Strategy is often an inspiring vision, floating high in the Clouds, while execution lives in Boxes—programmes, projects, and deliverables struggling to stay connected. The gap between them is where strategy either thrives or dies. Too many organisations pour effort into planning, only to watch their ideas drift, never fully landing in execution. So how do we bridge Clouds and Boxes to make strategy real? This story explores the missing link—and why getting it right changes everything.

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Bridging the Strategy-Execution Gap

The challenge with the Strategy that just floats.

Strategy. It’s a word that fills boardrooms, decks, and leadership retreats. It’s also a word that, too often, stays in the clouds—floating above the day-to-day reality of the teams tasked with delivering it.

I call this the Clouds and Boxes dilemma. I love to spot it, doodle it, and refer to it- 3 ITs right there!

The Clouds are the strategies, policies, and grand visions that define where we want to go; and
The Boxes are the programmes, projects, and initiatives—the tangible mechanisms that make things happen.

Here’s the challenge: strategy is only as strong as its ability to land. And too often, there’s a massive gap between the Clouds and the Boxes. I'm more of boxes and I've come to recognise the importance of the right kind of clouds.

The Disconnect: When Clouds Drift Too Far from Boxes

I've been very much enjoying my chats with Richard Copley summed up this challenge well when he said:

“There is planning associated with strategy, but most of what today is called ‘strategic planning’ is likely to be top-heavy on the strategic analysis and light on the real strategy formulation.

It is also top-heavy on the plans, which take a lot of effort, but are soon out of date.”
Richard Copley

I’ve seen this firsthand.

Leaders pour time into analysing trends, diagnosing problems, and crafting bold mission statements—but when it comes to execution, the connection is missing. Teams on the ground are handed vague directives, disconnected KPIs, and frameworks that don’t align with reality.

No wonder many organisations struggle to make their strategy stick.

Bridging the Gap: Making Strategy Tangible

So, how do we close the space between Clouds and Boxes? How do we make strategy real, actionable, and adaptable?

“It’s easier to see planning as the bit that sits in the intersection between strategy formulation and strategy execution.”
Richard Copley

In other words, we need a structured bridge that connects vision to action.

Resource it

Securing the different kinds of Resources required that are essential for resolving Wicked Challenges™. Not solely People but the Knowledge, Skills, Budget, and Time.

Collabor-it

Bringing colleagues together in the same room on the same page. Insights shared, dots joined, turn challenges into opportunities and outcomes!

FRAME It

Describing the situation so that all stakeholders engage and develop shared meanings. As a result, embrace a shared commitment on what success will mean.

INNOV-It

Encouraging innovative thinking to help make difficult choices and trade-offs and not be put off by the messy, combative, iterative ways decisions are often made.

Measure It

Scoring a realistic standard of success rather than a goal that is perhaps unrealistic. Towards improving Wicked Outcomes™ made-up of Solutions and Benefits.

Iter-It!

Committing to multiple iterations is essential to maintain flexibility and build confidence in the journey. Regular checkpoints provide accountability for the whole team.

That’s where I like to think about BIG PICTURE® and the Six ITs Framework to:

Visualise strategy—turning abstract policies into tangible, collaborative frameworks that teams can work with;
Prioritise alignment—ensuring that what’s discussed in leadership meetings directly translates into the execution layer; and
Enable continuous strategy formulation—because as Richard put it, “strategy formulation needs to be continuous.” The world moves too fast for static plans.

My Personal Experience: A Moment of Realisation

I remember sitting in a meeting where a leadership team was discussing their strategic vision for transformation.

It was compelling. It was bold. It was erm .. floating.

Meanwhile, the operational teams were buried in legacy processes, conflicting priorities, and an overwhelming sense of uncertainty about what they were actually supposed to be doing.

That was the moment it clicked. The problem wasn’t the strategy itself—it was the lack of connection between Clouds and Boxes.

What We Can Do About It

Here’s the reality:

📌 Strategy that doesn’t land is strategy that fails;
📌 Execution without strategic intent is just busywork; and
📌 Bridging the gap means creating alignment, clarity, and adaptability.

We can help organisations build that bridge. Through collaboration tools, strategic alignment workshops, and our Six ITs Framework, we ensure that strategy is:

✔️ Owned by everyone, not just leadership;
✔️ Continuously refined, not a one-off event; and
✔️ Tied to execution in a meaningful, human-centred way.

Watch out for the a BIG PICTURE® Playbook for Alignment coming soon!

The Question for You

What’s your experience with Clouds and Boxes?

Have you worked in organisations where strategy never translated into real execution?
Have you ever felt lost between the big vision and the reality of delivering it?

Let’s bridge the gap starting with a chat!