A skipper needs a good crew

It’s the summer of 1999, my girlfriend and I are sailing a Hobie Cat 16, about a mile off the coast of Datça in Turkey. We’re in a pack with 5 other Hobie 16, and 1 larger Hobie 18 Pacific, but going noticeably faster than the others.

The 2 guys sailing on the 18 footer are the organizer of the trip, who had been chartering boats for the last 20 years, and a friend of his. As we setup camp on the beach that night that guy asked us how we could have been faster on a smaller boat, given that he was with a pro.

And that’s the story I want to tell: a great skipper with a mediocre crew will get beaten by a good skipper & crew any time. In business, good vision and execution trumps great vision but poor execution.


The story actually started the night before we sailed off, when we all gathered to introduce ourselves. The organizer wanted to make sure at least one person per boat was an experienced sailor so he asked us about our experience. When I said I had sailed small boats since I was 7 or 8, he nodded at my girlfriend and said, “so that’s your crew then”. “Actually she is the skipper” we replied laughing. Not only she started sailing as young as I did, but both of us knew that she’s a better skipper.

When you sail a small boat, the roles are pretty well defined. The skipper controls the helm and the main sail, the crew is in charge of the jib (the front sail) and does ‘the monkey’, hanging on a trapeze outside the boat to stabilize it when the wind speeds up. The skipper manages the direction of the boat, taking in account currents and drift, yet the moment to moment interactions with the boat are actually fairly limited. Once the direction is set, the skipper tacks the sail and that’s pretty much the end of it. In contrast, the crew constantly adjusts the jib or the horizontality of the boat to maximize the speed. And with the higher position, he watches out for gusts of wind by looking at the shapes of the ripples on the water. It requires constant attention to the elements (wind, water and sometimes land).

If a boat was a traditional company, the skipper would be the CEO and the crew the COO; the former’s territory is vision, the latter’s playground is execution.

Operations is a multiplier for vision.

For a software company, operations is a vast domain. It goes from running the service (sysops) to the development processes and the company culture. It’s taking care of everything from keeping your servers alive to how much technical debt your code has. While vision gets talked about in the press and receives the accolades, execution remains in the shadows. Vision is what people see when things go well, execution is often in display when they go poorly.

All good companies understand that good operations is the breeding ground for an even bigger vision. True visionaries know that great ideas have to be well executed to make an impact.

And this goes at every scale of the company; as a manager, you may drive the vision for your project, but you have to pay as much attention to its execution. If not kept under control, technical debt will smother your ability to deliver on your goals. If you spend a lot of time tackling lots of small unrelated issues, there may be more systemic problems you should address. When you ship a great project, don’t think that a clear vision was all it took to be successful. It was most likely also built on solid execution.

So don’t let your focus on the product vision undermine your ability to execute. Every improvement to your operations will multiply the speed at which you can deliver your vision.

PS: the girlfriend in the story is now my wife; we do make a good team together.

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