How to Get Your Leadership Team to Think Strategically (Not Just Tactically)

Most leadership teams are great at reacting.

They solve day-to-day problems, put out fires, and keep things moving.

But ask them to think three years ahead,

Define strategic priorities,

Or challenge assumptions—and things stall.

That’s not because they’re incapable.

It’s because strategic thinking isn’t part of their rhythm yet.

The Tactical Trap

When your team is stuck in tactical thinking, you’ll notice:

Every meeting is focused on tasks and updates
There’s little to no long-term planning
Strategic initiatives start but fizzle out
No one’s pushing back on the status quo

If this sounds familiar, you’re not broken—you’re just missing structure.

3 Ways to Build Strategic Thinking Into Your Team

1. Set the Strategic Horizon
Define what “long-term” means for your company—1 year, 3 years, 7?

Give your team something concrete to think toward.

2. Ask Better Questions
Strategy lives in questions like:

- What must be true for us to hit our 3-year target?
- What’s a bottleneck we’re pretending isn’t there?
- Where are we over-complicating our business?

Add these to your meeting agendas to rewire the room.

3. Dedicate Time for Strategic Work
You won’t get strategic thinking in a meeting packed with updates.

Block time for strategic topics—ideally monthly—and create space to go deep.

What Changes When Strategy Becomes the Norm

Your team starts thinking like owners, not technicians or operators
You get proactive solutions, not reactive updates
Long-term initiatives gain momentum
You shift from managing the business to leading the future

Want to Build a Strategic Leadership Team?

I help owners lead teams that think ahead, act decisively, and execute with clarity. If you’re ready to shift from tactical chaos to strategic control, email me and let’s talk.

Steve@DYBCoach.com

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About the Author

As many of you know, my journey has been one of grit, grace, and transformation. At 19, I was a high school dropout, single father, and struggling paint contractor in Michigan. I later moved to Florida, where I faced both personal and professional hardships. With nothing left to lose, I turned to prayer—and was blessed with a relentless hunger to learn. I devoured books, attended seminars, and discovered better ways to streamline and grow my business—even through the Great Recession (and yes, I did hit the wife lottery along the way!). In 2014, I published How To Double Your Business and later sold the painting business, launching a new chapter: coaching others to grow their businesses. For the past 10 years, I’ve dedicated myself to helping business owners scale through the DYB System, while also drawing from frameworks like EOS, Scaling Up, and The Four Disciplines of Execution. Yet something was still missing—something more adaptive, integrated, and complete. Then I found Pinnacle. After months of research and interviews with other Guides, I joined Pinnacle. Their tools and strategies have exceeded every expectation. Now, as a Pinnacle Business Guide, I help leadership teams implement a custom-tailored operating system that draws from the best in the industry—but flexes with your unique business. It’s a dynamic, proven approach to achieve clarity, momentum, and lasting growth. I’m no longer taking on any more 1:1 coaching clients… Instead, I now specialize in working with visionary business owners who are ready to get their leadership teams aligned—around a clear vision, a focused strategy, and an actionable execution plan. With the tools and process I now have as a Pinnacle Business Guide, I help turn alignment into momentum, and momentum into results. If your business is growing—but your leadership team isn’t fully rowing in the same direction—let’s talk.