The Art of the Team Retreat

This blog originally appeared in eJewish Philanthropy.

Planning a retreat for a professional team is an opportunity to create a space filled with meaning, where colleagues have a sense of belonging and each person feels they are at the center of the experience. Priya Parker is an expert on this subject, writing about the “art of gathering” and the intentionality required to do this well. She notes that “gatherings crackle and flourish when real thought goes into them, when (often invisible) structure is baked into them, and when a host has the curiosity, willingness, and generosity of spirit to try.”

“Think of what you want to be different because you gathered,” she advises, “and work backward from that outcome.”

In the Jewish professional world, the need for this intentional gathering space feels more important than ever.

As program officers at the Jim Joseph Foundation, we were asked to plan a series of retreats for the foundation’s program team. After doing some research on strategies and best practices, we had our first retreat in March; two others will occur later this year. While each retreat will cover different areas, we wanted the thematic throughline to connect to the foundation’s Strategic Road Map and the aspiration to help people find “connection, meaning and purpose.”

We learned a lot after planning the first retreat, and knowing that other organizations are also exploring ways to come together in this moment, we are sharing five insights inspired by Parker’s wisdom and our experience:

1. Define the purpose and design around it.

Having a stated purpose helps to make planning decisions big and small along the way.

Our team had not met in person for a full day in years, since before the pandemic. We wanted people to have a very clear understanding of what our purpose would be on this special occasion, and we wanted our purpose to reflect the “core assumptions” of the Jim Joseph Foundation. We went back to our Strategic Road Map, with its emphasis on Judaism’s role in cultivating connection, meaning and purpose, and developed a purpose statement for the first of our three team retreats in that vein: “To center our purpose as we develop how we function as a team of teams and deepen our relationships with one another.”

2.  Invite to ignite the experience.

Designing an invitation that evoked the intended energy of the retreat inspired excitement and anticipation across the team.

Investing time in designing an invitation for an internal team gathering might seem superfluous, yet it was one of the most consequential aspects of our planning. For our colleagues who received it, the invite was the entryway to this first retreat. We named the retreat Kavanah (Purpose), which helped set the tone and give insight into what they could experience.

3. Structure with meaning.

It’s one thing to want to be together for a day enjoying each other’s company, knowing we’ve all experienced similar stresses since Oct. 7; but beyond that, we understood that the day needed to offer space at the right time for different experiences.

After learning what other organizations — including some of our grantee-partners — do in this regard, we structured our retreat to include spaces for wellness, Jewish learning, connection and teamwork, each portion led by a different member of our team. This included:

• Welcome and Breakfast
• Jewish Learning – Kavanah
• Purpose Stories
• Wellness Walk and Lunch
• StrengthsFinder: Team Strengths and Superpowers
• How We Meet and Work as a Team
• Wrap up and Next Steps

A day of mixed modalities helped us stay on track with our purpose and offered something for everyone, from the physical to the spiritual to the educational to the strategic.

4. Host with the most.

One of our roles for these retreats is to serve as the “planners,” setting an agenda and facilitating discussion. Additionally, however, we also serve as the “hosts,” which infers something different: that we have “guests.”

This conception of our roles played out before and during the first retreat. In the lead-up to the retreat, we shared frequent communications about what to expect. Once there, we distributed a welcome folder to each team member, which included an agenda and worksheets for break-out sessions; it also contained a personalized printout of their StrengthsFinder top-five strengths so that they could refer back to the content after the retreat. We gave space throughout the day for each guest to lead an activity, sharing their unique expertise and perspectives from both their professional and personal experiences. Finally, just as any good host would do, we ensured that meal time, held around a communal table, was nourishing in more ways than one.

While having an “anchor host” is critical, there is significant value in inviting others to help lead and shape different aspects of the gathering.

5. Close with intention.

Particularly since we were tasked with planning not one but a series of retreats, we wanted the end of the first to feel like it was a door opening to more.

Our concluding session started with meaning-making: Each person expressed what they learned throughout the day, and how they felt about being able to come together. We then agreed on clear action steps for the next few months, including experimenting with some team meeting adjustments to enhance our productivity and how we work together. All of these were designed to build toward our next retreat, which is called Chibur (Connection).

Closing thoughtfully helps not only to capture takeaways from the retreat but also to transition mindfully back into day-to-day work.

We recognize how fortunate we are to work in an organization that values and encourages spending time to gather in this way. The Jim Joseph Foundation also lives out this value through various grants that support wellness for grantee-partners and the broader Jewish ecosystem through investments in enhancing work cultures within Jewish nonprofits. Planning and experiencing this initial retreat, we now better understand how integral these spaces are in supporting talent and ensuring we have a strong Jewish communal workforce. After all, this workforce is ultimately what creates and implements Jewish experiences that are filled with connection, meaning and purpose.

Jenna Hanauer and Rachel Shamash Schneider are program officers at the Jim Joseph Foundation.