The Octane AI team on our retreat in Utah

What We Learned Planning Our First Ever Team Retreat

How We Changed Our Team Forever By Flying To The Mountains

Megan Berry
7 min readOct 16, 2017


Team retreats are an incredible way to bring a company together. If you are an all-remote company, like we are at Octane AI, I would say they are even essential. I’m going to share why it’s important and some tips to having a great team retreat.

Why Have a Team Retreat?

No better selfie than a hiking selfie

I’m a huge fan of remote teams. Working remotely expands your available talent pool, increases worker satisfaction and saves the company money in office costs (you can check out my complete guide to working at a remote company). But, the one thing you don’t have with a remote team is the ability to build strong in-person connections with your coworkers. This is where a team retreat is invaluable.

Team Retreats Increase Employee Engagement and Team Bonding

Credit: Officevibe, view the full infographic

Our company retreat brought us together in a way that exceeded any of our expectations. We ran an anonymous post-retreat survey and asked employees on a scale of 1 to 10 how much the team retreat facilitated team bonding: 70% said 10, 30% said 9, no one put anything lower. Can you think of any other activity companies do that have such universally positive results?

“Effective team building means more engaged employees, which is good for company culture and boosting the bottom line.” -Forbes

It’s a Huge Morale Boost to Finally “See” the People you Work With

Kelli does marketing. Daniel is an engineer. Both are maximum awesome.

On our team retreat I finally met in person some employees I had been working with for up to 10 months. A big part of the excitement for everyone was “OMG I finally get to meet ____!” Team retreats for remote companies are so different because seeing each other in person is rare and is a real reward in and of itself.

Companies with high employee morale outperform industry counterparts by about 20 percent. -Marketing Innovators Whitepaper

The team retreat increased our ability to see and hear people who aren’t working next to us. This helps us improve remote communication and makes us a stronger company.

So how did we do it?

Tips for Planning a Successful Team Retreat

In the beginning of October we had our first-annual team retreat in Park City, Utah with our team of 16 people.

Choose the Date with Employee Input and Far in Advance

We finalized the date for our company retreat about six months before going. We chose the dates by selecting a bunch of options and then having employees fill out a Doodle so they could tell us which weeks would work for them. This allowed us to plan out the retreat while minimizing the effect on employees’ other plans and vacations. As new employees joined after the dates were set, we told them the retreat timing during their onboarding so they could mark their calendars and make plans with their families.

We ended up having employees fly in on Monday and fly out on Saturday morning. This worked well for us, but you could certainly do variants of that (i.e. maybe fly in Sunday and fly out Friday) and be very successful.

Plan the Location After the Dates

Utah was gorgeous in the fall!

Honestly, there are so many great locations for a team retreat, it’s overwhelming. By choosing dates first, it allowed us to narrow down locations. We had thought about a beach trip, but for many of the beach locations we were considering, early October is still very much during hurricane season.

We researched, looked at prices and options, and eventually settled on Park City, Utah for our retreat. It was absolutely gorgeous and we were very happy with our accommodations and available activities. For next year’s retreat we will go somewhere else (we’re not sure where yet!) so discovering a new place can be part of the excitement of the team retreat.

Have Lodgings that Allow for Informal Gatherings, but Give Everyone Their Own Room

A multi-disciplinary hang of account managers, marketing, our CTO, an engineer and an executive assistant.

You want people to bond, but you want them to be able to do it on their own terms. For us that meant everyone had their own room, but we had a lot of common spaces where people could hang out and bond during free time.

Furthermore, DO give people free time. Having a schedule is important, but not every moment should be scheduled. Give people time to bond on their own or take some time to recover.

Start the Retreat with Company Vision and Goals

Our CEO Matt giving a presentation about our company vision

We started our retreat with a management presentation on company vision and goals. This helped set the stage for the whole retreat and got people immediately on the same page about what the company is trying to do. I highly recommend specifically talking about your vision state, tactical goals and your target customer. This helps align the team and all future conversations together.

No More Than Half the Time Should be Spent “Working”


Of course, we had some important work activities during the retreat. But the most important moments came from the “non-work” stuff. These were the moments that really brought us together more than meetings.

Have Events That Require Working Together and Getting Outside your Comfort Zone

This is collaboration. No shoes were harmed in the making of this photo

Related to the above, make sure you schedule activities that require working together and getting outside your comfort zone. For our team that was ziplining, hiking and swimming in a cave. We helped each other, we shared common experiences and some of us even overcame our fears to do it.

Have People Work in Different Groups from their Normal Teams

Milena (product), Rodrigo (design) and Elicia (account management) giving an awesome presentation. Content removed for confidentiality reasons.

We mixed people up into teams and gave them a challenge surrounding our company goals. The teams brainstormed amazing ideas to help us succeed and it also facilitated bonding between teams that don’t normally work together. We also discovered some previously unknown skills such as an engineer who makes beautiful presentations. Furthermore, in our post-retreat survey almost every employee mentioned this as an activity they thought was incredibly useful and/or fun.

Embrace Silliness

No employees were forced into costumes for the making of this GIF, it was all voluntary.

We have a long-standing rivalry in our company slack between Fast Parrot and Party Dino. When team members revealed their alliances and became willing to even go into costume to dance it out… well you can bet we ordered some costumes. This was an awesome moment at the retreat where we were all allowed to have fun and be silly together with no need for it to tie back to anything, beyond a good laugh. That being said, be careful not to force it. It has to come naturally.

Have a Final Send-Off Event

The whole team at our final dinner

We had a final dinner out and it was honestly one of the highlights of the event. The fact that everyone knew it was the final activity meant it was our time to say goodbye to people who were no longer just our co-workers, but also friends. We toasted each other and shared stories. We also shared how grateful we are to be working with each other.

In The End, Did We Feel It was Worth the Time and Expense?

The answer is a resounding yes. In our post-retreat survey 100% of respondents said that having a retreat next year was 10/10 important for the company.

You have to decide for yourself, but if you are a remote company, I encourage you to compare the cost of the retreat to the cost of an office. For us the retreat cost way less than we would spend if we had a traditional office and the level of bonding we got from this retreat was way more. The fact that we almost never see each other in person makes the retreat all the more valuable and meaningful.

I’ll leave you with a quote from one of our team members about the retreat:

“Just thank you so much for the opportunity to get to know one another better and for fostering an amazing culture here ❤”

If you have done your own team retreat, I’d love to hear your suggestions in the comments!

If you are interested in remote teams, also check out The Complete Guide to Working On A Remote Team.



Megan Berry

VP of Product @OctaneAI. Previously VP Product @RebelMouse, Community @Klout. Stanford grad.