02-07-2025
Mastering The Six Most Disruptive Enterprise Transformation Challenges
Jay Goldman, cofounder and CEO of Sensei Labs, co-author of New York Times bestseller The Decoded Company.
Enterprise transformation has never been more urgent—or more difficult. At OPEX Week 2025 in Miami, we hosted a Masterclass with senior leaders responsible for large-scale change across global enterprises, including participants from Amazon, American Express, eBay, Entergy, Pernod Ricard, the University of South Carolina and Vueling Airlines. Over lunch, they discussed six stubborn challenges standing in the way of transformation success. What emerged was a frank diagnosis—and a few emerging playbooks.
Here are the key insights we discussed, supported by industry research and examples from our customers.
1. Inconsistent Planning
Transformation planning is often inconsistent across phases, causing rework and delays. Participants advocated switching from annual to quarterly planning to reallocate budget and effort better.
However, even good planning fails without stakeholder alignment. Kearney reported that over 70% of planning transformations are undewhelming due to their narrow scope, as they're often treated as isolated system upgrades instead of enterprise-wide redesigns.
Move from episodic project management to strategic portfolio management (SPM). Use data and AI to align plans with execution, spotlight misalignments and reassign resources based on impact, not instinct.
2. Lack Of Benefits Tracking
Tracking transformation benefits is a recurring blind spot. Teams rely on lagging indicators and face pressure to show ROI prematurely. Finance demands clear metrics; transformation offices struggle to prove intangible value. A 2022 Kearney report noted that programs often double-count or conflate benefits, skewing investment decisions.
Tie execution to a shared KPI/benefits model with standardized definitions. AI can surface anomalies and ensure every project is tracked consistently, helping PMs focus on what matters most.
3. Manual Processes
Manual, spreadsheet-heavy processes still dominate, even in tech-forward firms. Automation is often pitched in business cases but rarely becomes reality. Governance swings from overly tight to completely hands off. The happy path is in the middle—agree on top-down, lagging success KPIs, give teams autonomy to execute and measure leading KPIs, keep governance to the required minimum, and automate as much as possible.
Automate processes and reporting to reduce low-value manual work. AI should free teams from routine tasks and elevate focus to exceptions and decisions.
4. Many Sources Of Truth
Conflicting KPIs and siloed data frustrate transformation leaders. Everyone thinks they're reporting on "net benefit," but each team defines it differently.
The risks are real. A July 2024 Wall Street Journal investigation showed how Amazon's Alexa team lost billions due to overconfident forecasts and inconsistent attribution—what one participant called "bulls--- with a confidence factor." As Harvard Business Review noted, failure to unify data across systems undermines scalability.
Create real-time dashboards as the single authoritative source. Use AI to automate calculations, surface anomalies and guide decisions with precision.
5. Ineffective Collaboration
Siloed teams, vague decision rights and "domain protectionism" remain stubborn barriers. Without a clear governance model and shared North Star, alignment breaks down.
Harvard Business Review reported in 2015 that 75% of cross-functional teams were dysfunctional due to unclear authority and accountability. Participants emphasized aligning individual incentives with shared outcomes.
Enable structured, cross-functional collaboration with shared tools and clear expectations. AI can eliminate redundant coordination and spotlight blockers early.
6. Short-Term Risk Management
Too many organizations manage for short-term milestones and neglect longer-term risks. Participants noted that post-consultant, many teams lack embedded structures to monitor and sustain progress.
FTI Consulting advises creating sustainable risk management frameworks, starting with a gap assessment and investment road map in talent and tech. Track risks and issues in a centralized system with clear mitigation plans. Let AI flag unmitigated risks, escalate them, and close the loop when resolved.
Customer Examples
We've had the opportunity to participate in thousands of large-scale enterprise transformation projects worldwide across virtually all industries. Along the way, we've observed the impact these changes can have on transformation outcomes.
• AT&T implemented real-time KPI tracking across more than 300 metrics, eliminating over 10,000 hours of manual reporting annually.
• OPDC, a Saudi Public Investment Fund portfolio company converting an offshore oil rig into a tourist resort, replaced manual risk tracking with automated workflows, improving compliance and executive visibility.
• A financial services customer cut manual input by over 50% by centralizing project intake, accelerating planning and alignment.
• A global defense manufacturer created a dynamic dashboard for steering committee updates, ensuring data accuracy without disrupting workflows.
• Ryder managed the Cardinal Logistics acquisition through real-time collaboration tools, enabling faster execution across integration teams.
• Unilever implemented structured governance reviews that cut manual follow-ups, improved accountability and reduced project overruns by 35%.
Takeaway
Despite the diversity of industries and geographies, the transformation challenges shared at OPEX Week were remarkably consistent. The emerging solutions were tighter alignment, consistent tracking, actionable data and shifting from episodic initiatives to continuous transformation. Tools matter, but mindset matters more.
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