leadership

When the Plan Lives in the Margins: Why Strategy Doesn’t Mean Execution

Margaret stood just outside her design team’s war room, watching them scribble on whiteboards and shuffle post-its. They were prototyping a feature she believed would revolutionize their software suite—a feature her board had greenlit months ago. Yet as she listened to their conversation, a hollow knot formed in her stomach. They were debating basic questions: Who owns this decision? How do we know if we’re done? Which priority takes precedence when two deadlines collide?

Her five-year roadmap hung on the office wall—bold objectives, clear milestones, market targets. But down here, in the day-to-day rhythm of ideation and problem-solving, that roadmap felt like wallpaper: visible, but irrelevant. These talented designers weren’t arguing about design principles; they were questioning whether any of their choices would truly matter. It wasn’t a lack of skill or good intentions. It was something subtler: the strategy existed, but it didn’t breathe in how people worked.
Margaret realized she was witnessing a familiar phenomenon: the gap between “what” to do and “how” to do it—and it wasn’t apparent on any spreadsheet. It lived in the unseen currents of leadership behavior, culture, and team dynamics. And until she addressed those invisible forces, the company’s best plans would remain just that: plans.

Why “Strategy vs. Operations” Misses the Point

Mid-market CEOs are trained to watch for tangible red flags—sales dips, client churn, talent turnover. But quiet teams are Few CEOs dismiss the importance of a strong strategy or efficient operations. Everyone recognizes that you need both. But most organizations treat them as separate realms:

  • “Strategy”: The realm of the C-suite—market analyses, vision statements, five-year projections.
  • “Operations”: The realm of department heads—budgeting, process flows, daily task lists.

When these two circles don’t overlap, magic falls through the cracks. You’ve seen it yourself:

  • A marketing plan calls for new messaging, but sales teams keep using outdated materials.
  • A product team sets delivery dates, yet customer support isn’t looped into feature testing.
  • Leadership preaches “innovation” but punishes missteps, so teams play it safe.

No single slide deck can bridge this divide. The missing link lies in how people show up: whether managers encourage questioning, whether teams trust each other to adapt when obstacles arise, and whether the company climate feels open enough for honest feedback.In other words, it’s not just “what” or “how”; it’s the “who” and “why” that stitches everything together.

The Invisible Forces: More Real Than You Think

Imagine strategy as a ship’s destination and operations as its engines. If you fuel the engines without setting a course, you’ll go nowhere. Conversely, if you set a course but the engines sputter, you’re stuck in port.

Those engines run on behavior, climate, and dynamics:

  1. Leadership Behaviors
    • It’s one thing for a CEO to endorse “risk-taking.” It’s another when managers implicitly reward only “sure bets.” People watch actions more than they listen to speeches. When leaders corner the lion’s share of credit or punish failure, employees quietly hedge their bets—undermining the strategy’s intent.
  2. Culture and Climate
    • Culture isn’t a mission poster on the wall. It’s the daily rhythm: Can you disagree without reprisal? Do people share bad news without fear? When candor is confined to email threads or whispered in hallways, incremental issues compound into systemic breakdowns.
  3. Team Dynamics
    • Teams are living ecosystems. If silos exist—whether between product and sales, marketing and finance, or junior and senior staff—each group operates on its own assumptions. Even a brilliant plan falters when nobody owns the handoffs.

When these forces align with strategy, execution becomes almost effortless: decisions cascade naturally, hiccups are caught early, and people feel anchored to a shared purpose. But when they diverge, the best intentions get lost in translation.

A Morning in the Trenches

On a recent Tuesday, Margaret dropped in on two fairly unrelated scenes:

  • In the customer-service bullpen, an agent wrestled with a complaint about a feature that didn’t match the promised workflow. The agent had no authority to escalate tweaks; his manager had to email product leadership—who might only react next week. That lag frustrated an already irate customer and demoralized a competent frontline employee.
  • Down the hall, a project manager huddled with engineers over crash-report data. They needed budget approval for extra testing resources, but the finance team was waiting on a formal project charter—again, a process buried three levels above. No one had paused to ask: Which is more critical—shoring up product quality or obeying the bureaucratic sequence?

Both scenes shared the same undercurrent: invisible friction that rewrote strategy into something unrecognizable at the front line. That morning taught Margaret that strategy’s power lies only in how it shapes each tiny decision—a lesson no boardroom slideshow can convey.

The Subtle Work of Bridging

So how do you fix what you can’t see? It starts with acknowledging that strategy implementation is a social act. Plans don’t execute themselves; people do. Here’s what Margaret and her leadership team learned as they rewired their approach:

  1. Observe Without Presuming
    • Margaret spent a week “walking the aisles,” not to “check up” but to quietly note patterns: Where did people hesitate? Who dropped projects when the first unexpected issue arose? When she merely observed—and occasionally asked, “What’s getting stuck here?”—leaders noticed they were blind to daily roadblocks.
  2. Surface Behavioral Contradictions
    • In a leaders’ retreat, they mapped out espoused values—“we value cross-functional collaboration”—against actual practices—“whoever controls the budget wins.” By naming these inconsistencies, they sparked honest debate: “Are we okay with teams raising silos if budgets are scarce? If not, what behaviors do we need to change?”
  3. Rebuild Decision Pathways, Not Just Org Charts
    • Instead of updating titles, they focused on crafting clear, context-rich decision guidelines: “If an urgent customer issue surfaces, escalate within 24 hours to a triage team that includes product, operations, and support leads.” This simple rule bypassed multiple signatures and put authority into people’s hands.
  4. Make Culture a Continuous Conversation
    • They reframed “culture audits” from annual surveys into weekly micro-check-ins: short Slack polls asking, “Did you speak up about a concern this week? If not, why?” Leadership reviewed results together and publicly shared corrective actions—no matter how small—to reinforce that feedback mattered.
  5. Empower Tension as a Signal, Not a Problem
    • Disagreement, when channeled properly, became a sign of health. Teams were encouraged to air “strategic friction” in a monthly forum where cross-departmental issues could be debated. By setting structured guidelines—listen more than talk, focus on solutions—they turned tension into alignment fuel.

Why This Matters More Than a New Plan

You don’t need another flashy strategic framework or a six-page action plan. If your company is mid-market—growing fast but still nimble—your real work lies in ensuring that any existing strategy lives in the everyday behaviors, norms, and conversations. Without this, a plan is just ink on paper.

When leaders shift from “We need a new strategy” to “How can we make our current strategy breathe?” they uncover the levers that actually move the needle. It’s quieter work—no big reveals or public fanfare—but it’s transformative.

Imagine a day when the design team debates not whether their choices matter, but how they can best serve the strategy. Picture customer-service agents empowered to solve problems without a week-long approval process. Envision a culture where tension between departments isn’t swept under the rug but channeled into optimal outcomes.

That’s the place where strategy and execution meet in real time. It’s less about charts and quarterly targets and more about the invisible forces that shape every choice your people make. When you fix that gap, you don’t just deliver on your roadmap—you breathe life into it.

Questions to Bring to Your Next Meeting

IfWhere do we send mixed messages?
If our actions reward risk aversion over intelligent risk-taking, what needs to change?

Which decisions still feel out of reach for frontline teams?
Are those decisions truly too big, or has the pathway been needlessly complicated?

How do we invite dissent as data?
When someone challenges our plan, do we treat it as a problem to silence or an opportunity to refine?

Are our feedback loops short enough to catch misalignment today—rather than six months from now?
What channels exist for a single employee to surface an issue that could impact strategy downstream?

If your answers reveal more “gray zones” than clarity, you’ve likely found one of those invisible gaps. And once you name it, you can begin to close it—so your strategy doesn’t just live on paper, but in every decision, conversation, and heartbeat of your organization.

We’re The Catalano Group

Our firm has consistently delivered leadership development that changes how leaders lead. Our team of psychologists, consultants, and coaches share a passion for pushing leaders to their peak.