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You Can't Steer a Sailboat Unless It Is Moving

The Blew By You on the Severn River in Annapolis, MD

Just about every business decision, whether it's the launching of a new product, the entry into an adjacent market, an acquisition, as well as many day-to-day tactics involves multiple variables, many of which cannot be precisely measured. This is what makes the game we call business so challenging.

The most analytical of us try hard to measure as much as possible, to run simulations testing various assumptions against a varied set of market conditions and potential competitor reactions. Sometimes we can objectively determine that our plans are justified. But mostly we find that at some point along our path we just have to make a decision whether or not we have all the answers. We have to take action!

Later we find that changing market conditions require our original paths be altered. Deciding when to change course from a currently successful path is often problematic. Getting lulled into complacency ensures that our good results will inhibit us from becoming better.

Decisions made in one department have an impact on others. Clear communication among team members is critically important to be able to react quickly and adjust to competition and changing market conditions.

What does all this have to do with a sailboat?

Each Wednesday evening a small group at our company, Purview in Annapolis, Maryland board a sailboat to race with the Round Bay Sailing Association on the Severn River. This is (mosty) a good natured but competitive race. My crew and I are novices and we are just learning how to get the most out of our boat in order to be competitive. Each week as we race we are faced with a constant stream of decisions.

And although we do this to relax, get out of the office in the nice weather and enjoy our friendship, each of our races is becoming more and more competitive; our experience is making us better sailors.

Even starting a race on a sailboat is an interesting choreography of zigs and zags as we each try to plot a path that gets us to the starting line just at the time that the race is starting. It’s interesting that no boat just sits at the starting line waiting for the starting gun. Neither do any try to “time” the start by plotting a perpendicular course to the starting line and hope that they don’t get there too soon, which would either cause a false start or potentially disqualify them from the race. Each boat’s goal is to be moving as fast as possible, in a direction that puts them near the starting line so that when the gun sounds they can quickly adjust and be their way.

To get started it’s important is to move as fast as possible in what appears to be the “right” direction.

Once the race starts, we try to plot a course that will get us to the first buoy as quickly as possible. And while that sounds pretty straight forward and logical, the direction we take is almost always not a straight line. Sailboats, as you might imagine, are subject to the winds that mother nature serves up. Seldomly does she blow from exactly the direction that will head us to our target on a straight path. And if she does, once we round that first buoy the next tack is sure to be different.

Make the most of the conditions you are given.

We can’t complain about the wind, its direction, or even the other boats, although we often find ourselves doing just that. We simply need to pick our direction and trim our sails. Hoping the winds will change or that we’ll be lucky enough to pick up a fortuitous rogue gust is generally a prescription for coming in last. Often getting to where we intend to go means that we have to take an indirect path to get there. Try as hard as we might, we can’t cheat by trying to head in a direction that the wind won’t permit. We’ve found this out the hard way.

It’s better to head where the conditions will take you and then tack back towards your target, then to try to out maneuver the conditions.

When it is time to change direction, we try to build up as much speed as we can and then quickly come about or jibe. This is especially important when there are only light winds and we are not making fast progress. The faster we are able to make this change the better our course and the faster our speed. Not turning the rudder fast enough and then not readjusting the tiller and retrimming the sails quickly enough afterward can cause us to lose ground to our competitors. We have to be continually learn and adjust to our mistakes.

You can’t turn a sailboat unless it is moving.

Trimming the sails is an effort in making continuous small adjustments. Often sailors hold the main sheet feeling for small changes in wind and constantly watching the tell-tales on the sail indicating your optimal trim. It is interesting to note that almost never during our race are the sails trimmed correctly.

Constant measurement and adjustment are required.

The direction of the tiller and the trimming of the sails are completely dependent on each other. If you change the trim of the sails you change the pressure on the tiller. And if you change the direction of the tiller, you will need to adjust the trim of your sail. Add a second or third sail and you increase the complexity of each of these maneuvers exponentially.

Each crew member needs to clearly communicate their intent prior to making a change or you may end up losing speed or heading in the wrong direction.

Sometimes we get on a great tack. The wind is in our favor and we pick up speed. This amounts to the ultimate joy of sailing; when everything conspires to enable you to catch the right wind and accelerate. But every sailor knows, that you can’t remain on one tack forever. So, while we enjoy this when we can and read its benefits, we still know we need to decide when to change direction.

Our success can seduce us into heading in the one direction for too long. But, sometimes, making too many adjustments when we have momentum slows us down.

When we first entered these races our intention was to just have fun. But what we have found instead are important lessons about teamwork, communication and decision making – an education that we wouldn’t have received had we been more diligent and decided to stay in the office. What we once thought would make us better sailors has coincidently enhanced our decision-making skills.


  • Buoy- A floating object of defined shape and color, which is anchored at a given position and serves as an aid to navigation or designates a leg of a race.

  • Come About- a sailing maneuver by which a sailing vessel, whose desired course is into the wind, turns its bow toward the wind so that the direction from which the wind blows changes from one side to the other, allowing progress in the desired direction.

  • Jibe- a sailing maneuver whereby a sailing vessel reaching downwind turns its stern through the wind, such that the wind direction changes from one side of the boat to the other. 

  • Rudder- a flat piece, usually of wood, metal, fiberglass or plastic, hinged vertically near the stern of a boat or ship for steering.

  • Sheet- a sheet is a line (rope, cable or chain)

  • Tack– a course or an approach

  • Tell Tales- usually a piece of yarn, string or plastic when attached to a sailcan be used as a guide when trimming (adjusting) a sail.

  • Tiller-a lever attached to the rudder used to steer.

  • Trimming- To adjust the sails so that their angle to the apparent wind achieves the most power possible

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