Making the Most of Your Planning Retreat

For some, the word “retreat” is a dirty word. It too often means a day (or more) spent in a windowless room engaged in conversations and discussions that rarely seem to do much to advance the organization. Even the word “retreat” suggests going backward instead of forward. Should it surprise us then that nonprofit board members recoil at the very mention of a “planning retreat?”

When it comes to strategic planning, however, a retreat can be an invaluable tool that can actually speed the planning process. Think about it this way: a good strategic planning process should engage the board (and often the staff) in grappling with some important and/or thorny issues. The board needs time to explore these issues and discuss them fully, and it is unlikely your regularly scheduled board meetings provide the time needed for this.

So, rather than have these important discussions in piecemeal over several meetings, or leave them to committees, consider carving out some time—unhurried and unencumbered by the regular business of the board—to “retreat” into a planning mode. Structured right, and well-facilitated, you just might find that the board retreat is where the board is at its most productive.

In our work with our clients, there is sure to be a retreat (or an “extended planning meeting”) at some point along the way. Our experience informs the recommendations that follow:

  • Many boards maintain the practice of having an “annual retreat.” As the date approaches they struggle to figure out what to do with the time. If you have to figure out why you are having the retreat, don’t have it. Don’t waste your board members’ time.
  • Plan the agenda carefully to maximize the time. Before you schedule the retreat, determine what it is that you really need to accomplish. If you could do the same thing in a regularly scheduled meeting or by sending it to the board in writing, don’t do it. Use the time to deal with BIG issues—with strategic questions—that truly need time and careful thought.
  • Don’t underestimate the value of this opportunity for board members to get to know each other in a different setting. I’m not suggesting you spend lots of time on icebreaker exercises, however. I’m suggesting you find ways to help board members get to know each other at a deeper level and, ideally, advance the agenda too.
  • While our experience suggests a 5-6 hour block of uninterrupted time works well for most retreats, we’ve also worked with organizations where the retreat was chopped-up into separate sessions on different days. In a few cases, we’ve had groups that have met on two successive evenings for 3-4 hours each. In another case, we worked with a group that separated their sessions by a few weeks, purposefully, so they could take ideas from the first session, explore them further, and then pick-up the work at the second meeting. These approaches aren’t ideal in maintaining continuity and cohesiveness, but they can work.
  • It’s hard to facilitate and manage a meeting and also actively participate in it. Consider the potential value of paying a professional facilitator to help you develop your agenda and manage a meeting that helps you achieve your desired outcomes. A good facilitator can help to manage the time, ask (and ask again) the tough questions, and ensure participation by all the participants.
  • Keep in mind that while a retreat is often a part of a strategic planning process, it should not be the process. We see a lot of “annual planning retreats” as just that—a once a year occasion to create the annual work-plan. These sessions are helpful but rarely strategic. You should anticipate that a planning retreat will be an aspect of almost any strategic planning process, but it will be just one part of a multi-step process.

In our experience, it is not unusual to find that board members can’t remember what happened at the last board meeting, but they can often recall quite distinctly what happened at the retreat that took place many months ago. The retreat offers an opportunity for some truly meaningful discussion and for important decisions that can shape the direction of the organization. Board members appreciate these opportunities.

Plan your retreat well, maximize the time together, and focus on the BIG issues, and you’ll find that retreats can be essential tools to advancing the work of your board and your organization.

You’ll find more strategic planning advice, like this post written by Starboard’s Jeff Wahlstrom, on our website: If you would like to talk with a member of our consulting team about your strategic planning process or facilitating your upcoming retreat, use our contact form to begin the conversation.