How to kick off your strategy event

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Are you stuck in the fog, like a ship adrift at sea?

The tool we are going to look at here is called the Sailboat exercise, but that's no excuse for an abundance of seafaring references, so I'll nip that in the bud already. The Sailboat exercise is fundamentally a process for gathering honest feedback from employees about the state of your team / product / company.

Variants of the sailboat exercise are used in different situations, e.g. within marketing (what marketing activities are holding you back, contra pushing you forward and generating growth).

Use the Sailboat exercise to recalibrate

The Sailboat is definitely useful in different scenarios, but I've found it of most use on "Team Day" events, or yearly Strategy Planning events. When it's time to recalibrate and ask things like: 

  • What's holding us back?
  • What's helping us grow?
  • What external factors are we sticking in our heads in the sand and not talking about?
  • What's been going well, or less well, and based on this - where do we head next.

A modern alternative to a SWOT analysis

In this respect, think about the Sailboat as a modern take on the SWOT analysis. There's nothing wrong with a SWOT, and you should certainly draft that too - but the Sailboat process is just a little less stale. It should be a fun, low pressure exercise at a time when your team is relaxed, and in a mindset to candidly assess the state of things — i.e. they’re removed from the stresses of their normal day jobs, and able to come up for air to think more holistically. And if you're on a "Team Day" or "Management Day" then you should all be in that zone - you should have your phones switched off until lunchtime! Or at least until you sneak out for a pee.

What's the Sailboat exercise?

Here's a simple step-by-step way of doing the Sailboat exercise.

  1. Gather your team in a room. Feed them coffee.
  2. Sketch on a whiteboard the sailboat and other items - as per this illustration. Make it fun! Draw a funky boat, maybe a pirate with a parrot. Whatever.
  3. Ask your team to (silently and independently) write down as many ideas/things as possible (1 per post-it note) into the groups below. Tell your team not to overthink, just to unload what's top of mind. Give them 25-30 minutes to carry this out.

The Sails:

What things are propelling us forward? e.g. strong team; competitive advantages we have; good processes.

The Wind:

What are the opportunities and positive things EXTERNALLY that are in our favour?  The winds that are blowing us in the right direction… (technology; shifts to sustainable behaviour; other societal trends that are relevant).

The Anchor:

What INTERNAL things are currently slowing your team / company down? Stuff that WE control: processes; governance; competitive weaknesses; areas to invest in; gaps in the team etc.

The Rocks:

The threats / negative things EXTERNAL to our organisation that we can’t necessarily always control. e.g. Tech disruptors; the economy; loss of key people;  things not currently being considered, but are risk points for the team going forward. (e.g. areas of tension; bottlenecks around scaling; competition).

The Island:

The things we should be aspiring to. (e.g. short-term objectives; medium-term goals; long-term mission etc etc).

  1. Each person should read out loud their post-it notes one by one, and place them on your lovely Sailboat illustration.
  2. After that, allow the team 3-5 dot-votes each, depending on the amount of people in your group. Their votes are for the points on the illustration they see as top priorities.
  3. You should be able to see the most salient focus points now, and that my friend, will help you and your team know what to focus on in your breakout sessions for the rest of your team day!


Useful tools, frameworks or further reading.

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