The Execution Gap: Why Strategy Still Fails in the Middle

In 2025, the most underleveraged asset in the strategy function isn’t capital, talent, or even insight. It’s visibility.

We recently came across a sharp piece from Cascade that reframes a problem many CSOs quietly acknowledge but rarely confront head-on:

You don’t own the strategy if you can’t see how it’s actually being executed.

Most strategy teams have planning covered. What’s missing is control over the “gray zone” — that volatile middle space where plans turn into actual work. Or don’t.

From Architect to Orchestrator

The role of the Chief Strategy Officer has moved beyond long-term roadmaps and boardroom alignment. Execution has become the differentiator — and visibility is the enabler.

Without line of sight into real-time progress, dependencies, and drag, CSOs risk being the person with the plan, not the person driving the outcome. And in a C-suite where credibility increasingly hinges on traction, that’s a dangerous place to be.

“If you're presenting a strategy in PowerPoint while others are running the business in real time, your relevance diminishes.”— Devina Patel, Strategy Execution Director, Cascade

Five Execution Questions Every CSO Should Be Able to Answer

In real time — not post-QBR.

1. Which initiatives are truly moving the needle — and which are just noise?

2. Where are we stuck — and why?

3. Are cross-functional dependencies slowing us down?

4. Is capital still flowing to the right priorities?

5. Where are we learning fast — and where are we repeating mistakes?
   

If answering those requires spreadsheets, syncs, or gut feel, you're not steering. You're reacting.

Why It Matters for CSOs

Execution visibility is the new leverage.With faster cycles and rising stakeholder expectations, the winning CSOs will be those who can do more than build the plan. They’ll be the ones who can see how it’s unfolding — and shape it in real time.

As Cascade puts it:

“CSOs who succeed today don’t just plan. They narrate progress — and they do it with data, not anecdotes.”

📌 Read the full article from Cascade

Because strategy doesn’t fail in the boardroom.It fails in the middle. And that’s exactly where your focus should be.