How to Have a Fantastic Staff Retreat in Eight Steps

An awesome shot from our retreat! 

If you are planning your company’s next in-person retreat, you are probably facing a mountain of questions about how to prepare and what you should aim to accomplish. Trust me, I’ve been there! There is so much to do both before and after that this post is part one in a two-part series about what to do both before and after your company’s retreat.  

In October, Spark Point gathered for our first post-pandemic, in-person staff retreat. Planning this gathering in the age of remote work and COVID precautions can be challenging. It certainly doesn’t help that if you look to the internet for tips and tricks on how to plan a company retreat, you are presented with endless listicles of generic advice that probably doesn’t fit your needs! Below are some takeaways from our retreat planning that I hope will help you build an experience that is productive, memorable, and meaningful to your organization and staff. 

  1. Get interactive feedback from your staff beforehand

Conventional wisdom says that it’s best to share a survey in advance of a retreat to gather ideas about content and other elements, but this approach is limiting. Yes, you should send a pre-retreat survey, but not about the content. Your pre-retreat survey should only include logistical questions like scheduling, location, food allergies, vaccination proof, transportation needs, etc. 

Instead, assign one staffer (ideally someone in operations or who works across organizational silos) to develop department-specific interview questions that are distributed to staffers in advance of a one-on-one interview. The assigned staffer should interview each team member (or select team members from each team) about what they hope to get out of the retreat and what sticky issues need to be addressed. This encourages more open sharing and active engagement compared to a static survey that is easy to ignore or rush through. 

For our retreat, I asked our new Managing Director, who started in September, to spend her first month interviewing each team member as a part of her onboarding process. She crafted questions for each interview based on her knowledge of each person’s role, then used those interviews to identify themes that informed the agenda for our retreat, ensuring that we addressed the most important issues at the retreat. The responses and themes from the interviews deeply informed our final retreat agenda and schedule. If you’d like a template of the questionnaire we used for our pre-retreat conversations, click here!

  1. No work during the retreat 

Nothing kills the vibe of a work retreat like…work! Get your retreat on the calendar as early as possible so that your staff has plenty of time to meet deadlines and complete deliverables in advance of the trip. Additionally, external partners and clients should be given no less than two weeks’ notice that you and your staff will be unreachable during the retreat. To really seal the deal, everyone should put up an out-of-office message conveying that they should only be contacted in case of an emergency. Although this can be scary, Spark Point has found that clients and external partners alike respond positively to firm boundaries and thus feel more comfortable communicating their own boundaries when they need them. 

  1. Build in time for fun and rest

Night owls, extroverts, morning joggers, don’t-talk-to-me-before-I-have-had-my-coffee – there is no telling the range of personalities and preferences that exist in your staff! Thus, your itinerary needs to model your company’s working hours. For Spark Point, that’s 10AM – 6PM EST. At our retreat, the time before and after this block was largely protected for independent activity or structured group activities like group dinners and games (always with a hard stop!). By honoring your staff’s outside-of-work preferences, you’ll foster an environment that is open and respectful, all while getting to learn about one another. At Spark Point’s retreat, one staffer was waking up barely 20 minutes in advance of the first session while another had already run several miles when they showed up!

  1. Distribute responsibility

As the leader of your organization, you will likely shoulder the heaviest burden in planning, budgeting for, and executing your retreat. But, don’t be afraid to ask others to help! If you opt to bring in an outside facilitator, this step may not be necessary. However, in the interests of budget and time, I chose to ask my teammates to help with facilitating various sessions.  Because we did the interviews at the beginning of the process, the topics on the agenda were relevant to everyone, not just leadership. This made it easier to ask people to engage in planning and facilitating conversations. 

At least two weeks in advance of the retreat, assign a staffer (or teams of staffers) to facilitate certain discussions and take detailed notes so you, as the leader, don’t have to do all the talking. This will help everyone feel invested while also saving money since you won’t have to hire a professional facilitator. And don’t stop there! Once you are there, assign teams to be responsible for necessary tasks, like preparing dinner, making sure the coffee is on (and that there’s enough!), and rounding up everyone in advance of activities. 

  1. Set ground rules at the beginning

Your retreat is likely to go off the rails quickly if there are constant interruptions or if a few people dominate every conversation. Before you dive into any sessions, set ground rules with everyone and normalize the expectation that everyone is empowered to politely point out if someone is violating those ground rules. At our retreat, we had “talking sticks” that we would raise when we had something to say, and we could only speak if the moderator called on us. Additionally, let staff know their voice will be heard by instituting a “Parking Lot,” a designated area of the retreat space with sticky notes so that if at any time, staff has an idea or question that would distract from the conversation at hand, they can “park” it there for a later discussion. Just make sure you go back to the parking lot later to make sure all of those issues are addressed.

  1. Check in on on the tough issues

Working from our couches, living rooms, and makeshift at-home offices has brought us all intimately into each other’s homes. We now see parts of our coworkers’ lives that were hidden from us before March of 2o2o: crying children, needy pets, roommates milling about in the background, etc. This seemingly new normal might cause us to forget that life is still really, really hard for many people, which might cause you to neglect the fact that your staff probably needs more support than they are getting. During your retreat, set aside a specific time to chat about the pros and cons of their current work environment – whether all virtual, hybrid, or in person – and any support (e.g. equipment, flexible work hours, scheduling blocks) that might be helpful in easing the cons and maximizing the pros. 

The work environment might not be the only thing you have to talk about that is difficult, but don’t skip over those challenging conversations. It’s much better to have them in person at a time when folks are not distracted by their day-to-day.

  1. Build in a lot of time for fun and casual conversations

Often, we set aside the time for a retreat and it becomes a catch all bucket for everything we don’t get to think about on a daily basis. But you can’t cover everything in one week, so prioritize the most important and universal strategic questions for your working sessions – the things that everyone cares about, not just you. This again is where those initial interviews are extremely important to your retreat’s success – the things that everyone or most people bring up are the things you need to be covering.

But it can’t be all work, otherwise folks won’t have the time and energy to get to know one another and have fun together. I was intentional about making sure that there was a theme for each day and that we had working sessions mixed with fun activities, team building, and down time. We had 3-5 hours of working sessions each day and the rest was fun and down time. Make sure you let people relax. 

For example, we took time out to visit clients and experience their missions. Here we are at a DC Scores game:

  1. Send a follow-up survey and tie up loose ends

After your team has had time to settle back into their work routine and retreat notes have been transcribed and placed in an easily accessible location, you’ll want to send a post-retreat survey that addresses any outstanding items. It’s great to ask about opinions regarding location and venue, but don’t be afraid to ask the questions that might have scary answers: Was this worth our time as a company? Did you enjoy the discussions and feel heard? Given the topics and problems addressed, how can the company do better in supporting you as a person and a professional? Do you think the company has a clear goal and vision as we move into next year? By being vulnerable and transparent in the questions you ask, your staff will likely feel comfortable responding in the same manner. And, it eliminates the frustrating experience of “Whatever happened with XYZ thing we talked about?”…Whoops. 
I hope that these planning tips will yield a retreat that actually addresses the issues and large strategic questions your company needs to flesh out. For Spark Point, we walked away with a better sense of connectedness, a firm foundation for approaching the coming challenges, and a group-curated Spotify playlist! Happy planning! And stay tuned for part two of this retreat series!

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