In partnership with

When I started university, my dad made me sit down and map out my entire four-year plan—every single class, every quarter, down to the last elective.

I protested with the righteous indignation only an eighteen-year-old can muster: "This is ridiculous. Why waste time mapping this out when it’s all going to change anyway?"

"Trust me," he said. "Just write it all down somewhere so you know you're meeting your requirements and can graduate on time."

I rolled my eyes (thank goodness it was a phone call!) but indulged him, pulling out my old-school planner and creating an elaborate grid. Once I got over my initial objections, the exercise became oddly satisfying—there was something comforting about simply having a plan. Without prompting, I found myself updating that four-year roadmap every quarter.

And because I had it (even as it constantly evolved), I was able to fit in a double major and a minor. I spotted opportunities I never would have seen otherwise, like realizing I was already halfway to a music minor just from orchestra credits. It saved me from scrambling through summer school or taking a fifth year. 

This is one of those moments where you have to give credit to your parents: My dad wasn't being absurd. He was being strategic.

Why You Keep Hitting Your Head

With that advice, my father intuited a skill that represents the most common gap standing in the way of leadership advancement—strategic thinking.

As Chief People Officer and throughout my coaching practice, I've repeatedly watched this pattern unfold. CEOs describe VPs marked for advancement as "too day-to-day, too tactical." VPs aspiring to the C-suite find themselves stuck because they can’t make the leap from doing the work to thinking about the work.

The feedback is always the same: "You need to be more strategic!"

Strategic thinking is the invisible marker that separates executives who plateau from those who become bona fide business leaders. It's what transforms you from someone who executes brilliantly within their function to someone who shapes the direction of the entire organization. Never has this been more critical than today, when companies desperately need leaders who can see around corners, anticipate challenges, and position their organizations for long-term success.

The irony is striking: such weight is placed on this elusive skill, yet few of us have been explicitly taught how to develop it. It becomes an insidious blind spot for even the most talented leaders.

So before we dive deeper into the topic, take a moment for honest self-reflection: 

• How strong is your strategic thinking muscle? 

• When was the last time you stepped back from the urgent to focus on the important? 

• Do you find yourself constantly reacting to events, or are you anticipating and preparing for what's next?

How to Break Through the Strategic Thinking Ceiling

To start, let’s ground the concept of strategic thinking with three fundamental shifts in perspective.

1. The Time Horizon Shift

   To jolt yourself out of the tactical day-to-day, extend your planning perspective by 1 to 2 timeframes. If you're planning in weeks, stretch to months. If you're thinking in months, extend to quarters. If you think in quarters, reach for a year.

   When you expand your timeline, patterns emerge that were invisible in the short-term view. Dependencies become clear. Opportunities reveal themselves.

2. The Altitude Adjustment

   To open up your aperture, think one level higher than your current perspective.  If you're focused on what your team needs, consider what your CEO cares about. If you're solving for one customer's problem, look for patterns across all customers. Doing so will illuminate connections, challenges, and leverage points not yet on your radar.

   Think of it like exploring a city. At street level, you see individual buildings. From a skyscraper, you see neighborhoods and traffic patterns. From a plane, you see how the whole city connects. Each altitude reveals insights you’re blind to in the others.

3. Scenario Simplification

   Instead of being paralyzed by infinite possibilities, focus on the 2-3 most likely scenarios. For a growth startup, that might be: base case, slight upside, major upside. The goal isn't perfect prediction—it's preparation. When you've thought through the likely scenarios, you can pivot quickly when reality unfolds.

You might read this and think, "Yeah, I can totally do that!" And you can.

But there's a fundamental gap between intellectual understanding—knowing what strategic thinking is—and actually practicing it under stress or overwhelm. It's the difference between abstract knowledge and muscle memory that only develops with practice.

The real challenge isn't intellectual—it's overriding the deeply ingrained habit of tactical thinking that's made you successful up to this point.

5 Ways to Build Strategic Thinking Muscles 

Building this muscle requires the same intentionality my dad brought to college planning: consistent practice, even when it feels unnecessary or uncomfortable. The key is to embed strategic thinking into your existing workflows rather than treating it as an additional burden.

Here are five practical ways to bake strategic thinking into your routines and workflows:

1. Embed Strategic Context in Regular Meetings: Make it routine to connect immediate work to larger goals. Try these phrases…

   • "Let's keep in mind how this supports our bigger goal of [X]."

   • "How do you see this fitting into our overall strategy?"

   • "This piece is important because it helps us move toward [key objective]."

   • "Quick check—how does this align with what we want to achieve long-term?"

2. Use Lightweight Strategic Frameworks: Don't let frameworks intimidate you. Use simplified, bite-sized versions and apply them selectively.

   • Quick SWOT check: "What's our biggest strength here? What's the most likely threat?"

   • Scenario thinking: "What if this goes really well? What if it doesn't?"

   • Strategic questions: "What's the bigger opportunity here?" or "How could this decision affect us in three years?"

3. Apply the "So What?" Test: When reviewing results or reports, dig deeper into insights. If customer satisfaction is up 15%, so what? What does that tell us about our strategy going forward? This simple question transforms data into strategic intelligence.

4. Weekly Strategic Reflection: Block time for strategic thinking with no agenda or deliverables—just thinking time. Ask big-picture questions like:

   • If we stay the same size, what are the implications?

   • If we triple revenue, what would we need?

   • If we don't get funding, what would we do?

   Don't get paralyzed by uncertainty. Remember scenario simplification? Spend 15-30 minutes sketching broad strokes for different scenarios. The 80/20 rule applies: a small time investment can get you most of the strategic clarity you need.

5. End-of-Week Learning Check: Set aside a few minutes weekly to capture clear lessons and next steps:

   • What worked well to move us toward our strategic priorities?

   • What should we adjust or prioritize next?

   • What patterns are we seeing that might affect our direction?

Your Strategic Thinking Trigger List

The more you exercise your strategic thinking muscle in those dedicated time blocks, the better you'll become at recognizing when everyday situations require strategic thinking. 

It will be challenging in the beginning. Day-to-day execution creates gradual blindness to change (like the frog-boiling analogy). Those scheduled moments invite you to step back with a refreshed perspective.

Meanwhile, watch for these characteristics in your day-to-day work. They're cues to expand your time horizon, level up your perspective, and simplify the scenarios:

• Long-term Impact: Market positioning, scaling plans, technology roadmaps, anything that influences your company's trajectory over several years

• High Uncertainty and Ambiguity: Emerging technologies or market trends, shifting customer needs, situations lacking clear precedent or answers

• Resource Allocation Decisions: Prioritizing limited capital, talent, or time between competing initiatives, major investments, or budget reallocations, trade-offs affecting multiple quarters

• Cross-Functional Impact: Projects affecting multiple departments, Decisions requiring broad stakeholder alignment, Changes that ripple across the organization

• Major Inflection Points: Growth plateaus or acceleration, Regulatory changes, Technology disruptions, Key leadership transitions

• Risk and Opportunity Identification: Situations exposing significant risks, potential breakthrough moments, competitive threats, or advantages

Take the Pressure Off "Strategy"

There's something about the directive for leaders to "think strategy" that implies you have to predict the future perfectly. That triggers a gut reaction of frustration: "I don't know! How am I supposed to know? I don't even know what I'm having for dinner tonight!"

But as I learned from my dad’s college planning exercise, this knee-jerk reaction quickly subsides. With regular practice, you'll build your capacity to think beyond the immediate, see connections others miss, and help your team navigate toward bigger goals.

Our goal isn’t perfect prediction—it's preparation. You're developing the mental agility to navigate uncertainty with confidence, the perspective to see beyond immediate pressures, and the judgment to make decisions that serve both short-term needs and long-term vision.

The ceiling is real, but it's not permanent. And the view from above is worth the climb.

Keep reading, keep leading,

Jess.

P.S. If The Left-Hand Column has resonated with you, consider supporting my work by clicking on one of the ads below. It's a small action that has a big impact!

Thank you for subscribing!

For more, follow me on LinkedIn 

jessyuen.com

The back office, built for founders

We’ve worked with over 800 startups—from first-time founders at pre-seed to fast-moving teams raising Series A and beyond—and we’d love to help you navigate whatever’s next.

Here’s how we’re willing to help you:

• Incorporating a new startup? We’ll take care of it—no legal fees, no delays.

• Spending at scale? You’ll earn 3% cash back on every dollar spent with our cards.

• Transferring $250K+? We’ll add $2,000 directly to your account.

Get started today.

Register for Pioneer: A summit for AI customer service leaders

Join the brightest, most innovative voices in customer service at Pioneer, a summit for exploring the latest opportunities and challenges transforming service with AI Agents.

Hear from leaders at companies like Anthropic, Boston Consulting Group, and more on how they’re building smarter support systems and why customer service will never be the same.

Register for Pioneer today