Why Most “Strategic Planning” Is Actually Execution Planning – And How To Fix It

Many organizations blur these lines. When an offsite is dominated by task lists, timelines, and KPIs it isn’t strategy – it’s execution planning mislabeled.

Why the Confusion Persists

This confusion shows up in predictable ways:

• Crowdsourcing Direction: Leaders invite the whole management team to “decide the strategy,” in the name of buy-in. They expect consensus; however, this dilutes clarity and accountability, leading to endless debates and watered-down direction.
• Strategy as Slogan: Treating strategy as a catchy phrase or annual event instead of a guiding North Star, differentiation disappears and alignment erodes.
• Execution Priorities Masquerading as Strategy: Organizations shift priorities year after year without anchoring them to a clear, enduring strategy, creating churn instead of progress.

Research from Harvard Business School suggests that up to 90% of organizations fail to executer strategy successfully, often because strategy and execution are not clearly separated or communicated.

The Leader Sets Strategy

When people hear “strategic planning” they imagine debate. Options weighed. Consensus built. A shared sense of ownership. It sounds democratic. Inclusive. Even noble.

But here’s the problem: strategy isn’t something you crowdsource. If you’re the leader, CEO, President, setting strategy is your job. Full stop.

How will we successfully compete in the market? Where will we play? What kind of talent will help us get there? Why do we exist? What will we explicitly choose not to do?

Anyone who has tried to wordsmith a mission statement with a group knows how this ends. The sharp edges get sanded down until a pleasant, forgettable statement emerges. Inclusive, yes. Directional, no. The leader’s role is to bring clarity and specificity, not to crowdsource it.

Advisors Provide Inputs, Not Decisions

Great leaders don’t work in isolation. They surround themselves with smart advisors: executives, board members, consultants, and their management team. These voices pressure-test assumptions and surface blind spots. The leader listens. Adjusts. Refines. But the decision still rests with the leader.

Think of a ship’s captain. The crew points out hazards and currents, but one person holds the wheel. If everyone steers, the ship goes nowhere.

Execution Planning: Turning Vision into Action

Vision without action is a daydream; action without vision is a nightmare. – Japanese proverb

Once strategy is clear, the organization must translate it into action. In larger firms, this is often the COO or Integrator role. In smaller firms, it’s shared across leaders. Either way, the role exists.

This is where teams answer: What must we prioritize this quarter? How will we measure progress? Who owns what? What trade-offs will we make when resources are tight? This work is critical. It just isn’t strategy. Mislabeling it creates confusion about roles, authority, and expectations.

Why This Distinction Matters

You might wonder: isn’t this just semantics? No. For three reasons:

1. Clarity of roles: When teams believe they’re deciding strategy together, frustration follows when the leader chooses otherwise. Clear roles prevent false expectations.
2. Efficiency: Offsites bog down when teams debate direction instead of aligning on delivery. Decisions stall. Energy dissipates.
3. Accountability: When “the strategy” belongs to everyone, it belongs to no one. Clear strategy sharpens execution ownership.

A Tale of Two Offsites

To illustrate, let me share two anonymized examples from companies we’ve worked with:

Company A: The Wandering Retreat
They gathered 15 senior leaders for a three-day retreat. The leader wanted everyone’s input on strategy, so the group brainstormed markets, debated product ideas, and workshopped mission statements. By the end of the third day, they had 27 sticky notes, three competing growth paths, and no decision. Morale was high in the room but execution fell flat back at the office. Six months later, they were still arguing about direction.

Company B: The Focused Offsite
Different company, different approach. The leader walked into the offsite with a clear articulation of strategy: “We will dominate the mid-market segment in Western Canada by offering the fastest turnaround times in the industry.” Full stop. The integrator then facilitated the team through execution planning: what does that mean for sales targets, staffing, and capital investment? Everyone left aligned, with clear quarterly rocks and KPIs. Six months later, results were measurable and the strategy was alive in day-to-day decisions.

The difference? In Company B, the leader did their job before the offsite.

Common Misconceptions About Strategy

Let’s clear up a few myths that trip leaders up:

1. Strategy should be democratic. Collaboration is healthy. Abdication is not. Leaders who avoid making tough calls under the guise of “team input” end up with muddled direction.
2. Strategy changes every year. Execution priorities may shift annually (or quarterly), but true strategy has a longer horizon. It’s a North Star that holds steady while tactics adjust.
3. Strategy is about slogans. A catchy phrase isn’t a strategy. Real strategy involves trade-offs, choosing what not to do. If your strategy could apply equally to any competitor, it’s not strategy.

How to Run a Truly Effective Offsite

So, if “strategic planning” offsites aren’t strategic, how should leaders run them? Here’s a blueprint:

1. Pre-Work for the Leader

• Articulate the strategy in writing before the offsite.
• Pressure-test it with advisors, not the entire team.
• Be ready to communicate it with clarity and conviction.

2. Use Planning Sessions for Execution

• Begin with the leader presenting the strategy.
• Use the bulk of the time for execution planning: setting priorities, defining metrics, and clarifying roles.
• Address resource allocation head-on.

3. Bridge the Gap with Alignment Tools

• Adopt frameworks like OKRs (Objectives and Key Results) or the One Page Plan to ensure strategic objectives are broken down into measurable outcomes and tracked across the organization.
• Regularly review progress, adjust tactics, and maintain feedback loops between strategy and execution.

4. Empower Middle Management

• Middle managers are critical for translating vision into results. Provide them with autonomy, resources, and training to drive execution and communicate the “why” behind strategic decisions.

5. Foster a Culture of Accountability

• Build a culture where accountability for execution is non-negotiable. Connect individual roles to strategic outcomes and consistently track performance.

6. Communicate Continuously

• Strategy should be a living conversation, not a static document.
• Cascade the plan across the organization.
• Set a rhythm of accountability (weekly meetings, monthly reviews, quarterly resets).
• Revisit execution, not strategy, unless seismic changes in the environment demand it.

But What About Buy-In?

Some leaders push back here. “If I walk in with the strategy, won’t my team feel excluded? Don’t I need their buy-in?”

Buy-in doesn’t come from co-authoring the strategy. It comes from believing the strategy makes sense, aligns with reality, and is worth committing to. The leader’s job is to communicate the “why,” paint a compelling picture of the future, and show how each person’s role connects to it. That’s how you earn commitment. False inclusion – pretending the strategy is up for debate when it isn’t – backfires. People feel manipulated when their “input” never really had weight. Clarity is kinder.

The Bottom Line

If you remember nothing else, remember this:

• Strategy is the leader’s job.
• Execution is the team’s job.
• Offsites should focus on planning execution, not creating strategy from scratch.

So, the next time someone invites you to a “strategic planning offsite,” ask: Are we actually setting strategy or are we planning how to deliver the one we already have? The distinction can mean the difference between frustrating debates and meaningful progress.

And for leaders, it’s a call to step up. Strategy isn’t optional. It’s your whole job.