4 Benefits of Company Retreats + 3 Planning Lessons that I Learned

At Awesome Motive, we’re a 100% remote team, and one of my favorite part of the year is our annual company retreat. We had our 4th annual company retreat two weeks ago, and it was better than all the past ones.

I say this every year because each year we improve from the lessons we learn.

After seeing the pictures I posted on my Twitter and Facebook profiles, several folks asked me if I could share the benefits we get from the retreat and what planning lessons I’ve learned.

Since this was our 4th annual retreat, and I have no plans on stopping, it has to be good.

Benefits of Company Retreat

We’re a remote company, and we rely on tools like Slack, Zoom, etc to stay connected as we work.

But there’s something really special when all of us get together under one roof. Below are the 4 biggest benefits we get from company retreats.

1. Renewed Energy towards our Vision

Company retreats are a great place to break department / team silos and have everyone galvanize around the bigger picture.

2. Hidden talents and stories

There’s a lot you learn about your teammates when you’re under roof. Maybe you lived in the same city several years ago or they’re a great chef or they’re an amazing photographer.

The stories you hear about people’s experiences are great for building deeper relationship.

3. Better Bonds

Nothing brings a remote team closer than a retreat.

Putting a face and person behind the avatar that you talk with on Slack is amazing. Sure there’s video chat and meetings, but they’re not the same.

Playing games, having a drink, having dinner on the same table helps you build tighter bonds and relationship with your team.

4. Hackathons

This is my favorite. We always end up doing cool stuff during hackathons. This year, we built SupportAlly – a tool to help our support team provide better support.

We also started working on several neat ideas that will turn into awesome features inside our products.

If you are thinking about doing a corporate retreat, I highly recommend it. DO IT. Trust me, you will not regret it.

Now that we have covered the benefits, I want to share 3 planning lessons that I have learned. These will help you plan a fun and productive retreat.

Lessons from Planning a Company Retreat

After planning 4 company retreats, I think it all boils down to 3 things. Location & length, Activities to do, and Managing costs.

Let’s take a look at each of them in details.

1. Location & Length

When planning a retreat, the biggest question you have to answer is where do you want to plan the retreat and for how long.

For the last 4 years, I’ve planned our retreat in Florida. Why?

Because I’m located in Florida. Second because we have great beaches and tourism. This past retreat was in Orlando.

I’m always tempted to do our retreats somewhere in the Caribbean or in South America, but since our team is global (majority U.S), it’s easier to just have it in the states and submit visa application for our international team members.

Our first retreat was only 5 days long, and it felt too short. The last 3 retreats have been 7 days, and it’s perfect.

Doing it in Orlando this year was good because we were near a major airport. The past 3 years we were in St. Augustine and Palm Coast (beach houses) which were definitely fun but airport commute was longer.

The best thing you can do is try to find connecting flights from same hubs. We use Delta, and it’s cool to have several of your teammates be in the same flight from Atlanta to final destination.

2. Activities to Do

Keeping everyone entertained and productive can be a challenging task.

In the past, we have done Jet Skis, mini-golf, bowling, pool tournaments, corn hole competitions, flag football, Catan (we love Settlers), and tons of other games.

The one that’s easiest to co-ordinate is Bowling (no matter your group size). As our team grows, some activities like Jet Skis aren’t feasible for large groups.

The first two days of our retreat is pretty relaxing. We eat, drink, swim, and have great conversations.

The third day, we have presentations where each team lead gives an overview of what has been done in the last 6 months as well as sharing the roadmap ahead. Each is followed by a Q&A, suggestions.

I also do a State of Awesome (townhall) style update which is tons of fun.

From than on the retreat is fairly ad-hoc with the exception of the Hackathon.

We dedicate 3 hours to build something awesome that our team can use, and the whole team works together to make it happen.

We have tons of breakout where team members can break into small groups to address a specific challenge that we’re having.

Sometimes results from breakouts can end up being a presentation for the entire team.

3. Managing Costs

Flying all the people to a central location, accommodations, activities, food, etc can all add up in cost.

The best way to start any planning is to set a budget.

We have had great luck finding luxury houses of VRBO. This past year, we used Luxury Retreats.

Aside from flights and venue, your next biggest expense is food.

In the past, we used to go out to eat every meal. This is fine if you’re a small team, but as your team grows this become hard to scale.

This retreat, we hired a private chef who worked at Disney before starting his own business. Probably one of the best decisions.

We had healthier food that taste great and it was cheaper. I was quiet surprised by how much cost effective this was. Not to mention the time you save from not driving to a restaurant and waiting is amazing.

Multiple course meals with options (that’s healthier and cheaper) — this is a no-brainer!

Booking in advance is another way you can save. For activities, always ask for a group discount. Most companies offer that (whether it’s bowling alley, jet skis, mini-golf, etc). They all have it.

Now it wouldn’t be a retreat post, if I didn’t share some pictures. Below are some that I randomly picked:

Hope you found this update helpful. If you’re thinking of planning a company retreat, then definitely do so.

Also don’t forget to checkout my article on 10 business mistakes that every entrepreneur should avoid.