Key Ingredients for a Joyful Family Retreat
By: Darcy Addison, Partner and Advisor
“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.” – Priya Parker, The Art of the Gathering
Is your family coming together for the first time in years? We believe that a great family retreat is more than just a gathering. It’s a chance to bring joy and gratitude into the conversation. A reminder of the unique position a family can play in philanthropy. A strategic opportunity to align multi-generational values with impactful giving. Therefore, we’re sharing our top 5 elements for crafting a successful retreat; which includes clear objective-setting, professional facilitation to navigate complex family dynamics, the establishment of a “safe space” for open dialogue, and creating moments of joy. A family retreat is surely a time when goals can be set – and mission, vision, and values are turned into action – but it’s also meant to be fun.
Find a Quiet and Comfortable Space
One of the most crucial and often overlooked aspects of setting the tone for a family retreat is selecting the right venue – what I like to call the “room where it happens” (a nod to Hamilton). This space should be free from distractions and inspire creativity. It should be comfortable for everyone, where every member is on equal footing. Ideal options include a boardroom at a law firm, a conference room at a foundation, or a private space at a nonprofit. Choosing a setting that is physically and mentally removed from the family’s usual environment encourages fresh thinking and allows for the “business of philanthropy” to receive the proper attention it deserves.
Also, don’t overlook food and snacks! A well-fed group is more productive, so ensure breakfast, lunch, and coffee (including any dietary restrictions) are taken care of before you begin. Everyone works better on a happy stomach. And you don’t want to be placing a lunch order in the middle of the meeting!
Create a “Safe” Space
While comfort is essential, creating a “safe space” is equally important. Family members should feel free to express differing opinions without fear of offending others. Inclusivity is crucial; everyone should have a voice during the retreat. To warm up the group, we often kick things off with icebreakers, especially if it’s an early morning start. Although some may resist these activities (or detest them!), they work wonders for setting the tone for the day and fostering dialogue. Starting the day with a shared memory or a laugh can pave the way for better collaboration and outcomes. Ideas include – taking a moment to share family rituals, or part of the lesser known family narrative. This is an opportunity to invite stories, pictures, and videos into the mix – after all, this is family. Break out the phones now – share the newest pictures!
Get on the Same Page
We like to begin each meeting with group agreements, inspired by our friends at 21/64, a next-gen training program for advisors. One of my personal favorites is “Assume Best Intentions.” In addition, everyone at the meeting should be respectful of each other, and setting expectations can lead to greater engagement. It’s respectful to agree on what behaviors are acceptable – and not acceptable (like phone use) – during the retreat. Start by addressing housekeeping items, like bathroom locations and encouraging participants to stretch or take breaks as needed. Hugs are welcome too!
Stick to the Agenda
Next, we do an overview of the agenda and intended outcomes for the day – to ensure everyone is aligned. The agenda should be thoughtfully crafted, defining specific goals; whether it’s revising a grant-making strategy or discussing succession planning. While it’s essential to stick to the agenda to cover all necessary items, flexibility is also key. Some discussions may require more time, and it’s important to thoughtfully plan for difficult conversations, allowing them to receive the attention they deserve.
Keep track of time to ensure you’re on schedule, and be prepared to arrange follow-up meetings for topics that need more discussion. Always keep the intended outcomes front and center: Are grants to be decided today? If so, make sure that happens. Do you need to vote on a new policy? Take that vote. Exploring a new field or issue area? Brainstorm ideas that everyone is excited about. Finally, end the retreat with a clear list of actionable next steps, assigned responsibilities, and timelines for implementation.
Work with an Advisor
It goes without saying that hiring a third-party facilitator, such as a philanthropic advisor, can lead to the best results for your family retreat. It may seem counterintuitive to invite someone outside the family, especially if you don’t see each other often. However, when discussing critical topics like succession planning or multi-year giving strategies, having an expert in the room is invaluable. According to “A Guide to Meaningfully Engaging Next-Generation Adults in Your Philanthropy” by The National Center for Family Philanthropy, using a third-party facilitator is a recommended strategy to foster inclusive, candid discussions, ensuring younger or less vocal members are empowered to participate. Advisors are there to facilitate discussions, especially when past family dynamics emerge. Advisors listen to what the family values – in order to turn those values into actionable plans – ensuring you have a roadmap to achieve your philanthropic goals at the end of the retreat.
By weaving together thoughtful structure and professional guidance, your retreat becomes more than just a meeting – it transforms into a lasting legacy of shared purpose. Ultimately, a well-planned retreat ensures that your philanthropy doesn’t just make an impact in the world, but strengthens the bonds of the family behind it.
About Grant Philanthropic Advisors:
We’re an independent firm helping clients to focus and maximize their philanthropy—in turn, strengthening the fabric of our communities. Founded in 2019, we help donors move from responsive patterns of giving by assisting clients to identify values and become more strategic in their philanthropy. Our goal is to help donors to become more effective as change-makers. We work with foundations (large and small staff teams), donor advised fund holders, multi generational families, individuals, philanthropy supporting organizations and corporations to design philanthropic strategies.