Why most transformations fail (and how to join the 30% that don't)

Earlier this month, I had the privilege of presenting at our cross-Community virtual event on "Strategy to execution: designing and measuring end-to-end operating models for successful transformation". After 15+ years working on complex global transformation programmes across industries, from retail giants to heavily regulated government departments, I've had the privilege of working with enterprises who have incredible strategic ambition for change and transformation. 

Most transformations don't deliver their expected results. But here's what I've learned: it's rarely because of the strategy itself, and it's certainly not because of the people involved. Everyone starts with good intentions and strong visions. The breakdown happens in that critical space between strategy and execution, specifically in how we measure and manage value delivery.

The real problem: investing in a depreciating asset

Imagine taking out car finance, being promised a residual value after four years, then two years in discovering that value is no longer valid and you're on the hook for a balloon payment. This is exactly what happens in most transformation programmes. Organisations invest millions over 18-24 months, then discover they can't track the benefits realised. They're left with a depreciating asset and no clear path to ROI.

During our session, I polled the audience on the measurement approaches within their enterprise. The results were telling: while a limited number of organisations measure outcomes consistently, many struggle with unclear prioritisation and inconsistent resource allocation. When asked whether business functions and IT teams operate in silos, the resounding majority said "yes, absolutely" with only one participant saying "no".

A model example for successful transformation: outcomes before solutions

Just before COVID hit, I was part of the team working with a global retail client on their global omnichannel strategy and subsequent transformation. This particular retailer had hit a revenue plateau and was lagging behind competitors in digital capabilities, its board needed a plan to return to profit and maintain its position as a leader in the industry.

Instead of the traditional approach of creating a strategy and then handing over to a delivery team to build the programme, leading to a disconnected long-term roadmap, we started with tangible business and customer outcomes. We built a robust commercial model grounded in customer and market research, coupled with a full market and internal capability assessment. Every initiative on the emerging roadmap was tied to measurable business value.

We created a cascading measurement framework using OKRs that connected these strategic ambitions down to squad-level metrics. Teams weren't just tracking their resource capacity or user story completion; they shaped their work to contribute to commercial success against a quarterly delivery cycle.

The results were remarkable. In six months, we rolled out click-and-collect to 324 US stores (they'd previously managed just 10% of these stores). When COVID hit and they forecasted losing 50% of physical store revenue, the operating model we'd established enabled them to pivot within three months, completely offsetting their projected losses with curbside collection, virtual try-on and enhanced e-commerce integration.

Three pillars for transformation success

Based on my experience during this engagement and many others with enterprises across industries and geographies, I've identified three critical success factors: