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Digital Transformations Gone Wrong: Five Red Flags and Fixes

Transformations die from silence, not technology. Spot the telltale signs early and cut a new path.

Transformations die from silence, not technology. Spot the telltale signs early and cut a new path.

Big transformations rarely implode overnight. They erode in small, observable ways. Catching them early is cheaper than apologizing later.

Problem: slow drift disguised as progress

  • Steering committees hear “dependencies being managed” while milestones slide.
  • Vendors show velocity charts, not value.
  • Business change is an afterthought, so adoption will miss.

Five red flags with fixes

  1. No owner for business change: Name a single accountable leader for adoption and training. Fund them.
  2. Architecture drift: Agree on non-negotiable standards and run fortnightly design spikes to prevent shadow decisions.
  3. Dependency roulette: Maintain a visible critical path with dates and owners; reforecast weekly, not monthly.
  4. Vendor opacity: Tie payments to delivered capabilities and quality gates, not hours. Add joint demos with business, not just PMs.
  5. Silent sponsors: If the sponsor is absent for two cadences, escalate to budget guardians. No presence means no priority.

Smart conclusions

  • Run a 30-day stabilization sprint: clear decisions, re-baseline, and communicate trade-offs bluntly.
  • Publish a one-page “if/then” for each red flag so teams act without waiting.
  • Transformation success is a governance problem masquerading as tech. Fix governance first.
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