Why Strategic Work Gets Stuck — And What Leadership Teams Can Do About It

Hey there, Megan here.

As you probably know, I work with a lot of purpose-driven leadership teams. And something I see over and over again is a pattern that makes it really hard for these teams to make real progress on strategic initiatives—even though they deeply want to.

Let me explain what I mean.

The Challenge of Leading While Pulled in Different Directions

Leadership teams are often made up of department or division heads who come together with the CEO, president, or executive director to work on organization-wide strategy. Their goal is to move the mission and vision forward. But in practice, here’s what usually happens:

Even though they’re technically sitting at the same leadership table, most leaders are still focused on their own departments. Their attention, their loyalty, and even their brain space tend to be pulled back to their own teams—even if they have strong second-in-command leaders.

It’s not because they don’t care about the organization as a whole. They do. Deeply.

But the gravitational pull toward their own areas of responsibility is just stronger than the pull toward the broader strategic work.

Why Strategic Initiatives Get Stalled

So, what happens when it’s time to work on a big, organization-wide strategic initiative—something that could make a huge impact?

It’s tough.

Even if the leaders agree it’s important, it’s hard to justify pulling time and energy away from urgent day-to-day operations to focus on longer-term strategy. That’s totally normal. I see it all the time.

But it becomes a real roadblock. Important strategic work doesn’t get the attention it needs—not because people don’t care, but because there just isn’t the space or structure to make it happen.

The Power of Stepping Out and Stepping In

Here’s where I often come in.

When organizations bring in someone external—like me—the leadership team makes the time. They come to retreats, offsites, or strategy sessions fully present and prepared. They clear their schedules, brief their teams, and commit to the process.

And something powerful happens:

They show up.
They engage deeply.
They collaborate.
They get real work done—all at once.

I’ve seen it over and over again. These sessions become a catalyst for progress, alignment, and renewed energy.

Giving Yourself (and Your Team) the Gift of Strategy

What makes these sessions successful isn’t just the content—it’s the time, the accountability, and the opportunity to think big and work together.

When leadership teams take a step back from the day-to-day, they reconnect with each other, the big picture, and the mission that brought them there in the first place. It’s a chance to work on the organization, not just in it.

When leaders give themselves the gift of accountability, the gift of time together, the gift of time to have the strategy work and collaborate deeply and meaningfully for the sake of the whole organization, they really show up.

And they love it. They actually enjoy having the space to be strategic, creative, and collaborative with their peers.

Because at the end of the day, they’re not just operational leaders. They’re mission-driven leaders who want to make a difference across the whole organization.

A Question for You

So here’s something I want you to think about:

What’s holding your organization back right now from moving forward on your biggest strategic priorities?

Maybe you already have a strategic plan. Maybe you have big projects that you know you need to tackle—but just haven’t had the time or space to do so.

Ask yourself:

• What’s getting in the way?

• Is it the constant pull of operations?

• Do you have the desire—but not the structure or support—to make it happen?

How I Support Leadership Teams

If that sounds familiar, this is where I can help.

I often work with leadership teams through retreats, workshops, and ongoing coaching. The most effective organizations I’ve worked with set up a cadence—like quarterly strategic sessions—so the work doesn’t just happen once and fade away. It becomes part of how they lead.

Between sessions, I stay connected with team members. They reach out with questions. We build in leadership development, creative problem-solving tools, and support for activating ideas within the organization.

The truth is, your team is smart and capable. But if those big things aren’t getting done, something’s in the way—and it’s worth exploring what kind of support or structure might make the difference.

Final Thought: Serve the Whole Organization

Imagine being able to return to your department not feeling scattered or stretched thin, but with confidence—knowing you’ve contributed to the organization’s larger goals.

That’s what strategic leadership looks like.

You’re not just serving your team—you’re serving the mission. And in doing so, you're enabling your team to thrive in ways they couldn’t on their own.

Let’s Talk

If this resonates with you, I’d love to hear your thoughts. I find the question of how leadership teams get strategic work done endlessly fascinating—and really important.

Let’s talk about it.

• Join my e-newsletter 
• Book a complimentary Coffee Chat with me

You've got this!

Megan

About Megan E. Mozina (she/her)

As Owner and Principal of Cresta Solutions, I serve as a strategic partner to purpose-driven leaders when they need their teams to innovate and collaborate in order to deliver on strategic change initiatives. To get there, I serve as a facilitator, consultant, and executive coach who leverages expertise in Creative Problem Solving, Team Building, Organizational Change Management, and Strategic Initiatives to ensure my clients get innovation-focused results. I bring over fifteen years of diverse experiences with purpose-driven organizations across four continents. To ensure that changes work and goals are achieved, I use my facilitation superpower to supercharge team collaboration and output. 

I hold a Masters from The George Washington University’s Graduate School of Education & Human Development and a Bachelors from the University of Wisconsin-Madison. I am certified in Change Management, Strategic Planning, and Creative Problem Solving (FourSight®), with additional formal training in Lean Process Improvement, Project Management, and People Management. I regularly present at regional and international conferences on topics such as facilitation, change management, and project leadership. I’m proud to have been a teacher in South Korea and a Peace Corps Volunteer in Honduras.

I’ve lived in five countries, so while I bring my Midwestern friendliness, work ethic, and accent everywhere I go, I see the world through a global perspective. I consume dark chocolate daily, can talk about books all day, and think that Lake Michigan might be my soul mate.

Learn more about my story here: https://www.crestasolutions.com/about.