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How asking “what if” saved me in Spain

by Chris Dyer

In March, I was fortunate to speak in Barcelona on the tenets of my book, The Power of Company Culture, in a keynote to top European business leaders. The reception was awesome—it is so inspiring to see attitudes about engagement changing around the world. As luck would have it, the speaking engagement fell over my wife’s spring break as a teacher, and she went along with me. We decided to have a good, old-fashioned road trip, and set out to see Spain and Tangier.

Leaving Barcelona, we hit Madrid and Toledo, had a quick lunch in Granada, and then headed to the southernmost part of Spain, the port town of Tarifa, to cross over to Africa. On our way, we received a message from our Tangier contact that the port there was closed because of bad weather. They redirected us to the port of Algeciras. Not a big deal, right? Just a small adjustment, right? Here is where the “what if” came into play.

Over the years, my team and I, as well as the teams and companies I consult with, have developed a habit. At the first sign of a little trouble, we start to ask this question. Asking “what if” when things are still okay, and not in full panic mode, allows those involved to easily think about possible outcomes and solutions before we have to deal with stress and deadlines.

My wife, dreaming of Tangier and our first visit to Africa, could not wait to get there. But we knew that we had to ask “what if” that port was closed by the time we got there. If, for some reason, our boat was cancelled, what would we do?

We did some research in the car, devised a plan, and had a fun and relaxed conversation about where we could go and what we would see instead. It may seem a little silly to be driving two more hours toward an open port and, at the same time, talking about what we might do if the worst-case scenario happened. The trick here is, we asked “what if” before there was stress and disappointment.

We reached the port at Algeciras, parked the car, and ran in to grab our tickets. The boat was to leave in fifteen minutes. As luck and weather would have it, all the boats were cancelled minutes before our arrival. People were yelling at the agents, arguments were erupting around us, and children were crying. Everyone in that port station seemed surprised. But not us. We had asked “what if,” and now we were ready. We sat down, opened our guide book and phone, and soon had our new hotel booked and sightseeing route set. Instead of Tangier, we would visit Gibraltar.

Raise your hand if you know where to find a UK colony on mainland Europe. If your hand is up, well done; but to many of us, Gibraltar is a mystery. On the tip of Spain is a small bit of land on a giant rock where the Mediterranean and Atlantic Oceans meet. It is a British, not Spanish, territory. This was news to us, too.

In the space of an hour, we went from tapas and Rioja to fish and chips and ale. The only thing most Americans know about Gibraltar is that is has something to do with a big rock. There is so much more! We also got to hang out with their famous monkeys, discuss Brexit, and be totally surprised at every corner. This wonderland of history was a place I might never have visited had the winds not kept us back from our original plans.

Preparation is a powerful tool. Asking “what if” allowed us to find the best options before we needed them, eliminating stress, fear, and an argument. The next time your team hits a small bump in the road, ask them to imagine the next few possible outcomes, and “what” to do “if” any of those come true.

Chris Dyer is the founder and CEO of PeopleG2, where he manages 30 full-time remote employees and 3,000 independent contractors. PeopleG2 is routinely ranked as one of the best places to work and has been listed as one of Inc.’s 5000 Fastest-Growing Companies. Having made the transition to remote during the recession in 2009 with stunning success, Chris Dyer is now a world-renowned expert on remote leadership and productive company culture.

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