You can read more about the Sailboat technique from Luke Hohmann's book Innovation Games. Luke also provides a free online tool to do these with distributed teams at www.innovationgames.com (choose Visual Collaboration Games).
Length of time:
Usually about 45 minutes to get through data gathering and insight generation.
This retrospective technique uses a sailboat as a metaphor for the team. The team identifies anchors (impediments) and wind (positive forces) and chooses an area to improve.
Either a large white board or a large piece of poster paper. Flip charts can be used, but in my experience are not quite big enough for most teams. They'll work in a pinch. Lots of sticky notes Thick markers
Not much required, other than having the materials in place. You may wish to pre-draw the sailboat.
The facilitator draws a large picture of a sailboat floating in the water, with about half of the space above and half below the water/boat. He/she then explains that we're going to use the sailboat as a visual metaphor for the team. On a sailboat, there are things that slow it down (anchors), and things that propel it forward (wind). Just like the sailboat, there are things that slow our team down, and things that propel it forward. The facilitator then asks the team to think of what is anchoring the team down and what is propelling it forward, and to start writing one anchor/wind per sticky note.
Sometimes people will be unsure if they should gather a bunch of stickies and then come up, or just bring them up as soon as they have one. I encourage the latter. As a facilitator, just keep an eye out for the energy in the room - you may need to prompt someone to go ahead and put their items on the board. When the energy starts to die down a bit, give people a fair warning that we'll wrap this part up in a moment. Once you see that everyone is done, get ready for the next step.
Ask the team to come up to the board and group sticky notes that seem related somehow. As they do it, ask them to read the sticky notes out loud. This part is a bit of a self-organizing activity, it may need a bit of facilitation to make sure that people are getting some value out of the grouping and that one person's opinion isn't dominating when creating the groups. Once the stickies are grouped, ask someone to label the groups. Typically this will result in one or a few large groups of sticky notes, which point out that there maybe a good amount of energy around addressing those items. You may ask someone to read all of the stickies at this point too, just to ensure nothing was overlooked.
Choosing what to do
Finally, you can ask team members to "dot vote" for the group or individual sticky they think should be worked on. I typically give everyone three votes, and they are allowed to use them however they please: place all votes on one sticky/group, distribute them around, or even don't use one. You can do this with drafting dots are simply everyone gets a marker and is on their honor to only place three dots. Total up the sticky/group with the most dots, and move into some root cause analysis and proposed changes to make!
The idea started from Luke Hohmann, and over the years has been modified a few times by many in the community.