One of a 72-person cohort, I spent the past week wrapping my head around the concept of servant leadership in preparation for a two-day retreat, the kick-off of my “Challenge Year” within the 2014 class of Leadership Tomorrow.

These are charged words, servant and leader. Amidst a collective whose ages range from 29 to 59, we each arrived with pre-formed notions of their definitions, either relating to or distancing ourselves from them. Over the next nine months, my cohort and I will use these concepts as a lens through which to discover and enhance our individual leadership styles, exploring our roles within the communities of family, friends, colleagues and the city and region at large.

One facilitator encouraged us to shout out words that we associate with leaders. We responded with attributes such as strong, visionary and responsible, while we associated qualities like service, empathy and faithful around the notion of servant. “Do you consider a good leader be service-oriented?” he asked, crossing out the word servant and replacing it with leader. “Is a good leader faithful or empathetic? What about a servant? Can someone who serves also be strong and responsible? Can they not have vision?” He crossed out the word leader and replaced it with servant as we questioned our long-held stereotypes.

During the retreat, we reflected on instances when our practice of leadership led to failure. We were asked to share these stories with each other and assess what we could have done differently. What if we had started by inspiring a shared vision or empowering others to act rather than hoarding power? What if we celebrated diverse view points, encouraging team members to employ their personal styles rather than demand that they follow orders or be punished for not approaching tasks exactly as we might?

Our discussion leader opened that session by sharing, not in a two-person group as we did but with the entire room, his story of being promoted into a corporate position after a decade of success with his company. Up to that point, his leadership style was based on the “Trinity of Fear” as he called it: the desire to look good, to always be right and to be in control. His team produced results based on his demands with little context or recognition; the senior officers rewarded him alone for the results that he was able to wrest from his staff.

Those behaviors made him a “good” middle manager but ultimately undermined his success with everyone in his new role. After six months, he had been written up by his colleagues, taken to task by the same senior officers who promoted him and was on the brink of being fired. He realized that what he had been practicing wasn’t the kind of leadership that anyone wanted to follow.

In another session, we were asked to list the five richest people in the world, the last five Men and Women of the Year named by Time magazine, the last five recipients of the Nobel Prize and the last five winners for Best Actor or Actress from the American Academy of Arts and Letters. As a group, we failed miserably. We were then asked to list five teachers or coaches who mentored us, five people who taught us something or helped us through a difficult time, and five people who made us feel appreciated. We completed the exercise with minutes to spare, allowing us to reflect on what it meant for those lists to differ.

While these explorations felt familiar, what took them to another level was the seriousness with which we, as a collective, approached our investigations and shared results. Through a storytelling model, LT was able to transform a room of type-A solo-achievers into a cohort of reflective human beings willing to publicly relate experiences that they would have never revealed to co-workers or even spouses.

Our watchwords were trust and openness, two qualities that we had originally associated with servants, yet were being applied to the notion of leaders. Elevating the importance of personal reflection, which many in the group had seldom done before, especially with journals, was one way we tapped into these dynamics. Using personal examples as a means of group learning was another. Over two days, we allowed ourselves to become vulnerable with each other, rewarding that courage with empathy — daring feats for people who were just a hair beyond being strangers.

While exploring my own past, I thought first of the servant leaders I’ve known. My first boss, Jordan, remains the paragon. After graduating first in his class from business school at USC he assumed the role of vice president of the firm, but he never considered any role beneath him. When I saw him bend to pick up trash during our property walks or make his own photocopies, I could see the depth of his commitment; he saw his role as that of a steward not overseer. His actions encouraged me to look for ways to pitch in rather than avoid the seemingly menial tasks that my parents had cautioned me against.

Their worst fear was that would be stuck in what they saw as servile positions; to be a leader in their eyes was to earn the right not to serve. While Jordan’s modeling helped me think differently about leadership while acting as a supporting team member, I didn’t have the skills to carry forward the heart of these lessons into my early management roles.

After Jordan, I worked under a series of bosses who thrived on the Trinity of Fear, withholding information as a means of control, spreading word of their own accomplishment while diminishing that of others and intimidating diverse voices of colleagues into remaining quiet. Surviving bad leadership conferred a badge of courage in my eyes, which is how I came to think that one earned a position of leadership. While a tested warrior in my own right, I didn’t realize that I had actually adopted their bad habits as I advanced within each organization, for mirroring their practices was how one advanced. When it was finally my turn to lead, I failed miserably, not understanding how my own leadership style contributed to those failures.

My friends will tell you that I’m a caring, thoughtful person. My peers and senior managers will say that I’m a dedicated colleague who always delivers, even under extreme pressure. Yet, some of my former staff have only known my Trinity of Fear side; back then, my method of dealing with tenuous circumstances–cascades of crushing deadlines, terrorist executive management–was to try to control everything rather than to inspire and empower others. I told myself that I was trying to protect my staff or toughen them up so that they could one day assume my role, but it was actually a result of my not understanding what a real leader is, which is to say, a servant and a steward of something greater than a single individual or viewpoint.

At the retreat, we acknowledged the potency of being vulnerable with others as being one trait of the leaders we most admired. Direct but gentle counsel and the application of empathy helped us learn in their presence. They gave us room to solve problems in our own way, shouted our praises when we succeeded, allowed us to fail, and when we did, encouraged us to try again. They didn’t seek to recreate themselves in us, but hoped that we might find our own path, knowing that the success of individuals leads to the success of teams.

When I applied for LT, I saw it as a means of increasing my network and gaining focus within my profession and role in the community. I was also compelled by the changes I’ve witnessed in colleagues who have graduated from the program. After nine months of exploring complex topics with similarly dedicated individuals, many of whom are today’s CEOs, senators and cultural leaders, I watched my friends become deeply skilled in team situations both large and small. I now see that they were modeling leadership in every aspect of their lives, no matter their actual role on a given initiative.

When asked for details, they were often hard-pressed to describe the results of their Challenge Year experience in only a few words, which I now understand when people ask me the same. Like the community in which we reside, LT is so great a network of concepts, systems and ideas, all effecting one another–the economy, arts and culture, the environment, basic needs, health and wellness, to name a few–that to consider one’s relationship to one of these areas interlocks with stewardship of all of them.

Little did I know that storytelling lays at the heart of LT, and at the heart of all good leaders, so there’s a chance for me after all.