Sagely is a digital-first, all-remote company. This strategy gives us significant advantages: hiring the best regardless of individual location, balance and flexibility for our team members. At the same time, it makes it significantly harder to build the camaraderie and psychological safety necessary for high-performing teams. So to make the most of our all remote team, we knew we needed in person time and decided to: host at least three company wide retreats each year.

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Before we dive into how we plan each retreat, let’s address the elephant in the room. Company retreats come with challenges. Half of our team are parents, and almost everyone has a pet, so a four-day trip every 3-4 months is not easy. Especially for the partners and grandparents holding things down at home. Also, navigating vacations and client engagements only furthers the complexity. Despite the challenges,  we continue to see the value and recommend them as a vital tool for remote teams.

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Q: How to plan a retreat from start to finish?

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We’re sharing the details of our thought processes and templates because we have seen, first hand, the value retreats and offsites bring to remote and hybrid teams. There is no replacing in-person interactions.‍

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1. Do not underestimate the time investment required to plan. If planning isn’t your thing, do not worry: the offsite-planning industry exploded post-pandemic. Using one of them can help pick a location, hotel, catering, etc. Even if you go that route, you still have significant decisions to make about the content and experience that you should not outsource for any cost savings.

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2. Start with Outcomes. Clearly define the intent and desired outcomes. Examples from our recent spring retreat: 

• Solidify & align on Sagely values & principles
• Improve the psychological safety of our group
• Jumpstart feelings of autonomy and creativity. ‍

3. Define a budget with a contingency buffer. Managing the budget is a huge part of any retreat planning. We use a pretty comprehensive budget-planning spreadsheet that we continuously improve. It helps for projections and comparing cities, but in the end, we’re realistic that it’ll always be a little off–hence a contingency buffer. We have also found that the size of the group dramatically changes options and pricing. It is significantly easier to plan for 10-12 people than 18-20 (and so on as you grow). Once you hit 20 people, it may be time to start thinking about those off-site planning organizations. Key learnings:

• Food and experience pricing varies significantly across locations, and isn’t always simple to estimate. 
• Costs are incurred over multiple months, typically 3 months, not just the month of the retreat.‍

4. Set a theme.  Once you have a budget and a location, a retreat theme helps with the experience and separates events. We try to give each retreat a theme based on location or venue. It’s not worth forcing one, but it helps with swag and experience planning if it makes sense. For example, the theme for our Nashville retreat was pretty obvious: making music!

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5. Learn from the past. Use feedback from your team to continue to improve, we utilize retrospectives, or retros, to ensure we receive feedback and use that as the starting point for planning.  Examples of feedback we incorporated: 

• Provide more outdoor time
• Breakout sessions for smaller  team collaboration 

6. Define stakeholders. A significant step in designing or building anything is identifying stakeholders, and retreats are no different. Define stakeholder groups and understand their needs, wants, and nice-to-haves. Find this out as early as possible (and also internalize that it will change… and probably change again [insert yoga emoji if thats an option]. Examples include:

• Exec and leadership team strong opinions on business and culture needs 
• Individual and team member experience 

7. Create an agenda but expect real-time changes. When creating an agenda, prioritize balancing group work, fun, and decompressing time. Don’t forget about time changes, not only to chosen location but for individual team members. Use learnings from past, stakeholder expectations and desired outcomes as the overarching framework. 

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8. Designate at least two people to lead execution and logistics and arrive early. Planning an experience for multiple people is no small feat. If you ever planned a party or a wedding you probably have some understanding of what we mean here. Getting there early to get a lay of the land is incredibly important. In a post-covid world, sharing responsibilities and adding redundancies  is essential. 

Ultimately, for a retreat to be great, you must have a high level of organizational self-awareness. Are you a serious company? A flashy group? Is altruism a key component? Are you family oriented? How seriously do you take yourself?

If you don’t know yourself, you’ll create experiences that feel inauthentic, forced, lame, and awkward. 

While it takes time, money, and effort to plan a retreat that has true value for the team, we continually see the benefits. From building strong relationships to providing time for collaborative deep-work time, the rewards are well worth the effort.

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