Good planning begins before everyone walks into the room
One of the biggest mistakes organizations make in strategic planning is assuming the process starts when everyone walks into the retreat.
The date gets scheduled. The room gets booked. Someone puts “Strategic Planning” at the top of an agenda. Then everyone shows up expecting that, over the next six hours, they are going to figure out the future of the organization.
That is asking a lot of six hours.
A good retreat can be an incredibly valuable part of strategic planning, but it should not be the first time people start thinking strategically. Before you start planning, you need to prepare and listen. And if I am facilitating the process, that work starts well before I walk into the room.
I want to understand what I am walking into
When I begin working with an organization, I want to understand as much as I reasonably can before I facilitate anything. I want to see the current strategic plan, finances, programs, staffing, organizational history, and relevant membership, client, or program data. I want to understand the major issues facing the organization and what decisions may be coming.
I do not need a 400-page data dump, and I do not expect an organization to have perfect information. But if we are going to make strategic decisions, we should have enough information to make informed ones.
If a membership organization is talking about launching a major new program, for example, I might want to know what participation has looked like in existing programs. What are members actually using? What might the new program cost? Is it expected to generate revenue? What might we stop doing to make room for it?
You do not need all the answers before the retreat. If you did, you probably would not need the retreat. But we need enough information to ask the right questions.
That matters for me as the facilitator too. I want enough context to know when the conversation is getting off course, when an assumption deserves to be challenged, or when there is a follow-up question that might get us somewhere more useful.
I want to talk before we plan
I also like to meet separately with the CEO or Executive Director and the Board Chair before a planning session. I want to know what each of them hopes we accomplish, what they think the big issues are, where they think the organization is headed, and whether there is a difficult conversation waiting for us.
And importantly: are they aligned?
I was once part of a Board retreat where the Executive Director came in with what was essentially a fully developed direction for the organization. It was not overtly presented that way, but as the retreat unfolded, it became clear that a lot of decisions had already been contemplated.
The Board Chair and much of the Board were not there yet. Some did not even realize that much work had already happened. Instead of moving forward with planning, the group had to stop and deal with a much bigger question about where the organization was actually headed.
Those conversations are much better to surface before the retreat than halfway through it.
As a facilitator, I am not trying to eliminate disagreement before everyone gets into the room. Disagreement can be incredibly productive. I just want to understand the dynamics so I can help the group work through them.
I want to hear from people who will not be in the room
Depending on the organization, I also like talking with people who may never attend the actual retreat. That could mean staff, members, program participants, funders, community partners, former Board members, or other stakeholders.
Sometimes that happens through interviews. Sometimes a focus group makes sense. Sometimes it is a survey. The approach depends on the organization and what we are trying to learn.
I also almost always like an anonymous Board survey before the retreat. It gets Board members thinking about the big questions before they arrive, but it also gives everyone a chance to raise something that might be harder to say in the room. That matters, especially when you have a few strong personalities who tend to dominate the conversation.
For me, all of that input is incredibly useful. I am listening for themes. Where do people agree? Where are the tensions? What keeps coming up? What surprised me? What does the Board actually need to wrestle with when we are together?
That does not mean every comment makes it onto the retreat agenda. Listening is not the same as taking a vote.
In one planning process, I spoke with a key funder who was disappointed that the organization had stopped some programming in a particular area. The organization had good reasons. Attendance had been low and the programs were not meeting the metrics they had established.
But the funder raised a different question: What happened in the larger community when those programs went away?
That changed the conversation. We did not simply conclude that the organization should bring the old programs back because a funder wanted them. Instead, the Board looked at the broader ecosystem. What were other organizations doing? What was no longer available? Where were the gaps?
They discovered a larger need that the organization was particularly well positioned to address. That helped shape new strategic priorities and ultimately created an opportunity for greater impact.
That is why I listen before I facilitate. I am not gathering input so I can tell the Board what its strategy should be. I am gathering it so I can bring better questions into the room.
Then we can use the retreat for what matters
By the time everyone arrives, I want participants to understand the basics of the organization and to have had an opportunity to think about the issues in front of them.
That is also why, when possible, I do not love attaching strategic planning to the end of a regular Board meeting, particularly if the Board only meets quarterly. People naturally arrive with operational questions and updates they have been waiting months to discuss, and suddenly half of our planning time is spent catching up.
The retreat should be different. For me, its highest-value purposes are choices and alignment.
What matters most now? Where are we trying to go? What opportunities should we pursue? What challenges do we need to address? What are we willing to prioritize? And just as importantly, what are we not going to prioritize?
My role as facilitator is to create the structure for those conversations, make sure we hear from more than the loudest voices, push when an answer needs more examination, help the group recognize where it is actually aligned, and keep us moving toward choices.
I am not there to hand you the answer. I am there to help your organization get to its answer.
The retreat is only one step
My general approach to strategic planning follows six broad steps: Prepare → Listen → Vision → Plan → Execute → Evaluate
The exact process changes depending on the organization. A small nonprofit with a seven-person Board will not need the same preparation as a statewide organization with a large staff, multiple programs, and dozens of stakeholders. But the sequence matters to me.
We prepare so we understand where we are. We listen so we understand the environment around us. Then we can start making decisions about where we want to go and how we are going to get there.
And yes, somewhere in there I will probably make you do an icebreaker. I know. I cringe at some of them too. But we often assume people around a Board table know one another much better than they actually do, and getting people comfortable talking with each other matters when we are about to ask them to have bigger conversations.
So before you start building the agenda for your next strategic planning retreat, start with two questions: What do we need to know? Who do we need to hear from?
Those answers should shape what happens when everyone finally gets into the room.
And if you are thinking about strategic planning for your organization, I would love to talk with you about it. This is some of my favorite work through True Compass Strategies. I love learning about an organization, figuring out the questions underneath the obvious questions, and helping a Board and leadership team work through where they go next.
The retreat matters. Just make sure the work starts before it.