You Can't Map the Terrain You're Standing In

Part one of two. An organization that knew exactly where it wanted to go.

They knew what they wanted before I started my contract with them. A membership model, and a partisan arm to go with it. They hired me to help them develop a strategic plan for the shift. The organization was young and fast and very good at what it did - better at registering voters than anyone else in its state, expanding into new cities, and increasingly frustrated that all of that work wasn't translating into political leverage they could feel. Their executive director knew where the organization needed to go. My job, at the outset, was to create the roadmap to get them there.
After months of data collection and facilitated planning discussions that helped challenge their previously held premise, they had the courage to change direction. 

It wasn't that they were wrong. It was that they hadn't fully wrestled with the implications of the shift, or considered alternate paths to achieve their goals.

I'm telling this story because, after seven years at Grassroots Solutions, I've just launched Greenbelt Civic Strategy (read to the end to learn more), and I'd rather show the work than describe it. So: here it is, in two parts.


My former colleague and I started by laying a foundation through a series of initial planning meetings to get aligned on goals, the parameters of the final deliverable, and a set of strategic learning questions to guide the process. We then moved quickly to data collection to inform the remainder of the planning process. We built the inquiry in two universes. One internal survey went to the board, staff, fellows, interns, and alumni: everyone with a stake in the answer. A second external survey went to partners, funders, and allies who worked alongside them and, in a couple of cases, competed with them for the same dollars.

Internally, about sixty percent said a more partisan posture would get them the power they were after.

Externally, not one person supported it. Forty percent were opposed outright. The rest were unsure.

Same question, two sets of stakeholders, diverging answers.

What the external universe surfaced wasn't a no. It was a set of caution flags the organization's leadership hadn't had room to weigh because they were so focused on executing (and rightfully so). Their access to campuses, the thing that made their signature program possible, existed because they were nonpartisan, and that access could have closed. Funding sources would have narrowed as well. They would have become a larger target in a state that had already shown an appetite for targeting organizations like theirs, at a moment when they had nascent compliance infrastructure, a small development team, and an executive director carrying the fundraising almost alone.

So we pivoted and began to ask the strategic planning committee different questions. What did power mean here? Their answer, at the outset, was a partisan arm. They wanted the ability to be partisan to build long-term power in their state. Once the definition of power widened to include the depth of their base, a real leadership pipeline, the standing to hold elected officials accountable, and the ability to say no to the eleventh coalition ask of the month, the partisan vehicle became one option among several. And not the first one.

Evaluate strategies around the current conditions without challenging existing assumptions and you get a memo about the current strategy. Define what the organization is reaching for and you get the strategies and programs that actually deliver it.


That engagement is old enough now to have an outcome.

The organization built the internal capacity: a development team, real operations, succession plans, an issue screen that let them decline things. The succeeding executive director built on all of it. And several years later they were able to move in a more partisan direction, because by then they had gotten as far as they could without it, the environment had changed, and endorsing candidates had become necessary rather than exciting. When they did it, their board and their most important external stakeholders were behind them.

They were right. They were early. The sequence identified through our inquiries and facilitation is what let them be right later.

This raises the harder question of why so many planning processes never get to the breakthroughs necessary for an impactful strategic plan.

Ask a room what the organization should do while everyone's current job is sitting in the room with them, and each person answers a slightly different question: what can I do from here, with this budget, this staff, my already overflowing plate, this year? Everyone answers honestly. The sum of the honest answers is this year with the verbs upgraded.

Compress the timeline, thin the budget, add an unstated mandate to avoid conflict, and the ceiling is set before the first interview. Those aren't constraints that a process simply works around. They're design choices, and every one of them lowers what the process is capable of returning.

Nobody decides this. It's just what a process does when no one has built it to do otherwise.


There's a second story worth telling, about an organization in the opposite position. This one knew something was wrong, and had known for a while. What it couldn't do was say so out loud.

In that engagement, the most consequential decision got made before a single interview happened. That's the next post.


Twenty years in this field has made me a little allergic to the phrase strategic plan, mostly because so many of those plans are a careful description of the present.


Grassroots Solutions, my professional home for the last seven years, is winding down at the end of this year, after more than two decades as one of the premier consulting firms in the progressive movement. Its legacy doesn't live in one place. It lives in the thousands of people who came through the firm and carry the craft into whatever they do next. For me, it will be through the creation of Greenbelt Civic Strategy and the work we will do together.

I’ll continue to use this space periodically to share examples and stories of how I approach my work, my partnerships with past and current clients, as well as thoughts and musings about our movement and our democracy. 

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What I'm Changing About Strategy Planning in 2026