Leadership lessons learnt from competitive sailing

Why Business Leaders Should Think Like Competitive Sailors

Over the years as I’ve moved more and more into leadership positions, I’ve come to the realisation that business and leadership within business have strong parallels with competitive sailing. The interesting thing I’ve discovered is that in business things move slowly and often there are major consequences for poor decisions, within competitive sailing the lessons can be observed and iterated on within a single afternoon of sailing.

Through my future posts, I’ll be diving into sailing scenarios and business parallels.

Sailing Scenario - Race Start

To start with today, we’ll introduce the idea of how sailors approach the start of a race and the first leg of the race.

In the leadup & start of a race, crews spend time doing the following:

  1. Observing the weather
  2. Planning & preparation
  3. Racing!

1. Observing the Weather

In the leadup to a race, competitive crews build as much prior knowledge (data points) as they can around expected conditions. Some of the important data points which are collected before hitting the water:

  • High-level meteorological forecasts to understand the forecasted macro weather events
  • Topography of the landscape and topography under the water (apparently this is called bathymetry or submarine topography) is important for understanding the flow of wind and water across the racecourse
  • Tide times in combination with the the submarine topography enable us to understand expected currents across the racecourse

Once on the water, competitive crews continue to acquire additional data points right up until the start of the race:

  • What are the wind conditions across the course
    • Are there areas with more or less wind?
    • Are there areas where the wind is coming from a different direction?
    • Is the wind direction oscillating back and forth?
    • Is the wind direction persistently changing direction?
    • Are there any indications of a major change to wind conditions? Storm clouds, smoke stacks, flags etc.
    • How is the topography affecting wind conditions? Is it as anticipated?
    • Are there rain clouds? How will they affect the wind conditions?
  • What are the water conditions across the course
    • Are there areas with flatter seastate or a rougher seastate? Why does it vary?
    • Are there areas with more/less tidal current than anticipated?
  • What are our main competitors observing?

2. Planning & Preparation

As the race start draws closer and closer, we need to plan our path to victory.

Planning and preparation involves:

  • Combining all the data which has been collected with other relevant information to create a strategy for how we approach the race
  • Ensuring the crew all know the strategy
  • Planning:
    • Planning where on the start line we want to start
    • Planning what happens immediately after the start
    • Planning our fallback options if things don’t go according to plan
  • Ensuring the boat is setup optimally for the anticipated weather at the start of the race
    • This is validated through multiple tests
  • A stopwatch is started to count down the time to the race start

Note: We can also look at planning and preparation from a longer-term perspective. I will cover this in a future post.

3. Racing!

In the final minutes & seconds before a race, boats are moving slowly and jostling for position, stress levels at this time go through the roof.

When the gun goes, the goal is to be optimally positioned with clear wind and moving at full speed. This is where the execution of our plans is critical.

Unfortunately, a crowded start line is the most likely place where plans can be disrupted, clear decisive thinking and adaptability is important. When plans do not go according to plan it is easy to be caught behind our competitors with sailing slowly with dirty air (disturbed wind) from our competitors sails. This is where a fallback plan helps to get to clear air as quickly as possible.

Business Parallels

Fortunately, with sailing there is a rapid feedback cycle with many more races to refine our approach.

In a business context where feedback cycles are significantly slower and the impact of failure are much higher, it’s critical to meticulously plan, continuously gather data, and be ready to adapt strategies swiftly in response to changing market dynamics, much like how sailors plan, prepare and execute at the start of a race.

There are multiple areas within business leadership which can learn from the above scenario. Perhaps the most obvious is the launch of a new product. In the planning phases of a new product launch, we need to:

  • Observe the current market conditions
  • Anticipate what the market conditions will be like at launch time
  • Identify possible major disruptions to market conditions
  • Develop our product strategy
  • Plan the launch
  • Plan what happens post-launch
  • Do some small tests of our product to ensure market fit
  • The best businesses will also have contingencies for when things don’t work out as planned
  • Ensure everyone knows the plan and what is needed from them
  • Pay attention to new data, be prepared to be wrong, and adapt when necessary

Share Your Insights

I hope you enjoyed this intro post, in future posts I’m looking to dive deeper into a range of topics. I’d love to hear about your thoughts, experiences and insights.

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