What Sailing Taught Me About being a Team Captain

In this article, I cover some of the problems I faced while getting my sailing/motorboat license and draw parallels between that experience and my day-to-day work as a “captain” of a creative team.

Published: Oct 08, 2019

Photo of sailboat on calm water by Jeremy Bishop on Unsplash

Photo by Jeremy Bishop on Unsplash

You’re on a 12-meter-long (40’) sailing yacht sailing straight towards the seashore – you know you’ll have to change course soon. A second sailboat is bearing down on you from left (port), and a long container ship looks like it’ll cut you off from the right (starboard). What do you do?

I wanted to learn what to do in situations like that so I could one day sail the Mediterranean, the San Francisco Bay and beyond. So I first took boating and seamanship classes to get a license to pilot sailing and motored vessel under 20 meters (65’) in length.

In this article, I cover some of the problems I faced while getting my sailing/motorboat license and draw parallels between that experience and my day-to-day work as a “captain” of a creative team.

The Problems I Faced

Going through the training and preparing for the practical and written tests was much tougher than I thought it was going to be:

The language: Sailor‘s speak is practically a sociolect, complete with its own vocabulary (e.g. a line is a rope), pronunciations (e.g. leeward is pronounced “loo’ard”) and syntax (Ready about means Ready to come about). My sailing course was in German, and even Germans say nautical language is similarly foreign to them.

The weather: I did my training in the Netherlands as Europe was experiencing a major heatwave. Temps were scratching 40° Celsius (104° Fahrenheit), some of the highest ever recorded there. One of my fellow budding sailors got heatstroke the first day and missed the rest of the training – even though we avoided being out on the water at noon.

The jackass instructor: Imagine your archetypical captain of a sailing ship in the era of European colonialization: volatile, barking orders, likely to make you swab the deck – or make you walk the plank. Apparently, my instructor missed the fact that those days are long gone. Each of the course participants had to accept his shouting, belittling and impatience, reasoning, “that’s just how he is.” I mostly had problems maneuvering around the docks. At one point, the instructor even stepped purposefully on my hand as I failed to throw the throttle quickly enough into reverse, barking, “Why aren’t you doing what I tell you to?”

Lesson 1: Know Your Crew

On board learning with me were two men and a woman. One of the men, a “gentle bear”-type, had lots of prior sailing experience. I knew I could rely on him to really crank some winches or show me how to stow the lines (ropes) properly. The woman was a quick learner and a wonderful listener. She explained lots of things to me when we were on lunch break.

You have to know the strengths and weaknesses of crew members so you can rely on them when you need them.

What that means for team leadership?: Ideally, a creative team is diverse in personalities and capabilities. It’s important for team leaders to recruit accordingly. And in the end, every one is in the boat together, so they’ve gotta get along and trust each other.

Lesson 2: Have the Right Equipment

It was the peak of summer, some of the hottest days on record. The sun beat down from above and reflected off the water from below.

I noticed how over the course of a day how the others on the boat reddened. One guy’s hat went overboard and I noticed how his concentration tanked without the protection.

My solution: I soaked two bandanas and spread them out over my head so my neck and cheeks were protected. And I wore a baseball cap on top of that, which protected most of my face. I also wore long sleeves, decreasing my sun exposure.

A picture of me sailing with a baseball cap and bandanas to shield myself from the sun

I wasn’t trying to win a fashion contest – just trying to protect myself from the sun

Having the right equipment helped me endure.

What that means for team leadership?: Having the right tools for the job helps you stay productive. Read about a few of my tools.

Lesson 3: You Need to Set a Course

We spent hours practicing the same maneuvers: tacking, jibing, “buoy overboard”. Often, we’d go in circles.

Still, whether before starting a set of maneuvers or after their completion, we always needed to set a general course.

Sighting a general course with a line-of-sight from the mast and bow to a distant fixed landmark

The instructor snapped at us whenever we’d complete a maneuver and the boat would continue to turn towards port or starboard. He gave us the tip:

“When you set a course, pick a landmark – a tree, a mountain, a smokestack – and sight that with the masts. The boat has to stay on that mark.”

What that means for team leadership?: Quarter targets, project milestones, OKRs and other team-level goals are your marks. Dashboards, JIRA epics, Kanban boards and team meetings are there to help you stay on course.

Lesson 4: Watch Your Telltales

Photo of telltales on a sailboat by Marcel Painchaud on Unsplash

Telltales; photo by Marcel Painchaud on Unsplash

A telltale is a little flag or cloth strip attached to the sides of a sail; if they’re fluttering in the wind, you know your sail is not trimmed properly.

Photo of a wind vane on a sailboat by Carl Nenzen Loven on Unsplash

Wind Vane; photo by Carl Nenzen Loven on Unsplash

A wind vane on the masthead (i.e. top of the mast) is used on larger sailing vessels to indicate the apparent (i.e. relative) wind direction.

Our instructor taught us to keep our eyes on the wind vane when changing course, reprimanding us whenever we glimpsed off at our target trajectory:

“Keep your eyes on the wind vane up there!!! THAT’s how you see where the wind is coming from – not from looking at the water!”

What that means for team leadership?: A person’s emotions are similar to telltales. For a leader, being able to reflect upon one’s own emotions helps to clearly communicate feedback or intentions. And reading teammates’ emotions is essential for talking about them and seeing things eye-to-eye.

Lesson 5: Give Clear Directives

When you’re on the water, the wind might be hissing or water crests might be slapping the boat. Your thoughts might be wandering. Or you might be fiddling with some rigging on the bow, far away from the helmsman.If you’re one of the crew, it would be dangerous to have to guess what the helmsman said.

Instructions need to be loud and clear to cut through the noise and avoid confusion.

What that means for team leadership?: Be clear about what you need, e.g.: “Based on the last user test, we need to explore ways to make the search results more understandable. I’d like you to do that since you’ve worked on the topic before.”

Lesson 6: Know the Rules – and Live by Them

Prior to the practical training on the boat, we had to spend two days in a classroom learning sailing and motorboat theory – everything from boat anatomy and physics to the rules and regulations.

We had to prove we learned the essentials in a multiple-choice exam. I studied for it using an app that cycled through all 300 possible questions until I got each one right.

While some questions are trivial (“What is a keel boat?”), others are important for traffic (“Boat A and Boat B are approaching each other on a crossing trajectory. Which boat has the right-of-way?”), and others are regard people’s safety ("What signal do you display in an emergency?).

It’s like driving: you and everybody else on the road need to know and follow the rules of the road. Otherwise 🚘💥🚙!

Coastal area with many boats on the water

Photo by Luke Bender on Unsplash

But it’s one thing to know the rules – it’s another to know when to break them. There’s one exception to the rules of sailing (and I’ll translate from German):

“Traffic laws may be deviated from if harm to oneself or others is immanent.”

What that means for team leadership?: There are several rules and regulations a UX/UI team needs to understand and follow:

On the other hand, skunkworks projects (working on under-the-radar projects) are one way to test out ideas that challenge the status quo. A/B testing is another great way to get data on politically-charged topics.

Lesson 7: Jackasses Make Horrible Teachers

Maybe I’ve gotten used to questioning authority, but my sailing instructor was a jackass. Interestingly enough, every one else taking the course agreed. So what was wrong?

I know that learning to maneuver a large yacht around a busy harbor, through a sluice, around huge container ships, etc., is potentially dangerous – that you have to react quickly and communicate intentions to other ships clearly.

Still, I learn best from others when:

What that means for team leadership?: Mentoring others means giving the good ol’ ego a backseat, being patient, encouraging mistakes, giving room to experiment, being open to different methods – and listening.

Lesson 8: Experience is the Greatest Teacher

Even at the end of the four days of on-the-water training, I still had tons of questions: “How do you read the weather?”, “What do you do if the boat starts taking in water?”, “How do you fish a real person out of the water?”

But while you can read up on what to do or listen to a sailor’s whale tales, personal experience itself is the greatest teacher.

Our instructor said:

“Your license is basically a license to practice and continue learning.”

That was my biggest takeaway from the whole thing.

What that means for team leadership?: No matter how much experience you have in design, technology or interpersonal relations, there’s always room to grow, always new things to learn and things to improve.

How Team Leadership Differs from Captaining

Obviously, creative/mental work is way different from physical labor. At least at our company, no one is going to die if we fail to meet a deadline or botch a release (although some stakeholders might like to kill ya).

As a crew member aboard a sailing vessel, its your job to perform tasks swiftly on command. Asking a bunch of questions or discussing options is just not called for. And it’s the captain’s job to coordinate execution.

But as a member of a creative team, it’s your job to engage in discussion with everyone involved and to explore options. And it’s the team leader’s job to enable collaboration.

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