Structured but Flexible: My Approach to Strategic Planning

My first two blogs in this series covered why a strategic plan is different from a comprehensive plan, and what needs to happen before anyone sits down to build one. This one is about the sessions themselves, and what happens in the room as the plan is crafted.

Letting the Group Lead

Call it the self-aware control freak in me, I know I can never have all the information that the people in the room have, no matter how good my discovery process has been. That is exactly why I walk into a planning session with no opinion about what a group needs to do. I bring the process, but they bring everything else.

Central to my approach is this: the people with the most contextual knowledge of an organization are the ones who should be building its plan. The participants have the background, the specifics of everything else that is impacting the work, and they are not short on ideas. What has likely been challenging is figuring out how to work through everyone’s ideas and priorities, together, cohesively.

That is what my approach seeks to support—a robust and thoughtful discussion, through a structured but flexible process, with an eye on the ultimate prize. A plan that you can and will implement. Otherwise, I have failed.

The journey I take with a group in developing an effective strategic plan never changes: the same stops in the same order, using the same method, every time. What changes is the answer, because that belongs to whoever is in the room, not to me.

Is it geeky to admit that when I pose the question for the session ahead, I get goosebumps? I do not know the answer, but the group does, and we are going to uncover it together.

Setting Off from a Shared Starting Point

Before your car’s GPS can provide you with directions to your destination (read: vision), it needs to know where you are leaving from. This applies equally for a strategic plan.

Identifying your current reality is the first critical step. I think of this stage as the five-story parking garage under the whole plan. Nobody sees it in the finished document, but without it, nothing aboveground is stable.

There are many possibilities here—we can look at agency data to see what it is telling us, examine trends that are shifting in our working context, or seek input about where community members are happy or frustrated.

A favorite approach I often use is what I call the ‘eras tour’. As part of this approach, a group takes a rapid scan of the agency’s past accomplishments and setbacks, present strengths and challenges, and future opportunities and threats, creating—sometimes for the first time—a shared landscape.

One city manager described how he saw this approach play out with his council.

"It wasn't debated," he told me. "It was open for each council member and staff to communicate what they believed was in our current reality. We didn't have to spend any time trying to further affirm what we thought were successes, or where we could improve."

A board member involved in another recent process said: "We came in with a mix of tenures and perspectives. Getting that shared context—really seeing where we were—was more valuable than I expected."

Seeking the North Star

With that shared context in place, the group turns to what it wants three to five years from now. I ask people to imagine future success and describe what would be distinctly different from today, specific enough that they would “know it if they saw it.” 

This stage is both inspirational and aspirational, but also rooted in the reality we have just established. People get to think bigger than their day-to-day lives allow, and that is by design. New ideas and divergent thinking helps the group consider what is possible.

A recent participant told me that during this stage, people who'd been involved in the organization for years got to see it with fresh eyes. For her, it offered real “light bulb moments” and the sense of "Oh, this is what we could be."

Bridging from Vision to What Is Holding Us Back

Only once a group knows where it wants to go can it see clearly what is standing in the way of that desired future. I have one hard rule here, and I hold to it: The group may not say "lack of" anything—be it funding, staff, or time. Those are symptoms, and they tend to get said with a shrug, like nothing can be done about it anyway.

One group I worked with thought their organization’s main obstacle was a lack of locally available living-wage jobs. Encouraged to reframe this, it became decline of local historic industries, something specific enough for the group to focus a strategy around.

Once obstacles are identified and put up on the wall for everyone to see, something shifts in the room. Group members have often been carrying around the same unspoken frustrations for years, quietly, separately, assuming they were the only one who felt it. Seeing it named tends to bring a sense of relief. One participant told me that having the space to name obstacles honestly—and agree on them together—was "really freeing.”

Crafting Strategy Becomes a Moment of Breakthrough

With the vision and the obstacles both up on the wall, the creative tension between them is where strategy emerges. Given where a group wants to go and what is in the way, what will the group actually do?

This part happens in two stages. First, the group works in smaller cohorts and they draft ideas that help finish the prompt "We intend to..."

The responses then get clustered together and named as strategies. Then we go up a level (call it the 30,000-foot view) and group initial strategies into strategic priorities, with a focus on creating three or four total strategies (five at most). By the end, group participants can all finish the same sentence: “Over the next few years, we will focus our attention on...”

Nothing comes off the wall during this process. Every card a cohort generated finds a home somewhere in the final structure, helping to weave in the specific creativity of that idea and elevating the work.

This makes the consensus real and personal. People know exactly how much they agree on because they can see their own words sitting inside the result.

"Nobody gave anything up," one participant told me. "You could see your own handwriting on the wall. Your ideas were there, and somehow we'd named what connected all of them."

The structure earns its keep long after the new strategic plan is adopted. The strategic priorities function as a filter for all future work, providing a framework for tracking accomplishments and reporting to the community.

The Implementation Plan: Staff Expertise in Play

Implementation is where the rubber meets the road. If a group does not have a clear timeline of who will do what by when, it becomes very difficult to get started. A process that leaves an agency without this crucial piece risks the success of the whole investment.

Before staff can plan the work of the first year, leadership should provide one last thing: success indicators. This is not a list of tasks, but rather a clear picture of what change leadership expects to see, usually within a two-year window.

In local government context, this is important so that staff are not trying to be psychic about what the governing body wants to see by way of results. The body names the destination, staff figures out the route.

Once that is settled, implementation becomes its own working session, often with a different group in the room. The people who set the strategic direction build the frame, but the people who will actually do the work should be the ones filling it in. They know what else is competing for their time and can bring all of their additional context and knowledge into play.

Ongoing Systems Will Support Success

The plan has been developed, and the governing body has adopted it. The implementation timeline has major projects and assignments. Is the work done? No.

Essential to make this a living, breathing guide to the organization are the systems that keep it visible. One city manager identified how he’s doing this—by adding a line to every agenda bill naming which strategic priority a proposed item or discussion will advance. When a councilmember asks for something new to be researched, city staff can check which strategic priority it ties to before it goes further.

This city manager has also scheduled quarterly check-ins against the plan and will hang a printed copy of the strategic priorities in the council chambers. Every time the council meets, they can easily refer to the document.

Knowing When my Work Is Done

By the time a plan like this is finished, the group has spent hours together wrestling with questions, and listening to and building on what each participant contributes. That is not a just a side effect of the process, it is the point of it.

One board member summed up it up: "We sat down and we worked through it together. I think people left feeling like we did something good."

As the facilitator, that is what I am aiming for.