Avoid These 5 Mistakes on Your Next Company Retreat

Akua Nyame-Mensah

Retreats are becoming more and more common in a post-Covid world. I’m not talking about leadership retreats–I’m talking about when everyone is invited. Increasingly, all-staff retreats are seen as a perk alongside free espressos, in-house lunches, and gym memberships. As someone who often presents at and facilitates retreats, I’ve seen far too many instances of retreats going horribly wrong. When leaders care more about prioritizing forced “fun” and the optics of the retreat, rather than going into it with clear people-first goals in mind, it can lead to professional and interpersonal disaster.

Many retreats take teams away from their families and their environment into windowless rooms with too much sitting, leading to dynamics reminiscent of high school popularity contests over drinks late into the night. Even when retreats avoid this dynamic, they still often struggle to translate the learning and insights gained offsite into actionable change in the office.

Leaders can study learning & development principles and directly apply this knowledge to better understand what kinds of retreats work, and the steps leaders can take to minimize some of the pitfalls I outlined above. Here are five of the biggest mistakes leaders make when planning retreats and how to avoid them.

Mistake #1: Not Knowing Your “Why”

Many retreats are held with a vague aspiration of “team-building.” Other times, the goal of a retreat is too focused on (forced) fun and getting people outside their usual environment just for the sake of it. And on the occasion that there are real and clearly defined goals, they often aren’t well-matched to the environment, activities, and circumstances of the retreat.

Sometimes companies hold retreats to brainstorm and focus on a particular problem, project, or objective, but this isn’t always a good idea either. For example, taking people out of their usual environment to somewhere unfamiliar in order to tell them big changes are coming is uncomfortable, can breed resentment, and doesn’t send the message that leadership is being mindful of the existing parameters of the workplace.

The result of these various scenarios is that a retreat has happened with a lot of big promises and very little commitment to actual change. If the “why” behind your retreat is to bring people together to make positive improvements in your company, it might be better to have a few focused days in the usual environment (remote or in-office) to dedicate towards particular benchmarks or projects.

In general, retreats should always be informed by a needs assessment, which can bring clarity around the goals, intentions, and outcomes of the retreat. Retreats, in my experience, function best as a retrospective on the previous year. With this goal in mind, combined with a needs assessment, teams can reflect while helping each other understand how their day-to-day successes and struggles relate to bigger goals. Ensure you get a good facilitator and plan for how learning on the retreat will translate to action days, weeks, and months after the retreat.

How do you make sure you have a purposeful retreat?

• Perform a needs assessment

• Get clear on your “why”

• Ensure the environment, scheduling, and program matches the findings of the needs assessment

Mistake #2: You’re not team building, you’re trauma bonding

There is a difference between team building and trauma bonding, but not always on retreats. Too much “team-building” on retreats happens because people are uncomfortable in a new situation. While sometimes being in a new environment can bring people together, if it isn’t done well, bonds happen over gossip, shared discomfort, and sometimes even over the company being the common enemy.

This is not to discount the importance of organic social time with colleagues, but thought needs to go into what activities and spaces actually create true bonds and relationships. At best, retreats can create bonding because participants feel safe, and relaxed, and find themselves in a new (albeit) comfortable environment with activities that make sense.

Planning a successful retreat needs to account for differences in ability and interest, and go beyond just “drinks at night.” When there is a lack of planning to ensure that everyone is included, it can fuel the “old boy’s club” mentality where those who gossip and drink get opportunities, and those who don’t get left behind.

How do you ensure that your retreat is team building?

• Be intentional and inclusive—make sure that the only activities aren’t an open bar and a dance floor

• Inquire into what your team would actually value in a retreat, whether it’s games, outdoor activities, pottery, or other activities

• Ensure all activities, sessions, and programming are purposeful and accessible

Mistake #3: Overpacking the schedule

Retreats are costly, so organizers and leaders understandably want to get the most out of them—but one sure way to sabotage your retreat is to overpack your schedule. Overpacking a schedule can look like too-long sessions, too few breaks, and not enough time to digest new information.

How to combat this? We know that most of us can pay attention for about 20 minutes before losing focus. This means making sure you have short sessions, or at the very least, that you break up presentations into chunks.

Besides allocating presentation time according to L&D standards, it’s also important to give adequate breaks. Most of us work optimally with a break every 75-90 minutes—if people are sitting for long periods in a windowless room, more breaks might be better to prevent exhaustion.

Retreats can be emotionally and energetically taxing—people want to fit in, they don’t want to say the wrong thing, and they’re exhausted from sitting for eight hours straight whether it’s in a beautiful environment or under fluorescent lighting. One especially underrated stressor on participants is that they’re outside their usual scripts for moving through the workplace. Even though the people are the same, navigating retreats is completely different from navigating day-to-day life at work.

How do you ensure that you’re not overpacking your schedule and overwhelming your participants?

• Respect people’s attention spans: Keep sessions under 45 minutes, keep speaking time under 20 minutes per presenter

• Allow adequate breaks: no one sits for eight hours straight either at home or in the office. Allow adequate time to breathe, go outside, or decompress—especially if you’re in one room with no windows

• Overestimate how long things will take: Transitions, setting up for sessions, and cleaning up after meal breaks often take longer than you think. Build in spacious time so that your staff and your team aren’t stretched thin

Mistake #4: Not hiring a planner

Leaders sabotage their retreats by burning out their staff long before the retreat even happens. If companies aren’t hiring an external planner, then they are essentially adding another full-time job to HR, or to admin, or to whoever else takes on the burden of planning a retreat. This job is made even more taxing by giving these roles to staff who don’t know anything about booking vendors, event spaces, and so on.

How do you arrive at a retreat with a happy team?

• Hire an external planner and a great facilitator

• Allow your team to focus on their usual work so they’re arriving resourced rather than resentful

Mistake #5: Poor post-retreat implementation

It’s easy to dream big when you’re outside your normal environment. If you’ve chosen to hold a forward-looking retreat rather than a backward-looking retreat, the steps you take during the retreat need to fit the environment you’re returning to.

Translate the retreat learning into tactical steps, or else there will be a big gap between the reality and the fantasies of implementation. If, during the retreat, you decide to start planning for a future merger, for instance, will there be check-in meetings about it? Will team members who are spearheading that project be given additional support and learning to make sure they can follow through?

Don’t take your team offsite to tell them everything must change immediately while they’re out of their comfort zone with no facilitator. Anxious and under resourced teams will not be able to sustainability do their job AND manage change—keep plans to a manageable scale and ensure key players have adequate support. Without realistic expectations and the appropriate resources, employees may burn out and become detractors.

Planning during a retreat to implement new habits and routines is work. Leaders need to prepare ways to use the new skills and to create continuing opportunities to learn.

How do you catalyze realistic change through a team retreat?

• Offer your team spacious time and opportunities for skill upkeep and continued learning after the retreat ends

• Keep in mind internal and external conditions even while on offsite retreats

• Beware the one-off workshop—avoid these without also planning for future follow-ups or times to check in on how the skill implementation is going

• Ask what follow-up activities and ongoing support employees need after the retreat in order to create tactical next steps.

If you’re taking your employees away from their usual environment, home, and family, you should ensure you have a good reason for doing so. Well-done retreats can be transformative and help employees feel appreciated, but a bad one can breed resentment, frustration, and employee turnover. Put in the time, energy, and learning to do a retreat right, and you’ll be able to create lasting change, a restful and regenerative break, and help your team look forward to their next goals with new tools and skills.