The general premise is simple: picture a sailboat on the water with a person in the boat and a large sail. Ahead of the boat is a bright sun—or sometimes an island—which represents the destination we’re heading toward. Behind the boat, squiggly lines represent the wind, giving us forward momentum. Below the surface, an anchor drags across the seabed, slowing the boat down. Just ahead of the anchor is a massive rock—the big watch-out, the looming threat that could capsize the boat if not addressed.
Normally, this is all drawn on a board so that everyone can see the metaphor in action and immediately grasp the concept.
Now here’s where the real magic happens: the sailboat exercise revolves around four key questions.
This question sets the destination—the high aspirations, objectives, and goals that drive the team. It opens up conversations about motivation, vision, and alignment. Often, as people share their bright horizons, it sparks moments of realization: “Oh yeah, me too! I want that outcome as well.” Some facilitators steer the group toward specific goals, especially for project-based discussions. But for general team alignment, I like to leave it open, allowing personal and professional motivations to surface.
Momentum matters. Here, we highlight what’s already working in our favor—the wins, strengths, and positive forces pushing us forward. This part of the exercise is uplifting. Even when a team feels stuck, I challenge them to identify small victories. “You’re all here for this session—that’s already momentum. What else?” More often than not, once they start looking for wins, they find plenty.
This is where we get real about the struggles—both internal and external—that are slowing us down. By this point, trust has been built, and people start sharing candidly. Lack of resources, burnout, internal misalignment—whatever the blockers, calling them out brings relief and fosters camaraderie. The team realizes they’re not alone in their frustrations
These are the looming threats that haven’t hit yet but could derail us if we’re not careful. Restructures, budget cuts, external shifts—this is where leaders get an invaluable window into what their team is worried about. It’s also a chance for leaders to be transparent and share their own concerns. By the end of this conversation, the team has clarity on where everyone stands.
Fresh ideas and tips to fuel your growth
Beyond team alignment, the sailboat framework is a powerful tool for business strategy, storytelling, and personal development.
Think of the sailboat as a dynamic alternative to a SWOT analysis:
For example, let’s say your company aims to reduce carbon emissions by 100% by 2030 (bright horizon). You’ve already achieved a 20% reduction and are making steady progress (wind in sails). However, supply chain challenges and slow policy changes are making it difficult to accelerate progress (anchors). Meanwhile, unpredictable government regulations or shifts in public sentiment could disrupt your plans (big rocks). Mapping this out makes it easier to prioritize next steps and communicate with clarity.
Great stories follow the sailboat structure. Take any compelling brand story:
Let’s say you’re marketing a fitness app:
By structuring messaging this way, you create a compelling narrative that resonates with your audience.
The sailboat exercise is just as effective for self-reflection and goal-setting. Here’s how you can apply it to your own growth:
For instance, if you’re working towards launching your own business, your bright horizon might be financial independence and creative freedom. Your wind in sails could include relevant skills, supportive mentors, or past entrepreneurial experience. Your anchors might be self-doubt, procrastination, or lack of funding. And your big rocks could be economic downturns, market saturation, or unexpected personal setbacks.
By laying it out visually, you gain clarity and can start addressing what’s holding you back.
Until next time—keep moving forward.
Serge
