The Way of Strategy

Know yourself. Read the terrain. Shape the outcome.

Launching Spring 2026

Today’s leaders are navigating a world defined by shifting conditions, limited visibility, and constant change. Technical skills and good intentions are no longer enough—leadership now demands awareness, adaptability, communication, and strategic clarity.

The Way of Strategy is a deep leadership development program that helps leaders learn to navigate complexity using lessons drawn from the trail. Participants develop the skills to read terrain, understand timing and conditions, choose paths intentionally, manage pace and energy, handle obstacles, and steward healthy culture—all while building the capacity to lead people through demanding environments.

Who It’s For

This program is designed for:

  • Executives and senior leaders who are responsible for strategy, culture, and change

  • Managers and emerging leaders who guide teams, projects, and day-to-day execution

  • Organizations seeking alignment across levels during periods of transition or uncertainty

Whether you’re setting direction or guiding the group up the switchbacks, every leader on the trail needs to understand how strategy, communication, and stewardship work together.

What You’ll Gain

Strategic Navigation

Learn to read terrain and conditions—market forces, organizational dynamics, timing windows—and make choices that align your team with reality rather than wishful thinking.

Communication and Alignment

Build the skills to communicate clearly across distance and difference, reducing friction and enabling teams to move together instead of fragmenting apart.

Adaptive Leadership

Understand how to adjust pace, reroute when necessary, and move through obstacles without losing cohesion, morale, or shared purpose.

Culture and Stewardship

Explore how healthy culture is created and protected—through shared language, trust, psychological safety, and responsibility for the environment you lead within.

Personal Resilience & Self-Awareness

Strengthen your ability to stay grounded, steady, and effective when the elevation kicks up, the weather turns, or conditions change without warning.

Why This Approach Works

Trails demand what modern leadership requires:

  • Orientation instead of certainty

  • Awareness instead of control

  • Coordination instead of command

  • Stewardship instead of exploitation

  • Shared purpose instead of zero-sum thinking

The trail offers a strategic language that avoids adversarial “win/lose” framing and instead focuses on how groups move through complexity together—a more relevant model for organizations, communities, and periods of rapid change.

Facilitators

David Huff and Jen Zuckerman

David and Jen bring together decades of experience in leadership strategy, systems change, and human-centered design. At the intersection of their work is a shared belief: lasting change begins with clarity, connection, and a deep respect for people and place.

Jen brings deep expertise in coalition-building, philanthropy, and social impact strategy. With a relational and responsive approach shaped by her upbringing in a globally minded home, she creates spaces where diverse voices are heard, trust is built, and meaningful partnerships take root.

David draws on a rich background in corporate leadership development, Eastern philosophy, and strategic facilitation. With a style grounded in storytelling, reflection, and experiential learning, he helps leaders navigate complexity with wisdom and purpose—guiding them to slow down, see clearly, and lead with intention.

Together, David and Jen help individuals and organizations align who they are with how they lead. Their work is both strategic and soulful—inviting teams to think systemically, lead authentically, and cultivate the kind of leadership our world needs now: grounded, wise, and rooted in shared purpose.