There’s a phrase that gets thrown around in nearly every leadership conversation I hear:
“You need to think more strategically.”
It’s said in boardrooms.
It’s written into performance reviews.
It’s listed as a core executive competency.
And yet, when you pause and ask a simple follow‑up question—What does that actually mean?—The room often goes quiet.
That silence is exactly why my recent conversation with John Hillen, a leader whose career spans business, government, academia, and the military, resonated so deeply. When someone has served as a CEO, a board chair, a senior government official, a professor, and a strategist across multiple domains, you pay attention—not because of the titles, but because of the pattern recognition that comes from living leadership at scale.
What emerged from our discussion wasn’t theory for theory’s sake. It was something far more valuable for today’s executives: a practical, human, and teachable way to understand strategy and strategic thinking—not as abstract concepts, but as everyday leadership disciplines.
The Strategy Gap Hiding in Plain Sight
Here’s the paradox most organizations are living with today:
We demand strategic thinking from leaders at every level, but we rarely teach them how to do it.
Many executives can point to a strategy course they took years ago in business school. Others have participated in annual off-sites where strategy is discussed behind closed doors by a small group of senior leaders. But very few have been given a shared language, a repeatable process, or a practical framework for thinking strategically as part of their daily work.
As a result, “strategy” becomes a vague expectation rather than a usable skill.
People confuse strategy with:
- Goals
- Vision statements
- Mission declarations
- Values posters
- Incremental performance improvements
Those things matter—but they are not strategy.
And when leaders don’t clearly understand the difference, organizations drift. They stay busy. They stay reactive. They execute well on today’s tasks while slowly losing their grip on tomorrow.
So What Is Strategy, Really?
At its core, strategy is a complete game plan.
It is a blueprint that moves an organization from where it is today to a position of greater advantage in the future.
Not just growth.
Not just scale.
Not just efficiency.
Advantage.
A real strategy answers a set of interlocking questions:
- Where are we going?
- Why is that future better than our current position?
- What will we do—and just as importantly, what will we not do—to get there?
- In what sequence will things happen?
- Who is responsible for what?
- How do different moves reinforce each other?
- Why should customers, partners, or stakeholders choose us over alternatives?
Strategy is not a slogan. It’s a system of choices.
And strategic thinking is the mindset that allows leaders to navigate those choices with clarity, confidence, and coherence.
The Telltale Signs of a Strategic Mind
One of the most useful ways to understand strategic thinking is to recognize it when you see it.
Strategic leaders tend to share several characteristics:
They Think Big Picture
They don’t get trapped by the issue directly in front of them. They zoom out. They look for patterns. They ask how today’s decision shapes tomorrow’s reality.
They Think Long‑Term
While others are optimizing for this quarter, strategic thinkers are asking how today’s moves position the organization years from now.
They Think in Systems
Analysts break problems apart. Strategists connect them. They understand how internal capabilities, market forces, competitors, customers, and culture interact as a whole.
They Challenge the Status Quo
Strategy implies change. Movement. Transformation. A willingness to say, “What got us here may not get us where we need to go next.”
They Are Inherently Optimistic
This is critical—and often overlooked.
To imagine a better future, you must believe one is possible.
Research consistently shows that effective leaders share a common trait: optimism. Not blind positivity, but grounded belief that problems can be reframed into opportunities and that deliberate action can shape outcomes.
Without optimism, strategy collapses into fear management.
Reframing Problems into Strategic Possibilities
Every organization has problems. That’s not a flaw—it’s a sign you’re alive.
What separates strategic leaders from reactive ones is how they frame those problems.
The default response to a problem often looks like this:
- Sales are down → Who messed up?
- Costs are up → What’s broken?
- A product is underperforming → What went wrong?
This framing invites blame, defensiveness, and short‑term fixes.
A strategic framing sounds different:
- What future outcomes are possible here?
- What strategic options do we have?
- What would have to be true for each option to succeed?
Simply asking “What would have to be true for this to work?” shifts the entire tone of the conversation. It invites creativity, analysis, and collaboration rather than finger‑pointing.
The problem hasn’t changed—but the mindset has.
And that mindset opens the door to strategic dialogue instead of tactical firefighting.
Ideas Are Necessary—but Not Sufficient
Executives often pride themselves on idea generation—and rightly so. Innovation matters.
But strategy is not an idea contest.
High‑growth organizations are often rich with ideas—sometimes too rich. They have dozens, even hundreds, of possible paths forward. Without discipline, that abundance becomes chaos.
Strategic thinking requires structure.
It means pushing ideas through a set of frameworks that test them against reality:
- External market conditions
- Internal capabilities
- Competitive dynamics
- Financial logic
- Organizational readiness
Only after ideas survive that process should they earn investment of real time, money, and resources.
This is where many leaders stumble. They fall in love with the possibility before doing the hard thinking.
Strategy asks leaders to slow down—to commit to the process—so that speed later is purposeful rather than frantic.
Why Leaders Struggle to Make Time for Strategy
Here’s an uncomfortable truth: most leaders know strategic thinking matters—and still don’t do it consistently.
Why?
Because three of the most important leadership activities rarely feel urgent:
*Thinking Strategically
The big‑picture, future‑oriented work gets crowded out by immediate demands.
*Developing Other Leaders
Coaching takes time, and time feels scarce—until you realize developing others is how you escape operational overload.
*Building Strategic Networks
Relationships outside your organization—peers, competitors, thinkers—often get postponed until they’re desperately needed… which is too late.
The urgent wins over the important.
And organizations pay the price years later.
Strategic leaders protect time for these activities because they understand something fundamental: the future doesn’t build itself.
A Strategy That Worked—But a Business Model That Didn’t
One of the most instructive leadership stories shared in our conversation came from a capital markets firm attempting to democratize access to stock trading.
The mission was powerful.
The technology was brilliant.
The strategy was sound.
But the business struggled.
Why?
Because the business model didn’t align with what customers actually valued.
The company thought it was selling software. Customers didn’t want software—they wanted access. They wanted the use of the platform, not ownership of the technology itself.
Once leaders understood that distinction, everything changed.
The pricing model shifted.
The revenue engine transformed.
The organization became profitable—not just visionary.
This is a lesson every executive needs to internalize:
Customers don’t buy what you love.
They buy what solves their problem.
Strategy without a viable business model is aspiration.
A business model without a strategy is fragile.
You need both.
Strategy Evolves—Just Like Organizations Do
One of the most powerful examples of strategic evolution is Netflix.
It didn’t just change products. It changed what kind of company it was—from distributor, to technology platform, to content creator.
Each shift required:
- New capabilities
- New talent
- New systems
- New metrics
- New leadership behaviors
Strategy is not a one‑time decision. It’s an ongoing dialogue between the organization and its environment.
Leaders who expect stability in a world of constant change are setting themselves—and their teams—up for disappointment.
The Executive Takeaway
If you lead people, teams, or organizations today, here’s what this journey reinforces:
- Strategy is a blueprint, not a buzzword
- Strategic thinking is a skill, not a personality trait
- Optimism is a requirement, not a nice‑to‑have
- Ideas need discipline, not just enthusiasm
- Time spent thinking, developing others, and building relationships is never wasted
Most importantly:
Strategy should not live in a secret room, discussed once a year.
It should be part of everyday organizational life.
When leaders make strategic thinking accessible, teachable, and repeatable, they don’t just create better plans—they create better leaders.
And in a world defined by complexity and change, that may be the greatest advantage of all.
Listen to the full episode on C-Suite Radio: Disrupt & Innovate | C-Suite Network
Watch the episode: DI 140 “Strategic Thinking Made Simple | Dr. John Hillen on Leadership, Innovation & Change.”
This article was drafted with the assistance of an AI writing assistant (Abacus.AI’s ChatLLM Teams) and edited by Lisa L. Levy for accuracy, tone, and final content.
