How to train yourself to think like a strategist
Most people think strategy is about answers. But good strategists know it starts with the right kind of questions.
It’s not about having a genius insight drop from the ceiling. It’s about training your mind to zig when others zag, to see the angle no one’s watching, to pause before solving the obvious. That’s not intuition. That’s learned.
Here’s how to train yourself to think like a strategist, not just a doer.
Stop solving, start noticing
The first habit to unlearn is premature problem solving. Most of us are trained to act quickly, fix fast, move forward. Strategists do the opposite. They slow down and observe.
Great strategy starts with pattern recognition. But you can’t see patterns if you’re always reacting. Start noticing what most people ignore. Small changes in behavior. Outlier data. Comments customers make offhand. The weird question no one on the team wants to ask.
In psychology, this is called attentional control. It’s the practice of noticing your own focus and moving it with intention. Strategy lives there, in the subtle shifts, not the loud moments.
Use tangents to unlock new directions
Tangential thinking is the art of mental misdirection. It’s what great comedians, inventors, and planners do instinctively. They move laterally before they go forward. They ask, “What does this remind me of?” not “What’s the most efficient solution?”
When Volkswagen launched the Beetle in the 1960s, a time of muscle cars and horsepower, it didn’t pretend to be what it wasn’t. It leaned into its oddity. “Think Small.” It was strategic not because it shouted louder, but because it reframed the question. That’s tangential thinking in action.
To build this skill, practice taking your current challenge and mapping unrelated metaphors onto it. What would this look like if it were a game? A religion? A garden? It might feel ridiculous, but it’s a tool to escape the gravity of the obvious.
Think in human tensions, not just business goals
The strategist’s brain sits between business logic and human behavior. It sees both. A campaign objective might say “increase leads,” but a strategist rewrites that as “how do we earn trust from people who feel burned?” The question changes the approach.
Psychology tells us that behavior isn’t driven by facts, it’s driven by emotion, context, and tension. A great strategist knows that behind every decision is a tug-of-war between fear and aspiration, between risk and reward.
Train yourself to spot the human dilemma beneath the commercial objective. That’s where strategy starts to breathe.
Zoom out before zooming in
In advertising and branding, strategists are taught to build narratives from a wide-angle lens. You can’t write a meaningful tagline without first understanding the cultural, market, and human context it’s being born into.
Strategic thinking often begins with systems thinking. Who are the players? What incentives shape their behavior? Where’s the leverage? The point isn’t to be exhaustive it’s to connect dots that others miss.
Build the habit of zooming out. Before solving, step back and map the forces in play. Use simple tools: mind maps, circles of influence, even napkin scribbles. Strategic clarity rarely arrives in bullet points.
Let go of being right
Strategy is about navigating uncertainty, not eliminating it. One of the worst instincts to bring into strategic thinking is the need to be right.
Instead, practice intellectual humility. Test competing hypotheses. Get comfortable in the “I don’t know yet” zone. The best strategists aren’t the ones who win every debate, they’re the ones who stay curious longest.
As the ad world’s most famous planner, Jon Steel, once said: “Strategy is a story, not a spreadsheet.”
And stories get better when you keep rewriting them.
Be boring, then brilliant
The most effective strategies often feel obvious in hindsight. But they usually come from someone doing the boring work first. Digging through transcripts. Watching customer behavior on video. Reading dull research reports with fresh eyes.
The strategist doesn’t skip the grunt work. They find meaning in it. And then, only then, they turn the insight into something sharp, surprising, and sticky.
Brilliance without grounding is just flair. But when insight comes from the soil of the problem, it sticks. It persuades. It moves.
Final thought: practice outside the brief
If you want to train your brain to think strategically, don’t wait for a strategy brief to land on your desk. Pick a brand and reverse-engineer its success. Watch people shop and guess what drives their behavior. Study what didn’t work and ask why. Watch stand-up comedy. Read behavioral economics. Eavesdrop in public. Notice how people change their minds.
Strategists build their thinking the way athletes build muscle, by repetition, curiosity, and pushing into discomfort.
So, no, it’s not just a gift. It’s not about being “the smart one in the room.” Strategic thinking is a discipline. You can train for it. And in a world full of action, the ones who pause to think differently will always have the edge.