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Ajay Yadav is the CEO and founder of Roomi, a positive way to search for co-living experiences. 

Depending on the stage of the company and the unique set of challenges it currently faces, retreats can have entirely different purposes and metrics for success.

When our COO, Alex Larsen, began planning our first retreat at Roomi, we were less than a year out of beta, and entering a high-growth phase in the increasingly competitive shared-housing space. We had decided to shift our company hierarchy away from a relatively flat structure as we hired new team members with varying experience levels and responsibilities.

We also wanted to fix some discord that had arisen after opening a second office on the West Coast, and better connect with remote employees working in different continents.

Here is the approach that helped us walk away from our retreat feeling unified and prepared for the milestones we hoped to reach in the coming months.

Look at the Big Picture

If you're looking to plan the perfect retreat, start by outlining your goals. Are you hoping to reward employees? Celebrate a milestone? Introduce a new leader? Solve a product or culture problem?  

We wanted to grow our company, unite the founding team members under our mission and vision, and achieve both clarity and solidarity around our business strategies. After all, as we continued to expand, these were the leaders who would pass down our culture to new hires, and if they got it wrong, the consequences would have been tough to reverse.

We decided the best way to accomplish our goals was to create an environment where our team could band together to brainstorm, hash out challenges, enjoy personal time, and bond over tasks and events. With those objectives in mind, we began to look into locations. Unless your budget allows you to head somewhere exotic (making inconvenient travel significantly more tolerable), minimizing travel should be a priority.

Given that we wanted to integrate communal leisure activities and it was winter, we thought snow sports would be a great option. About half of our team had experience skiing or snowboarding, which presented an opportunity to help one another learn -- an attitude of helpfulness we hoped would bleed into other areas. Since it was a reasonable travel distance from our base in New York City, we opted to host our retreat in Vermont.

Select the Appropriate Venue

Selecting the appropriate accommodations and setting expectations is critical for setting the right tone to meet your desired outcomes. For example, a large luxury hotel may be the perfect setting for the retreat of an established, mature corporation, but it won't create the opportunity for those organic interactions walking to the refrigerator or gathering to watch the news in the common area.

Since we wanted a more intimate, self-contained setting that fostered community while also allowing for privacy, a large ski lodge was perfect. Some people shared a room, but we had prepared the team to anticipate sharing during the trip (after all, we are a shared-housing platform!).

Larger companies may have to be more creative about accommodations if they're striving for a similar vibe.

Plan With a Purpose

Because we had so much to achieve, we carefully planned to maximize our time together. We opted to stay for five weekdays in order to make time for strategic business planning as well as relaxation and bonding.

To get the ball rolling, we fostered a comfortable setting where no brainstorming idea was deemed too "silly." We also tried to get creative about turning objectives into fun activities, and made a conscious effort to intermix new people from different departments so that everyone could come together during challenges and competitions.

We found that the below format worked well:

  • Group exercises: In preparation for the trip, we had everyone in the company test the experience in order to undergo the user experience from beginning to end. Each employee documented the process to be used in a product improvement brainstorming that took place during the trip. This exercise was particularly helpful, since everyone brings a unique perspective on business perspectives, and it allowed the entire team to contribute to our product in a meaningful way. Our product manager was then able to modify his product development roadmap to integrate the best new ideas.
  • Breakout sessions: We took stock of areas where we could inject innovation or solve challenges in each of our business units (product, marketing and operations), and designated interdepartmental teams for hour-long sessions to address the top four-to-five needs.
  • One-to-one check-ins: Alex and I met with each team member to discuss evolving roles and responsibilities, explaining new assignments and year-end goals that would move both the company and the individual forward. Having that clear breakdown of responsibilities would help each employee better understand how to involve the rest of the team.

To ensure a balance of work and play, we integrated both free time and several lighthearted activities as well, including downtime, teambuilding games, and communal participation in cooking meals and cleaning up.

Even with the most careful planning, unforeseen issues will arise, and you should take them in stride. But generally, working in advance as much as possible and pushing non-critical items will help ensure that you achieve your goals, both for your business and for your team's wellbeing.

Once you've got a plan, look forward to enjoying a productive and memorable time together.