Seven Important Considerations Before Planning Your Next Team Retreat

Have you been charged with helping to plan your team’s offsite or summer retreat? Here are some tips to make sure the time is productive and engaging for everyone. If your team can’t step away from their desks for one day a year, you may need to evaluate why. Research shows that teams are more productive and innovative when they take time out to reflect upon their objectives, processes and culture and make changes accordingly.

1. Onsite or Offsite?

This could be compared to a “staycation” vs. a vacation. We all know which one we’d rather do! Honestly, either can work but I find that getting offsite helps people to psychologically unplug. People are less tempted to pop into their office during break and can’t be taken hostage by a colleague who “just needs a minute.” If going off site is too costly, consider asking a colleague at another organization to swap spaces. Take measures to protect the time If you stay onsite.

2. Outside or Internal Facilitator

It is hard to facilitate a conversation, capture the key points, synthesize the takeaways and be a participant at the same time. Bringing in a facilitator allows each person to be fully present and participate. Some teams bring in a HR business partner as a facilitator, just be sure that doing so will not stifle honest conversation. A good rule of thumb is that a facilitator will spend about one hour preparing for every hour of content. If you don’t bring in someone else to facilitate, divide and conquer by having people take responsibility for different portions of the day. Ask for time keepers, scribes and people to help with set up/clean up so not everything falls on one person.

3. Always Engage the Most Senior Person

Regardless of who facilitates, it is important to truly understand the leader’s hopes and objectives for the day. Alignment and buy-in from the top are crucial. Some good questions include, “How would you describe the team climate?” and “Imagine people are leaving the retreat. What do you want people to say about their experience?” or “What would it look like if we got this right?” A quick check in beforehand with each person on the team can help shape the content and target of focus of the retreat too. The worst team retreat I ever facilitated was when I had no contact with the team leader despite my attempts. I was blindsided! He arrived late to the retreat, was responding to email during the session, took a phone call and left early. Here is the message he sent to the group…other people are more important to me than you are. He missed the chance to show up and be fully present – just one day of the year! This was a team that was plagued with infighting and low engagement. Go figure!

4. Get Real

There is not much value in having a team retreat if the real conversation takes place the next day around the water cooler. You want to create a trusting environment that encourages people to let their guard down. Here is the surefire way to help your team get real—the most senior person must role model vulnerability. This sends the message that no is perfect and that people can be honest with themselves, which is the prerequire for being honest with each other.

5. Balancing Goal Setting and Team Building

All work and no play can make for a dull retreat. I find that a blend works well, though requires at least one full day, if not two days. Many leaders also want to find a way to celebrate the year’s successes. I worked with a leader who admittedly was so focused on goals that the team was longing for some words of praise and acknowledgement of hard work. Her compliments were couched with worry that the team shouldn’t get too comfortable or take their eye off the ball. If delivering heartfelt appreciation doesn’t come naturally, partner with other members of the senior leadership team who can authentically convey the enthusiasm and positivity that is needed. Our firm often uses the StrengthsFinder assessment as a way to help each person articulate their unique contribution to the team. This is a perfect prelude to goal setting and ensures that there is alignment of talent and task.

6. Unscheduled Time and Overnight Retreats

Plenty of team building can take place outside of the formal retreat – maybe it’s an early morning run for a few folks or a nightcap at the bar. It is important to make these optional with no repercussions for opting out. The leaders must always be sensitive to each person on the team. Does a nursing mother need time and space to pump? Is there someone in recovery who is not going to feel comfortable going to the bar? One of my favorite retreats was at a beautiful lodge overlooking a lake. During our day, we each had time to reflect on a key question. Some people chose to chat together, others walked quietly, some journaled. The secret here is to give people choices.

7. Push the Reset Button

Rituals have been around for thousands of years. They bring groups together, create bonds and promote hope. If your team has struggled, ask yourself what issues from the past need to be put to rest. For example, on my own team we devoted some time to talking through the year’s disappointments at our annual meeting. It cleared the air and helped us move past the hard moments we experienced. It felt like there was a collective exhale, fresh energy and a renewed commitment.

Lastly, it’s ok to NOT have the retreat. If your retreats have become stale, predictable and frankly boring, its ok to take a year off. Or better yet, mix it up and try something completely new!

Sara Regan, President of Strengths Now, has 25 years of experience working with teams and designing impactful retreats to drive business results and strengthen collaboration. Contact us to book now or learn more.