Five invisible disconnects that derail strategy (and how to fix them)

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Jul 18 2025 by Molly Lebowitz Print This Article

In fast-moving environments, the pressure to deliver has never been higher. Leaders are expected to cut costs, accelerate results, and reinvent their organizations - all at once. But even the most ambitious strategy won't drive value if the execution is not aligned. When strategy and operations drift apart, organizations stall. Priorities get muddled, and projects sprawl and fizzle. Talent burns out.

That disconnect doesn't always show up in obvious ways. More often, it creeps in slowly, through unclear mandates, competing goals, or rigid systems that don't flex with market shifts. Here are five common signs that strategy and execution have fallen out of sync - and what you can do to reconnect them.

Disconnect #1: The Vision Black Hole

Sometimes, a strategy looks great on paper but never makes it into the real work of the organization. It's discussed in boardrooms, compelling value proposition agreed to, and it's then left to fade. Middle managers and delivery teams are left wondering how their day-to-day responsibilities connect to any broader vision and project goals begin to sprawl.

What it looks like: Functional leaders do not communicate strategic priorities, projects are kicked off without a clear business case or value proposition, teams pursue siloed and disconnected goals, and teams are unable to effectively partner cross-functionally.

What to do: Make strategic alignment part of the operating rhythm. Use a structured cascade, such as an OKR (Objectives and Key Results) framework, that translates strategy into clear, measurable goals across every level of the organization. Overcommunicate the strategic goals at all levels, connecting the strategy to a "why," such as competitive forces or a market shift. Revisit transparent progress against the goals often - not once a year. Whether in team meetings or quarterly reviews, keep reinforcing how today's work ladders up to the long-term plan.

Disconnect #2: Too Many Priorities, Not Enough Focus

When everything is labeled "strategic," teams can't focus. People end up juggling too many initiatives with no clear sense of what matters most. Leaders push forward new requests, but without a system for trade-offs, work piles up faster than teams can manage it.

What it looks like: Fire-fighting mode, missed deadlines, burnout, and conflicting demands from different corners of the organization.

What to do: Start by creating a centralized forum - ideally with executive visibility - where leaders commit to what the organization will and won't take on. Understand the capacity of your team and dedicate a portion of capacity for the named strategic initiatives. Reinforce priorities visually with portfolio dashboards and roadmaps. And adopt a reprioritization mechanism (some call it an "interrupt process") to make room for critical new efforts without simply layering them on top of existing commitments.

Disconnect #3: The Org Chart Isn't the Operating Model

Most things worth doing require collaboration across multiple functions. But too often, ownership is unclear. Teams duplicate efforts, work at cross-purposes, or drop the ball entirely.

What it looks like: Silos, political turf wars, and inconsistent execution across departments. Teams protect their status, work in isolation, or fail to align timelines and goals.

What to do: Avoid confusing structure with coordination. Align cross-functional teams early - ideally during the chartering phase of major initiatives. Invest in defining an operating model that maximizes contributions from multiple teams. Be explicit about who owns what, how handoffs will work, and what success looks like across groups.

Culturally, reinforce shared accountability by tying team contributions to joint outcomes, not just individual wins. For example, some large tech companies have started to tie a portion of individual incentive compensation to achieving specific cross-functional shared goals.

Disconnect #4: Change Fatigue and Stakeholder Apathy

Organizations that layer change on top of change - without showing progress - eventually hit a wall. Employees tune out, and stakeholders disengage. The next transformation effort meets resistance before it begins.

What it looks like: Poor adoption, "we've seen this before" skepticism, and quiet quitting.

What to do: Shift from top-down updates to two-way conversations. Instead of only broadcasting the "what," invite dialogue around the why and the how. Own the entire narrative on what has brought us to this point and acknowledge past missteps. Get creative with tactics like stakeholder working groups or change champion networks to generate buy-in from the ground up. And above all, don't rely on passive communication. Tell the story and show how change connects to real wins.

Disconnect #5: Strategy That Doesn't Evolve

Execution connected to strategy is great, but a good strategy is never static. Markets shift, customer needs change, and what made sense in January might not hold by June. When organizations cling to outdated plans, execution continues - but in the wrong direction. Management needs to have a healthy tension with teams to be able to reprioritize when needed, and employees expect a company to make sharp decisions to stay relevant.

What it looks like: Declining relevance, stalled growth, and teams investing in efforts that no longer make sense.

What to do: Build in the flexibility to adapt. That means connecting strategic planning tools (like OKRs or product roadmaps) to execution in a way that allows real-time shifts. When strategy changes, don't bury the lead - communicate it with humility and urgency. Strong leaders are willing to say, "Here's what's changed, and here's why we're going in a different direction." Try to keep tracking mechanisms consistent to reduce churn. Then, reallocate resources based on where you're headed - not where you've been. If you skip this step, you risk wasting capacity and eroding trust.

Don't Let Execution Be the Weak Link

A strategy is a plan of attack on paper, but the value only comes when you execute on the strategy. Since humans generally steer execution, we must rely on human connection, communication, and engagement to tie execution to strategy.

Left unaddressed, the disconnects outlined here can quietly derail even the most well-crafted plans. For leaders, the work isn't just to set a bold direction - it's to clear the path for teams to act on it. That means spotting the gaps early, building mechanisms to course-correct, and staying agile as priorities shift. So don't just launch your next strategy, ask: Have you cleared the path to deliver it?

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About The Author

Molly Lebowitz
Molly Lebowitz

Molly Lebowitz is the managing director of the tech industry at Propeller, a management consultancy that helps leading organizations accelerate transformation and navigate complexity. She has extensive experience helping technology organizations tackle large-scale, complex operational challenges and transformations.