How You're Killing Your Strategy's Momentum: ClearPoint Strategy Founders Series
Co-Founder & Alabama Native

Ted is a Founder and Managing Partner of ClearPoint Strategy and leads the sales and marketing teams.

Ted Jackson is the co-founder of ClearPoint Strategy, a B2B SaaS platform that empowers organizations to execute strategic plans with precision. A Duke and Harvard Business School alumnus, he brings over 30 years’ experience in strategy execution—including 15 years with Kaplan and Norton on the Balanced Scorecard. Ted works closely with customers to ensure the software meets unique challenges, continually refining the platform with his global expertise.

You may not even realize it.

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You know the feeling: Your new strategic plan is finally off the ground. Leadership is energized. Departments are engaged. The launch meeting felt like the beginning of a turning point.

Then a few months go by… and you’re still finalizing objectives. There’s debate about which projects should be included. Success metrics are still a moving target. You’re not quite sure who owns what. The initial momentum has faded, and the strategy feels more like an unfinished to-do list than a living, guiding force.

And you start to wonder: Is this even worth it?

I’ve seen this play out more times than I can count. The truth is, most strategies don’t fail because they’re bad ideas. They fail because they stall. That stall happens when we unintentionally kill our own momentum.  

Here are five ways that happens—and what to do instead.

1. You’re Treating Strategy Like a Project, Not a Process

Too often, organizations pour their energy into building the strategy—and then stop. They wait for every performance indicator to be perfect, every initiative to be fully scoped, and every objective to be polished.

The Fix:

Don’t wait. As soon as your plan is about 80% complete, start your review cadence. Schedule regular, quarterly strategy meetings. Even if you don’t have all your KPIs figured out yet, begin by talking about the goals. What’s going well? What’s not? Let the conversations evolve as you build out the details.

Momentum comes from movement—not from waiting for perfection.

Video: How to Run an Effective Strategy Review Meeting

2. You’re Only Talking About What’s Going Wrong

Strategy reviews often turn into post-mortems. Everyone focuses on what’s red or yellow—what’s behind schedule or underperforming. And while that’s important, it’s also a surefire way to drain energy from the room.

The Fix:

Celebrate the green. Highlight wins. Recognize individuals or teams who are driving progress. People respond to encouragement. Celebrating success builds energy and reinforces the behaviors you want to see more of.

3. You’re Trying to Tackle Everything at Once

If your strategy has dozens of objectives, KPIs, and initiatives, trying to review everything in a single meeting can be overwhelming. You run out of time, conversations lose focus, and nothing gets the depth it deserves.

See: 5 Mistakes You’re Making in Your Strategy Review (and how to fix it)

The Fix:

Break your strategy into themes and hold shorter, focused meetings on one theme at a time. Assign a facilitator, stick to the agenda, and give each topic the time it needs. This structure brings clarity and prevents overload—two things that are critical to keeping your strategy moving forward.

4. You’re Not Adjusting the Plan When Things Change

Let’s say Q1 doesn’t go as planned. You fall behind on your targets. And instead of adjusting, you keep pushing forward like nothing happened—hoping the numbers will turn around.

That’s not strategy. That’s denial.

The Fix:

Your strategy should be a living document. If AI, tariffs, regulations, or other external factors shift the playing field, update your plan. You can keep your original targets as a reference, but give yourself permission to adjust based on new realities. That’s why frequent review meetings exist—to keep your strategy relevant and actionable.

Free eBook: How to Lead Effective Strategy Review Meetings

5. You’re Not Connecting Strategy to Daily Work

Lack of strategic alignment is one of the biggest momentum killers of all. When employees don’t see how their work contributes to the strategy, they disengage. Strategy becomes something “the leadership team does,” not something they’re part of.

The Fix:

Translate the strategy down to departments and individuals. Assign ownership to objectives, KPIs, and projects. Recognize contributions. And most importantly, help people articulate where they make the biggest difference. When someone can say, “Here’s how I support our strategy,” you’ve got momentum.

Keep the Momentum

Momentum doesn’t come from motivation alone—it comes from structure, habits, and clarity.

If your strategy feels stuck, it’s probably not because the goals are wrong. It’s because the organization isn’t reinforcing progress in the right ways. Schedule the meetings. Celebrate the wins. Focus the conversations. Adjust when needed. Make the strategy part of daily work.

That’s how you build a strategy that moves.

Simplify your execution with ClearPoint Strategy. Book a free demo with a strategy expert to see how software helps automate planning, project management, reporting, and more!