The Elephant in the Room on Strategic Planning Day

Forty minutes into a strategic planning day, someone finally says the thing everyone in the room had been avoiding. The room falls silent. A few people glance at their coffee cups. The facilitator, who spent a lot of time preparing questions about priorities, resources, and community, is now standing in front of a conversation they didn’t plan for.

As a facilitator, this has happened to me more than once. It's rarely a surprise to the room. It's usually a surprise to me, because by the time it surfaces on planning day, it's already been the elephant for a while.

That's why I now ask every client in their kickoff call: is there anything unresolved that could pull focus during our session? A leadership dispute. A values disagreement. A program nobody wants to be the one to end. I'm not expecting a tidy answer, and there is no judgment attached to whatever the answer is. But it changes what I can do with it.

Why the Question Comes Before Planning Day, Not During It

A strategic planning session is built for a specific kind of work: aligning on direction, weighing options, building a shared plan the board and staff can unite behind. It isn't built to mediate an unresolved conflict that needs its own time, its own process, and often its own set of questions. Those are different jobs, even if it’s the same group of people working through both.

That's what I’m checking for when I ask about tricky topics in advance: whether the day I’m preparing for is the day the room is going to need.

What Happens When It Surfaces Mid-Session Instead

I prepare for a strategic planning day with real care. Questions sequenced, activities scoped to what I understand about the room, time budgeted to the minute. If halfway through, the actual work in front of us becomes something else entirely, I’m not equipped in that moment to facilitate it properly. Not for lack of general skill, but because that topic deserves its own preparation: research, targeted consultation, sometimes individual conversations before anyone is in a group setting at all.

Squeeze the discussion into the day anyway, and the strategic planning work is what gets sacrificed. The resulting plan comes out thin, because the attention is elsewhere. Try to work through the real issue with whatever time is left, and it gets a rushed pass at something that deserved better.

Neither one gets done well.

When the Deadline Is the Real Problem

Sometimes the pressure isn't coming from inside the room. It's coming from a funder or a provincial or national sport organization that requires a plan on file to maintain membership or funding conditions by a certain date. That deadline is real, and I'm not going to tell a board to ignore it.

But there's a difference between meeting a deadline for the sake of it and meeting it well. If your organization has something that genuinely needs to be worked through before you can plan strategically, that's worth raising directly with whoever holds the deadline. Funders and federations often deal with organizational complexity, and a proactive, honest conversation about your circumstances tends to land better than a plan built to check a box on time.

Two Ways Forward

As I see it, there are two options. The first is to work through the elephant on its own, then come to strategic planning once it’s resolved.

The second is to put it into the plan. Name it as a strategic outcome and key initiative with its own timeline, something the board commits to working through properly, rather squeezing it into a single planning day.

This does two things. It takes the deadline pressure off the topic itself, since it's now embedded into the plan's timeline instead of one afternoon. And it gives the topic the process it actually needs: the right information, the right voices at the table, enough time to reach a decision the organization can stand behind.

The Plan Doesn't Need Every Answer

A strategic plan doesn't need every hard question resolved before it's written. It needs to be honest about which questions are still open, and clear about how the organization intends to work through them. That's not a gap in the plan. That's the plan doing its job.

If you already know what your organization's elephant is, or you suspect there might be one, that conversation is worth having before a planning day gets booked, not during it. Let's talk about what that could look like for your board.