What Can Sailing Expeditions Teach About Building Resilient Teams

Before the sail catches wind, before the open water stretches wide, there’s work. A lot of it. A sailing expedition doesn’t begin with adventure; it begins with spreadsheets, weather forecasts, team briefings, and double-checking gear that better be watertight.

The same is true for any other teams. In fact, the reason why we think sailing is such a powerful thought exercise for team leaders everywhere isn’t the romance of the waves, but the very real alignment, planning, and interdependence it demands.

With the global team-building services market valued at $4.5 billion in 2024 and leadership development forecasted to hit $10.2 billion by 2033, organizations are clearly hungry for strategies that go beyond trust falls and PowerPoints.

Since the best ideas come from the most unusual of places, we think there’s a lot that land teams can learn from a sailing crew. Here’s why.

The Focus on Planning & Preparation

In sailing, you never just “wing it.” Before you even touch the water, there’s a long checklist to get through: planning your route, checking the weather, assigning roles, inspecting gear, and building contingency plans for when (not if) things go sideways.

Great teams are built the same way. Before jumping into a big project or product launch, resilient teams take time to align around three critical elements:

• Clear Objectives: Just like a skipper needs to know where they’re headed (and where the rocks are), teams need clarity on their destination. This might mean setting OKRs for a quarter, outlining KPIs for a marketing campaign, or creating a detailed timeline for a product rollout.
• Well-Defined Roles: On a boat, there’s no time for debates mid-crisis about who’s supposed to pull which rope. The captain steers, the navigator plots, the deckhand trims the sails — everyone knows their job. In the workplace, that translates to clearly defined roles on a cross-functional team. This way, everyone knows what to do even in a high-pressure environment.
• Thorough Preparation: Sailors don’t wait until they’re in open water to discover a leaky hull. They check everything beforehand. For teams, this means pressure-testing ideas before launch, preparing FAQs before a big stakeholder meeting, or rehearsing a demo before presenting to investors. The fewer surprises, the smoother the journey.

As a passenger, you want to know that the team manning the boat or yacht is prepared for anything. Say you book a BVI sailing trip to relax and enjoy the scenery. Wouldn’t you want to make sure the onboard crew is experienced and well-trained?

The same is true for your clients and business partners. They would rather work with a well-forged team that can get them out of any “hot water” situation.

Why Day‑to‑Day Collaboration Matters

Out on the water, everyone’s involved — adjusting sails, navigating shifting winds, bailing out (hopefully metaphorical) water. The everyday grind of life at sea isn’t glamorous, but it’s where real teams are forged.

It’s also where the cracks show. Tired crew members snap at each other. Mistakes happen. The weather turns. This is where the power of communication shows itself — if a team can’t communicate openly when things get rough, they’re not going to make it very far, whether they’re on a boat or in a boardroom.

Resilient teams are built during the storm, not in the calm. Facing tough conditions together — a tight deadline, a product that needs reworking, or a sudden leadership shake-up — can either splinter a team or bring them closer.

The difference? Open communication.

Teams that feel safe sharing bad news, asking for help, or admitting mistakes build a kind of deep, unshakable trust.

Crisis Reveals Character (and Leadership)

Every skipper knows you can’t always predict every storm, but you can prepare for how your team responds.

In the office, teams face their own storms: product crashes, PR crises, major clients walking out, or sudden layoffs. These are the moments when hierarchy flattens and teams either break apart or come together. More often than not, it’s not the strongest, most talented person who leads — it’s the one who stays calm, listens well, and helps others keep moving.

Here’s what sailing can teach you about leading through chaos:

• You need to be flexible: Sticking to the original plan is a great way to capsize in a storm. Resilient teams learn to adjust course fast, reprioritizing tasks, shifting roles, and making tough decisions with limited information.
• Training is essential: In a crisis, people lean on what they know, not what they hope.
• Calm communication wins: Barking orders and spreading panic don’t work on deck or in Slack. The most effective leaders in turbulent moments are the ones who communicate clearly, give space for input, and keep egos out of it.

Wrap Up

Escape rooms are fun, but if you want to learn true leadership, you should try sailing instead. The sea may be salty, but its lessons are pure gold: plan well, communicate better, and trust your crew. That’s how real teams weather any storm — metaphorical or otherwise.