Mickey Drexler, the 80-year-old chairman of clothing brand Alex Mill, knows the power of connection. We’re inspired by his passionate advocacy for open communication in the workplace. He has built a reputation for his down-to-earth demeanor. One way he builds rapport with his colleagues is by asking them basic, open-ended questions about their work and home lives. This kind of conversational touch is a deliberate show of his conviction that the most persuasive, effective leadership flows from real relationships.
Drexler is a retail legend as former chief executive at Gap and J.Crew Group. He likes to be called “Mickey,” even in congressional hearings. His inclination says that he—and likely we—want to lower the barriers of hierarchy to create a more collegial space. Drexler’s remarkable achievements in the apparel industry range from turning around Ann Taylor to making Gap a $14 billion retailing juggernaut. He’s the guy behind the successful brands like Old Navy and Madewell. For 16 years from 1999 to 2015, he was a director on Apple’s board.
In a recent chat, Drexler explained why bridging relationships between team members—or lack thereof—matters to a T.O.D. He stated, “You have to connect to the team. You can’t be in your ivory tower… You don’t learn in a bureaucracy [or] in an office.” This philosophy aligns with findings from a March 2023 survey by the Pew Research Center, which indicates that employees increasingly value having connections with their managers.
The notion of empathy and transparency in leadership is further supported by Deepali Vyas, who notes that “managers that master the balance of emotional intelligence and not being so rigid — that’s a good boss.” Which is why Drexler is the perfect embodiment of this sentiment, having made an empathetic approach to management his mission.
Instead of having a connotation associated with the role, Drexler would rather focus the role’s perception on leadership. He prefers a less formal, more collaborative and collegial approach. Most importantly, he understands that the deepest learning happens between people—not through the lens of a bureaucracy’s organizational chart. This conviction has driven his efforts in creating an inclusive workplace culture where all perspectives are amplified.