“If you stare at these things long enough, you’re supposed to be able to see some kind of hidden, three-dimensional picture.” — Brodie Bruce (Jason Lee), Mallrats
On the first day of my business strategy class each term, I show the students a slide that is truly mind-boggling in its visual intricacy. The slide, which was meant to depict the operating environment in Afghanistan in 2009, remains a unique internet punchline about the futility of complex slideology.
“If you Google ‘PowerPoint slide from hell‘, this is what you’ll find,” I explain as I reveal the image.
At the time, we referred to it simply as the spaghetti chart. It was a hot mess of tribal, local, and national entities and traced their interconnectedness via colored lines and nodes – an image in time of the systems of systems at play in the Graveyard of Empires. Most people who tried to make sense of it scoffed like they were trying to see the sailboat in a three-dimensional picture.
But 15 years after it first appeared, it made its way into my classroom. Why? Because that hot mess illustrated something that few people truly appreciate or understand. A strategic competitive environment – regardless of where that competition is occurring – is truly that complex. When you try to visually map the various actors and their inherent interrelationships, it will look like a bowl of spaghetti.
It underscores an immutable fact about strategic leadership: success at that level demands mastery of strategic thinking.
THE ANATOMY OF STRATEGIC THINKING
The linkage between strategic thinking and leadership might seem like a blinding flash of the obvious on the surface. It’s not. And it’s where most strategic leaders fail. In their 2015 book, Leading with Strategic Thinking, Aaron Olson and Keith Simerson spend most of the opening chapter defining exactly where each concept comes from and what to do with it. Their premise is simple to state but harder to practice: strategic thinking sits at the intersection of three disciplines that rarely get mentioned in the same paragraph, cognitive psychology, systems thinking, and game theory.
Cognitive psychology governs how you manage your own biases and blind spots – the mental shortcuts that convince you a problem is simpler than it actually is. Systems thinking pulls you back a different way, broadening the slate of factors you weigh before deciding which lever to pull. Game theory keeps you honest about something strategists love to remind people: you’re never operating in isolation. Every move invites a countermove, and a plan built without an opponent in mind is doomed to fail.
Layer leadership over all of that and the model sharpens further. Strategic thinking without leadership, Olson and Simerson argue, risks becoming an exercise in intellectual self-gratification. In the same vein, leadership without strategic thinking risks action without direction, a good leader executing the wrong plan with tremendous energy. Strategic leadership emerges when someone can do both: set the mission and the vision, then cut a credible path to reach it.
THE PRICE OF NOT THINKING
The value of strategic thinking isn’t really in doubt. Or at least shouldn’t be. Convincing people to make room for it is the hard part. In a 2017 Forbes article, Brendan Keegan, who spent twelve years running corporate turnarounds, puts it bluntly: companies losing millions a month aren’t failing for lack of talent; they’re failing because nobody carves out time to think past the next dumpster fire. His fix is a 90/10 rule – spend ninety percent of your time working in the business and ten percent working on it. That ten percent pays for itself many times over, mostly by exposing and eliminating tasks and habits that shouldn’t exist in the first place.
That distinction, working in versus working on, is really a description of strategic thinking’s core value proposition. It’s the only kind of thinking that prioritizes asking whether you’re solving the right problem before you get too deep into solving the wrong one. Critical thinking sharpens the analysis. Entrepreneurial thinking finds the unconventional angle. Strategic thinking steps back far enough to see cause and effect play out several moves ahead, then works backward to what needs to happen today.
None of this is a soft skill anymore. The World Economic Forum’s 2022 Skills Outlook found that at least seven of the ten most in-demand workplace skills draw directly on strategic, critical, or entrepreneurial thinking. Organizations that treat it as optional are vying with competitors who hold a decisive advantage from the outset.
FIVE SKILLS THAT SEPARATE THE STRATEGIC LEADER
So, what separates a strategic leader from the rest of the pack? To answer that question, simply weave the frameworks together and let the patterns – another key strategic thinking train – emerge. Five skills separate strategic leaders from leaders who simply stay busy basking in the glory of a comfort zone they’ll never find again.
1. Manage your own bias.
The mental models that accelerate your decision-making also make you wrong in predictable ways. Strategic leaders build in habits, a second opinion, a devil’s advocate, a pause before deciding, that catch blind spots before they harden into decisions.
2. See the whole system.
When pressed, most people default to a checklist mentality: find the one or two causes closest to the event, fix those, and move on. Strategic leaders worry less about what they know than what they don’t. They ask what else is influencing the outcome and whether the obvious fix treats a symptom rather than the real problem.
3. Anticipate the countermove.
Nothing you do happens in isolation. Competitors, colleagues, and circumstances all react to your moves, and a plan that assumes a passive world is a plan built to fail on contact. No plan survives first contact with a rival (or the enemy) – that’s a truism you don’t want to forget.
4. Protect the time.
Strategic thinking never shows up on the calendar uninvited. It has to be scheduled, defended, and treated as real work, not the thing you get to once the inbox is empty. Carve out that time and let your brain percolate.
5. Translate vision into execution.
Formulating strategy and delivering it are two different muscles, and many talented people have only one. The strategic leader sets the mission and vision, then builds the credible, disciplined path that turns intent into results.
None of these skills is exotic on its own. What’s rare is doing all five consistently, especially under pressure, which is exactly when they matter most. That’s what makes a successful strategic leader.
