What does it really mean to lead today? That’s the big question tackled in the latest Dscoop Roundtable conversation — and the five leaders at the table didn’t hold back.
The conversation began with reflections on the complexity of team building, especially as workplaces evolve with shifting expectations around family ownership, team building and leadership styles.
The group also shared honest reflections on the missteps that come with marketing and hiring, and covered the importance of setting clear expectations, building trust and recognizing when to pivot or provide more support.
They also explored the emotional weight leaders carry. They spoke about how isolating the top role can feel at times — the quiet burden of protecting culture, making hard decisions and maintaining stability even when things are uncertain behind the scenes. They opened up about the personal impact of leadership, including the challenge of managing stress, staying energized and remaining authentic with their teams. Each panelist emphasized the need to foster a workplace culture where team members feel safe enough to share ideas, admit mistakes and challenge the status quo. The leaders discussed how creating this kind of culture requires intentionality, vulnerability and consistency.
The conversation also surfaced another shared theme: the difficulty and necessity of letting go. As their businesses grew, several leaders had to transition from hands-on doers to facilitators of others’ success. That evolution required building systems, trusting others with execution and redefining what success looks like from the leader’s seat. They acknowledged that growth often means changing their own behavior, not just the behavior of their teams.
Throughout the discussion, a sense of connection ran deep. The leaders acknowledged that while their businesses differ in size, geography and structure, many of the leadership struggles are the same. Being able to openly discuss those challenges with fellow Dscoopers — peers who understand the stakes — was an energizing and affirming experience.
This Roundtable is a powerful, unscripted exchange that reveals the human side of leadership — the doubts, decisions and personal growth that come with guiding others. For anyone in a leadership role, the conversation offers insights, encouragement and real-world perspective from those who are walking the same path.
