In this episode of Chasing the Insights, I talk to leadership expert Chris Duprey.

Chris talks to us about how leader training is non-existent today and why that needs to change.

Chris Duprey has built his career—and his life—on the belief that every person has untapped potential waiting to be discovered. A former Army officer turned business leader and coach, Chris thrives on helping others uncover what’s possible within themselves, guiding them toward breakthroughs that create lasting impact.

His journey began in the 82nd Airborne Division, where a pivotal lesson from his mentor taught him the power of listening and being present. That moment set him on a lifelong path of self-awareness and leadership, emphasizing disciplined initiative and fostering a culture where people could find their own solutions. Chris carried those principles into his role as a company commander, where he focused on developing paratroopers into leaders and bringing out their best.

After transitioning from the military, Chris led teams in the business world and earned his graduate degree at Quinnipiac University. Along the way, he was deeply influenced by mentors like Adam Barlow, who instilled a relentless drive for excellence, and Marcus Sheridan, who demonstrated the transformative power of communication and energy. Chris’s work is also shaped by his studies in mindfulness and leadership, from books like 10% Happier to Start With Why.

Today, as a partner at The Question First Group, Chris helps leaders and teams have better conversations, build deeper connections, and achieve breakthroughs. His mission is simple: to create leaders who create other leaders. Whether he’s working with a sales team or guiding an executive, Chris’s goal is always the same—to help people be just a little better today than they were yesterday.

Outside of work, Chris channels his creativity as a musician, playing bass guitar and writing lyrics for his band. He’s also a devoted father, whose kids constantly remind him of the importance of explaining the “why” behind any action. Inspired by his own father’s warmth and belief in him, Chris strives to make others feel valued and included—whether at a backyard barbecue or a boardroom meeting.

Chris believes that with self-awareness, intentional communication, and a commitment to growth, anyone can achieve extraordinary things.