The “Be More Strategic” Trap

(And What It Actually Means)

15 years ago, my manager told me to be more strategic. The scene is still fresh in my head. I was responsible for user experience at PayPal, and we went through my thoughts on it in front of a whiteboard. I felt well prepared and forward-thinking. Until I learned I was not. And I guess we’ve all heard it, and actually, I have said it since then myself to my direct reports plenty of times. It’s the classic feedback given in one-on-ones, usually delivered with a thoughtful nod:

“You’re doing great work, but to get to the next level, you need to be more strategic.”

Cue the internal panic. When my manager dropped this line on me, I had absolutely no idea what he meant. I did what any driven professional would do: I panicked, bought all the classic strategy books, and downloaded every SWOT, PESTLE, and OKR template I could find on the internet.

I filled out boxes. I made elaborate slides. But it didn’t feel right. It felt like I was doing paperwork. I didn’t feel “strategic.”

Today, sitting on the other side of the table as a leader, I realize why those templates failed me. Being strategic isn’t about filling out a grid. It’s a completely different way of processing and communicating information.

Here is what being strategic actually means, how leaders spot it, and how you can train that muscle without reading a 500-page textbook..

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What Being Strategic Actually Means

At its core, strategic thinking is the ability to rise above the daily tactical grind. As one seasoned product manager on Reddit’s perfectly summarized the shift:

“ICs finish tasks. PMs define outcomes. ICs react. PMs reframe. ICs ship. PMs steer.”

When you are tactical, you focus on completing the puzzle piece in front of you. When you are strategic, you are looking at the picture on the box to make sure your piece is going in the right place. It means recognizing patterns, anticipating roadblocks, rather than just an order-taker.

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How Leaders Know You’re Strategic

As a leader today, I don’t look for who has the prettiest framework, or is the loudest person in the room, or has the best storytelling skills, or the prettiest slides. I look for specific behavioral cues. I know someone is thinking strategically when they exhibit these four traits:

1. The 360-Degree Storyteller

They can take the exact same initiative and tell the story from completely different angles depending on the context. When executives say “think strategically,” they really mean “think like a business person.” A strategic thinker doesn’t just talk about user features; they talk about the P&L, the cost of sale, market forces, and how the initiative impacts the company’s bottom line.

They tell the story coherently over weeks. It might evolve through feedback loops and gaining new insights, but the backbone of the strategic story remains stable.

2. The Audience Chameleon

They can discuss a project with a junior developer in the weeds, and then pivot to present the exact same initiative to the Board of Directors—speaking the native language of both. They embed their work into a broader, constant context and are able to give fact-based advice that demonstrates that they’ve put themselves in the shoes of the senior person’s and company’s context.

3. The Core Keeper

In a sea of noise and distractions, they ruthlessly protect the core elements that actually drive value.

It’s almost a cliché at this point to quote Steve Jobs and say, “Strategy is knowing what to say NO to.” But it’s incredibly hard to practice if you’re not truly owning and embracing the strategic narrative.

When you lack a deep conviction in your strategy, every request from a stakeholder feels urgent. Every shiny new market trend feels like a must-have. You end up trying to please everyone, which inevitably leads to building a bloated, disjointed product—or burning out your team on low-impact tasks.

A true strategic thinker acts as the gatekeeper for the team’s focus. Leaders know someone has mastered strategy if they are able to

• protect the core by delivering the "strategic no," rejecting even great ideas by using the overarching narrative as a shield against distraction.

• possess the courage to kill active zombie projects the moment they misalign with that core, completely ignoring the sunk cost fallacy.

• embrace brutal trade-offs, recognizing that true prioritization isn't ranking fifty tasks to do eventually—it’s drawing a hard line at the top five and throwing the rest away, fully comfortable with the reality that choosing one path means actively sacrificing others.

4. The Evidence-Based Narrator

Their ideas aren’t just gut feelings, but they also aren’t afraid to take a stance. A great strategy is ultimately an educated bet. As another seasoned PM shared: “The most misunderstood thing about strategy is that it’s a bet, a gamble on some future that you believe will come true. Best practices can only get you so far; at some point, you have to form a point of view and have conviction in it.”

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Good News: You Can Train Your “Strategic Muscle”

My key learning is that strategic thinking isn’t an innate talent; it’s a muscle you build. And at some point in your career, you know that your training paid off. It’s a gradual process. But personally, I knew I made progress when I was able to sit in a board room, confident enough to share the strategy, because what I presented was more than just slides. It was clarity, backed up by experience, insights, knowledge, and data.

Where to Get Started: My “Messy Miro Board” Method

Whenever I step into a new role, I don’t start by writing a strategy document. I start by setting up a completely chaotic, messy Miro board.

This board becomes my single source of truth. I throw everything in there: raw data points, customer insights, Ideal Customer Profiles, and competitive intelligence. But most importantly, I collect quotes. I write down the exact phrases and recurring themes other executives use, so I can learn to speak their language natively.

For the first few weeks, it’s just noise. But eventually, the matrix starts to reveal itself. I begin to see how the scattered facts and figures relate to each other, and the first rough draft of a strategic story emerges.

Here is the secret: I don’t hide this messy board. I share it with my PMs, my peers and my boss. I slap an “Early Beta” label on it and use it to fact-check my assumptions and validate my early lines of thinking. I treat building the strategy exactly like building a product—developed in small, iterative chunks and constantly validated with my “users.”

How to Train Your “Strategic Muscle” (Exercises)

Once you have your messy board established, building your strategic muscle comes down to reps. Here are a few exercises, ranging from daily habits to deep-dive sessions, to help you level up.

Lightweight Daily/Weekly Exercises

• The Executive Empathy Hack: Take five minutes on a Friday and write down what you believe are the top three overarching priorities for your boss (and your board). Then, look at your calendar and task list for the upcoming week. If your tactical output doesn’t map directly to their strategic priorities, you are out of alignment.

• The Meeting Meta-Analysis: During your next cross-functional meeting, stop focusing solely on your department’s update. Actively listen to the other teams (Sales, Marketing, Support) and try to connect the dots. Ask yourself: “How does what Sales is struggling with right now impact what Engineering needs to build next month?”

• The “Why Are We Doing This?” Audit: Take one regular, recurring task you do every week. Trace it all the way up the chain. Why do you do it? Who consumes it? What business metric does it ultimately move? If you can’t connect the dots to a macro goal, you might be executing just for the sake of executing.

More Complex Monthly/Quarterly Exercises

• The Pre-Mortem Drill: Pick a major initiative your team is about to launch. Now, imagine it is exactly one year from today, and the project was a catastrophic failure. Write the story of why it failed. What macro-environmental shifts did you miss? What internal bottlenecks did you ignore? This forces you out of tactical optimism and into systemic, strategic realism.

• The Competitor Roleplay: Block out two hours and pretend you were just hired as the Lead PM for your biggest competitor. Your sole mandate is to steal your current company’s market share. Where are your current product’s vulnerabilities? What feature would you build to exploit them? How would you position your marketing? To be strategic, you have to be able to look at your own work from a hostile, external perspective.

Personally, it took me at least 5-8 years until I “felt” I was strategic and walking into a board room was no longer scary but exciting. I didn’t present slides anymore. I presented my product perspective on the future of the business and was curious to get challenged and receive insights from the board to further polish my thinking and my storyline.

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The Takeaway

You don’t need another textbook or a complicated matrix. You need to elevate your perspective. Look at the whole board, understand who you are talking to, find the data that matters, say “no” to the distractions, and make a confident bet. That is how you become strategic.

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From Reactive Execution to Proactive Leadership

Master the product discipline and become a confident, trusted leader. Stop chasing C-Level wishlists, shuffling roadmap slides, and burning out by Friday evening, and start driving real strategic impact.

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