A Road Trip Teaches Four Women Leaders Unexpected Lessons

Lewellen-exec road trip2 March 28, 2022 By: Christina Lewellen, CAE

Sometimes it really is the journey, not just the destination. Four female association leaders discovered that on a road trip that ended up challenging their perceptions of each other—and themselves—while bonding over their shared profession.

The nature of a road trip is that it’s often filled with surprises, and ours certainly was—in many unexpected ways.

Three of my fellow women executives and I were signed up to participate in a retreat-style professional development event in a remote area of North Carolina last fall. For the time it would take to fly and transfer to the lodge, we figured we might as well drive. Sara Wood, CAE, executive director of the Public Media Business Association, Nicole Araujo, CAE, client engagement director at Mighty Citizen, and Lindsay Currie, CAE, executive officer at the Council on Undergraduate Research, and I loaded into a minivan in the wee hours of a chilly morning and headed south.

By the time we returned to our point of origin, we had spent more than 12 hours in that van together, and we couldn’t have imagined the strategic troubleshooting and profound leadership lessons that would emerge as the miles flew by.

Talking Points

As four leaders who have built our careers in association management, we had plenty to discuss between pit stops and road closures. We talked about the impact of the pandemic, the challenges from our C-suite vantage points, and what we wished we had known earlier in our careers. We also discussed what our jobs are going to require of us moving forward and how we’ve had to evolve our leadership styles to reflect the current needs of our staff, board, customers, and colleagues.

We explored how small associations are agile, and perhaps larger organizations should take a page from their book coming out of the pandemic. Other than a few stops for gas and snacks, we powered toward our destination discussing just about every challenge and opportunity in today’s world of association management.

We weren’t just filling time as we drove, we were co-creating a masterclass in modern leadership.

We weren’t just filling time as we drove, we were co-creating a masterclass in modern leadership. We knew while it was happening that it was a special opportunity to discuss challenges and support each other. What struck us a few months later is that the value of what we experienced would likely resonate with a broader audience—which is why we will be presenting “Modern Leadership and Strategy: Lessons from an Exec Road Trip” at the 2022 ASAE Annual Meeting & Exposition in Nashville.

“Humans did not evolve to exist in isolation, and we have to remember this as we develop our leadership skills,” said Wood. “Community is critical to modern leadership, and sometimes we find that community in unexpected places and experiences.”

Leadership Personas

One of the more surprising aspects of the trip was the exploration we did around our personas as leaders. The pandemic was hard on everyone, and we each had our own experiences to share about how it shaped—and continues to shape—us as individuals. As we discussed our unique perspectives, however, we started seeing some obvious threads of commonality. 

First, we observed that the pandemic had changed us—not just in the obvious ways, but in more subtle ways that didn’t strike us until the road trip. For example, if we asked 100 people who know the extremely gregarious, outgoing Nicole Araujo, where she falls on the introvert and extrovert spectrum, they’d probably unanimously say that her name is in the dictionary under extrovert. However, she reflected that as one of her first trips back after lockdown, our party-of-four van ride felt more comforting and natural to her. She usually gravitates toward crowds, on this trip, she relished the intimacy.

 “A wide network is valuable in the work I do. Creating a tight-knit tribe, that comfortable space to openly discuss topics, generate ideas, and reflect without judgment is equally as essential,” Araujo said. “We have to seek out opportunities to connect in truly authentic ways, and the road trip showed me a new opportunity—and how much I needed that.”

We also discovered there’s something about being positioned in a car that is inherently conducive to having a vulnerable discussion. We were all facing forward and looking at the horizon, not at each other. With little distraction from work and family, we were stuck in that van and focused on listening to each other. By isolating the nature of our interaction to primarily auditory, the self-proclaimed “extreme introvert” in our mix, Lindsay Currie, was able to join the discussion in a surprisingly unguarded way. “I’m not always quick to open up and lay my challenges out on the table for group discussion,” Currie said. “Something about the dynamic of being in a car created a safe environment. I knew I would get guidance without judgment, and the discussion just felt easier to me as an introvert.”

Guided by a GPS and interrupted only by occasional gas station stops, we defined on our road trip what it means to be in our generation of C-suite leadership—which is much different than what it was just a few short years ago. Our trip turned out to be the most memorable and resonant professional workshop of our careers. By the time we put the van in park at our destination, we felt empowered to tackle whatever lies ahead of us as leaders. 

Christina Lewellen, CAE

Christina Lewellen, MBA, CAE, is executive director of the Association of Technology Leaders in Independent Schools in Winchester, Virginia.