Why Strategic Planning Fails at the Top-And How to Fix It

Unpacking the hidden causes of executive-level strategic failure, and proven ways to rebuild from the top down.

Why Strategy Fails—and How You Can Fix It

As a strategic planning facilitator, I’ve sat with many CEOs and leadership teams who feel stuck - not because they lack vision or effort, but because their strategy simply isn’t landing. It might look polished, but something’s off: the team’s spinning its wheels, goals keep shifting, and there’s a growing disconnect between ideas and action.

If this sounds familiar, you’re not alone - and more importantly, it’s fixable.

Strategic Failure: What It Looks Like in the Real World

Strategic failure isn’t always a dramatic crash. Often, it looks like this:

• Everyone’s busy, but progress is vague

• Priorities keep shifting

• Mid-level leaders are unclear or disengaged

• The same issues resurface quarter after quarter

• Teams execute in silos instead of collaboration

If you’ve experienced this, you’re likely facing not a business problem - but a leadership alignment problem.

Why Executive Planning Problems Happen

1. Vision Without Alignment

You may have a vision - but is your whole leadership team interpreting it the same way? Often, different leaders have different takes on what success looks like. That misalignment leads to fractured priorities, unclear messaging, and misused energy.

Fix: Through successful Strategic Planning Re-align your leadership team around a shared vision. Get clear on what you’re trying to achieve and how you’ll get there- together.

2. Strategy Without Ownership

It’s one thing to design a strategic plan. It’s another to drive it. When no one owns the outcomes, strategic documents collect dust, and progress stalls.

Fix: Assign accountable owners for each strategic pillar. Embed check-ins. Make results visible. The best plans are lived, not laminated.

3. Communication That Doesn’t Cascade

If strategy doesn’t reach the frontline in a clear, relatable way, your people will fill in the blanks -or disengage completely.

Fix: Communicate early and often. Explain the “why” behind each decision. Make strategy part of daily dialogue, not just leadership retreats.

The A.C.T. Framework: A Simple Structure to Realign Strategy

To help executive teams reset their strategy, you can use a practical method called the A.C.T. Framework:

A — Align Vision and Priorities

Start by bringing every executive leader onto the same page - no assumptions, no ambiguity. Clear alignment at the top filters down to clarity across the business.

C — Communicate with Consistency

Use a shared language around goals and priorities. Ensure every team knows how their daily work supports the bigger picture.

T — Track What Matters

Review performance data regularly. Adjust quickly. Celebrate wins. Make sure accountability isn’t abstract - it’s attached to real progress.

Governance Matters: Strategy Needs Strong Structures

Many executive planning problems come back to weak governance. When accountability is vague, decisions take too long, or the board lacks visibility, even strong strategies can unravel.

In my facilitation work, I help CEOs and boards:

• Define decision-making rights

• Align long-term goals with operational capacity

• Introduce simple, trackable reporting rhythms

• Build in succession and sustainability planning

It’s not about adding complexity - it’s about creating the confidence to lead decisively.

Global Proof: Strategic Failure Isn’t the End - It’s a Turning Point

IBM under Lou Gerstner

In the early ‘90s, IBM was bleeding cash and rapidly losing relevance. Lou Gerstner didn’t save the company with a new product - he did it by reshaping culture, aligning teams, and repositioning the company from selling hardware to delivering business solutions. It was a full strategic reset from the top down - and it worked.

Microsoft under Satya Nadella

When Nadella took over, Microsoft was seen as outdated. He simplified the vision, restructured teams, shifted to cloud-first thinking, and rebuilt the culture around learning and empathy. Strategic clarity and leadership alignment turned the company into a market leader again.

Your Turnaround Can Start Today: A Real Client Example

A professional services firm here in Perth came to me after a frustrating year. They had a plan - but no traction. Teams were working hard but not together, and strategic projects kept falling off the radar.

Through two facilitated strategy sessions, we:

• Realigned the executive team on their 3-year vision

• Prioritised key initiatives under 5 strategic pillars

• Created a 90-day action sprint with named owners

• Introduced quarterly leadership reviews to track progress

Three months later, they saw measurable momentum, improved internal engagement, and, most importantly, a renewed sense of purpose.

Strategic Misalignment Checklist for CEOs

Ask yourself:

• Are we all clear on the company’s 3-year destination?

• Are roles and responsibilities tied directly to our strategic goals?

• Do our people understand how their work supports the bigger picture?

• Are our board and leadership team in sync - or working in silos?

• Are we tracking progress consistently, and adjusting with agility?

If you answered “no” to two or more - your strategy likely needs a reset.

Strategic Planning Is a System - Not a One-Off Event

The most effective strategic plans I’ve seen don’t come from a single workshop. They come from systems: a structured cadence of planning, reviewing, and refining that empowers leaders to stay focused - even when the day-to-day gets noisy.

That’s why I help CEOs and executive teams build not just plans, but sustainable systems that:

• Support real-time decision-making

• Create accountability across levels

• Align with board governance and reporting

• Engage people from top to bottom

Because the best strategy is one your entire business can live out - not just admire.

Let’s Make Your Strategy Work

If your executive team is stuck in a cycle of planning but not progressing, it’s not a failure—it’s a flag. And it’s also your opportunity.

Let’s talk about where you’re stuck—and how to reset with clarity and momentum.
Book a confidential executive discovery session

You’ve built something worth leading. Let’s give it the structure, clarity, and action plan to grow with purpose.

FAQs about Strategic Planning for Executive Teams

1. What causes strategic failure at the executive level?

Strategic failure usually stems from misalignment, unclear ownership, and poor communication. If leaders aren’t united on the vision - or if the strategy doesn’t translate into daily action - it can quietly unravel, even if the plan itself looks strong.

2. How do I know if our executive team is misaligned?

Signs include shifting priorities, inconsistent decision-making, disengaged teams, or repeating the same discussions without resolution. If your top team can’t clearly and consistently articulate your key goals, alignment is likely off.

3. Can an external facilitator really help with planning?

Absolutely. A strategic planning consultant brings an outside lens, breaks through internal blind spots, and ensures every voice is heard. More importantly, they help you move from big ideas to a structured, actionable roadmap that gets lived - not shelved.

4. What’s the first step to fixing a broken strategy?

Start with a strategic alignment session. Reconfirm your vision, assess where your team is currently focused, and identify where things are off-track. From there, build a refreshed roadmap with short-term sprints and clear ownership.