The great escape: A founder’s guide to retreat planning

Sean Hoff, founder and managing partner at corporate culture agency Moniker, has been helping companies plan meetings, retreats, and incentive trips since 2013. In a typical pre-pandemic year, Sean said his team received roughly 50-60 inquiries a year and planned an average of 20 trips a year. 

But today, as leaders and teams emerge from pandemic lockdowns — and, in many cases, navigate what it means to work in a remote or hybrid model — those numbers are rising dramatically. “We've probably had 50-60 inquiries in the last two months,” Sean said. “All of these companies are emerging out of the pandemic, into the light, and recognizing they need to connect and engage their teams.” Many companies are considering a retreat for the first time, he noted, while regulars are coming back, too.

With unspent budget funds remaining after not gathering in person for a year or two, companies are ready to invest in their teams. For some, it’s important to create an opportunity for collaboration and to engage in planning and project work; for others, the focus is on thanking employees and connecting socially. 

“We’re seeing a shift in the agendas that our clients are interested in creating,” Sean said. “Whereas remote teams, especially, used to fill a meeting agenda with working blocks, leaders are much more interested in offering people the chance to connect and relax right now.” 

While retreats may have fallen in the “nice-to-have” category for some before the pandemic, many founders are realizing the event is a “must-have” to nurture culture and fuel growth today.

If the idea of devoting time, money, and energy to planning a retreat feels overwhelming, know that we’re here to help you get your head around the what, why, how, and where of it all.

While most of the information we’re offering up here relates to multi-day, offsite retreats, the principles and many of the planning considerations apply more broadly to shorter events closer to home as well. With that, let’s hit the road!

The why: An investment in company culture

If you’re looking for statistics to support a decision to gather your team, you likely won’t find definitive numbers to back a retreat, specifically. The right balance of palm trees, excursions, and cocktails won’t necessarily correlate to a 3x increase in new customers or a measurable jump in your net promoter score. The impact, like company culture itself, is hard to define.

“Companies we work with tell us the benefits are mostly intangible, but they’re significant. The biggest plus, founders tell us, is seeing employees express a renewed commitment to the company and to their roles,” Sean said.

There is data to support the benefit of this increased engagement, if not the retreat itself. The connection with their job and their colleagues that employees experience as they gather together can translate to increased productivity and, potentially, company profit. 

The Workplace Research Foundation found that upping an investment in employee engagement by 10% every year can raise a company’s profit by $2,400 per person. Overall, research has shown that employee engagement leads to better performance, less burnout, and improved retention.

Sean added that feedback from retreat participants supports the idea that these experiences improve retention. “We’ve had employees tell us on post-event surveys, ‘You know, I was considering taking a new position, but after spending a week with my colleagues, I realize how much I love this place.’”  

Those intangible but essential elements of company culture enhanced by a retreat can also be paired with more actionable and measurable results for teams who devote some portion of time to planning and project work. 

“We’ve had CEOs tell us that new products and services have come from the time teams have spent collaborating on retreat, whether through brainstorming sessions, hackathons, or casual conversations at the hotel bar,” Sean said.

Another benefit, especially in today’s tough hiring climate, is the opportunity to promote a regular retreat as a recruitment tool. “Retreats can generate great content — photos and videos, for instance — to use as marketing collateral to show a company’s culture,” Sean noted. 

At a companywide retreat, the opportunity for cross-team collaboration is also a win. Creating time and space for folks from different departments to better understand one another’s roles and contributions to a common goal bolsters community connections and provides opportunities for new initiatives that fuel growth.

The what: Are we meeting, retreating, or both? 

If you’re considering planning an offsite getaway for your team, it’s important to be clear about your goals from the get-go to create an experience that meets your needs and delivers the desired results. 

At Moniker, conversations with clients interested in planning a retreat begin with a discussion of goals. “The first thing we ask a prospective client is the purpose they have in mind because that, together with the budget, will determine the sample locations and agendas we can offer.” 

Generally, if you’re a founder thinking of gathering your entire team for an offsite experience,  you’re likely considering either what Moniker refers to as a “meeting,” with a multi-day agenda built around working blocks with some time for recreation; or, a “retreat,” where the focus is primarily team building and social connection while providing some space for collaborative work time. 

In the most general terms, Sean said, “A founder either wants to create the opportunity for their team to hang out and get together to celebrate something, or they want to get together because they find that meeting in person is more efficient or effective than day-to-day working from home. Often, it’s a combination of the two.”

To clarify goals and plan a retreat that helps you reach those objectives, put in some time before you get into event details to reflect and review any insights you’ve gathered about how your team is feeling about their roles and about the company and any concerns they may have.

Do you have a recent engagement survey? Feedback from past events? Anecdotal info from team members or coaches around the current culture landscape? If not, consider sending a brief survey ahead of planning to get your team’s pulse, and use the information you have to shape an experience that is responsive and inclusive.

The where and the how: Big picture thinking for founders

Once you have a clear understanding of why you want to bring folks together and what you hope to achieve as a team, you’re ready to think through the key aspects of planning. 

Quick note: If you’re looking for a step-by-step retreat planning guide, Help Scout has a great one that dives into all the nitty-gritty details, but know that this is not that. Instead, this will provide a founder’s-eye view of why a retreat matters and unique considerations you, as a leader of the team, should keep in mind. 

1. Consider the cost — and the benefit 

There’s no doubt that cost can be significant depending on the scale of the retreat you’re planning. If dollar signs are flashing as you consider the travel and other expenses related to a team retreat, consider the broader context of this investment in your team. For values-driven founders, this people-first perspective is key.

David Heath, co-founder and CEO of mission-driven apparel company Bombas, noted that the expense of the company’s annual, five-day, company-wide, nonworking retreat, which cost $300,000 in 2019, is an important indicator of how the business values its team. “I find it important to keep investing in our people and doing things like company retreats because, honestly, the most important thing at Bombas is its people — it’s what makes everything run so well and is the biggest contributing factor to our success.”

Describing the benefit of the significant investment of financial resources for each retreat in an article in Inc. Magazine, he said, "It's about the laughs, the bonds, and the relationships that form," he says. "Of everything we do, the retreat has by far the best ROI."  

If you’re a remote team, it can be helpful to think about the budget in the context of cost savings you’ll likely see from not renting an office space or hosting regular in-person events. And it makes financial sense for both co-located and remote teams to make this investment in retention if you consider the cost savings in employee turnover. According to Gallup, the cost of replacing an individual employee can range from one-half to two times the employee’s annual salary.

According to Sean, as a basic rule of thumb, figuring about $1000 per-employee per-day for an all-expenses paid retreat (food, lodging, transfers, activities) in the U.S. (and in some international locations), is a good starting point. “If everybody's in their own room and you’re going to cover all basic expenses, that number is a good indication that you’ll have everything covered. From there, if a company indicates a larger budget, we can begin to expand options in terms of types of hotels, locations, and other variables.” 

2. Understand the scope of the effort

As a founder, think about the role you want to play in planning. If you have a small team, you may take a hands-on approach and work closely with members of your operations team to plan; if your team is larger, you’ll likely want to assign an internal lead to manage the process and work with an external planning group. 

But before you hand out what might seem like a plum assignment, know what you’re asking. “Founders will often present the planning role to a team member with the intention of offering them a fun, new responsibility, but it can become all-consuming and, really, a full-time role toward the end of the planning process,” Sean said. “Founders should be aware of what they’re asking and how it might affect their team member’s other responsibilities.”

To alleviate the pressure on one person, consider forming a committee to help with planning tasks. “People like to be involved in planning a retreat,” Sean noted. “If you can divy up the tasks between a few folks — three tends to be a good number — it will be less overwhelming for the lead planner and also allow other team members to feel invested in the event and the outcome.”

A planning firm can be invaluable in improving efficiency and offering cost savings — given the time you’ll save internal team members when experts are leading research, logistics, and planning. This is especially true if you’re planning a destination that requires air travel, transfers, and complex lodging arrangements.

However the planning management and tasks are divided, be aware that this is likely a six-month planning process from start to finish. “We’ve planned events in less time than that,” Sean noted, “but it’s not fun.”

3. Pick the right time and the right place

As you consider when and where to gather your team, keep a few points in mind regarding scheduling. 

First, you can save money on travel and lodging by opting to plan an off-season event (fall and spring, generally, versus summer or winter). 

Second, be aware of existing internal deadlines (new product releases scheduled and publication deadlines, for instance) before you commit to a date. You won’t be able to avoid all conflicts, but thinking through how the time away will impact your team’s ability to fully engage and enjoy the experience is important. 

Third, if you’re planning to invite family members to join the retreat, consider school vacation schedules and other relevant aspects that might affect family life. That consideration applies to location, as well — think about destinations that will accommodate the full range of ages and interests (a planning firm will be a big help in this area). 

And speaking of location, the world is your oyster — sort of. The size of your team will play a big role in where you go and the lodging that will work to accommodate, as will whether your team is co-located or distributed. If distributed, choosing a central location or alternating between locations in the U.S. and abroad can be a good approach to ensure that team members feel the burden (and excitement) of travel is shared equally.

Finally, if travel is still difficult for your team given pandemic-related restrictions or hesitancy among team members to travel, know that a virtual retreat is still a great option, as are dual retreat tracks for in-person and virtual attendance. Moniker and other planning firms have leaned into this new online experience and have a lot of wisdom to share, and companies are offering up lessons learned during the pandemic, so there are great resources to tap into if you opt for this route.

4. Be aware of your role on the agenda and your personal needs

As you’re contributing to planning the experience your team will have during the retreat, think about your engagement in the event as a founder as well.

When planning the agenda, Sean suggested setting the tone on the first full day of the event by presenting opening remarks.

“I encourage the founder or the CEO to get up in front of everybody and offer a welcome address, including housekeeping, expectation setting around rules and behavior guidelines  — around alcohol and social events, specifically — and make sure there's no gray area,” he said. “It’s important to remind team members that, despite the fun planned for the days ahead, this is a work trip and they will be expected to adhere to standard policies and behavior guidelines throughout.”

With the housekeeping covered, there’s further opportunity in that opening session to engage your team, share your gratitude, and inspire both work and fun for the rest of the week. Whether you offer an update on company growth and a look toward future goals, host a panel with leadership team members, or invite team members to share on current projects or initiatives, focus on making the most of the time with your entire team to meet your goals for the retreat and express your appreciation.

From there, as you engage with your team throughout the week, pay attention to your own energy and capacity to engage effectively.

In a post he wrote for Buffer’s blog, the company’s co-founder and CEO, Joel Gascoigne, said that acknowledging his needs as an introvert has allowed him to engage more fully and re-charge throughout the company’s retreat. He makes a point to get out and take a walk by himself during the day, especially between presentations or ahead of team-wide gatherings. “​​I have found that it absolutely is possible for me to enjoy the whole week, as long as I remember to be aware of my energy levels and take care of myself,” he wrote.

And, if you’re an extrovert, keep the needs of your introverted team members in mind. Sean noted that “many of the founders and CEOs we work with are extroverts and very comfortable in front of crowds. Their vision for a retreat might be a high-energy, consistently social experience, but that can be really draining for introverts on the team. I encourage founders to remember to give people time and space to recharge and to understand that if someone chooses not to participate in all the activities, that’s not a reflection of a lack of commitment to the company or to the experience.” 

Create an agenda where attendance expectations are clear and proactively message that not all events are mandatory. This can relieve anxiety and help ensure everyone is engaging in a way that is aligned with their capacity for social interaction.

To build an agenda that includes the right mix of activity, rest, and collaboration for you and your team, check out ideas from Buffer, Moniker, Zapier, and Wildbit — all of which have hosted multiple successful company-wide retreats and have great ideas to share.

Finally, as a founder, consider offering a concluding address to your team at the end of the retreat. “Wrap-up remarks are a great way to thank everyone for coming and to offer your own takeaways as a founder, which will send everyone home with a summary of the shared experience and prompt them to reflect on their own experience and gratitude,” Sean said. If timing for a final address is a challenge given staggered departures, an email or video message is another option to close out the retreat.

The gift of perspective

Ultimately, all the steps you take and every dollar you spend toward a retreat reflect a commitment to your team. 

“If I were to just draw one single summary of the key benefit of planning a retreat,” Sean said, “it would be the power it has to offer a leader and a team perspective around people. At the end of the day, a business is built around — and through — a team. Without your people, the company doesn't run. Reminding yourself and the people who are helping grow your business every day of the connection to a shared goal, and sharing appreciation through the experience, is a powerful gift.”