Course-Correcting Failing Transformation Programs Early

Stuart Barry

CTO Consulting

Stuart Barry is a Principal at CTO Consulting and a seasoned Release Train Engineer and Program Delivery Lead across government and regulated industries. He works with clients to re-align digital transformations for sustainable, scalable outcomes.

Enterprise transformation programs are among the most ambitious undertakings an organisation can launch—and among the most likely to underperform, stall, or fail outright. With decades of combined experience across government, financial services, healthcare, and infrastructure, my colleagues and I have seen firsthand what distinguishes successful programs from the rest. 

Here’s the hard truth: most programs don’t fail suddenly—they drift. The failure is rarely a single decision or moment. It’s a series of seemingly minor deviations, compromises, or misreads of context. The good news? These signs are almost always visible early—if you know what to look for and are willing to act decisively. 

Warning Signs of a Program Losing Altitude 

Common warning signs include: 

1. No Shared Vision Across Business and IT 
   Projects kick off fast, but without a shared north star. According to Mark Stones, “Misalignment between business objectives and delivery teams creates friction and slows down delivery momentum. The program becomes a collection of disconnected initiatives.” 

2. Stakeholder Engagement is Superficial 
   When stakeholders are ‘informed’ but not ‘engaged’, decisions stall and adoption plummets. Scott Childs, who has worked with both government and private sector transformations, observes: “One of the earliest signs of risk is when key stakeholders delegate too much and disengage from shaping outcomes.” 

3. Inadequate Change Management and Benefits Realisation Planning 
   Transformation without change is just technology implementation. Kate Cribb, who has led enterprise-wide transformation efforts in sectors like health, consumer, and logistics, reflects: “Leaders must anticipate impact on operating models, not just systems. If users are not prepared or don’t see value, benefits evaporate.” 

4. Siloed Decision-Making 
   Programs run like independent workstreams without integrated governance. Mark Pavkovic, with extensive experience in program rescue and assurance, notes: “When decisions are made in silos, you see misaligned roadmaps, rework, and missed dependencies.” 

Decision Triggers: When It’s Time to Intervene 

Recognising the signals is one thing; knowing when to act is another. Here are key triggers that experienced leaders use to re-evaluate a transformation program: 

• Benefits trajectory diverges from the business case 
  Even if deliverables are being met, if forecasted benefits are slipping, it’s time to pause and reassess. 

• Governance no longer reflects decision velocity 
  If steering forums become ceremonial or decisions are escalated by default, the program is no longer governing itself. 

• Program teams are busy, but the business is disengaged 
  Transformations are not IT projects. If business users aren’t showing up or are ‘too busy’, the program is likely missing its change management mandate. 

• Vendors start leading program planning conversations 
  This signals internal capability fatigue or a lack of ownership. 

As Mark Stones, who has overseen major ERP and cyber uplift programs, puts it: “A program reset isn’t a failure. It’s an executive maturity marker. I’ve had more success rebooting at 60% confidence than pushing forward with 90% denial.”

Reset Levers That Work 

Course-correction doesn’t mean starting over. The best leaders use targeted reset levers: 

• Re-baseline for value, not just time and cost 
  Shift focus from deadlines to outcomes. Validate what value is still realisable and adjust accordingly. 

• Re-sequence delivery around quick wins to rebuild confidence 
  Find achievable, meaningful use cases that demonstrate traction and re-energise stakeholders. 

• Replace centralised control with distributed empowerment 
  If central governance is a bottleneck, shift to empowered delivery teams with tighter alignment to line-of-business outcomes. 

• Conduct an ‘architectural reset’ without rebuilding the solution 
  Revisit the business architecture and integration assumptions. Often, simplifying the interface between change initiatives is more impactful than reengineering the platform. 

What Experienced Leaders Do Differently 

At CTO Consulting, we’ve supported transformations from both the inside and outside—whether managing service integration (SIAM), modernising ERP platforms, or re-aligning digital strategies with capability uplift. 

What sets successful leaders apart isn’t perfection; it’s pragmatism and timing. 

• They act early, before failure is visible on the balance sheet 

• They protect the trust equity built with business users, not just the Gantt chart 

• They treat transparency as a strength, not a risk 

As I often say to program boards: “You can fix a broken schedule. You can’t fix eroded trust.” 

If your transformation program is starting to drift—or if you’re inheriting one that already has—don’t wait. Act. The earlier you intervene, the more leverage you have to redirect it. 

Let’s normalise early resets as a sign of leadership, not of weakness. 

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