When Strategy Fails Before It Starts

Failure doesn't always come from the outside. Sometimes, it’s baked into the leadership structure before the first milestone is even set.

In a recent role, I was brought to shape and launch a £90 million strategic transformation programme, a bold, future-facing initiative that required sharp vision, modern tools, agile governance, and cross-functional alignment.

During the interview process, I received a strong verbal commitment from the departmental director that the organisation was open to modern ways of working. I was assured that although Excel was still heavily used, there was openness to adopting agile tools such as Trello, Asana, and Jira to support visibility, momentum, and shared accountability.

The green light was given, and the brief was clear: “We need fresh thinking. We want to do this differently. We want this to succeed. And we want your experience and insight to modernise”.

But once inside, the reality diverged from the rhetoric.

The Disconnect: When Leaders Say “Agile” But Mean “Control”

Very quickly, it became apparent that the departmental director, who had recruited me to lead, insisted she play a hands-on critical role in the programme development.

Agile workflows, transparent boards, and iterative planning, all of it was either misunderstood or rejected outright. Instead, a hard line drawn around waterfall delivery and a demand for monthly Gantt chart updates via Excel. This wasn’t just a preference; it was an imposed constraint. And it wasn’t aligned to the programme’s complexity, innovation focus, or speed requirements.

The effect? A sluggish start. Confused teams. Duplicate stakeholder engagement. And a growing gap between vision and execution.

Stakeholder Chaos: When Silos Compete, Stakeholders Suffer

A case in point: stakeholder engagement.

I attempted to introduce a department-wide stakeholder mapping process, using collaborative, real-time tools to centralise engagement efforts and reduce duplication. But each team insisted on maintaining its own Excel-based tracker, guarded like intellectual property, resulting in multiple, uncoordinated contacts being made to the same stakeholders.

Frustration mounted among board-level oversight ( the people responsible for the budget allocation), damaging the credibility of the programme before it even launched. Internally, the fragmentation highlighted a deeper issue: the multiple teams within this department had never worked in unison. There was no common stakeholder taxonomy. No shared CRM logic. No standard definition of engagement outcomes. Just isolated efforts, fighting for relevance and visibility.

Vision, Mission, Outcomes: Without Alignment, They’re Just Wall Words

Programmes of this scale require more than financial investment. They demand alignment, upwards, downwards, and sideways. That alignment starts with a shared definition of the vision (why we’re doing this), the mission (how we’ll achieve it), and the defined outcomes (what success looks like).

When senior leadership isn’t aligned on these fundamentals, or worse, when one leader actively seeks to control rather than empower, it sends contradictory signals to the organisation. Teams become hesitant. Momentum stalls. Innovation dies under the weight of status reporting.

In this case, the departmental director’s desire to control and revert to “safe” methods had a chilling effect. Agility was seen as a threat. Change became a battleground. Newly recruited project management staff resigned (clearly stating it was solely due to the chaos caused by the Departmental Director). And the programme’s credibility took an early, avoidable hit.

Trust in Strategic Leadership: The Non-Negotiable

Trust is the currency of change. When a contractor is brought in as an Interim Head of a new £90m programme, especially to shape and launch a high-value, high-risk initiative, they must be empowered to lead, not managed into compliance.

A strategy consultant isn’t there to do things the way they’ve always been done. They are hired to show a better way. If that intent is undercut by internal politics or fragile egos, the business not only loses its edge—it squanders its investment.

What I’d Do Differently Next Time

1. Formalise Alignment in Writing Upfront

   During the onboarding and scoping phase, I would clearly define the operating model, tools, delivery principles, and reporting expectations—with executive sign-off. Verbal agreements are too fragile when challenged by hierarchy, egos, or fear of change.

2. Assess Change Readiness Before Launch

   I would run a pre-programme cultural and change readiness diagnostic. This would surface resistance points early, giving me a mandate to address misalignment before it becomes sabotage.

3. Secure a Programme Sponsor with Backbone

   A CSO needs a senior sponsor who can uphold the strategic direction when departmental silos push back. At the point of recruitment, I thought I had that. Next time, I’ll ensure that the sponsor is visible, vocal, and prepared to back reform over comfort.

4. Design for Transparency and Accountability

   I would lean even harder into visible, public roadmaps and programme boards—inviting collaboration and removing the ability for anyone to independently alter direction without scrutiny.

5. Hold a Leadership Alignment meeting —Early

   Getting all relevant leaders into the same room to align on shared principles, roles, behaviours, and escalation pathways is a must. Without that, everyone builds their own version of success—and failure.

6. Maintain my confidence in modern ways of working

   I have been fortunate to design / re-design and launch a variety of large scale programmes throughout my career. Yet this experience bruised me, and had me question every single one of the skills I take pride in.

   
   

In Summary

Failure in business transformation is rarely due to a lack of tools or talent. It’s almost always due to a failure of alignment at the top.

No amount of agile boards or stakeholder mapping can compensate for misaligned leaders who don’t trust each other or the experts they bring in. In these moments, the role of the CSO is not just to drive strategy, it’s to expose misalignment early, and, when necessary, challenge it head-on.

The good news? Every failure brings sharper clarity. The next time I step into a £90m programme, I’ll bring these lessons and ensure alignment isn’t assumed, but actively and collaboratively built.