Work with Vince
Most of the work I do begins when someone reads or hears something where I surface the underlying dynamics of an experience they recognize—something they’ve felt but hadn’t yet been able to make sense of—and we begin a conversation.
That conversation might be about exploring what’s actually happening beneath the surface: how uncertainty is showing up, where assumptions may no longer hold, and what kind of orientation would be most useful now. From there, the work takes shape in different ways, depending on context and fit.
How This Work Often Takes Shape
What tends to shape these engagements is a shared recognition that the challenge requires a different way of seeing—one grounded in a new operating environment, where leadership, systems, and uncertainty interact in practice.
From that initial conversation, the work tends to take shape in a few common ways—always guided by resonance, context, and fit.
This work is most useful for leaders who sense that familiar approaches are no longer sufficient—and who are willing to question their own frames, not just their circumstances. It’s less suited to situations looking for quick answers, predefined solutions, or validation of an existing plan.
- Speaking
and facilitated conversations
I’m often invited to speak with leadership teams, boards, or broader audiences as a way to frame complexity, surface shared challenges, and help groups orient to the conditions they’re navigating. These sessions are less about delivering answers and more about creating the conditions for better thinking together
- Board-level
engagement
In some cases, ongoing dialogue leads to board involvement, where a system-level perspective, pattern recognition, and judgment under uncertainty are most useful. These relationships tend to develop over time, grounded in trust and a shared understanding of the work.
- Ongoing
advisory or mentoring relationships
For a small number of leaders, the work continues through periodic conversations focused on sense-making, decision-making, and navigating moments of transition or ambiguity. These relationships are selective by design and shaped by mutual fit.
An Invitation
If this way of seeing resonates, the next step is usually a conversation—simply to explore whether there’s a fit and what might be most useful now.
Vince Gennaro © 2026