How to Actually Think More Strategically

You Keep Hearing You Need to Be "More Strategic." But What Does That Actually Mean?

Your calendar is full. Your inbox is overflowing. Your boss keeps saying, “Think more strategically.”

But when? And how?

You know that thinking more strategically could help you get ahead, but no one tells you what that actually means in your role, when to do it, or where to start.

So you try to take action.

Maybe you:

• Block off "thinking time" on your calendar, but when the time comes, you don’t know what to focus on, so you give it up for something urgent.

• Write long memos or slide decks outlining your ideas, but no one reads them.

• Fall into analysis paralysis, searching for the perfect data point to validate your idea until weeks pass and nothing moves forward.

Sound familiar? You're not alone.

I’ve received this feedback before and had no clue what it meant. I was working long hours, delivering on all of my goals, and getting positive feedback from key stakeholders. But my manager told me I needed to be more strategic. It was frustrating and confusing, but eventually, I figured it out.

Why “be more strategic” is frustrating advice

Strategy is one of corporate life's most overused and least defined words.

It shows up in performance reviews. It’s written into job descriptions. But no one tells you how to do it.

Being more strategic isn’t about doing more. It’s about thinking differently. Taking a step back, connecting the dots, and making deliberate choices.

As this great video describes, strategy is simply a plan to create value.

And the good news? It’s a skill you can learn.

Three Steps to Thinking More Strategically

Step 1: Ask the right questions

Most professionals get stuck in execution mode because they never step back to ask better questions.

To think strategically, you need to understand your organization’s priorities and the broader industry landscape.

You should be able to answer confidently:

• What are my organization’s top three priorities right now? How does my work contribute?

• What’s happening in our industry? Are there new competitors, regulations, or technologies we should be paying attention to?

• Where is the business headed over the next three to four years?

You can explore answers to these questions by reading industry publications, following interesting people who write about your space, attending conferences, talking to customers, and networking with peers.

Example: I needed to address increased employee attrition during a challenging business period. On the surface, I could have immediately reacted to higher attrition, stated we had a problem, and applied generic solutions (i.e, ask for comp increases, implement stay interviews, etc.). Instead, I should step back and look internally and externally to explore:

• What specific roles or skills are we at risk of losing? Do they matter to our business priorities?

• What’s causing employees to consider leaving? (Compensation? Leadership changes? Workload?)

• What are competitors offering that we’re not?

• Where can we invest in employee experience without increasing costs?

By asking the right questions first, you avoid reactive decisions that don’t address the real problem.

Step 2: Develop a clear point of view

Gathering information is a start, but strategy requires forming a perspective.

Once you’ve done the research, ask yourself:

• What do I believe should happen next?

• Why does this matter?

• What’s at stake if we do nothing?

Try to distill your perspective into one to three sentences. If you can’t summarize it briefly, you don’t fully understand it yet.

A simple way to structure your thinking is the "What, So What, Now What" framework:

• What? (What’s happening?)

• So what? (Why does it matter?)

• Now what? (What should we do?)

Example: Instead of just saying, "We need to improve retention," develop a clear, strategic point of view:

• What? Employee turnover has increased by 15% in the last six months, and exit interviews show that lack of career growth is a top reason people leave.

• So what? If this trend continues, we risk losing high performers and increasing hiring costs, which is troubling given tight budgets.

• Now what? We should introduce a targeted internal mobility program that helps employees see a future within the company without requiring big raises or promotions.

Strategic thinkers don’t just describe problems. They define the path forward.

Step 3: Articulate your point of view to others

A good strategy doesn’t matter if no one understands it. Great ideas die in bad communication.

To get buy-in, make your message land.

• Be brief. Get to the point. Don’t bury insights in long decks or emails.

• Speak in business terms. Tie your idea to revenue, efficiency, or company goals.

• Adapt to your audience. Your presentation to a VP should be different from your presentation to a peer.

Example: Instead of sending a long email about employee turnover, frame it in a way that drives action:

"We’ve lost 15% of employees in the last six months, and data shows career stagnation is a driver. If we don’t address this, we risk losing top talent at a time when hiring budgets are frozen. I recommend launching an internal mobility initiative that requires minimal budget but increases retention."

Presenting your strategy clearly and concisely makes it easy for decision-makers to engage and act. Most people think being strategic means adding more complexity. In reality, the best strategic thinkers simplify their message, making it easier for decision-makers to act.

Final Thought: Anyone can be a strategic thinker

Strategic thinking isn’t about working harder. It’s about:

• Asking better questions

• Developing a clear point of view

• Communicating insights in a way that gets buy-in

It’s a skill. And like any skill, it can be practiced and improved. Proactively block time on your calendar and use your “thinking time” to practice the steps outlined above. You’ll be seen as more strategic in no time.

Until Next Time,

Winston

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