How Do I Know If My Strategy Plan Is Executable?
Most leaders don't ask this question until something's already gone wrong. The plan looked solid when it landed. It had priorities, a task list, some measures attached to each goal. It came from a firm with a name your board recognized, and it cost enough that nobody wanted to say out loud that they weren't sure what to do with it. Looking buttoned up and being executable are two different things, and the gap between them is where most strategic plans quietly die.
I hear this constantly from leadership teams: they paid good money for a plan, and a year later it still hasn't moved. I can usually tell within the first twenty minutes whether it's going to move or whether it's going to sit in a shared drive getting reviewed once a year, right before the next one gets commissioned. Here's what I'm actually looking for.
Start Five Years Out, Not At The Task List
The test I come back to most often has nothing to do with the plan itself. I ask leaders to think five years ahead and tell me how they'll know they've achieved it. Not what they hope happens. What people will actually be doing differently. What the results will look like operationally, in the day-to-day running of the organization.
Most leaders can describe an aspiration. Far fewer can describe a behaviour. If the answer stays at the level of "we'll be more sustainable" or "we'll have stronger community trust," that's not done yet. Those are values, not outcomes, and you can't execute toward a value. I'm looking for something concrete enough that a staff member two levels down could read it and know whether they're doing it or not. Can you name, behaviourally and operationally, what done looks like? If you can't, the plan hasn't actually been finished. It's been drafted.
Four Things I Check Before I Trust A Plan
Once I've heard how someone defines done, I move into the plan itself, and I'm checking four things every time.
What's actually being measured, and does it inform anything. Plenty of plans have measurement attached to every goal, and plenty of that measurement is a survey or a feedback form that gets collected and filed. If the data doesn't tell you whether or not to change course, it isn't measurement. It's a tick box that lets someone say they did measurement. That's staff time and salary spent producing information nobody acts on, which is its own kind of waste.
Whether ownership is actually clear. Not "the programs team owns this." A person. And not just a name attached to a line item, but a person who understands what they own, where it starts, and where their authority ends.
Whether the capabilities and resources exist to get there. This is the one I see skipped most. A plan can name the right priorities and still have no chance, because nobody asked whether the organization has what it takes to execute them, or whether capability still needs to be built.
Whether there's budget behind what they've said they're doing. Priorities without a dollar figure attached aren't priorities. They're intentions.
Why This Keeps Happening
Here's what frustrates me about how a lot of these plans get built in the first place. A firm hands off a document with almost no real clarity on how to get it living inside the organization, and it's dressed up to look like they have. There's something to measure, there's a task list - it reads like a plan.
A blueprint isn't the house. A strategic plan isn't the change.
But those tasks were never mapped to a budget or to what the organization can actually do. I've had leaders tell me, "I have a plan, but I have no idea where to start with it." That's the tell. If a leader can't answer that question about their own plan, what was the plan for?
And then there's what gets charged for it. Organizations pay a great deal of money for what amounts to text on paper and a few spreadsheets. The real work, the work worth paying for, is getting that plan living inside the organization. I also have real feelings about what gets passed off as measurement in these documents. If it's a survey or a round of feedback with no mechanism for turning what you learn into a change, it's not meaningful measurement. Meaningful measurement tells you what people are doing differently. If I had to boil strategy down to one thing, it's choices and decisions. The real question is whether leaders are equipping their people to make choices that align with the plan, and whether anyone can tell if they're making the right ones. Strategy isn't a document. It's a way of operating.
What It Feels Like In The Room
I get pushback when I walk leaders through this, sometimes real defensiveness, and I expect it. I'm challenging something big, something they likely paid a lot of money for, and I'm asking them to sit with the fact that they don't yet have what they need to get it moving in a way that actually changes anything.
Some push back hardest on the measurement piece. They believe what they have is fine, right up until I ask whether any of it has ever changed a decision. Once that lands, most people get it.
Others are relieved. They finally have a way to get things moving that produces real change instead of more of the same, and there's something freeing about naming that out loud instead of quietly wondering why the plan from eighteen months ago never went anywhere.
I've Been That Employee
I've lived the other side of this too. Earlier in my career, in a leadership role, I had tasks assigned to me out of a strategic plan, sitting in a spreadsheet with loose measures and vague definitions. At first glance it looked practical. But the tell was that I genuinely didn't know how to get any of it done, or what the actual steps were to get there, so it never got done. No one followed up. It never came up at the leadership table. We didn't review it against anything.
I'd open that spreadsheet every so often and then quietly close it again, because I didn't have the clarity I needed and I wasn't sure it was my place to say so. And because leadership wasn't treating those priorities as something that mattered, I didn't either. They never guided a decision or shaped a discussion in any meeting I sat in. When I asked colleagues about it, they shrugged too. It wasn't anyone's fault exactly. We just didn't have a strategic culture, and a plan can't build one on its own.
What To Do This Week
If you're reading this and recognizing your own plan in it, don't wait for the next planning cycle to fix it. Call me, or take one of the questions above straight to the consultant who built your plan and watch how they answer it.
I also put together a short self-check you can run against your own plan in about two minutes, along with the eight questions worth asking before your consultant's engagement wraps up. [Grab the self-check here.]
A plan that looks finished and a plan that's actually executable are not the same thing, and the difference is almost never visible from the outside. It shows up the first time someone tries to act on it.