When I think of great companies, there’s one thing that sets them light-years ahead of their competition. It’s not their product, it’s their people.

And how do these companies attract and retain the best talent? An incredible culture! Creating great culture is my job as CEO.

The original Proof team (Chris, Austin, JP, and Dave) in Annapolis.

As Proof has grown from JP, Chris, and myself working out of JP’s basement to a full-time team of 14 in Austin, I’ve been focused on one thing — how do I take the right steps today to build a culture that my employees enjoy, that emphasizes our collective values, and that scales over time? I’m obsessed with building a strong culture, and nearly every conversation I’ve had with investors and other founders over the last year has focused on this topic.

"If there’s one theme that they’ve constantly harped in these conversations — it’s to take the time to invest in your people, give them the resources they need to grow in their roles, and wait to reap rewards for years to come."

With this in mind, I knew it was time for Proof to plan our biggest company retreat yet: Proof Camp!

This year’s Proof Camp logo.

I wanted to create an event that employees would get excited for every year! When I read articles about Buffer’s retreats around the globe or Zapier organizing a retreat for their remote team, my brain started racing, thinking about how I would plan Proof’s first off-site in Texas.

This is the story of how I planned and ran our biggest retreat yet — I hope it’ll help you when planning a company retreat of your own.  

Set a Date

My first goal in planning our company retreat was to get a date on the calendar.

This task, while seemingly easy, is one of the hardest things to do. Planning a company retreat is expensive — you’re not only paying direct costs to rent a venue, for food & drinks, and for activities — but you are also paying indirect costs in terms of days away from the office. Honestly, there’s never going to be a “good time” to do it.

At one point, I even debated having the retreat.

As a seed-stage startup, especially one in growth phase, this is a tough dilemma. I thought we could save some money and host our retreat at the office. But ultimately, I realized that the benefits from an off-site retreat outweighed the cost. In the long-term, I was confident this event would help our team function as a cohesive unit and align on our goals for the upcoming quarter and year.

In early May, I sent a poll out to our team to find a date that worked for everyone. My advice here is to make sure you take this step early enough so that you can choose a date that works for all your employees — we had two team members flying in from the Northeast, so this was especially critical for us.

After some back and forth, we finally settled on our dates: July 16th-19th, 2018.

Choose a Theme, Set Big Goals!

Now that we had a date, it was time to pick out a theme. Being that our company retreat would fall in the middle of summer in Texas, I wanted to make this an event that took full advantage of the outdoors and the relaxed feeling that summer evokes. Swimming, time spent outside, relaxation…

And that’s how we came up with our yearly retreat theme: Proof Camp!

Choosing a theme was an important part of the planning process because I wanted to create a fun event that the team could look forward to year after year. Summer Camp brings back fond memories for me, and having the team BBQing, hanging out in the pool, playing cornhole, and sitting around a campfire is something that I knew would get my team fired up!

I turned to my head of marketing and graphic design wizard Austin to create a logo for the event. One of my goals with Proof Camp was to make the event reproducible, something that we could host every year at the beginning of Q3. By making a logo and shirts, we could create an event that stayed at the top of our mind all year. When new employees come on board, they’d hear stories from Proof Camp and get excited about the next Proof Camp.

At our all-hands meeting, I presented the idea for a retreat. Our band of engineers, marketers, and customer success gurus got super pumped about spending summer days in the Texas Hill Country together, and now it was time to start setting some goals for the event.

The two main things I wanted to accomplish from Proof Camp, if nothing else, were:

  1. Get aligned on goals for the quarter (and the year ahead)
  2. Walk away better friends and with lasting memories

If at the end of our three and a half days together, we could do these two things well, we’d be on our way to creating an event I’d want to continue hosting year after year.

Life at Proof Camp

On day one of Proof Camp, we packed up our bags and carpooled from our office in Downtown Austin to a house southwest of town, near Lake Travis.

It was an incredible house with a swimming pool, a fire pit, a basketball court, backyard games, and nearly every creature comfort we needed. Here are the keys steps and evetns that made our days at the house an absolute blast:

We Hired An Awesome Outside Facilitator

Juan Gonzalez (co-founder of the Growth Institute) leading a discussion on effective leaders.

The best decision I made when planning Proof Camp was deciding to use an outside facilitator for our programming rather than hosting the event myself. After consulting my network, I was referred to Juan Gonzalez, one of the co-founders of the Growth Institute in Austin.

Juan is charismatic, intelligent, and great at developing systemized approaches for growing teams. He has advised executives and companies around the globe, and his experience was essential in helping execute our plan of attack for the quarter and year. During our retreat, he led programming every day to get us thinking more strategically and more focused on setting goals for every part of our business.

Over our varied sessions, we aligned on a mission for the company, prepared a one-page strategic plan for each department, prepared a strategic plan for the company, talked about our core purpose, set a Big Hairy Audacious Goal (BHAG), refined our x-factor, identified our vital functions, and reevaluated our priorities.  

Our BHAG for Q3 2018.

He seamlessly integrated case studies from some of the world’s biggest companies — Starbucks, McDonald’s, Microsoft, Amazon — into his presentations to help guide our discussions. Juan also had the unique talent of helping our team open up to our most vulnerable and honest states so that we could know each other better.  

Most importantly, by having Juan facilitate the retreat, our team was pushed to our limits. He was comfortable challenging us and making us question why we did things certain ways.

Another added benefit of Juan’s presence was that I was able to participate in these conversations — and think alongside my team rather than guide the conversation from above.

Our Axe Throwing Adventure

On the first night of Proof Camp, we ventured off-site for a team building exercise at Urban Axes Austin.

I don’t know if you know the concept, but it’s pretty simple. They give you an axe, and you throw it towards a dart board. Our team had a blast here, and the folks at Urban Axes were incredible — helping organize a bracket competition that brought us all into the spirit of this funky sport. It’s harder than it looks!

The Proof Olympiad

On the second day of Proof Camp, we hosted the Proof Olympiad. My co-founder Chris was Mr. High School Hero, Captain of the Football team, All-Star Golfer, and the perfect candidate to facilitate our field day at Proof Camp. He paired us on to teams of two and then scheduled nine activities that got our team bonding and competing.

Pre-game stretching before the Proof Olympiad.

Here was the schedule of events:

  1. A Super Soaker Relay Challenge — The team that knocks over the plastic cups with a water gun fastest wins.
  2. Knockout Basketball — An old schoolyard favorite.
  3. Big Club Golf — See what team can get the ball into the hole in the fewest strokes (using an oversized Golf set).
  4. Home Run Derby — Played with ping pong balls rather than baseballs for an added challenge!
  5. Relay — We competed in 3 relay events — Sprint, Dizzy Bat, and Beach Ball.
  6. Water Chug — Whoever drinks the glass of water first wins.
  7. IPO Challenge — Ring the bell with a frisbee.
  8. Water Balloon Fight — We taped Alka-Seltzer tablets on notecards, and placed them on our shirts to easily see when you were knocked out.

Balancing Work with Play

Our hill country view from Proof Camp.

Another important thing to consider when planning your company retreat is how you split the time up every day. I aimed to make each day varied to keep our team stimulated, excited, and focused on our goals. We spent roughly 6 hours a day doing work (both normal day to day tasks and planning for the quarter) and 6 hours a day relaxing, sitting by the pool, and playing games outside.

JP, our CTO, loves to take selfies at company events.

Maintaining a good mix of work and play is a big element of a successful retreat. It helps make the days enjoyable but still helps your team walk away with a productive product.

We ordered the best brisket on the planet — Franklin BBQ.

Celebrate Your People

An important part of the retreat was an event I planned for the last night. I wanted to include an element in our retreat that celebrates our people for big milestones — in particular, their work anniversary.

On the last day of Proof Camp, we honored all three work anniversaries that had recently occurred in the last quarter. We went around the room, shared our favorite stories about those team members, and showed our collective appreciation for their hard work and contributions to the company. We started a new tradition of giving everyone a custom bobblehead of themselves on their 1-year anniversary.

It was a special time and many on the team told me it was their favorite part of Proof Camp.

Collect Feedback, Improve, Repeat

I’m not an expert when it comes to planning a retreat — I’ll be the first to admit it.

But like many things in the world of startups and life, the best way to get better at something is to dive into the deep end, head-first. For our first all team retreat, I’m incredibly pleased with our results.

Our team bonded and walked away better friends, stronger coworkers, and more aligned on our company goals.

I knew that planning a retreat would be an expensive endeavor, but I can’t overemphasize how valuable the experience was to our team. It’s been almost a month, and we’re still sharing stories about fun things that we learned and experienced during our time at Proof Camp.

In terms of what I’d change next time, I received some valuable feedback from my team that I hope will help you if you ever plan a company retreat. The overarching piece of feedback I received was that I needed to provide an agenda for activities. Not providing an agenda made it hard for many of my employees to plan phone calls or meetings while we were out of office, and the lack of a timeline made the time harder to enjoy. This is something I will definitely change for the next Proof Camp.

From our company retreat, we implemented a new strategic planning system that’s increased our productivity on both a team and company level. And our team returned to the office with a fire in our belly.

We set a new goal of 1,000,000 winning split tests for customers by 2025, refined our mission statement, and have a new appreciation for each other as coworkers and friends. And most importantly, I’m excited for Proof Camp #2 in 2019!

If you’ve had a great experience company retreat planning or attending a company retreat, tell us why in the comments below!