The User Experience Journey of a Company Retreat

Even when we design and facilitate offsites for ourselves, we struggle with the challenge of knowing exactly what to cover and how to broach difficult conversations. Here's how we coach teams, including our own, to overcome those inevitable challenges.

Twice a year, we shut down NOBL for three days to gather someplace secluded and answer a very hard question: if we were to start NOBL today, knowing what we know now, what would we do differently?

We call this retreat a Metamorphosis because the goal is to emerge a better organization for our customers, as well as ourselves. We reflect on everything: our products, services, processes, policies, and even our vision and mission. Nothing is sacred, except for our commitment to help others.

These retreats are the “cocoon stage” between who we are and who we want to be, during which we know we have to find some bridge between our personal opinions and shared ideals to build something great. The burden to be good at such discussions is heavy—we do this for a living, after all! We remind ourselves that things we like may have to change, and that things we dislike may have to stay the same. Even with these reminders, our retreats tend to follow a familiar pattern:

  1. First, we develop a rational, regimented plan. We do our prep work and parcel out our time in neat blocks with clear facilitation plans.

  2. Then, the plan fails. Tensions arise without any clear way to address them. We struggle with balancing the demands of the present with the attention we know the long-term deserves. Our neat agenda gets thrown out the window, and for the briefest moment, we look around at each other unsure how to move forward.

  3. And then the real work begins. We dig in because of our shared commitment to one another. We tackle the tough issues one at a time and celebrate each small step we’re able to take together. We find new reserves of creativity and uncover new insights into the business. We leave exhausted but in full embrace.

We just completed another Metamorphosis this week, and it followed the same pattern. We came in knowing it would be challenging because we doubled the size of the company in the last six months—yet, we still had that shared moment of uncertainty and unease.

Yes, even us enlightened “experts” have to struggle to create something new; in this case, a new NOBL (expect some radical changes from us soon!). Even our years of experience helping the Fortune 500 and startup darlings of the world can’t immunize us from it. However, we’re able to overcome that moment because we know to expect it, we know what causes it, and we know how to process it without turning on one another.

If you’re planning to take your team on a retreat soon, remember:

  1. The “groan zone” is real. Between imagining possible futures and then deciding on a single course to take is a region of cognitive space dubbed the “groan zone,” where your brain rejects the winnowing of choices. It feels unpleasant, uncomfortable, and even hopeless while you’re in it. Knowing that it’s a natural part of the process helps you cope with it.

  2. Take small steps forward. Instead of panicking at the enormity of the task ahead and wondering if you’ll ever get it all done, break it down into the smallest possible unit. What’s one thing you can do right nowto address it? What’s the very next thing? Once you’ve made a little headway, it can be encouraging to look back and realize that yes, you can do this.

  3. Allow for errors. Give your teammates the space to screw up, backtrack, or just be wrong. We have an “amnesty” policy: at any time, someone can announce “amnesty” while introducing an idea or proposal. This means that they can change their mind or withdraw the idea as they see fit, giving the team the freedom to test out new concepts without fear of being judged.

  4. Don’t cancel breaks or bonding time to make up for lost “progress.” It’s tempting to put aside fun in favor of the “real work,” but there will always be more work than time, and difficult debates will always stretch to the time you allot. To maintain clarity, your brain needs to occasionally step away from the problem at hand. As always, we’re not saying that you should do trust falls, but do build in some activities to lighten the mood and exercise your brain in different ways, like Powerpoint Karaoke.

  5. Hire us to help you through it. We couldn’t NOT remind you that we do indeed design and facilitate team retreats.

Lastly, we suggest that you go offsite with your team to discuss what’s working (or not) no less than twice per year. For us, these retreats are priceless opportunities to completely reimagine a team’s possibilities together.

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