The Retreat-Planning Playbook: A Starter's Manual

Planning a company getaway for the coming new year? Here are tips on how to save money, re-energize your team and company.

learn more about Kelsey Raymond

By Kelsey Raymond


Opinions expressed by Entrepreneur contributors are their own.

For a day and a half each year, our team members turn off computers, ignore email, wear matching T-shirts and play ridiculous games. No, we're not crazy -- we're focusing on team development and company improvement. We do this through our annual company retreat.

Related: 6 Ways to Go Above and Beyond the Average Work Retreat

Having fun is absolutely one of our goals, but that's not the only reason we host our retreat. A retreat's purpose should be tailored to the stage the company is in and to its team's biggest challenges.

At Influence & Co., we use themes to define each retreat's goals. In our earlier years, we focused on our product offerings and a better understanding of our clients' needs, but now that we've begun to grow, we're concentrating on team bonding. This past year, in particular, we determined new company values, and our retreat offered the perfect opportunity to introduce them to our team.

We've found that by creating a clear theme and purpose for each retreat, we can better communicate the getaway's value to our people and make sure everything we plan aligns with our objective.

Here are some of the ways we've found to make our retreats successful.

A retreat doesn't have to break the bank.

I've heard a lot of company leaders say that they can't afford to put on a retreat for their teams because they don't have enough profits at the moment. I'd counter that by saying that a company retreat doesn't have to be expensive.

For example, the first retreat we hosted was simply an afternoon at my co-founder's house. Our 15 team members ordered pizza (with a coupon), hung out on the patio and had some activities planned. The whole thing probably cost us $200.

As our team has grown, we've upgraded our retreat plans a bit, opting for an overnight retreat at an event center in mid-Missouri. With transportation, lodging, food, beverages, matching shirts and other swag, we've ended up spending around $400 per person on the retreat, but that expenditure is 100 percent worth it, given the value that our retreats bring.

The ROI that retreats can produce

Speaking of value, there's plenty to be found in a company retreat.

Depending on their individual retreat goals, different companies will gain a different level or type of value. For us, some of our greatest achievements have been the incredible innovations we've implemented in our service offerings, workflow and culture.

Our annual Mini Startup Weekend event has launched new roles, new technologies and our company intranet; and we'll soon start developing our newest initiative, I&Co. Content University.

We've also realized that our retreats boost our team's energy. After the retreats, we always get messages from employees saying they're even more excited about their roles and our company's future. An energized, inspired team brings more value to any company.

Then, there are the new team member friendships. You can't really put a value on friendships -- though Gallup's research has cited how having a close friend at work correlates with other positive feelings about your job.

Related: 4 Ways Companies Foster Productive Co-Worker Friendships

Best practices

No matter what the retreat's goals or the value companies want to achieve, there are a few best practices for a truly worthwhile and memorable retreat. Take a few pages from our playbook:

1. Create opportunities for those who don't work closely to get to know one another. We create such opportunities by pairing people up as roommates for the two-day, one-night retreat. We also put people into teams with others they don't work closely with and leave a lot of down time for people to socialize.

2. Keep everyone connected. We used an employee engagement app called Bonfyre to keep everyone in the loop on the agenda, to post pictures and share thoughts about the event. It was a great way to connect before, during and even after the retreat. Plus, our team members loved sharing their memories with everyone on the platform (without having to cloud their personal Facebook feeds to do so).

3. Choose one activity focusing on company improvement. Again, fun is a priority, but the team still needs to accomplish something. Our company improvement activity for the past two years has been a Mini Startup Weekend during which employees share ideas about company improvement, work in teams to further develop those ideas and pitch them to the company founders. The team gets a say in the company's direction, and leaders get to hear fresh -- and awesome! -- ideas.

4. Include a mix of physical and non-physical activities. Remember that employees have different abilities and desires to participate in physical activities. For this reason, we plan a mix of physical team-bonding activities, such as a blindfolded obstacle course, and mental activities, such as competitions to build the tallest tower from spaghetti and marshmallows. Including different types of activities ensures that everyone on the team gets a chance to participate and feel included.

Related: 4 Unexpected Benefits of a Company Retreat

With these best practices, organizations can host retreats that give employees the space to not only have fun and reenergize, but also grow the business. For those just starting to implement retreats (and those who already have them), reach out and let me know what you've learned.

I'd love the opportunity to learn from other companies' experiences.

Kelsey Raymond

Entrepreneur Leadership Network Contributor

CEO of Influence & Co.

Kelsey Raymond is CEO of Influence & Co., a content-marketing firm specializing in helping companies showcase their expertise through thought leadership. Influence & Co.’s clients range from venture-backed startups to Fortune 500 brands.

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