Sailboats and Project Management

I love to race sailboats.

(To an outsider, a sailboat race usually falls somewhere between incomprehensible and watching-paint-dry boring. Trust me – it’s very, very different when you’re on the boat!)

I’ve raced everything from one-person dinghies to a 45-footer (14 meters) we owned until my wife noted she preferred adventures that didn’t involve frigid Pacific Northwest water. Currently, three buddies and I share a couple of Etchells-class boats – fast, fun, cheap, and easily sailed with two to four people per boat. We race them Thursday nights against other Etchells’ and similarly sized boats.

Etchells War Kanu
An Etchells – not ours – sailing upwind.
Image credit: By Bilby (Own work) [CC BY 3.0], via Wikimedia Commons.

Recent races reminded me of some aspects of project management too often ignored even by experienced project managers.

Do Your Job

The four of us (and various guests) trade off jobs on the boats. For one race I might steer, for another cover the midboat (trim the mainsail, call tactics), for the next run the bow (jib and spinnaker).

On one recent race, the helmsman kept looking around to see how we were doing against our competition. The third time he did it, the tactician said quite directly, “You have one job tonight. Drive the boat.”

Steering a sailboat in a race requires unblinking focus. Lose concentration for an instant, and you lose five to ten seconds, often the difference between winning and losing a ninety-minute race. To be successful, we each have to do our own jobs as best we can, and spend no time worrying about whether or how well someone else is doing his or her job. Person X may not be as good a driver as person Y, but for this race X is driving. We won’t help him or the boat by taking focus from sail trim to see how he’s doing or to offer “suggestions,” and he will make the boat go the opposite of faster by looking at what we or other boats are doing.

The same goes for a project. When you’re a member of a project team, focus on your job. Leave coordination, organization, and so on to the project manager (or team lead, if you don’t have a designated “project manager”).

If you’re the project manager and also playing a role (e.g., as a lawyer contributing substantive knowledge and work), separate those roles as best you can. When you’re lawyering, focus on the that’s-why-I-love-being-a-lawyer stuff. When you’re managing the project, step away from your lawyering proclivities.

Of course, there are times during a race that a crew member will ask for opinions, such as, Think there’s more wind over there? Also, good sailors are constantly offering information about what they’re sensing (e.g., I feel less wind here). Both are essential. It’s trying to do someone else’s job – i.e., not trusting – that’s counterproductive.

Get Your Head Out of the Boat

While the helmsperson focuses on steering, the other crew must remember there’s a whole world beyond the fiberglass hull that keeps us afloat. There is so much to attend to in a boat such as an Etchells that simply trimming the sails and adjusting the maze of control lines can become a full-time job.

But someone has to deliver information about context. The wind looks lighter ahead. We are clear to change course without running into the reef. Orcas off the starboard bow! And of course, that other boat is on a collision course with us, and they have right of way.

In other words, be aware of related activity happening around you. (Where we sail, the occasional appearance of orcas is deemed pertinent information.)

On a legal project, the stakeholders possess a wealth of critical information that’s “outside the boat,” not directly on point for the legal matter at stake but crucial to your ability to approach it in a manner that makes the most sense for the business. Cultivate good working relationships with their administrative assistants, for example, and remember that your job is to help the stakeholders achieve their business goals – within certain bounds, of course.

Likewise, the interpersonal relationships and interactions of team members are a big part of project successes. So are the management and leadership skills of you, the project manager.

Get your head out of the boat.

To Finish First, You First Have to Finish

These informal, friendly races start inside a bay, pass through the narrow, shallow (but sandy, rock-free) entrance and out to a buoy some miles away, the head back into the bay, a course that gives the slower boats one last chance to gain by outmaneuvering the stiff, swirling currents.

In one race, the tactician and helmsperson had a disagreement on when to change course as we entered the channel that led to the finish line. The upshot: we shhh’d to a stop as the keel dug into the soft, sandy bottom.

The lesson is that you have to avoid doing the “stupid stuff” to deliver great work, and running aground because we weren’t all on the same page certainly goes in the stupid-stuff column. No damage, and we got free within twenty seconds, but we coughed up first place after ninety minutes of good sailing.

On a project, make sure you understand when your resources will and will not be available – and what, or who, could cause their availability to change. Know the dependencies that tasks have on each other, so that a chain of dependencies – A depends on B, which requires C to be completed first – doesn’t cause you to miss a deadline. Make sure the client’s expected cost aligns with what you expect to spend, whether or not there is a formal budget – and ensure that the cost doesn’t exceed the value you’ll deliver. List the things that can go wrong (project risks), and take steps to minimize or work around the more significant issues.

You can’t deliver great work if you can’t get it all done in a timely manner.

As experienced (though not great) sailors, and as experienced project managers, we shouldn’t make these mistakes.

But we do.

It’s better to avoid them, but the next best thing is to acknowledge and address the issue quickly and smoothly.

That’s the way to win more races – and succeed on more projects.

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