How to Improve Strategic Thinking Skills
Killer Innovations with Phil McKinney
Release Date: 04/22/2025
Thinking 101: A Pause, A Reflection, And What Might Come Next
Killer Innovations with Phil McKinney
Twenty-one years. That's how long I've been doing this. Producing content. Showing up. Week after week, with only a handful of exceptions—most of them involving hospitals and cardiac surgeons, but that's another story. After twenty-one years, you learn what lands and what doesn't. You learn not to get too attached because you never know what's going to connect. But this one surprised me. Thinking 101—the response has been different. More comments. More questions. More people saying, "This is exactly what I needed." It's made me reflect on why I started this series. Years ago, I was in a...
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Mental Models - Your Thinking Toolkit
Killer Innovations with Phil McKinney
Before the Space Shuttle Challenger exploded in 1986, NASA management officially estimated the probability of catastrophic failure at one in one hundred thousand. That's about the same odds as getting struck by lightning while being attacked by a shark. The engineers working on the actual rockets? They estimated the risk at closer to one in one hundred. A thousand times more dangerous than management believed.¹ Both groups had access to the same data. The same flight records. The same engineering reports. So how could their conclusions be off by a factor of a thousand? The answer isn't about...
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Numerical Thinking: How to Find the Truth When Numbers Lie
Killer Innovations with Phil McKinney
Quick—which is more dangerous: the thing that kills 50,000 Americans every year, or the thing that kills 50? Your brain says the first one, obviously. The data says you're dead wrong. Heart disease kills 700,000 people annually, but you're not terrified of cheeseburgers. Shark attacks kill about 10 people worldwide per year, but millions of people are genuinely afraid of the ocean. Your brain can't do the math, so you worry about the wrong things and ignore the actual threats. And here's the kicker: The people selling you fear, products, and policies? They know your brain works this way....
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The Clock is Screaming
Killer Innovations with Phil McKinney
I stepped out of the shower in March and my chest split open. Not a metaphor. The surgical incision from my cardiac device procedure just… opened. Blood and fluid everywhere. Three bath towels to stop it. My wife—a nurse, the exact person I needed—was in Chicago dealing with her parents’ estate. Both had just died. So my daughter drove me to the ER instead. That was surgery number one. By Thanksgiving this year, I’d had five cardiac surgeries. Six hospitalizations. All in twelve months. And somewhere between surgery three and four, everything I thought I knew about gratitude…...
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Second-Order Thinking: How to Stop Your Decisions From Creating Bigger Problems (Thinking 101 - Ep 6)
Killer Innovations with Phil McKinney
In August 2025, Polish researchers tested something nobody had thought to check: what happens to doctors' skills after they rely on AI assistance? The AI worked perfectly—catching problems during colonoscopies, flagging abnormalities faster than human eyes could. But when researchers pulled the AI away, the doctors' detection rates had dropped. They'd become less skilled at spotting problems on their own. We're all making decisions like this right now. A solution fixes the immediate problem—but creates a second-order consequence that's harder to see and often more damaging than what we...
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Make Better Decisions When Nothing is Certain
Killer Innovations with Phil McKinney
You're frozen. The deadline's approaching. You don't have all the data. Everyone wants certainty. You can't give it. Sound familiar? Maybe it's a hiring decision with three qualified candidates and red flags on each one. Or a product launch where the market research is mixed. Or a career pivot where you can't predict which path leads where. You want more information. More time. More certainty. But you're not going to get it. Meanwhile, a small group of professionals—poker players, venture capitalists, military strategists—consistently make better decisions than the rest of us in exactly...
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You Think In Analogies and You Are Doing It Wrong
Killer Innovations with Phil McKinney
Try to go through a day without using an analogy. I guarantee you'll fail within an hour. Your morning coffee tastes like yesterday's batch. Traffic is moving like molasses. Your boss sounds like a broken record. Every comparison you make—every single one—is your brain's way of understanding the world. You can't turn it off. When someone told you ChatGPT is "like having a smart assistant," your brain immediately knew what to expect—and what to worry about. When Netflix called itself "the HBO of streaming," investors understood the strategy instantly. These comparisons aren't just...
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How To Master Causal Thinking
Killer Innovations with Phil McKinney
$37 billion. That's how much gets wasted annually on marketing budgets because of poor attribution and misunderstanding of what actually drives results. Companies' credit campaigns that didn't work. They kill initiatives that were actually succeeding. They double down on coincidences while ignoring what's actually driving outcomes. Three executives lost their jobs this month for making the same mistake. They presented data showing success after their initiatives were launched. Boards approved promotions. Then someone asked the one question nobody thought to ask: "Could something else...
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How to Improve Logical Reasoning Skills
Killer Innovations with Phil McKinney
You see a headline: "Study Shows Coffee Drinkers Live Longer." You share it in 3 seconds flat. But here's what just happened—you confused correlation with causation, inductive observation with deductive proof, and you just became a vector for misinformation. Right now, millions of people are doing the exact same thing, spreading beliefs they think are facts, making decisions based on patterns that don't exist, all while feeling absolutely certain they're thinking clearly. We live in a world drowning in information—but starving for truth. Every day, you're presented with hundreds of...
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Why Thinking Skills Matter More Than Ever
Killer Innovations with Phil McKinney
The Crisis We're Not Talking About We're living through the greatest thinking crisis in human history—and most people don't even realize it's happening. Right now, AI generates your answers before you've finished asking the question. Search engines remember everything so you don't have to. Algorithms curate your reality, telling you what to think before you've had the chance to think for yourself. We've built the most sophisticated cognitive tools humanity has ever known, and in doing so, we've systematically dismantled our ability to use our own minds. A recent MIT study found that students...
info_outlineMost people react to change. They adapt, adjust, and scramble to keep up. But a small group sees change coming. They prepare for it, shape it, and position themselves to win. Their edge? Strategic thinking skills.
In this article, you'll learn six powerful strategic thinking skills and five proven exercises to sharpen your thinking, decision, and act. You'll move from reacting to shaping. From being caught off guard to staying three moves ahead.
Let's build the mental toolkit that visionary leaders use to navigate uncertainty—and turn disruption into opportunity.
What Makes a Mindset Strategic?
Strategic thinking isn't about obsessing over efficiency or micromanaging tactics. It's about seeing the big picture, anticipating what's next, and setting direction when others stall. Strategic thinkers operate with four key traits:
- Long-term orientation – They think in years, not days.
- Pattern recognition – They connect signals others miss.
- Comfort with uncertainty – They decide with incomplete data.
- Proactivity – They shape the game, not just play it.
That mindset lays the foundation. Now, let's break down the six core strategic thinking skills.
6 Essential Strategic Thinking Skills
1. Ask "And Then What?"
Second-order thinking separates amateurs from pros. Don't just consider immediate consequences—look downstream. What happens next? What unintended effects might show up later?
Netflix mastered this. Studios focused on short-term streaming revenue. Netflix saw user data as leverage for producing original content—and flipped the game.
2. Think in Probabilities, Not Certainties
Ask, "What's the chance this works?" instead of "Will this work?" Keep a decision journal. Estimate outcomes. Then, reflect and recalibrate. That's how you develop judgment.
3. Weigh Opportunity Costs
Every yes is a no to something else. Strategic thinkers force themselves to list three alternatives they're giving up before choosing a path. That habit exposes trade-offs others miss.
4. Use Inversion
Flip the question. Ask, "How might this fail?" Use pre-mortems before major projects. Thinking like this isn't pessimism—it's prevention.
5. Envision Multiple Futures
Don't chase predictions. Instead, map out a few plausible future scenarios. Prepare for each. That's how you build flexibility into your strategy.
6. Strip Down to First Principles
Start from what you know to be true. Then, build up. Forget how it's "always been done." That's how Elon Musk questioned the high cost of rockets—and built SpaceX.
5 Exercises to Strengthen Your Strategic Thinking
- Pre-Mortem – Identify failure scenarios before you start.
- 10/10/10 Test – Ask how a decision will feel in 10 minutes, 10 months, and 10 years.
- Future-Back Planning – Start with your desired outcome and work backward.
- Perspective Shifting – Analyze decisions from multiple points of view.
- Strategic Questioning – Use prompts like "What would change my mind?" or "What's the non-obvious move?"
These sharpen your thinking. Repetition turns them into instinct.
Make Strategic Thinking a Daily Habit
You don't need hours. One thoughtful decision a day is enough to start. Try this:
- Create mental triggers. Pause when you feel rushed.
- Partner with someone who thinks differently.
- Schedule 15 minutes a week to think long-term.
- Reflect after decisions. Note what worked—and what didn't.
Over time, you'll default to asking better questions and spotting better options. That's the real power of strategic thinking skills.
One Skill. One Decision. One Advantage.
You don't need to master everything overnight. Just choose one skill. Apply it to one big decision this week. Watch what changes.
Strategic thinking isn't just for CEOs—it's for anyone who wants to stop reacting and start shaping their future.
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