Strategy to Execution: The Challenge of the Messy Middle

To kick off the month of June, we brought together a group of enterprise leaders from across sectors to explore a question that continues to dominate leadership conversations:

How do we build a better system to deliver better outcomes? 

In the room, we had a group of leaders from across banking, insurance, retail, telecommunications, education, automotive, professional services and not-for-profit organisations.

On the surface, these leaders appear to come from very different contexts: different customers, regulatory environments, strategies and competitive pressures.

Yet, when I spoke with them, I found the conversations remarkably similar.

4 conversations shaping leadership today

1.Execution: Turning strategy into value as the competitive advantage 

The first conversation is execution.

Because most organisations don't have a strategy problem. Most organisations have an execution problem. 

The challenge is turning intent into outcomes. Turning investment into value. Turning ambition into measurable impact.

In an environment where products, services and technology can be copied faster than ever before, execution is increasingly becoming the competitive advantage.

Not strategy. Not technology. Execution.

The organisations that can align strategy, investment, teams and delivery faster than their competitors will win.

The question to consider: What is the biggest blocker between strategy and execution in your organisational context today?

2. AI: From experimentation to operating model change

The second conversation is AI.

It's impossible to gather a group of leaders today and not discuss it. But the conversation is changing rapidly.

Twelve months ago, many organisations were exploring AI. Running pilots. Testing use cases. Experimenting with productivity.

Today the question is becoming much bigger: How does AI change how we deliver value? How does AI change our operating model?

The opportunity is no longer simply automation. The opportunity is redesign. Redesigning work. Redesigning flow. Redesigning how organisations create value.

Which raises an important question: How much of your AI effort is improving existing work versus re-imagining how value gets delivered?

3. Constraints: Doing better with the same 

The third conversation is constraints. Because we're all trying to execute within limits.

Funding is constrained. Capacity is constrained. Talent is constrained.

Yet expectations continue to grow. Most organisations aren't being asked to do less. They're being asked to do better with the same.

The challenge is no longer simply asking: "What should we start?" 

The more important questions are: " Are we clear on where we will win and how we will play? What should we stop?"

4. Leadership: Navigating continuous change

And finally, leadership.

Because none of the previous three conversations happen without leaders.

If execution is the challenge, constraints are the reality, and AI is the disruptor, then leadership is the multiplier.

Today's leaders are expected to navigate ambiguity, make decisions faster, create clarity, foster psychological safety, enable experimentation, and guide organisations through continual change.

At the same time, many of the leadership muscles that made us successful in the past are being challenged. The environment increasingly rewards adaptability, learning, collaboration and curiosity. [Refer to my 5 roles of today’s leader for more details.]

Which leaves us with two final questions: Do we have the right muscles to lead in today's environment? And what is our role in redesigning work for the future?

The challenge is not strategy. The challenge is the messy middle. 

Participants completed a diagnostic using the SSH Strategy to Execution pattern that outlines 4 essential steps.

Leaders assessed their confidence across the critical elements required to translate strategy into outcomes, from vision and customer understanding through to leadership, portfolio management and delivery.

Across sectors, the results were remarkably consistent. What was striking was not where confidence was high. It was where confidence collapsed.

We have become better at delivering work than deciding what work matters. 

Confidence was high at the beginning and end of the system. Most leaders felt confident in their organisation’s strategic direction. Most also felt they had established delivery practices and mechanisms in place.

The lowest confidence sat squarely in the middle – where leaders need to translate strategy into customer value, outcomes, priorities and delivery decisions.

The sentiment from the leaders in the room was strongly aligned:

“Strategy and alignment are not the same thing.” “Difficulty moving beyond KPIs and activity measures.” “OKRs are a tick-box exercise.”

“We need to: Grow, comply, enhance and experiment. This means nothing gets stopped.”  “Every initiative is important.”  “Work continues despite stop decisions.”

“Too focused internally than on the customer.” “Functional siloed empires.” “HIPPO decision making.”

“Orgs know they need to change. Many are struggling to create the space to do it.” “Quarterly is now too slow.”  “Organisations are struggling to balance commitment with learning.”

In other words, the challenge was not creating strategy. The challenge was converting strategy into behaviours, decisions, outcomes and ways of working that consistently create value.

Organisations spend most of their time in delivery – and it is the area where they are most comfortable to play. This translates to the delivery practices and areas where they’ve invested heavily, with less investment into the systems that connect strategy to delivery.

These challenges are not new. We have proven patterns to overcome these challenges. 

During the Forum, we shared learnings, proven approaches and recommendations to these challenges.

Translating strategy into action through a redesigned system of work .

• Align leadership measures, incentives and behaviours to strategic outcomes, value creation and organisational learning.

• Build the capability to define meaningful outcomes that connect strategy, customer value and delivery priorities.

• Create a clear golden thread that links strategy, investment, outcomes, work and customer impact.

• Design governance, planning and delivery systems around value realisation rather than project execution.

Creating focus

• Establish a single view of priorities that enables deliberate investment decisions and clear organisational focus.

• Match demand to available capacity by creating visibility of work, flow and organisational constraints.

• Build the discipline to make explicit trade-offs, stop low-value work and continuously reallocate investment to the highest-value opportunities.

• Create the capacity for deep work, learning and innovation by subtracting before adding new initiatives.

Leading differently

• Shift decision-making closer to the work through clear decision rights, empowered teams and outcome-based accountability.

• Organise around value to deliver customer outcomes through cross-functional collaboration rather than functional silos.

• Evolve governance and performance measures to reinforce adaptability, learning, experimentation and value delivery.

• Embed customer understanding and feedback into planning, prioritisation and delivery decisions.

• Develop leaders who balance challenge and care, creating the conditions for both high performance and sustainable outcomes.

Adapting to a changing environment

• Redesign operating models to harness AI, automation and human capability as an integrated system of work.

• Move from annual planning and periodic governance to continuous planning, adaptive funding and ongoing prioritisation.

• Build organisational adaptability through shorter feedback loops, faster learning cycles and evidence-based decision making.

• Create sustainable capacity for change by simplifying work, reducing unnecessary complexity and intentionally designing recovery, learning and improvement into the system.

• Treat workforce capability, wellbeing and work design as strategic enablers of transformation rather than separate initiatives.

Even though the challenges discussed at the Forum are not new, they are hard to get right and require continuous attention and improvement. In an environment shaped by AI, increasing complexity and constrained capacity, they have never been more important to address.

The organisations creating the greatest advantage today are not simply delivering more work.

They are creating greater focus, faster learning and stronger connections between strategy, customer value and execution.