"What do you mean the buses aren't here?"

I was on the island of Kauai with about 150+ C-Suite executives, VPs, senior management and top 1% ad sales performers—and their wives. This gaggle of sun-kissed tourists was freshly showered after a day of volcano tours and shopping, and patiently waiting to be picked up for a perfectly timed sunset dinner at the oceanfront restaurant we'd reserved months in advance.

We were on an "incentive travel" vacation. Which, if you're unfamiliar, incentive travel is a kind of employee performance reward certain businesses utilize in lieu of or in addition to bonuses.

In this former life, I was what you call a "Trip Director." You know those people you see in front of large groups holding up silly signs with "group" names?

Yep that was me.

This was how I was able to get paid to be a travel writer for eight years.

And I have to say it was one of the best gigs I've ever had.

It was also one that taught me a lot about anticipation and thinking critically in the moment.

With these trips, nothing was ever left to chance. They were run like a traveling Disney World. Every moment had to be magical. Things like "perfectly timed sunsets" were critical. Every food allergy, weather condition, even force majeure had been accounted for.

What we hadn't accounted for was that the two massive buses scheduled to take us to the restaurant hadn't showed up yet. And the sun wasn't going to hang out in the sky and wait.

Now, I was brand new, and this was my first trip. So while all the senior directors were on their phones frantically trying to track down the missing buses, I did the only thing I knew how to do, which was to entertain, crack jokes and keep guests distracted from impending doom.

As I eyed the sun dropping further, and my former stand-up persona was trying to come up with the "top ten reasons it was better to dine just AFTER sunset," three huge tour buses pulled up. I was so relieved to see them dropping off guests, because I was running out of material fast.

The problem was, these still were not our buses.

I immediately went to the lead trip director and said, " Hey let's ask these guys to take us anyway."

I mean Kauai is a small island. There are maybe a handful of tour bus companies and I was certain an arrangement could be made between them.

The woman said, "We can't just take their bus." Naturally I replied, "Why not?" She looked at me scathingly and said, "Because that's impossible."

Now, this woman was a local. She was from the mainland, but lived on Kauai, sharp as a tack and was regularly tapped to spearhead my company's trips. So, when she said this, I believed her.

Still, it nagged at me. So I sought out the CEO of our tour company, the woman who hired me - a copywriter with zero trip directing experience - and threw out the idea. She immediately went to the first bus, hopped on, spoke with the driver for a minute or two, and the next thing I knew, all 150+ of us were loaded onto the buses and whisked off to our destination.

When we arrived, the sun had barely dipped a toe into the horizon. It was perfect, and our guests were none the wiser. Crisis averted.

Even the senior trip director told me I'd done a good job.

I've noticed time and again when people are presented with a new way of doing things, especially if it's in the clutch, they balk. They revert to the age-old mindset of, "that's not the way we do it."

In fairness, a small percentage of the time, a certain idea or ideas may have been rigorously tested and truly did not work. However, the majority of the time the idea either didn't work at a specific moment in time, done a specific way OR it wasn't even entertained at all.

But most of the time, the knee-jerk reaction is flat out "no."

What if next time someone throws a kooky idea out there, the gut reaction is "yes?"

What if next time, instead of saying "Why would we do that?" You say, "Why not?"

It's easier than you think. What I do is consider the bigger picture. I elevate my perspective as high as possible.

Take this instance for example. The most likely outcome was that our buses would eventually show up, but the guests would miss sunset. The worst case scenario would be that no buses come and they missed the dinner all together.

How does asking the bus driver affect either of those scenarios?

It doesn't. The worst case scenario of asking the bus driver if we could commandeer his bus was that he said, "no."

If you can start to think of every situation from the most elevated point, it's much easier to make critical decisions. Think about the end goal first and ask yourself:
​
🤔 What is the most important thing you want to happen right now?
🤔 What is the best case?
🤔 What is the worst case?
🤔 What is the cost of asking "Why would we do this?"
🤔 What is the cost of asking "Why not?"

Katrina "Why not?" Turner

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