“You keep using that word. I do not think it means what you think it means.”
— Inigo Montoya, The Princess Bride
Sometimes, in meetings, I play a little game with myself.
Every time someone says the word “strategy,” I take an imaginary shot.
I don’t recommend this as a real exercise. For a number of reasons, but primarily because you will not make it through the meeting. My personal record is 15 minutes before I would have been, at best, completely useless and, at worst, a cautionary tale.
Strategy.
It’s one of those words that sounds important, feels important, and gets used so often that it starts to lose any real meaning. Everyone wants one. Everyone says they have one. And yet, if you ask five people in the same room what “strategy” actually is, you’ll get five different answers.
Why “Strategy” Has Lost Its Meaning
I’ve seen it from every angle.
I’ve presented what I thought were clear, thoughtful strategic plans and gotten the feedback, “This is great, but how do we actually do this?” I’ve also delivered work that was grounded in execution, with clear direction and defined next steps, only to hear, “This feels too in the weeds. We need something more high level.”
Same word. Completely different expectations.
Strategy Is a Set of Choices — Not a Deck
So what are we actually talking about?
At its core, strategy is a set of choices. Not a list of ideas. Not a collection of tactics. Not a deck that makes everyone feel like progress has been made.
Choices.
What are we going to do? What are we not going to do? Where are we going to focus our time, energy, and resources in a way that moves us toward a defined outcome?
That sounds simple. It’s not.
Because making those choices requires alignment, clarity, and a willingness to leave some good ideas on the table in service of better ones. And that’s usually where things start to get uncomfortable.
What Usually Gets Labeled “Strategy” (But Isn’t)
A lot of what gets labeled as “strategy” is actually one of three things.
Sometimes it’s vision. Big, directional thinking about where an organization wants to go. Important work, but not the same thing. Vision tells you where. Strategy tells you how you’re going to get there.
Sometimes it’s a plan. A detailed list of actions, timelines, and deliverables. Also important. But that’s execution. That’s the “how we’re going to do it,” not the decision-making framework behind it.
And sometimes, if we’re being honest, it’s just a collection of ideas that haven’t been prioritized yet.
None of those are inherently bad. They just aren’t strategy.
Which is why so many conversations around “strategy” feel like they’re missing something. Because the room isn’t aligned on what’s actually being asked for.
Four Questions to Align Before You Build Anything
So before you build anything, present anything, or react to feedback, there are a few questions that are worth putting on the table early. Not as a checklist, but as a way to get everyone speaking the same language.
What are we trying to change?
Not what are we trying to say, or launch, or promote. What are we trying to change in behavior, perception, or outcome? If that’s not clear, everything that follows is going to drift.
What does success look like?
In real terms. Not abstract language. Not “increased awareness” unless you can define what that actually means. What would be different if this works?
What decisions are we making?
This is the one that gets skipped. If the “strategy” doesn’t clearly outline where you’re focusing and where you’re not, it’s not a strategy. It’s a brainstorm.
What level are we operating at?
Are we talking about direction? Or are we talking about execution? Because both are valid, but they are not interchangeable. A lot of frustration in these conversations comes from people reacting to the wrong version of the work.
Once those questions are answered, the work gets easier. Not easy, but clearer. You can build something that actually meets the moment instead of trying to guess what version of “strategy” the room is expecting.
Because the goal isn’t to use the word correctly.
It’s to do the work that the word is supposed to represent.
And ideally, to make it through the meeting without needing a drink.
If you’re working through what strategy actually looks like for your organization — not the word, but the work — let’s talk.