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What’s in an offsite?

By Leah Weitz on August 5, 2014

A few days into my marketing internship at Cloudability last summer, my mentor asked me a question that made my stomach flip: “Have you thought about coming to the offsite?”

The offsite: three days and two nights of all things Cloudability, the whole company tucked away at some remote location with only each other for company. I envisioned company-wide meetings, presentations, and brainstorming sessions; I also envisioned trust-falls. Lots and lots of trust-falls.

With less than a full week of work under my belt and the offsite only two weeks out, the idea made me feel woozy. I knew my mentor, Aaron. I’d also been introduced to the CEO, Mat, the co-founder, J.R., and my desk-mate, Samuel. Past those four, my onboarding at Cloudability had been such a whirlwind that my already undependable memory had utterly failed me on any other name, and I’d only somewhat begun to assign faces to desks. For every name that I knew, there were five that I didn’t; and even those who I could confidently hail in the hallway were hardly friends at this point. Three days straight with this crew? Oh boy.

But I went. Of course I went. That’s what internships are for.

That’s me in the aquamarine shorts, looking extremely proud of my new Cloudability sweatshirt.

Now, it’s a year later. As you may have guessed, I’m still here. Rather than the subject of the longest internship ever, I’m working full time as the Marketing Communications Coordinator— managing our blog, social accounts, and more. If you’re thinking it’s crazy that I went from That Intern Who Proofreads Stuff to Almighty Content Overlord in one year, then I’m right there with you. How the heck did I reach this point?

Well, as it turns out, something happened at that offsite— even without trust-falls— that doesn’t happen across a desk, over the top of a computer monitor, or even during a walk to the food carts. Somewhere between the road trip to central Oregon, the brainstorming sessions, the sleepy breakfasts, the s’mores, and, yes, the bonding games, I came to understand the people around me. Not just their names and their roles— though that was extremely helpful— but their stories. Their pets. Their food allergies. How they met their significant others. What they do when they can’t find the conference room on the hotel map. What kind of books they read during downtime. The faces they make when going over a waterfall in a white water raft.



Sure, the technical word for these people is “coworker.” But after the offsite, I finally understood why they kept throwing around words like “team”— even “family.” When you get to know someone as a person— when you respect, understand, and genuinely care about each other— working together and helping each other is a no-brainer. You want to make each other proud.

I came back from my first offsite to a changed world. If I needed help on something, I knew who to ask, knew they would help,  and felt no shame in being honest about my confusion. If I finished a project, I could high-five whoever was walking by— and know that whichever member of the team happened to stroll past first would be genuinely excited about the work I’d done. As my trust in the people around me grew, so did my enthusiasm, my responsibilities, and my sense of belonging. I am an important part of this team. We all are.

Last week’s offsite. Say cheese!

I’ve got three Cloudability offsites under my belt now, and each has been as vitally important as the rest. With every new team member (and we’ve more than doubled since last summer), the process of learning, connecting, and appreciating starts again. It’s just as important for the old-timers to welcome and learn from our new team members as it is for the newest engineers, account managers, UX designers, and yes, interns, to build a sense of belonging.

Of course, the offsites are also where we do the bulk of our coordinating for the next quarter, getting everyone on the same page in terms of goals, OKRs, status updates, and departmental battle plans. It’s important stuff, obviously, but probably best saved for a different blog post. Just trust me when I say that our world domination efforts are going swimmingly— work helped in no small part by the camaraderie that only play can foster.

I’m pitching trust-falls for the next one.

Being in the know feels great