Why “Being Strategic” Feels So Hard (And What to Do About It)

In reviewing the feedback from my recent leadership survey, something came up that I get asked about all the time.

“How can I be more strategic in my role?”

Leaders at every level said they feel pressure to think and act more strategically but many leaders aren’t sure how to make it happen.

In fact, I was working with a leadership team recently when one of the Directors pulled me aside.

“Vanessa,” she said, “I keep hearing that I need to be more strategic. But honestly, I’m not even sure what that means.”

I appreciated her honesty because she is not alone.

Strategic leadership is one of the most talked-about competencies in business and one of the least understood. Most leaders know they’re supposed to be strategic but are unsure what that looks like in practice.

Why is there so much uncertainty?

Well, real strategic leadership is not just a single activity. It has three distinct parts.

Here are the 3 components of strategy:

1. Strategic Thinking

This is the foundation. Strategic thinking is the habit of stepping back and asking: Is this the right approach? It’s about questioning your assumptions, looking at your work with fresh eyes and being willing to challenge the way things have always been done.

2. Strategic Planning

Once you’ve done the strategic thinking, you need a strategic plan. Strategic planning is where you take your vision and translate it into clear priorities, timelines and responsibilities.

3. Strategic Implementation

This is where strategy lives or dies. You can think brilliantly and plan meticulously, but if your team isn’t executing against the plan, and you’re not following up, it won’t move the needle.

So how strategic are you, really?

Here are a few honest questions to ask yourself:

1. Do you schedule time in your calendar specifically for strategic thinking?
2. Do you have a clear plan that your team can actually reference and follow?
3. Do you hold regular check-ins to track progress on strategic priorities?

If you answered “not really” to most of these, not to worry.

The good news is that strategy is a skill, which means it can be learned and developed.

This is exactly what we can build together

If you’re reading this thinking, “I get it, but I don’t know how to make this stick inside my team’s culture”, that’s exactly the gap my work is designed to close.

Whether it’s through one-on-one coaching, my training program called “Execute Strategically” or a series of team strategy sessions, we can build a plan together. I’d love to hear more about what that could look like for you and your team.

If this feels right for you, I would be delighted to help you turn your strategic intention into consistent action.

If you’re ready to make that shift, let’s start a conversation. Reply to this email and let me know how you need support.

Thank you for sharing!

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