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7 Tips For Planning Remarkably Productive And Effective Board Retreats

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At the end of a recent strategic planning retreat, each participant shared brief reflections on the day. Board and staff 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 we had, and how they felt hopeful 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 board retreats he had attended, this was the best one. It was so gratifying to receive such 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 or staff teams.

In this post, I’ll share how we design these retreats so you can run effective ones of your own. With that in mind, here are the seven principles that we use to design and lead impactful strategic planning board retreats.

Essential Principles for Effective Board Retreat and Strategic Planning

Principle 1: Figure out the most important conversations the group needs to have right now.

The board retreat design always comes from thinking about how the group can spend the time together in the most productive and worthwhile way possible. That means knowing what to focus on. 

That’s why we start out by asking this question: “What are the most important conversations for this group to be having right now?” 

We have limited time together, which means we need that focal point. So we start with that question, and we keep asking it along the way. We guide the group to productively deepen our connections to one another, the organization’s mission, and the changes that the organization is working toward. 

If there’s any doubt throughout the day about how to move forward, we go back to that question. 

Principle 2: Collaborate with a design team to guide the strategic planning or board retreat processes. 

The design team is made up of four to six representative members of the staff and board who weigh in on retreat agendas. We work with them to learn about their vision for planning. During that 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. 

The point of this process is related to that first principle. We want to know: Are we having the right conversations? We go back and forth and keep adjusting the agenda until we hit the sweet spot and make sure we go into the retreat feeling confident that we’ll have the most productive conversations possible.

Principle 3: Conduct a board assessment, survey, or discovery interviews before the retreat. 

In order to learn more about what the board or staff members need, we customarily include a board assessment or survey and conduct discovery interviews as part of the retreat planning process. 

In the assessment, we ask about board roles, 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 nonprofit strategic planning directions that we can draw on or, for a larger process, customize to the organization. 

These assessments and interviews are a chance to share and be transparent about the good, the bad, and the ugly about what’s going on with the board, staff, or organization. Reviewing the results gives board and staff members the opportunity to reflect on organizational strengths and challenges, which helps them understand what is most important to focus on at the retreat.

Don’t worry: Most teams or boards have weak spots—and that’s OK! You can only strengthen your work together when you’re open to discussing it and how you need to improve. So, bring courage, directness, honesty, and compassion to the table when discussing the places where you want to get better.

Principle 4: Create a vision and a plan to execute it. 

We often include visioneering and planning in the day. In addition to building relationships, this is the best stuff of what the group does. 

Why? Because creating a cohesive vision for the organization is important, as the board and staff members are all able to buy into its ambitions and goals. Plus, people get excited about creating a vision together and a plan for next steps. Capturing this is priceless in terms of developing alignment around the vision and team priorities.

Principle 5: Ensure board retreats are interactive. 

Our strategic planning retreats or board governance processes are really interactive. Whether the retreat is virtual or in person, we spend a lot of time in breakout groups. 

We do this because having these groups gives participants a chance to deepen relationships and learn from one another. Some group members are less comfortable speaking in a larger group, so breakout groups are also a built-in way to ensure that each person’s perspective is heard and honored.

Principle 6: Conduct a retreat evaluation and share this feedback with the design team.

After the retreat, we conduct a retreat evaluation and share this feedback with the design team. We do this because we want to hear what participants found to be most effective and keep course correcting to make sure our work is as effective as possible. 

In that evaluation, we ask about which conversations were especially useful and what participants wished that the group had explored.

Principle 7: Have follow-up meetings (if possible). 

When possible, we include follow-up meetings. For most boards or teams, the work we’ve generated in these meetings adds additional work to their already-full workloads. After all, taking steps to improve your organization takes work. Having a consultant check in about this helps keep the work that was generated at the retreat on track. 

Evaluation and continued discussion help to fortify the gains made during the retreat. Our hope is that the transparency, communication, development of the vision for the organization, engagement and participation of the members, evaluation, and continued purposeful discussion will grow throughout an organization. We’ve found the greatest success with our partners with those key elements.

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

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