Why We Do These Skift Retreats, And Why You Should Too

NOTE: In what has become somewhat of a tradition at our company Skift, I write a memo every year after our Annual Retreat. This was the memo I sent after our 2015 trip to Medellin. And thus is it this year too, after a very successful year four in Montreal. This memo gives you more context of the place of Retreats in our company, and why I think *every* company should explore doing such retreats. I am posting a slightly edited version below.

“If you are tired of Skift, you are tired of the promise of travel.”

That, in essence is what our promise is to you Skifters, and to the global travel industry: that we are eternally curious about the business and creative possibilities of travel and what that means to the world at large.

Every year there are two seminal moments at Skift that keep our curiosity journey fresh: one is our flagship Skift Global Forum in NYC every fall, now in its fourth year. The intensity and dedicated effort each one of you puts into making it the best freakin travel conference on the planet, and the feeling of pride you get seeing your work brought to life, is among the biggest professional highs you will ever experience. All of our collective efforts has quickly made it the ONE gathering of all the people defining and building the future of travel. For those who are new to Skift, I can guarantee that at the company dinner the last night of the Forum, when you are dead tired, you will feel that collective high and will get why we put the superhuman effort into the Forum and the importance of this achievement to the team.

The second is our Skift Annual Retreat, where we re-energize and rededicate ourselves to our cultural promise. Four years into having retreats — Iceland, Colombia, Cuba and Montreal this week — we still reap enormous visible and invisible benefits from them, way beyond the week of the retreat. I can honestly say we come out of these changed in our relationship to the company and each other, where the easy camaraderie and becoming lifelong friends with each other, learning perhaps way too much about each other, is the whole point of it. And while the main purpose of these trips is to have fun, we also get a behind-the-scenes peek at the business of travel in every destination we go to, and we learn a lot.

I wrote this for Inc.com in 2014, right after our first retreat to Iceland:

There are two ways to think about company culture. It’s either a set of perks and platitudes designed to make employees feel good about themselves for working somewhere — or it’s a strategic function that helps keep your employees aligned with your brand, and your brand aligned with your customers. You can already guess which I’m going to say is better. What’s more important is to understand that your culture is only as deep as you make it….The best employees — the ones who’ll drive innovation, break barriers, and grow into a new generation of leaders — aren’t motivated by workplace comforts or feel-good HR policies. They’re motivated by the opportunity to do their best work, to understand their customers better, to discover new ways to think about markets and opportunities, to connect with their peers more effectively around their core work, and beyond work.

This still applies to our Retreat and gives you a sense of the meaning they create for each of us and for the company culture and brand.

The Internal Promise of Skift

There is a straight line that connects our Retreat to one of our main Core Values here at Skift: Humane, always default to making professional + personal lives of our team better. This reflects in our hiring philosophy. We lay out what you should expect from working here, and how we want to help your career to blossom at, and even beyond Skift.

Many of you have seen me talk about this above, this is the audacious promise we strive to keep every day at Skift. We are not there yet, we may not ever be there for everyone, but the journey towards it will continue as long as I am here.

Selfishly, another hope of mine is one day when you are older, you will sit down with your kids or grandkids and tell the story about this one small and special place you helped create that made an important difference in your life. That for a moment in time, you were part of this special family that made a tiny but permanent dent in the universe. That this one imperfect, intense guy helped you on your way in life.

Here’s to dreaming of more retreats.

I love you all.