Navigating Leadership Pitfalls: Insights from the Caldwell Conversations Conference

The medical profession often faces the temptation to cut time short on patients with mental health concerns due to low reimbursement metrics. Balancing this reality with authentic servant leadership was just one of the thought-provoking discussions at this year’s Caldwell Conversations Conference. Bringing together alumni and current Fellows, the event fostered meaningful dialogue on the challenges of servant leadership under the theme of Navigating Leadership Pitfalls.

The conference featured a diverse panel of alumni and student storytellers, including Frank Gordon (’85), Amanda Rose (’06), Raven Solomon (’08), Juan Lopez (’26), and Josiah Keilison (’16). Developed and facilitated by Cary Strickland (’07), the event was structured around three guiding questions exploring leadership challenges on societal, relational, and personal levels. Each section was introduced by two speakers who shared stories of their own leadership pitfalls, setting the stage for small-group discussions focused on struggles and strategies for staying true to one’s values.

Balancing Societal Expectations with Servant Leadership

The first discussion examined how leaders can navigate external success metrics while remaining aligned with the principles of servant leadership. “We realized that the servant leader’s hierarchy of priorities is the inverse of society’s current hierarchy of priorities,” commented Sandra Younger (’75). Attendees engaged in exercises to categorize and prioritize common societal values, identifying those that truly reflect leadership consistent with their core beliefs.

Leading with Compassion Over Competition

The conversation then shifted to relational challenges, emphasizing leadership driven by empathy rather than comparison. Frank Gordon reminded the group, “Robert Greenleaf’s tombstone reads: ‘Potentially a good plumber; ruined by a sophisticated education.’ This serves as a reminder that while some of us have had the privilege of higher education, many have not—and that’s okay. A great leader understands this fact, checks their ego at the door, and leads with humility.” Alumni and students shared personal experiences where competition and pride hindered effective leadership and explored strategies to cultivate compassion in their roles.

Overcoming Personal Challenges: Imposter Syndrome & Perfectionism

The final segment focused on internal struggles, particularly imposter syndrome and perfectionism. In small groups, participants discussed resilience-building techniques and how evolving definitions of success impact self-perception. “As a seasoned alum, I hoped to offer guidance, but I found myself just as inspired by the incredible resilience and quality of the current and recent Caldwell Fellows. Their excellence is a testament to the program’s ever-rising bar,” reflected Trevor Gadson (’90).

Now in its eighth year, Caldwell Conversations continues to provide a vital platform for alumni and students to engage in leadership development within a supportive community. With growing participation and enthusiasm, the conference remains a cornerstone for fostering meaningful connections and leadership insights.