For project strategies to soar, don’t skip those in the middle

“We have a weak middle management team,” a CEO told me recently. “I need to overhaul most of that layer in my organization because projects stall unless my senior executives get into the weeds. But when they do, they can’t focus on the strategic work they’re supposed to be doing.” But when this CEO added that he didn’t want his middle managers “wasting time” learning the strategy, that’s when I knew what was going on.

This wasn’t a weak middle management issue. It was a classic case of strategy being defined in isolation, and high-value execution being expected in a vacuum. The very people responsible for delivering the work had no idea why they were doing it. Without that clarity, they were never going to get it right.

The symptoms

When the people responsible for delivering your strategy don’t actually understand what the strategy is, cracks start to show. Projects take too long and cost too much. Executives get involved in details they shouldn’t be touching, and decisions stall because middle managers miss clear direction on what success looks like, forcing executives to drive all decisions. But because executives then try to do more than one job, decision-making slows down even more than when they tried to delegate it in the first place.

And even when projects are delivered, success is measured by completion, not by achieving the required business results that move the organizational needle.

From the outside, it looks like a middle management issue because you don’t know a project wasn’t set up for success until you’re mostly through execution. Even though the problem started before the work actually began, the finger pointing unfolds: “We need stronger players,” “They just need to be more strategic,” “Our project management process is broken.”

Often, executives restructure, layer more governance, or add even more process in attempts to accelerate execution. However, delivery just slows down even further because they’re operating within a flawed system. When the operating model itself doesn’t connect strategy to execution, more structure just adds friction and frustration.

The root cause

Middle managers, both functional team leaders and project managers, are the execution engine of your organization.

They’re the ones leading the teams and turning strategy into action, not just managing people and tasks. They’re either driving momentum or destroying it — either one comes down to how clearly the path is defined and why it matters. But most middle managers are asked to deliver without the information they need to sit in the driver’s seat.

Project managers are handed initiatives tied to strategic goals, but no one helps them connect the dots between the work and the business outcomes they’re supposed to support. Functional managers, on the other hand, are focused on budgets tied to people and operational tasks. Their performance is measured by how well they keep the lights on, not whether their teams actually help move the strategy forward.

Then, when strategy-focused projects show up, no one knows how to prioritize them. The project people can’t push the work through without help. The functional managers don’t make it a priority because nothing in their goals or metrics tells them they should. And it all breaks down, not because the work isn’t important, but because no one understands why it matters or how to make room for it. They don’t know why they’re doing their work. They’re just told to deliver the project.

So they do. They focus on the plan, track timelines, and manage risks. They check the boxes, but when they don’t understand what the project is meant to accomplish, they can’t make the right decisions. They can’t adjust when things change nor lead the work in a way that drives outcomes, because no one has told them what outcomes actually matter. Then middle management is blamed for poor execution and executives jump in. It’s not that they’re not capable, but they haven’t been given the context to deliver the results leaders expect.

This disconnect isn’t about execution. It starts much earlier. Strategy is defined at the top, in isolation, and then handed over like a task list with predefined dates and fuzzy goals. And when the work gets delivered but the business outcomes needed to move the business forward don’t materialize, everyone’s frustrated, not because the strategy was wrong but because the people delivering it didn’t know what success looked like in the first place.

The solution

If you want better execution, start by making business strategy everyone’s responsibility, especially for those in charge of delivering it. Here’s how:

1. Involve middle managers early. Don’t hand them predetermined scope and timelines, and expect flawless execution and high ROI. Bring them into the strategy conversation while there’s still room to shape the work. They’ll tell you what’s realistic and flag risks you didn’t see coming. Project managers are future predictors, and functional managers know the real workload they already have on their plates.
2. Share the why, not just the what or when. Make sure your delivery leaders know why this work matters, how it ties to business outcomes, and what success actually looks like. If they don’t understand the context, they’re just managing tasks. When they do, they can make smarter decisions, lead their teams with purpose, and adjust when things change, because they know what they’re solving for. They can’t lead effectively or make real time decisions if they’re left guessing.
3. Shift the conversation from outputs to outcomes. Stop measuring success by how much got done. Perfect outputs that don’t drive the right business outcomes are a waste of time and resources. Start focusing on the impact of that work. What changed? What value did it deliver? That’s what matters. Get your managers thinking this way.
4. Teach middle managers how to think like business owners. Most organizations train middle managers in tactics like how to run meetings, manage tasks, and follow processes, but not how to think like business leaders. If you want them to lead, you must invest in building their strategic muscle. They need training, coaching, and context to go from task managers to outcome owners. When they understand the bigger picture and what success looks like, the shift happens fast. We’ve seen even junior team members shift their entire mindset and show up with a completely different level of ownership and confidence in as little as a few days when they’re shown the right way to think about and deliver their work.
5. Make alignment part of the job. Build a system that keeps strategy connected to delivery throughout the entire lifecycle. Strategy isn’t a one-time handoff. It’s a constant conversation. You need to bridge the gap from strategy definition, to strategy execution, to strategy realization so everyone stays focused on outcomes, not just activity.

If your middle management team doesn’t understand the strategy, you don’t have an execution problem. You have a leadership problem.

Before you start reorganizing or adding more oversight, take a hard look at whether your strategy has been clearly communicated to the people doing the work. Better yet, ask them. If they can’t tell you why they’re doing what they’re doing or what success looks like, don’t be surprised when it doesn’t advance the business.

If you want better outcomes, start with alignment. When your people know what they’re doing, why they’re doing it, and what success looks like, strategy delivery accelerates without the need to replace your entire middle layer.