Board Retreats: Strategic Centering through Learning, Engagement, and Follow Through

Board retreats might feel like obligations, things Heads and Board Chairs think they are supposed to do (“We’ve always had one in August.”). They become routine, numbingly rote. At their worst, they become bloated versions of regular board meetings, full of reports and showing-and-telling. Board members leave such gatherings in a kind of stupor, with no perspective on how what they have heard relates to their role as school trustees and fiduciaries.

Without an understanding of the possible benefit of a good board retreat, heads and board chairs tend to shorten them over time as though the retreat is a necessary evil, a waste of time to apologize for. Additionally, since the Pandemic, more and more schools have had as many as half of their board members join remotely, even when those members live in the area. This is an unhealthy practice as it limits the ability of the board to work together well both in moments of strategy creation and in times of crisis.

Given the critical demands on schools, board retreats must be better. Board chairs and heads in particular must carefully interrogate what they want to come from the retreat. Making the board retreat effective may also require reestablishing clear expectations for board member engagement. In short, they have an obligation to prepare for the retreat (and indeed all meetings), and to engage thoughtfully in it. Conversely, if board members are going to commit the time and energy to a retreat, the construction and planning for the retreat must be sound and engaging. Hearing reports for extended periods of time is rarely, if ever, deeply engaging. If this is the retreat in store, someone should apologize for it!

What is good work for a board retreat?

Work that provides the necessary learning for the board. For a board to be successful and provide the requisite strategic leadership, it needs professional learning. Too many boards make decisions based on intuition or blindly accept anecdotal impressions as truth. There are two types of necessary board learning: inside out and outside in.

• Inside Out: this learning allows the board to take a close look at a strategically critical aspect of the school’s work, building the board’s understanding in a way that provides the necessary perspective. For instance, if the school has a program that, inspired by the strategic plan and because of innovative leadership, is becoming distinctive, a deep dive into that program can inspire a conversation about how to catalyze that success. In addition, it should inspire a conversation about how to best support innovative and differentiated programming at the school generally.
• Outside In: this learning begins with a topic that all schools are facing (think about AI, regional demographic shifts, new understandings of how students learn best, and economic changes affecting the independent school market, or the shrinking pool of outstanding teachers). This type of board learning starts beyond the individual school, builds perspective, and then applies it to the individual school. There are times when there are significant topics on the horizon that heads have spotted, but the board has no way of identifying or recognizing the potential impact on their school in the future. A board retreat is a good setting to help the board build some perspective long before they have to be simply reactive to it. There are boards who have been discussing AI, for example, for years. Other boards have learned about critical market shifts long before a shrinking market affected the admissions pipeline.

What support does the head and board need to make the retreat valuable?

Access to outstanding expertise. Preparing an excellent board retreat requires selecting sources of good counsel for both pre-reads and perhaps in bringing in an outside speaker/facilitator. This outside speaker/facilitator might be someone from the faculty with an exceptional level of knowledge on a topic such as AI, it might be an expert in a given field, or it might be someone who is experienced in facilitating critical, and at times difficult, conversations with boards.

What preparation is requisite?

Maybe none. If there is preparation required of the board, it should be highly relevant and manageable in less than an hour. If the reading is not additive, don’t assign it. While we might want to ask more, the law of diminishing returns is in play here. As a rule of thumb you want to be able to refer to the reading without feeling as if everyone is pretending to have read it. (A hot-take: I think there should be some sort of accountability for board members based on an assumption that they have done the reading. For instance, as a means of beginning a deep-dive conversation, ask them to write for five minutes on what they believe were the most critical take-aways from an article. Not only is it a great way to begin a dialogue, but it also sets clear expectations for board member engagement without ever having to become shrill. If they haven’t done the reading, they are more likely to do it next time.)

What are the desired outcomes?

Seeking board engagement in a retreat is part of a positive outcome but it is likely not enough on its own. Knowing what outcomes you seek is necessary in planning well for the retreat itself. It is necessary to have answers to questions like these before completing planning:

• What are the learning objectives (be specific)?
• How will you know that the learning objectives have been met?
• How will board members participate?
• How will you ensure all board member voices are given space?
• What counsel are you seeking from the Board?

What will be the retreat follow-up?

No matter how engaging, no matter how successful the retreat felt in the room, its value is not determined in the room that particular day. Without a nuanced understanding of how the retreat fits into the bigger picture of the board’s work, its value is likely severely limited. The retreat should be relevant to the board’s established work. It should fit in as a puzzle piece. It may be helpful to think of this in fill in the blanks:

• This retreat is relevant to our strategy because…
• This learning will allow the board/board members to…
• This will pave the way for …
• We need to do this because…
• The board needs to have a deeper understanding of threat/ opportunity/ context/ reality

It is vital to have a follow-up communication with the board reflecting back key takeaways and intended learnings. Note: this is most effective if it is co-designed by the head and board chair. The key learning from the retreat will drift away if the head and board chair fail to steward the board attentively.

The board retreat should always be a part of strategy creation or strategy advancement. The line between strategy and the retreat should be clear and oft-repeated at the beginning and end of the retreat, as well as after the retreat. The retreat can be a way of moving strategy back toward the center of the board’s dialogue, and given that it is so easy for a board to drift from its strategic center, this can be the superpower of a well-planned, well-executed board retreat.

Please don’t hesitate to call on us if you’d like a thought partner in your board planning or retreat planning processes. We will always be glad to hear from you.