What strategic leaders do differently

Reader,

When I entered my first leadership role, I started to realize the importance of being strategic, but I didn’t always know how to do that well.

This email is for any rising leader who wants to be more strategic and make strategic conversations possible with their team.

Strategic planning time.

One of my first experiences at a new job was participating in annual strategic planning. I admit, I didn’t really get it.

We were asked questions like:

How much revenue do you think we can bring in next year?
What should our goals be?
What resources do we need to achieve those goals?

I remember thinking, "I have absolutely no clue what we can do. I’ve never done this before."

Funny thing—after I had done it before, I still found those questions challenging. It felt like I was guessing at numbers that would determine our budget, staffing, resources, and more.

This is how many rising leaders feel about strategic planning too. That’s because those meetings weren’t really about strategy. They were about prediction.

Strategy, on the other hand, is about perspective.

But being strategic is far more than looking ahead to decide goals.

Being strategic begins with asking better questions.

Recently, I worked with a rising leader to rethink the roles on her team. Until that point, the team’s structure reflected the past far more than the future.

Instead of asking:
How can we adjust these roles to better reflect what we need now?

We asked:
If we could start again and design roles for where we are now and where we want to be in five years, what would they look like?

The first question would have kept our thinking stuck in what is. The second question freed us to imagine something new.

But what if you can’t make big changes? Why ask questions that aren’t even possible?

Right?
Wrong.

Strategy is about how you could approach your work to achieve your vision. It’s about possibility. And it requires stepping out of the day-to-day reality of what is.

Finding a higher vantage point.

Imagine hiking in a jungle. The vegetation is thick, there’s no trail, and you’re not quite sure you’re going the right way.

Then you spot a small hill to the east and decide to climb it. From the top, you can see all the way back to the beach where you started. You turn toward your destination and see that just ahead, the trees open up.

Now you know exactly where to go.

That’s what being strategic does. It brings you up, out of the day-to-day, and helps you see farther and think critically about where you’re going and how to get there.

Perspective makes progress possible.

Because that rising leader and I began with better questions—and took time to think at a higher vantage point—our final decisions came easily.

When we shared the plan with stakeholders, the feedback was unanimous. One person said something that stayed with me: “These roles have been stuck for a long time, and no one took the time to rethink them until now.”

That’s the power of perspective.
The team had all the potential they needed; they just needed to look at it differently.

Staying stuck is a choice.

What’s remarkable is how little time it actually takes to think strategically.

We spent just two-and-a-half hours together:
30 minutes catching up.
30 minutes reviewing notes.
90 minutes reimagining a new staff structure from scratch.

Those roles could have stayed the same until they were forced to change. But instead, one rising leader paused, asked better questions, and thought strategically about what was possible.

Every time you’re stuck, there’s an opportunity to:
Find a higher vantage point (ask better questions).
Be strategic (think critically and explore possibilities).
Choose a new direction.

You don’t have to stay stuck or feel boxed in.

When to be strategic.

Senior leaders are used to being strategic all the time. It’s a muscle they develop over time.

For rising leaders, here are daily opportunities for strategic thinking:

At the start of your week—choosing priorities that align with the big picture.
Before any meeting—clarifying the purpose and how you’ll use the time well.
When giving direction—making sure your team understands not just what to do but why it matters.
Before adding a new priority—thinking critically about what’s most important to your larger vision.
After setting a priority—identifying the best way to accomplish it.
At the end of your week—reflecting on your team, culture, priorities, and progress.

It only takes a few minutes to pause, find a higher vantage point, and think strategically.

The cost of daily work that isn’t strategic is great. Every year, organizations waste enormous time, energy, and resources doing what they’ve always done.

That’s why leadership is so valuable. Great leaders are always strategic: always thinking ahead, always considering the best way forward.

And always making sure people know what to do, why it matters, and how to take action together.