Nonprofit Board Strategic Planning Retreats: 7 Tips to Make Them Remarkable

At the close of a recent strategic planning retreat, each participant shared brief reflections on the benefits of the strategic planning day. Nonprofit staff and board members  spoke about how meaningful it was to come together and get to know each other better, how much they had learned through the conversations, and how they felt hopeful and positive about the ways in which their visions for the organization were translated into concrete plans. One comment was particularly memorable; a long-time board member shared that, of all the nonprofit board retreats he had attended, this was the best.

Wow! It was gratifying to receive the positive feedback. As I headed home, I felt a strong sense of appreciation. This is the feedback that The Ross Collective is consistently receiving about the processes we’re running for board members or staff teams.

And to be honest: We’ve refined our process over the past few years so that it is stronger than it was at the beginning. When we started out, we weren’t as consistent in receiving highly positive feedback from every group. Each time something did not work as effectively as expected, we reflected on what happened and thought about how to build the next process even better.

7  steps to create impactful, successful board planning retreats or nonprofit strategic planning retreats

Here are seven principles that The Ross Collective uses to design and lead impactful board or strategic planning retreats for nonprofit organizations:

1. We define your organization’s  strategic priorities

These processes always focus on the question: What are the most important conversations for this group to be having now based on the organization’s strategic priorities? We’ll start with that question and keep asking it along the way. We bring many ideas for how to structure team conversations. We may start with our organizational mapping tool to frame the conversation.  But the design always comes from thinking about how the staff and board members can spend the time together in the most productive and worthwhile way possible. Coming out of a long period when we could not gather, in-person time (if possible) feels especially precious. We guide the group to productively deepen our connections to one another, the organization’s mission, and the changes that the organization is working towards.

2. We collaborate with a Design Team to guide strategic planning agendas or board retreat processes.

The Design Team is four-to-six representative staff and board members who weigh in on retreat agendas. We’ll conduct a kickoff meeting with the Design Team to learn about their vision for planning. During our Discovery Process we learn about the organization and its work. Then, we build a draft agenda and share it with the Design Team to get their feedback. We want to know: Based on what we’ve talked about, are we having the right conversations? We keep adjusting the agenda until we hit the sweet spot.

3. We conduct assessments and interviews before, during and after the strategic planning process

We customarily include a board assessment or survey and discovery interviews as part of the process. The Ross Collective uses our proprietary board assessment that asks about board roles and board functions as well as board composition and the path to equity. This assessment is based on the qualities of strong boards from Boardsource and our commitment to equity on boards. We have other assessments around fundraising or strategic planning directions that we can draw on or, for a larger process, customize to the organization. 

Taking the assessments and reviewing the results gives board members and nonprofit organization staff the opportunity to reflect on organizational strengths and challenges. These assessments and interviews are a chance to share and be transparent about the good, the bad, and the ugly. Hopefully your organization has a lot of good! Most teams or board organizations also have some weak spots and that’s okay. You begin to strengthen your work together when you’re open to discussing it. We bring courage, directness, and compassion to the places where you want to get better.

4. We build a strategic vision and nonprofit strategic plan together

We often include visioning and planning in the day. In addition to relationship building, this is the most important activity that the group does. People feel excited to create a vision together and a plan for next steps. Using your organization’s core values to create a cohesive vision for the organization is important, as the board and staff members are able to all buy in to its ambitions and goals. Capturing this is priceless in terms of developing alignment around the vision and team priorities.

5. Every process is interactive

All strategic planning retreats or board governance processes are really (really!) interactive. Whether the retreat is virtual or in-person, we spend a lot of the time in breakout groups for small group discussions. This gives participants a chance to deepen relationships and learn from other staff and board members. Some group members are less comfortable speaking in the large group, so breakout groups are also a built-in way to ensure that each person’s perspective is heard and honored.

6. We evaluate and learn for future nonprofit board retreats

We conduct a retreat evaluation and share this feedback with the Design Team. We want to hear what participants found to be most effective and keep course correcting to make sure our work with groups stays as effective as possible. We ask about which conversations were especially useful, and also whether there was something that participants wished that the group had explored.

7. We include follow-up in the strategic planning process

When possible, we include follow-up meetings in the contract. For most boards or teams, the work we’ve generated in these meetings does add additional work. Having a consultant check in about this helps keep the work that was generated at the retreat on track.

We are intentionally inclusive and drive participation from the very start of this process with a new nonprofit organization. Since a key concept in strategic planning is cohesiveness within the team, we focus strongly on developing a vision together. 

After that, we work to continuously engage and communicate with the Design Team to ensure that we’re drafting a plan that meets the goals of the nonprofit organization. Afterwards, evaluation and continued discussion helps to fortify the gains during the retreat. 

Our hope is that the transparency, communication, developing the vision for the nonprofit organization, engagement and participation of the members, evaluation, and continued purposeful discussion will grow throughout an organization. We have found the greatest success with our partners with those key elements.

Get started with your nonprofit organization’s strategic planning or board retreat!

Does this sound like the kind of strategic planning or board retreat process that would enhance your organization’s work?