In terms both of creative, meaningful board involvement and of the generation of high-level planning guidance, an intensive strategic work session – or what is commonly known as a “retreat” – involving your board, CEO, and senior managers is one of the most powerful ways to kick off your nonprofit’s annual planning cycle.  By “retreat,” I mean an event that involves your Strategic Governing Team’s spending at least a full day together in a setting away from the office, engaged in working through a common agenda.  A well-designed retreat can generate high-level guidance not only to the Strategic Change Portfolio planning stream, but also to the operational planning/budget preparation stream that proceeds separately from, but concurrently with, the Portfolio process.  A retreat can also produce valuable spin-offs, such as:

• Enhanced knowledge about your nonprofit’s operations and its internal and external environment
• Strong feelings of ownership – of both the Strategic Change Portfolio process and of the substantive planning outcomes (such as an updated vision statement)
• A more cohesive Strategic Governing Team as a result of working closely together in generating important outcomes
• The esprit de corps that comes from engaging in exciting and even fun work

However, as you may have learned from bitter experience, only meticulously designed retreats are apt to produce such impressive results, and you are likely to rue the day that you gather your whole Strategic Governing Team for a haphazardly planned session.  On countless occasions over the years, while interviewing board members as part of retreat preparation processes, I have heard disgusted accounts of retreats that have gone awry, wasting everyone’s time and insulting their intelligence.  The sour taste from such “retreats from hell” tends not to fade away quickly, making board and staff members quite reluctant to embark on another retreat adventure anytime in the foreseeable future. One of the highest prices of holding a poorly designed retreat can be the estrangement of your board members from the planning process.

The key to a productive and emotionally satisfying retreat is a well structured and facilitated retreat design process that involves selected board members (perhaps your planning and development committee, the governance (or board operations) committee, or an ad hoc design committee) and the CEO in thinking through all of the key elements of the retreat, often with the assistance of a professional facilitator:

• The objectives to be tackled:  for example, to update values and vision; to identify and discuss strategic issues; to brainstorm possible change initiatives
• The structure of the session:  for example, that breakout groups will be used to do much of the work, that dress will be casual, that participants will stay overnight
• And the blow-by-blow agenda to guide participants through the process

In addition to the three basic components of your nonprofit’s retreat design, the following factors have helped to ensure the success of hundreds of retreats that I have facilitated or participated in over the years:

• The key design elements are described in detail in a memorandum from the retreat design committee that is transmitted to all invited participants at least a month before the retreat.
• Breakout groups led by board members are employed to generate substantive planning outcomes and to ensure active participation.
• The breakout group process is defined in enough detail that everyone knows what they are expected to do.
• The board members who have agreed to serve as breakout group leaders are provided with sufficient orientation and training to ensure success at doing their very visible job.
• No formal decision-making is attempted during the retreat, in order to prevent premature, “seat of the pants” judgments that will be regretted later, as new knowledge and more in-depth deliberations lead to different conclusions than those reached in only a day or two together.
• The follow-through process is thought through before the retreat takes place.
• Professional facilitation is employed to keep deliberations on track and to make sure that the objectives are fully achieved.

Sending a detailed retreat design memorandum to all invited retreat participants will serve two important purposes.  In the first place, it is intended to provide invited participants with enough detail to understand what is going to happen, so that they will not be needlessly apprehensive about the event.  In my experience  even highly successful people whom you would expect not to spend a minute fretting about an upcoming retreat tend to worry about the possibility of being put in an embarrassing position by some kind of “touchy-feely” exercise or, even worse, wasting their time or being bored out of their minds.

Such a formal and detailed retreat design memorandum serves another very important purpose: signaling to everyone involved the seriousness of the retreat.  Everyone knows in advance that far from being a “ho-hum” event, the retreat will address very important questions through carefully designed structure and process.  Not only will you not waste your time, you will think twice about missing the experience.  The fact that the design memorandum comes from several board members, the CEO, and the professional facilitator symbolizes that participants’ peers, not just an outsider, shaped the design and are willing to take public accountability for it.

Well-designed breakout groups can play a critical role in making a retreat a more powerful experience.  For one thing, involving several board members as breakout group leaders is a very effective way to expand ownership of a retreat, for two reasons:  giving them a serious stake in the process; and providing them with an ego-satisfying experience.  As owners, board members are far more likely to work hard to make the retreat successful, rather than merely sitting back as neutral observers and judges.  However, if your retreat design incorporates the use of board members as breakout group leaders, you cannot afford to let any leader look less than capable in the role; faltering publicly would embarrass anybody, and public embarrassment is not soon forgotten.  So part of the retreat preparation process is preparing board members to play their leadership role, which can include developing breakout group process guidelines  and providing a thorough orientation and training session for breakout group leaders.

Of course, employing breakout groups can also generate much more content than can be produced by a group doing all of its work in plenary session, and breaking people into smaller groups is a sure-fire way to promote more active participation.  Having people participate in three different groups over the course of the retreat diversifies interaction, which is an excellent way to enhance intimacy by breaking down stereotypes and deepening people’s understanding of each other. Breakout groups can also contribute to making your retreat a more satisfying theatrical experience, adding fun and excitement, which should be a top-tier retreat design concern.  Keep in mind that in the process of generating content, such as an updated vision statement, you want people to be excited and to enjoy the experience; if the process feels boring or onerous, ownership will decline.

One good technique for enlivening the retreat experience is to require that all breakout group participants assist in reporting back to the plenary session on their groups’ deliberations.  You can picture the scene:  eight members of a breakout group standing by their flip chart sheets taped on the wall, describing sheet-by-sheet what they came up with and taking questions from the floor.  I trust that this sounds far more dynamic than everyone sitting in a room working through an issue together.  You should also keep in mind that requiring every breakout group member to participate in reporting back to the whole group is an effective way to keep people’s attention focused on their assigned tasks throughout the retreat; after all, to let your mind wander is to risk not being able to explain your group’s work during the plenary reporting session.