The Sailboat Exercise – Reflect Like a Strategist

Some reflection tools are practical. Others are powerful. The sailboat exercise is both.

Imagine your team as a boat sailing across open water. You’re in motion—but what’s propelling you forward? What’s holding you back? What’s on the horizon? What obstacles might you hit? In this episode, Michael introduces a tool he uses often in leadership coaching: the Sailboat Exercise.

It begins with four questions:
1. What is the wind in our sails?
2. What is anchoring us down?
3. What are the beacons on the horizon?
4. What are the barriers in our way?

These questions invite teams to reflect visually and holistically. When used with stickies on a whiteboard or in a digital collaboration space, they surface both energy and friction, goals and risks. They help teams move past surface-level blame to focus on systems, processes, and shared progress.

One team Michael worked with used the Sailboat Exercise after a difficult term. They surfaced themes of motivation, misalignment, and hidden fears. More importantly, they left with renewed direction and a shared commitment to steer forward together.

This tool isn’t just for a crisis. It works for quarterly reviews, strategic planning, or any moment when your team needs clarity and cohesion. It’s a way to name the forces that shape your journey—and then act on them together.

🧭 Download: Sailboat Reflection Worksheet