What makes a strategic planning process fail - and it's not the plan

After a decade of facilitation, I can usually tell in the first hour whether a strategic planning process is going to produce something real. It's not the quality of the materials. It's not the size of the room or the catering budget. It's something in how people are sitting, who's looking at their phone, and whether the executive director makes eye contact with their board chair.

Strategic planning processes fail for predictable reasons. Not because the consultant used the wrong framework. Not because the data was incomplete. They fail because of the things that were true before anyone walked into the room.

The plan is never the problem

I've seen beautifully written strategic plans accomplish nothing. I've seen rough, imperfect plans galvanize a team for three years. The difference was never the document. The difference was whether the people who needed to own the plan actually shaped it.

When a consultant - or a board committee, or an executive director working alone - writes a plan and presents it to the organization for ratification, the plan is already compromised. It doesn't matter how good the thinking is. If the people who have to live with it didn't help build it, they won't fight for it.

The signs I watch for before we even start

There are a few things that, when I see them in the intake process, tell me we need to do some work before we can do the planning work.

The first is a board and an executive director who aren't aligned on why they're doing this. If the board wants a plan to satisfy a funder and the ED wants a plan to get clarity on staffing, those aren't the same process. We have to name that before we start, or we'll spend five months making both groups quietly resentful.

The second is leadership that wants the process to be fast. Not efficient - fast. There's a difference. Efficient means we're thoughtful about where we spend time and energy. Fast means someone has already decided what the plan should say and wants the process to confirm it. That's not planning. That's theater.

The third is an organization that has skipped the hard conversation. Every organization I've worked with has at least one thing that everyone knows and no one says out loud. Sometimes it's a program that isn't working. Sometimes it's a board member who's been a problem for two years. Sometimes it's an ED who isn't sure they want to stay. A strategic planning process will surface these things. If leadership isn't prepared for that, the process will get derailed by them.

What I do about it

Before we design a process, I do an intake conversation with the executive director and at least one board leader. I ask direct questions: What has to be true for this process to succeed? What are you worried about? What would you be relieved to finally have out in the open?

The answers to those questions shape everything that follows. Sometimes they tell me we're ready to plan. Sometimes they tell me we need to do some organizational development work first. Either way, I'd rather know that in week one than discover it at the retreat.

The goal of strategic planning isn't a document. It's a shared understanding of where you're going and why - clear enough that people can make decisions aligned with it on a Tuesday afternoon without calling a meeting. That only happens when the process itself is honest. And honest processes take a little courage to begin.

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If you're thinking about a planning process, here's how I approach it.