Stabilize
A season for steadying, when something load-bearing is asking for attention before the big directional questions can get a fair hearing.
Sixty to ninety days
The KindTru approach
The real work of strategy is making choices, and a plan earns its keep to the extent that it records those choices and helps you act on them.
Strategic planning is usually described as the process by which an organization produces a three-year or five-year plan. I understand why, since that is the most visible part. Still, I have come to think the description puts the emphasis in the wrong place, and I suspect it explains a great many plans sitting in a great many drawers.
How I see it
If the plan is the point, a thin planning season produces a thin plan and the whole effort feels wasted. If the choosing is the point, then even a short afternoon leaves you better off, because the choices got made and everyone knows what they are.
Understood as choosing rather than producing, planning becomes less a document and more a practice: looking honestly, deciding, putting resources behind the decisions, and adapting as you learn. The document is one artifact made along the way, and I have come to think it is not the point. That matters most for a small organization, I suspect. If the plan is the point, a thin planning season produces a thin plan and the whole effort feels wasted. If the choosing is the point, then even a short afternoon leaves you better off, because the choices got made and everyone knows what they are.
Aspiration is the enjoyable part, and I say that with affection, because I enjoy it too. A room full of people who care about the same mission can produce a stirring five-year vision in ninety minutes, and it will feel like real progress. In my experience the difficulty arrives later, when that vision meets a budget that cannot carry it, or a board member who quietly disagreed in the room and said nothing. So I would ask the plainer questions first. Where are we strong? Where is the strain? And one I have watched change the temperature of a room: what does the board think the staff thinks?
One more thing seems to matter for an organization your size. The question “what does the community need?” has an answer that never really changes (more than any one organization can provide), so I have found it more useful to ask “what can we deliver excellently, given who we actually are?” That one has an answer, and the answer is a strategy.
As for how a good process moves, I think of it in eight movements: Prepare, Listen, See, Make Meaning, Choose, Build, Execute, and then Learn and Adapt. Choose is the one most processes skip, and skipping it is why so many plans feel unreal to the people asked to carry them.
Community surrounds all eight. The people you serve are not a consultation step to be finished early and ticked off. Their voice belongs wherever a choice is being made about work that affects them.
What can we deliver excellently, given who we actually are?
How a good process moves
Choose is the one most processes skip, and skipping it is why so many plans feel unreal to the people asked to carry them.
Community surrounds all eight
What kind of planning?
If there is one thing on this page I would plant a flag on, it is this: the most expensive mistake in our field is running the wrong kind of planning process. A five-year visioning retreat is exactly right for one organization and genuinely hard on another, and the difference is usually the season the organization is in rather than its size or its budget. I have found it helps to give those seasons names. None of them is better than another.
A season for steadying, when something load-bearing is asking for attention before the big directional questions can get a fair hearing.
More good work than the organization can sustain, where what is needed is a choosing conversation more than a planning document.
Solid ground, where the question is how to strengthen so the organization can keep its promises at the size it wants to be.
A shifting landscape, where the organization may be steady but planning has to watch as carefully as it commits.
The deep questions, about what this organization is for and what shape it should take next.
The standard
Across the planning rooms I have sat in, the processes that changed anything seemed to share the same properties. I hold our own materials to this list, and you are welcome to hold me to it.
Fifteen is more than any one process will carry perfectly, so I offer it as something to review against rather than a bar to clear.
Where to start
01 · Understand
02 · Act
03 · Thrive
Planning tends to go better when everyone starts from the same picture, and that is what I built the KindTru assessment to give you: the key categories of organizational health, answered confidentially by the people who know the organization from the inside, and returned as a report your leadership can read in an evening. From there, the Facilitation Kit helps your board spend one hour on one decision, and the Action Plan keeps a record of what it decided, with owners and dates. When the decision is about direction, the Strategic Planning Kit turns your own results into a half-day retreat your team can run (an agenda, a script you can speak from, choosing exercises and a plan on a page), and the Planning Room holds the guides and tools for every kind of planning. Check-ins and Board Development help you keep it going through the year. All of it comes with the same one-time $299.

The guide
Everything on this page at more length, along with the parts that would not fit: how each season tends to go, the tensions that surface along the way, and how to size all of it for an afternoon rather than a season. I wrote it so that an organization could run a good process without me. It is free, and I will treat your email address with respect.
Whatever you use, and whether or not any of it is ours, I hope the planning goes well. I hope it leaves your organization steadier than it found you, and a little clearer about what you are choosing.