To keep your board functioning like a well-oiled machine, efficiently and effectively driving your local Main Street organization forward, consider having a board retreat, which is a worthwhile workshop of sorts that’s dedicated to aligning board members on strategic goals and creating consensus. But, you can’t simply throw together the plans for your board retreat because this experience requires careful planning to make the most of having all of your board members gather together. Here are six tips to plan a productive retreat:
1. Fulfill Your Mission
The reason your organization exists is to fulfill its mission, whatever that may be, specifically. Your board is an instrumental part of that process, and they should be engaged and involved. A board retreat offers the perfect opportunity for everyone to regroup, reconnect and recharge, but it must have a clear purpose. Just like your mission statement, determine the why behind the board retreat, what it does and it’s objectives. Ask yourself, what are you seeking to accomplish?
2. Reenergize and Reengage Your Board
Use your board retreat to reignite the passion for the mission in board members and help form personal connections, which can foster board cohesion over the long term. Kickoff conversation with a “mission moment” or inspiring icebreaker that reminds everyone of their personal commitment and the common desire that’s shared amongst leaders.
3. Review Roles and Responsibilities
One key to a long-lasting, and effective Main Street program is an engaged and active working board. If the board possesses a strong understanding of roles an responsibilities and functions as a collaborative team working toward shared goals, then leaders will report positive impact on organizational performance. If you haven’t done so already, provide board members with an expectation sheet or agreement for board members to review and sign. Expectations of your board members should include attendance at meetings, making a personal donation, serving on at least one committee, acting as an advocate for your cause and helping with fundraising. During the retreat, consider having board members complete a self-assessment of how they did during the previous year, individually and as a board.
4. Plan for the Year
Most importantly, your board retreat should be used to prepare and plan for the year ahead. Review your strategic plan and/or work together to set a strategic direction that’s supported by the organization’s vision. Identify and set short-term and long-term goals, as well as action steps for implementation. And don’t forget to make specific assignments! Nothing gets done that doesn’t have a champion.
5. Raise More Money
Your board retreat represents a fantastic opportunity to engage board members in giving and getting. Discuss the importance of 100% participation and provide specific opportunities for each board member to get involved in the fundraising process. Remind them that fundraising isn’t just about raising funds for the nonprofit organization. It’s about inspiring people to want to give and support your mission. It’s about reaching people and not just their wallets.
6. Networking and Socializing
If possible, hold your retreat in a different location, or even a different community. Get out of the office and secure an outside facilitator, which will enable staff members to fully participate (if appropriate). A good facilitator will be able to keep discussion on point, keep to the agenda and move things along nicely. Also, if you want your board to work well together, they will need to feel comfortable so don’t forget to provide ample social and networking time. Don’t be afraid to loosen things up!
Example: Uptown Partnership 2022 Board Retreat
Last month, Uptown Partnership (UP) in Martinsville, Virginia held its first-ever board retreat to engage, encourage and reenergize board members as they commit to the organization’s mission, vision and overall goals; develop a strategic direction that’s supported by the organization’s recent community-driven Visioning Plan; and brainstorm development and fundraising opportunities to ensure viability. While they didn’t travel outside of the community, it felt appropriate to hold the organization’s first board retreat inside their new office / meeting space in Uptown Martinsville. It was symbolic of the fact that they’ve physically and positively made their presence known in the district, and it worked for this training!
The local Main Street organization invited staff from the Virginia Department of Housing and Community Development (DHCD) to facilitate the retreat, and through a series of presentations, exercises and conversations, UP board members:
- Learned why a healthy, viable downtown (or Uptown) is crucial to the economic health and civic pride of the entire community and how the Main Street Approach effectively guides the organization’s roadmap to revitalization;
- Strengthened internal board culture, which will help the organization improve performance, engage and energize volunteers, build consensus and cultivate strong collective wisdom;
- Revisited the organization’s Transformation Strategies to gauge their overall effectiveness; and
- Reflected on and recognized the importance of fund diversification, as well as the need to develop a fundraising plan, one that outlines how to foster thoughtful supporters and investors that champion the organization’s mission.
As the organization’s leaders left their first-ever board retreat, everyone was energized and ready to tackle the work that’s needed to build a highly successful and sustainable Main Street program!


