Set the right expectations for the retreat and have fun

Ah, the alternately celebrated (or possibly dreaded) company retreat. I have planned three company retreats for my team at Cirrus Insight. Our last two retreats were in Nashville and Atlanta, and this September we’re going to Chicago. On these retreats, my team and I have had a lot of fun and laughs while getting a lot of work done, too. So what goes into a successful company retreat? And how do you strike the right balance between work and fun?

Set Expectations

Right off the bat, it’s important to address the language surrounding company retreats. The word “retreat” makes it sound like a spa vacation. If that’s what you’re buying for your team, that’s awesome. But if, like me, you’re planning a work retreat, you need to set the right expectations. If your team thinks it’s a vacation and you think it’s a work session, there’s going to be disconnect. Share your plans with a small representative group at your company to get feedback and draft an agenda. When your agenda is ready, circulate it company-wide a couple weeks before the retreat.

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At our first retreat in Nashville two years ago, we made the mistake of announcing the meeting time for the next morning the night before. By the time we made the announcement, folks were already ramping up for a big night on the town. The next year in Atlanta, we did a much better job of communicating our schedule. Everyone was aware that we’d be meeting at 8:30 a.m. for breakfast and starting our program at 9:00 a.m. sharp. That way, everybody could plan their evening activities to match up with the next morning’s expectations.

Plan Ahead

The retreat is likely to be the most remembered event of the year for your company, but make sure it’s for the right reasons by planning ahead. What will make the retreat a great experience? What will make it productive? You want people talking about how much they accomplished and how much fun they had when they return to work. If they only had fun, they’ll talk about it, but it won’t have a lasting impact on your company. And if they only did work, they’ll think the retreat was a waste of a trip. It’s combining work and fun that makes a retreat remarkable for your team and your company.

When planning ahead for our Atlanta retreat, we sent out a pre-retreat anonymous survey. We asked every employee:

• What do you like most about working here?

• What could be improved about working here?

• What does our company do particularly well?

• What does our company need to improve?

• What would you predict for our future one year from now?

People said the company’s biggest strengths were executing on our product roadmap, launching creative go-to-market campaigns, delivering great sales demonstrations and providing personal support. Intra-company communication, especially between our two primary teams and locations – engineering in California and marketing/sales/support in Tennessee – overwhelmingly needed the most work. These answers helped us plan our agenda by identifying important trends that we needed to address when we were all together.

Have Fun

Your company retreat could be the only time all year that your employees will all be together in person. There will be a lot of handshakes, hugs and laughs. This unstructured social time is important so that your employees can get to know each other as people outside of work.

For our retreat, we have people coming from Irvine, Calif., Knoxville, Tenn., Atlanta, Ga., Chattanooga, Tenn., Brooklyn, N.Y., Brookfield, Conn. and Portland, Ore. We learned in our pre-retreat survey that everybody’s favorite thing about working at our company was their colleagues – their creativity, ideas, intelligence and energy. We want to provide ample time for all of our employees from across the country to get to know each other.

Two social activities that will always be on our retreat agenda are a big family-style meal and a pingpong tournament. People talk about the pingpong tourney all year, so it’s become a cornerstone of our shared company culture. This year, we’ll be enjoying a deep dish pizza banquet at Giordano’s. The following afternoon, we’re going to see the Cubs play at Wrigley Field.

Work Hard

All play and no work turns a retreat into a mere vacation. It won’t have the long-lasting value that you want. Bringing your whole company together is a unique opportunity to get everybody on the same page. You want your employees to head back home feeling like they accomplished something significant, and re-energized regarding the direction of the company and the value of their personal contribution.

For our upcoming retreat, we reserved a meeting space at the University of Chicago to do work between our fun activities. We’re going to spend Friday divided up into small groups. Each group will be made up of team members from engineering, design, marketing, sales, support and success.

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Everybody will get a sense of how each department and individual contributes to making the company function as a cohesive unit. The idea is to build understanding and empathy. The following day, we’ll spend time focused on our next big product release to energize everybody about the present and future direction of the company. Finally, we’re going to ask each person to start working on a project of their choice that they can present by the end of the retreat on Sunday. We’ll each be able to show off something amazing to the group and celebrate each other’s personal efforts before we head back home.

Whatever you do for your company retreat, as long as you set expectations, plan ahead, have fun and work hard, it’ll be well worth the time, energy and expense. It’s almost impossible to overestimate the return on investment for a retreat that gets everybody smiling and working together.
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Brandon Bruce is co-founder of Cirrus Insight, a bootstrapped software company in Knoxville, Tennessee. Cirrus Insight automatically keeps Salesforce CRM up to date for sales teams. It intelligently syncs emails and appointments from Microsoft Office 365 and Google for Work to matching leads, contacts, accounts, opportunities, and cases in Salesforce. Cirrus Insight also includes power tools for salespeople in Outlook and Gmail including email tracking, follow up reminders, and mail merge templates. Brandon enjoys cycling and once rode his bicycle across Death Valley as part of the Furnace Creek 508. He finished in 35 hours and 7 minutes.

The Young Entrepreneur Council (YEC) is an invite-only organisation comprising the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship programme that helps millions of entrepreneurs start and grow businesses.

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