The Strategic Planning Trap
ALIGNMENT, EXECUTION 2025-11-06 Robert Courser

November Is Planning Season

November is when executive teams huddle for annual strategic planning. Off-sites, board decks, vision statements: this is the season of bold ideas and polished PowerPoint slides.

But here’s the hard truth: strategy is taught; execution isn’t. And that’s why so many brilliant strategies collapse under their own weight within months of the new year.

At Line-of-Sight℠, we see it every year. Organizations invest enormous effort in creating strategy, but far too little in operationalizing it.

The Pitfalls of Strategic Planning

Even the most forward-thinking companies fall into predictable traps:

  1. Planning as ritual. The focus is on producing a polished plan instead of creating a system that can actually be executed.
  2. Ambition without clarity. The goals are bold, but they don’t cascade into actionable priorities for teams.
  3. Metrics that miss the point. Leaders measure internal activity rather than customer value and impact.
  4. Execution assumed, not taught. Leaders hand teams a plan and expect flawless delivery, without equipping them with the discipline of execution.

The outcome? By March, teams are already improvising, reinterpreting, or ignoring the plan. The strategy hasn’t failed; execution has been neglected.

Shifting the Focus: Designing for Execution

The most effective organizations use November planning not just to decide what to do, but to ensure everyone knows how to do it. That requires embedding execution discipline into the planning process itself.

Winning leaders:

  • Pair strategy with execution pathways. Every goal must be matched with a clear operational plan.
  • Involve mid-level leaders in planning. They are the ones who will translate strategy into daily action.
  • Align metrics to customer outcomes. Stop tracking busyness, measure impact.
  • Treat planning as a system, not an event. Annual planning isn’t a binder, it’s the launchpad for continuous execution.

A Case in Point

One Line-of-Sight client, a global services firm, discovered their annual plan was essentially a shelf ornament, a glossy binder that looked impressive but rarely shaped daily work.

By reengineering their planning process with an execution lens, they:

  • Integrated Line-of-Sight assessments into the planning cycle.
  • Required each strategic priority to include a defined execution roadmap.
  • Held leaders accountable for execution clarity, not just strategic vision.

The result? When the new year began, execution wasn’t an afterthought, it was already in motion. By spring, they weren’t revisiting assumptions; they were delivering results.

November Reflection for Leaders

As you finalize your 2026 plans, ask yourself:

  • Are we designing for execution, or just documenting ambition?
  • Will our managers and teams know how to act on this plan?
  • Are we equipping leaders to teach execution with the same rigor we teach strategy?

If you can’t answer yes, your strategy is at risk, before the year even starts.

The Line-of-Sight Commitment

This November don’t let your strategic plan become another glossy binder collecting dust by March.

Plans don’t fail because they’re bad. They fail because execution isn’t built in.

At Line-of-Sight, we equip leaders with the clarity, tools, and accountability to turn strategy into momentum from day one.

Before you finalize your 2026 plan, let’s make sure it’s built for execution.

👉 Contact us: info@thelineofsight.com, or Book a Strategy Alignment Session: https://calendly.com/robertcourser

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