When the Map Fails: 580,300 Steps, 414 km and the Unwritten Rules of Resilient Leadership
(Voir ce lien pour la version française)
Disclaimer: Any resemblance to real persons, living or dead, or actual events, or actual organizations is purely coincidental.
We got off the bus in Lucca, Tuscany, Italy, and there was a huge crowd we weren't expecting to see near the bus stop. Lucca is a pretty small city with a population of 89,000, located on the left of Italy's boot, on the thigh (this is how I remember Italy's map!).
The ancient walls rose before me like an impossible organizational challenge; 414.5 kilometers of walking stretched ahead, 8955 meters of elevation to conquer, and countless unknown variables between here and Rome. I didn't realize then that I was embarking on the most profound leadership education of my life, one that would fundamentally transform how I approach organizational change.
Superhero costumes were everywhere, with participants dressed in blue, white and red outfits, holding circular shields with a star in the centre. Some were Captain Americas, other were Superman or Spiderman, and the cosplayers' costumes was a great contrast to this walled city that dates 180 BC.
The architecture of Lucca is something that strikes you the first time you set foot into the city, with the Renaissance fortification encircling the main part of the city, 4km length and 223 meters in circumference. It replaced in 1648 the original Roman fortification that was erected as early as 180 BC, a military castra (camp), common of Roman Empire.
It was beginning of November 2014, with a clement weather, cool autumn breeze, and colourful foliage, and the racket of chanting participants disturbed my attention and took it away from the hidden beauties of this ancient city. The contrast between these modern celebrations and ancient stones mirrors what happens when traditional organizations first encounter agile methodologies, disorienting but potentially transformative.
Later I discovered that The Comics & Games Festival was one of the major of the type in Europe, inaugurated in 1965, it is held starting end of October and extending a few days into November, in conjunction with All Saints' Day.
The Path and Its Purpose
This was my first trekking experience. The plan was to walk from Lucca to Rome, on the Via Francigena, covering 414.5 kilometers with an elevation gain of 8955 meters. The route was pretty much unknown to hikers in 2014, and there were very few people walking it in groups. The road is also called Roman routes, and was built in the 6th century by Lombard population who needed to connect their cities. From the end of 8th century, and the annexation of northern Italy to the Kingdom of the Franks in 774, the Pope Hadrian I called for the route to be known as Via Francigena, literally "road originating from France". The destination of the road is set to be Rome, and the first written description of the route is in the report of Sigeric, archbishop of Canterbury.
Like the organizational transformations I would later lead, this journey had ancient foundations but required modern navigation. The well-worn path still demanded constant vigilance and adaptation.
For someone like me born and raised in country governed by theocracy, where religion has made a lot of damages, I am "allergic" to religions. I believe in what Harari says about religion: "religions are filled with fictional stories, invented by people" and that "people are free to believe in gods if they find it helpful, but there is no need for gods in order to live a good life. Morality doesn't mean 'obeying gods'. Morality means 'liberating yourself and others from suffering'".
Standing before ancient monasteries with my skepticism of organized dogmas, I learned something essential about transformation leadership. The most powerful organizational change doesn't come from imposing belief systems. It liberates people from meaningless paths. The best transformations don't demand blind faith in leadership manifestos. They create tangible improvements in everyday lives.
Although Via Francigena is a pilgrimage route, and it requires to carry "Credentials", a kind of let-in permit allowing you to lodge in monasteries along the way, you don't need to be religious to undertake the journey. The simple fact that you are using the trek to reflect and to discover new horizons is enough to carry this document rich in intangible meaning.
The Transformation Connection
Trekking has had an immense impact on my strategy to company-wide change management and organisation transformation. My capacity to understand the road, know the history and context of the path I am walking on, reflect on what I want to accomplish by undertaking a trek are the most important parts of my preparation. Once the mission and purpose defined, gathering information about the trail, structure it and transform it to lived knowledge are other ingredients of more than 2000 kilometres I have walked in Italy, through French Alps, in Scotland, in Japan and in Portugal.
When leading any transformation, understanding context is vital. The company's legacy systems aren't just technical challenges. They carry cultural and historical significance for long-tenured employees. By learning the "history of the path" before attempting changes, we can avoided resistance that would otherwise derailed any transformation attempts.
Companions on the Journey
When trekking, you should know your companions and evaluate their capacity, knowledge and strengths, their resilience and perseverance and see if they fit the objectives you are trying to achieve. Some treks are more about reflecting and even though they spread over 400 kilometres, you won't have to ascend much, and as far as you keep the daily objective in mind, you can allow yourself an unsteady pace, and some wondering around. On the other hand, some treks like the ones in the French Alps, are demanding.
The French Alps trek broke people differently than the leisurely Italian countryside. With more than 1500-meter daily climb on hostile terrain, no water for kilometers, and mountain cabins seemingly never getting closer, I watched trekkers who talked confidently at breakfast abandon the path by noon. Your digital transformation or cultural change has identical breaking points. The executive who championed the initiative disappears when the legacy systems prove more entangled than expected. The enthusiastic early adopters revert to old methods when the new approach requires genuine sacrifice.
If you are walking with companions, you want to know if they can surpass the physical barriers, push themselves to go above when they are facing a mountain they have to ascend. The first days will be fun walking and discovering the mountain, but without perseverance you will never finish the route, and you risk turning around and quitting. It is a constant negotiation with yourself, reflecting on your capabilities, thinking about the purpose of the journey, and reminding yourself that with each ascending you gain elevation, you come across a new perspective you didn't see before, and that will set your next summit in perspective.
There are ups and downs everyday, literally and metaphorically, as by each ascending you gain confidence in your capacities to conquer your fear of "not being able", and that the reflection along the way, and the final view from the summit, something most people will miss because of not walking this trail, is your reward to keep going.
Mountains teach brutal leadership truths. Each ascent confronts you with your fear of inadequacy. Each summit rewards you with perspective invisible to those who never climb. Each descent reminds you that achievement is temporary. Most organizational transformations fail not from lack of vision, but from inability to navigate these emotional terrains.
Finding the Path
I classify the Via Francigena on the easy side of the spectrum. Although we had rearranged the steps to walk about 30 to 35 kilometres per day, some days went as far as a marathon, about 42 kilometres of walking. The trail wasn't as organised as today, with a well-designed website and an application you could download on your phone. Trekkers like us were reliant on the map provided by a few previous trekkers, and a paper map, accompanying the official book of the route. The signposting was not maintained in many areas and being lost in reflection could cost us a few more kilometres of walking when getting lost in Italian countryside. Our automated cerebral algorithm was searching for signs every few steps, to ensure we are on the right track.
Our eyes frantically searched for trail markers at each fork, our brains becoming pattern-recognition machines devoted to finding painted stripes on trees and rocks. This is precisely how effective transformation leaders operate, hyperaware of leading indicators, constantly adjusting based on subtle market signals that others miss, never allowing comfortable momentum to blind them to directional shifts.
Discovery Through Openness
When arriving in any city, the excitement was still there, because you get to knock on the door of some of the oldest monasteries in Europe. You never know who will open the door, how many people are living inside behind the tall walls, what your room will look like, what you will eat and what discussions you will have with the habitants of the monastery. Everyday was a novel discovery of the sceneries, architecture, thoughts, scents, people, flavours and perspective. A curious polymath mind like mine felt in heaven as the variety of information gathered was so rich, and the discussions strengthened the interconnections between all these novelties.
The monastery door creaked closed behind us, offering blessed silence after pushing through the day's walk. This threshold moment, moving from chaos to calm, from action to reflection, is precisely what organizations systematically eliminate in their transformation efforts, yet it's where the deepest insights emerge.
Maintaining an open-minded attitude was what made the journey so enjoyable for me, as despite my past relation with religion, I seek opposite perspective in everything to challenge and question my point of views, and see the blind spots I am not able to notice. I find that our vision of any topic is like the one from an arrowslit in a castle: a narrow vertical aperture that although we think provides a wide view of the landscape, is limited by the width of our own knowledge.
Every organization peers through its own arrowslit: narrow vertical apertures in the castle of industry experience. The most transformative leaders I've worked with deliberately seek the view from other castle windows.
I carry Socrates' paradox with me on every trek and into every boardroom: "Knowing that you know nothing is the true form of wisdom." The most dangerous transformation leaders are those convinced of their certainty. The most effective are those who maintain Socratic curiosity while still moving decisively forward, certain of the destination but humble about the exact path.
The Value of Silence and Reflection
There is a richness in connecting with those behind the tall doors, in pushing a heavy monastery door, in discovering the hidden world behind it, in connecting with the ones who spend their time in reflection and silence, more than the majority of the human-beings on this planet. We are flooded with distraction and the unique experience of not having any network on my phone for 20 to 30 days, or books to read, made my focus so sharp, my ears wide open, my senses more receptive and my thoughts sorted. There is another world beyond the messiness of noise and clutter we are flooded in, and the luxury of silence and reflection is only offered to those who are ready to give up the frenzies of modern society, even for a few days.
The Summit View
More than 2000 kilometres walked by foot ascending 58784 meters, 5 months in a lifelong, and a lasting impact on change and transformation. The summits I conquered in my treks are countless.
Each of my steps across the 414.5 kilometers of Via Francigena taught me something corporations pay millions to consultants to learn: transformation isn't measured in grand announcements. It is a daily commitment. Organizations track the wrong metrics, focusing on the destination rather than the quality and consistency of each step.
Knowing how your organisation is adapted to the transformation treks it undertakes is a wonderful way of discovering forces you were not aware of. The capacity of daily walks or how much each individual is able to deliver per day, the resilience of your organisation and adaptability to follow the plan A, and switch to plan B or C or come up with another plan if things don't work out. The perseverance to start a big meaningful journey, pass the excitement of the first step and be steady in achieving each step over a long-distance trek, without abandoning the path and heading back. The capacity to be aware of the arrowslit through which you see the world, and the openness to discover other perspectives, even if they are totally opposite to your beliefs. The ability to trust in the summit you are trying to achieve, and communicate its beauty around you, to inspire those who are in doubt of the destination, and lead them to the summit you have envisioned. The aptitude to focus on getting to one destination, breathe in the achievement, take in the view, and prepare for the next destination, as "the fool who walks will go further than the intellectual who sits".
The monastery bells of Rome finally rang for us after 414.5 kilometers, 8955 meters of elevation gain, and countless blisters. But the real achievement wasn't reaching Rome. The real achievement was in the daily decision to continue when giving up seemed wiser. Your organization stands at its own Lucca now, with a distant Rome calling. The question isn't whether you'll face mountains, get lost, or doubt the path, because you will. The question is whether you've built the muscles needed for the journey that matters most.
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Disclaimer: Any resemblance to real persons, living or dead, or actual events, or actual organizations is purely coincidental.
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