprising that the answers to last week’s question were so varied.  Like most processes, leading and executing strategy is one where each step is critical, although the exact order and intensity of each step may sometimes vary given the situation.  Also, a common thread to notice across all the items: leading and executing strategy is an inherently social process.  The key steps of successfully leading strategy involve the ability to motivate others toward a common vision and goals and then enable and celebrate their successes.

Additional Reading
Chernside, Bradley. (2019). The Only Way Is West: A Once in a Lifetime Adventure Walking 500 Miles on Spain’s Camino de Santiago.  Bradley Chernside.
Easnes, Russ (2019). The Walk of a Lifetime: 500 Miles on the Camino de Santiago. The Walker Press.
Foster, Elaine and Joseph. (2015). In Movement There is Peace: Stumbling 500 Miles along the Way to the Spirit.  PsyConOps.
Justino, Beth. (2018). Walking to the End of the World: A Thousand Miles on the Camino De Santiago. 2018. Mountaineers Books.
Kevin, Tony. (2014). Walking the Camino: A Modern Pilgrimage to Santiago. Scribe Publications.
Piper, Alisa. (2017). Sinning Across Spain. Victory Books.
Prince, Victor. (2017). The Camino Way: Lessons in Leadership from a Walk Across Spain. American Management Association.
Soper, Katherine. (2020). Steps Out of Time. Stellaire Press.

Additional Listening
Brennan, Leigh. (2021-2022). The Camino Café.
Mullins, Dan. (2017-2022). My Camino – The Podcast.
Whitson, Dave. (2019-2021). The Camino Podcast.