Three Steps to Handling the Unexpected

When my friend Sam invited his new girlfriend Robyn to join him for a sailing trip, he was relatively new to the sport. He had pretty strong skills but not a lot of experience. She had neither.

They were expecting it to be a long sail — about seven hours — and spent several days preparing. They assembled maps and prepared their route. They planned to stay close to the coast in case they needed to pull in, though there were a few short crossings where they would be unprotected. They shopped for food, packed emergency supplies, and made sure others knew their intended route.

On the day of the sail, the weather was overcast but they decided to go anyway. Several hours into the trip — as fate would have it right in the middle of one of their crossings — the wind picked up, and dark clouds blew in. Directly in their path, less than a mile away, was a thunderstorm. They were exposed, with lightning crackling around them.

But Sam is a level-headed guy. And what he did — smack in the middle of the action, when most of us would panic — was astounding: he stopped the boat.

He aimed the bow of the boat toward the wind so the sails would go slack. Then he turned to face Robyn and began to discuss options. They could try to go back. They could try to go around the storm. They could try to wait it out. Or they could try to run through it.

The conversation didn’t take long because they didn’t have a lot of time. They weighed the options and the risks and decided to run through it. The waves were big and Robyn got seasick, but they made it through fine.

After the trip, we all had dinner, and I asked Robyn whether she wanted to go sailing again.

“Tomorrow,” she responded. I commented that she must really like Sam.

“I do,” she said, smiling. “But it’s not just that. We prepared. We knew we might encounter a thunderstorm or any number of other things.”

“And you knew how you would handle them?” I asked.

“No — the opposite actually. We knew that there were too many variables to have a plan for all of them. We knew we would need to make decisions on the fly.”

What they needed — and what they had — was a plan for how to handle the things they didn’t know how to handle. How to be smart, in the moment, without being cocky.

“I think the best thing Sam did,” she continued, “was not pretend he knew what he was doing. I love him for that. He didn’t posture. He didn’t rush into anything. And he didn’t push me into anything. But he didn’t freeze, either. We paused, we talked, and even though we were in a scary situation with imperfect information, we made a thoughtful decision fast.”

That’s as good a description of powerful leadership — and powerful living — in the twenty first century as I can imagine.

We live and lead in a world of imperfect information, guaranteed surprises, and unpredictable occurrences. Storms, both real and metaphorical, are waiting to happen. Trying to predict their arrival is futile. Trying to eradicate their risks is fantasy. And, even though we may have planned meticulously, believing that we’re prepared for whatever the future will bring is folly. The most successful people are able to navigate ambiguity.

But if we can’t possibly know what will happen tomorrow, how can we be prepared? We need to be prepared to be unprepared.

In the face of the unexpected:

    1. Stop the boat. If momentum is driving you to make a decision quickly, then, as Sam did in front of the thunderstorm, turn the bow toward the wind and let the sail go slack. If you’re in a meeting, take a bathroom break. In your office, get up and take a walk. In other words, do what we so rarely give ourselves an opportunity to do: think. Paul Petzoldt, legendary mountaineer, environmentalist, and founder of the National Outdoor Leadership School, used to say that the first thing you should do in an emergency situation — once you know it’s safe — is smoke a cigarette. Proverbially, anyway.
    2. Assess Your Actual Options. Don’t waste time wishing things were different or trying to force-fit your previous plan to the new, unforeseen situation. Start with a blank slate: think about the outcome you want given the new situation, the information you have at hand, and the resources available. Then lay out your options.
    3. Sail. Based on your new assessment, make a decision, and commit. Even if the decision isn’t ideal, even if it’s not giving you everything you hoped for originally, accept that it’s the best under the circumstances and move forward without hesitation.

    No matter how much preparation we do, navigating our way through a new economy, a new competitive landscape, or a new team will constantly put us in situations for which we are unprepared. Becoming comfortable acting in the face of the unanticipated is a huge asset.

    After that day, Sam and Robyn continued to sail together, and their relationship grew. One day, they went out on Sam’s boat and, in a calm expanse of open sea, Sam got on one knee and, unexpectedly, asked Robyn to marry him. Robyn paused, but not for too long, and then, relying on all her newfound sailing experience, knowing there would be a life of surprise awaiting her, she said yes.