Strategy to Execution: Different Geographies, Same Messy Middle

Earlier this year, at our Strategy to Execution Forum in Asia-Pacific, we asked a group of leaders a simple question: Where are you most confident in your organisation’s ability to move from strategy to execution?

What emerged was what we started calling the messy middle. Leaders were relatively confident at either end. They could articulate strategy and they had established delivery practices. But confidence dropped when we got into everything required to connect the two: understanding value, defining outcomes, connecting work to strategy, making prioritisation decisions, aligning capacity and creating the conditions for teams to deliver.

One comment from the Asia-Pacific group captured it particularly well:

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

This comment stayed with me, but it also left me curious. Was this an Asia-Pacific pattern? Was it particular to the organisations or industries represented in the room? Or were we seeing something more systemic?

At SSH Live in London last week, we ran the exercise again. This time the room included leaders from global organisations representing North America, the UK and Europe. A different group of organisations, industries and geographies. 

The result? A remarkably similar messy middle.

The messy middle is clearly visible - and SSH Live in London helped clarify it

The challenge is in the connections between strategy and execution. The conversations at SSH Live gave us some useful signals about what those connections actually require.

Signal 1: Strategy may exist. That doesn't mean it is usable.

In Asia-Pacific, we saw relatively strong confidence around strategy, but an important distinction emerged: strategy and alignment aren't the same thing. London reinforced that.

Leaders talked about strategy becoming more tactical as it moves through the organisation, greater clarity in the short term than the longer term, and challenges with communication. They also reflected on a lack of clarity about what the organisation is optimising for, and the mindset and principles required to enable strategy delivery.

Interestingly, some of this clarity exists at team or departmental level, but not consistently across the enterprise, making it harder to navigate the silos and siloed thinking they reinforce.

For me, this shifts the question. It isn't simply: Do we have a strategy? It is: Can people across the organisation see it, understand it, and use it to make decisions?

A beautifully articulated strategy that doesn't drive change isn't doing much work.

Signal 2: We talk a lot about customer value. Creating a shared definition of it is harder.

The Asia-Pacific group surfaced the tension between being customer-led and remaining internally focused. SSH Live group in London made that tension more tangible.

Some identified challenges with getting close enough to customer needs, defining the target experience, and measuring the impact. Even in organisations with strong product and UX capability, leaders described slow feedback loops inhibiting a deeper understanding of value end-to-end.

This matters because customer insight isn't enough on its own. It needs to flow from: Customer need → Value → Outcome → Investment → Work. When this chain breaks, we can have very customer-focused teams operating inside a system that aren't consistently optimising for customer value.

Signal 3: Outcomes may be one of the weakest pieces of connective tissue

This was one of the strongest signals for me from London. Across the London group, we heard:

• "Output vs outcome thinking"

• "We don't define + measure at a meaningful level"

• "I've not seen OKRs being used consistently across the enterprise, even with pockets of good practice"

• "OKRs? What OKRs?"

There was also a very practical challenge around annual OKRs and the effort required to revisit them quarterly.

This echoes what we heard in Asia-Pacific, where leaders talked about the difficulty of moving beyond activity and KPI thinking, and the risk of OKRs becoming another tick-box exercise.

I don't think the answer is simply better OKRs. The deeper capability is translating strategic intent into a small number of meaningful, measurable outcomes, and then using those outcomes to decide which bets we place, which we don't, and when we pivot.

Signal 4: The Golden Thread is where the mess becomes visible

This may be the most interesting commonality between the two groups. In Asia-Pacific, leaders described the challenge of connecting strategy, investment, outcomes and work. Priorities multiplied. Everything became important. And stopping work remained difficult. In London, this connection, or lack of connection, was made very explicit.

We heard:

• "We don't stop work not linked to strategy."

• "Our work is not measured, nor connected. There is no golden thread."

• "We don't have a good way to visualise this connection. No tooling to support."

There were also comments about change fatigue, funding and macro-environmental factors. 

Making work visible and connecting it to strategy sounds simple. In practice, it forces choices about what we continue, what we defer and what we stop. This is why I've become increasingly interested in the Golden Thread of Value. 

Can we see all the work happening across the organisation? Can we trace why it exists? Can we connect it to an outcome and ultimately to strategy? And, perhaps most importantly, can we stop it when we can't?

Signal 5: Strong delivery capability can mask a strategy-to-execution problem

In both Asia-Pacific and London, confidence began to recover as we moved towards delivery. 

Delivery itself wasn't universally the problem. Leaders described established delivery cadences and ways of working, while also identifying challenges with accountability, delegation, and cross-functional collaboration.

The conversations surfaced three important distinctions:

• Having a delivery cadence doesn't necessarily mean we're learning quickly.

• Having empowered teams doesn't necessarily mean they're working on the highest-value problems.

• Being good at delivery doesn't necessarily mean we're delivering the right things.

This means that we can optimise how work flows through delivery without fixing how the organisation decides what work should enter the system in the first place. That, for me, is a big part of the messy middle.

So, what changed between Asia-Pacific and London?

Not as much as I expected. We now have two groups of leaders, spanning organisations across Asia-Pacific, North America, the UK and Europe, wrestling with remarkably similar challenges.

Across both conversations, we heard about translating strategy, defining value, shifting from outputs to outcomes, connecting portfolios to strategy, stopping work, breaking through silos, aligning scarce capacity, and shortening feedback loops.

The conversation at SSH Live in London didn't change the pattern. It helped us understand the pattern more deeply.

The messy middle isn't a single broken process. It is the collection of organisational capabilities required to translate strategic intent into choices, and choices into action.

For years, organisations have invested heavily in strategy. And they have invested heavily in delivery. Perhaps the next opportunity is to invest just as deliberately in what connects them.

The goal isn't simply to execute more effectively. It's to make better choices about what matters, where to focus scarce capacity, what to stop, and how quickly we learn.

Strategy = Execution. 

And the messy middle is where we make that connection real.

For further reading: If you'd like to explore the Strategy to Execution pattern in your organisation's context, please refer to our Quick Learn Strategy to Execution | Sooner Safer Happier.