Transform Your Family Dynamic: The Magic of a Retreat

It’s great for families to bond over dinner or vacation, but it’s also important to have meetings with purpose and intention. That’s where the idea of a “family meeting” or “family retreat” comes in. These gatherings provide a structured environment for families to achieve specific objectives and have intentional conversations. They can also be used for educational purposes or to reinforce trust, strengthen relationships, and pass down important values. With a little planning, these moments can be just as enjoyable and fulfilling as casual get-togethers—all while helping you achieve a shared goal.

Whether you call it a family meeting or a family retreat, the idea is the same: to create a space where you can come together and have meaningful conversations with fewer distractions. At the same time, they help create lasting memories that will be cherished for years to come.

The Devil Is in the Details

When it comes to planning a family retreat or assembly, it’s important to consider the dynamics of your family. After all, every family is different, and what works for one may not work for another. Take the time to understand your family’s specific needs and goals before you start planning.

Once you’ve defined the purpose of the retreat, you can begin shaping an agenda that meets your family’s needs. That includes coordinating with subject matter experts to ensure that your family gets the most out of the experience. Be sure to set expectations and ensure that everyone is on the same page before the retreat begins. By putting in the time up front, you’ll improve the odds that your family retreat is a success—and that everyone leaves feeling closer and more connected.

Keep in mind, for smaller families, meetings and retreats can be shorter and less formal. Larger families may require a more complex and structured retreat. As your family evolves and grows, make sure your family meetings and retreats keep pace with your changing needs.

In addition, family meetings and retreats can also be a time to celebrate milestones and achievements. Whatever you hope to achieve, allow enough time for planning, as organizing a family meeting or retreat can be daunting. But the planning process can also be a gateway to building relationships and bonding with family members. By working together to plan a successful gathering, you can strengthen connections and see others in a whole new light. 

No One Size Fits All

When it comes to planning family meetings and retreats, there is no one-size-fits-all approach. In smaller families, one person may assume responsibility for planning, while larger families may require a small group of family members to own the logistics. That includes determining who needs to attend and what the meeting objectives are. When there is a committee—or other representative body making plans—be sure to cast a wide net for ideas and agenda topics and allow for input before finalizing them.

While all families should consider the importance of organizing and planning logistics, those with a family office can leverage its centralized position to help with this task. The office can take point on road mapping the agenda items, setting goals for the meeting, and ensuring that all participants are prepared. This will vary based on the objectives you hope to achieve, whether it’s specific problems that need to be solved, making important decisions, planning for an upcoming transition, or simply checking in with family members and gathering feedback.

Agendas can cover a variety of activities, from education and discussions about a family enterprise to philanthropic planning and events that promote family bonding. Depending on the complexity of the situation, these activities can be accomplished in one day or span multiple days. Consider the timing of gatherings as well. Many families decide to gather one to two times a year, with shorter one-day gatherings more frequently throughout the year for larger families. Annual get-togethers with a longer two-to-three-day retreat every other year are also common. Successful agendas often intersperse social activities—like welcome dinners and icebreakers—with breakout sessions that explore family and business history, current challenges, and philanthropy discussions.

Families may also hold retreats that revolve around a specific theme, such as a “newlywed” weekend catering to new members who have married into the family. These retreats can be an ideal way to welcome newcomers while sharing the family’s values, an overview of its business, and how the family makes collective decisions. These types of gatherings also help to build stronger relationships between different branches of the family. They provide a fun and engaging way to clarify which opportunities are available for spouses versus lineal descendants, while also fostering a sense of camaraderie and togetherness.

When deciding on a location, be sure to choose an alluring destination that will boost participation and excitement. On the other hand, families with an operating business may decide to host the retreat on-site or in the same city or town as the headquarters, allowing families to tour the business facilities periodically.

What About Kids?

Children can be delightful additions to a family gathering, depending on the nature of your agenda. Whether to include them often depends on the different types of participants who will be attending. For example, if your family has a business, you may have shareholders who are of different ages and levels of involvement. Keep in mind the age when children gain ownership and what their role is in the business. While younger children may not participate in formal shareholder meetings, having them in the vicinity of discussions can increase transparency and reduce uncertainty, which can help shape future stewards.

In addition to learning about the family business, children can also benefit from being around family members they don’t see very often. This can help build and strengthen relationships, which is important for maintaining a sense of connection and togetherness among family members. By observing adults navigate difficult conversations, disagree, have conflict—and then move on—children can learn important skills that they can use to integrate family values into their day-to-day lives while establishing a foundation for future involvement. 

What are some kid-friendly ideas? Develop savings plans for allowances, share life lessons from the family and/or its business history, or give them a say in family philanthropy discussions. The gatherings can also provide a window into different charitable causes that younger generations might be interested in supporting someday. By giving children a voice in these discussions, families can help build their self-esteem and ensure they feel like valued contributors. It’s also a great way for everyone to hear fresh ideas and perspectives.

Measuring Success

Over time, frequent, well-run gatherings ultimately lead to better-functioning families. When handled effectively, they foster improved communication and a deeper appreciation for the upside of healthy conflict. Participants discover hidden talents, learn from each other and figure out how to work together while gaining a stronger sense of the family’s history and values.

In the beginning, family meetings might feel somewhat awkward. But with time, they become more ingrained—and valuable. Many families find it helpful to partner with an external advisor to facilitate the family retreat and ensure effective follow-up. By delegating that aspect, you can unlock the magic of a transformative retreat while immersing yourself in the experience.