Make the Most of Your Team Retreat with These Six Steps

An extended team strategy session (sometimes called a team retreat, team off-site, or team deep dive) has been scheduled. After comparing what look like impossible calendars, simply finding a day when the full team is available feels like a huge success. First hurdle surmounted!

With the day booked, you turn your attention to planning a full-day agenda. The team desperately needs this time to step back, focus, and get aligned as a team. You know the opportunity to have this extended time together is hard to come by and therefore precious, and you want to be sure to plan a session that makes the most of everyone’s time together.

Of course, no two team retreats are the same, and the most important tip might be to know your context, know your audience, and plan accordingly. However, there are a set of steps that we follow consistently and find applicable across all the various contexts and clients with whom we work.

Six Steps to Prepare a Home Run Session

1) Be clear about your goals, and design around them.

It may seem obvious to say, but so many people blow past this step. What are your goals for the day? What do you really need to accomplish? What information and conversations truly need the attention of the full team, versus what can be effectively communicated in an email or covered in other meetings? There are a hundred different ways you could spend your time together, and without a clear purpose the day will not be maximized.

We often aim to distill the goals into sets of three, such as Connect, Learn, and Align or Learn, Assess, Decide. Learning is almost always one of our primary goals because we believe teams need to stay curious and open to possibilities as well as invited into opportunities to learn about the the current state and future vision of the organization. As my colleague Tara Tucci-Exilus has written, “Organizations that learn, change. And organizations that change thrive in the long run.” Whatever your goals, get clear about them and design the day around them.

2) Create your agenda.

With your goals in mind, you’re ready to develop an agenda. In a typical 4-6 week preparation period, without fail the agenda is going to change. Nonetheless, start somewhere and put some stakes in the ground. Write a first draft of the agenda that breaks the day into chunks of time for each goal and topic. The task of simply assigning times to each goal and topic usually reveals some overlap in priorities and forces getting honest about how much time can realistically be dedicated to each topic for discussion. Lastly, please put yourself in the shoes of a participant and be sure to include reasonable breaks in the day, as well as start and end times. As a three-time nursing mom, I can tell you that some of us really need the breaks.

3) Conduct pre-retreat interviews and/or survey.

You know what they say about making assumptions. One of the most important things you can do to make the most of your team retreat is to do sufficient homework so that you can design an agenda that meets people where they are, and not where you assume they are.

One way of learning is to interview team members in advance of the retreat. Ask questions and listen to understand their needs, experiences, ideas, and pain points. One of the worst things that can happen is that you design a full-day agenda thinking people need only a quick update on one topic, only to find out on the spot that there are a lot of different opinions that require dedicating the full morning to the topic. Pre-retreat conversations help you avoid this misstep.

Interviews can be brief (30 minutes), and you can always choose a select few to interview if time is an issue. You’d be surprised how often interviews unearth new information or context that gives you new perspective on how to most effectively approach the day. Stay curious and be willing to learn.

Another way you can gather information from participants is to release a simple pre-retreat survey. A survey may be preferable over interviews if time is limited or if the group is too large to interview. When we conduct surveys, we often include a mix of deeper questions about people’s experiences and perspectives on an issue, and some lighter questions that can help us plan engaging energizer and connection activities.

4) Create your content.

Do not underestimate the time it will take to create your content, and by that I mean your presentation slides, handouts, participant workbooks, etc. Let me say that again, do not underestimate the time it will take and do not procrastinate! It is true that some conversations can emerge organically and shouldn’t be over-orchestrated. However, it’s our experience that the best retreats are those that have been thoughtfully planned and designed.

Below are a few of the things we always take into consideration as we’re developing content for a team session.

  • Opportunities to connect: How might we create space for team members to connect as people and strengthen relationships? This might include an opportunity for deep 1:1 conversation that helps team members better get to know their colleagues on a personal level, or light energizers that spark laughter and creativity. Even if it’s only 10 minutes here and 15 minutes there, it’s our experience that opportunities for connection positively contribute to the success of the day, and ultimately the success of the team.

  • Facilitation: How will you approach each agenda item, and how will you help the team move through each topic? Know your audience, and have a plan to keep them engaged. Design the content in a way that will facilitate progress toward your goals. Try to anticipate any spots where team members will get stuck. Make discussion questions and activity instructions clear.

  • Doing the work in the meeting: How might you design the session to enable the fastest possible launch afterward? One of the worst feelings is leaving a full-day retreat feeling bogged down by a day’s worth of work just to type up notes and synthesize takeaways. To avoid this, design notetakers in the presentation slides and frame the content in such a way that it forces the group to synthesize during the meeting.

  • Accessibility and inclusion: How will you make sure that everyone attending will be able to equally participate and contribute? Some people like printed handouts, while others prefer to engage with their laptops. Most people cannot read 10 pt. font no matter how much you want to pack it all onto one slide. Also, how will you create the conditions to invite all voices into the conversation and encourage honest dialogue? Mix up moments for individual think time, small group conversation, and full group dialogue, with the goal of giving all participants a chance to contribute to the conversation. As you design content, always keep your participants in mind and what you can do to ensure a positive experience for them.

5) Assign pre-work.

One of the most effective ways to maximize your retreat time is to front load some of the baseline learning to a pre-read or pre-retreat exercise. Just as we invest in designing the session content, we put equal effort into developing a pre-read that can be shared in advance and gives everyone a chance to get on the same page before the session. The time in the session, then, can be spent on confirming and refining, as opposed to learning.

6) Communicate clearly.

Share your agenda, important logistics, and pre-work expectations with participants 5-7 days in advance of the meeting. Don’t leave people guessing about the goals of the day. Be proactive and open about the goals and what they can expect. Knowing the goals of the day helps people come ready to work. Even if specific pre-work isn’t assigned, the day’s objectives might prompt participants to have certain conversations with their teams in advance, pull together information they anticipate being relevant to the conversation, or flesh out their perspective on a particular issue. Clear communications not only tells people what to expect, it also gives you a chance to set a positive tone for the retreat before the day even begins.

Let it Roll

If you invest in the six steps above, you are ready to rock. You’ve done your homework and prepared a solid day with a lot of intention. Sure, the day will not go exactly as planned. Even with significant preparation, we often find ourselves in situations where we toss or streamline content on the spot in order to be responsive to how the conversation and session unfolds.

In addition to preparing for the day itself, be sure to give some thought to how the session you’ve planned might fit in with the team’s ongoing strategy. Will the retreat be a single one-off session, or will it be one of several thoughtfully designed touch points as part of a longer arc and ongoing process? In our experience, the best deep-dive days are the latter. So much energy goes into planning a great day, but if it’s not part of a bigger picture journey then it becomes this moment in time that quickly fades into the past. Situate the retreat in a sustained process that team members can begin to anticipate.

Hopefully these tips help you get the most out of your next team retreat. Follow these steps so you can go confidently into the day knowing you’ve done what it takes to maximize the extended time together. Now let it roll, trust the process, and have some fun.