Book Review: Digital Transformation – Survive and Thrive in an Era of Mass Extinction

Although already published in 2019 (more than 5 years ago), this book points several concepts still very relevant in the fast changing world of Digital Transformation. Below a summary of these concepts and recommended actions

In Digital Transformation, technology visionary Thomas Siebel offers a compelling and pragmatic guide for business leaders confronting the rapidly converging forces of cloud computing, big data, artificial intelligence (AI), and the Internet of Things (IoT). These technologies are creating an extinction-level event for legacy business models. Siebel contends that digital transformation is not optional—it is a matter of survival.

Drawing on his experience as founder of C3.ai, Siebel presents a clear strategic playbook and numerous real-world examples that demonstrate how companies across sectors can reinvent themselves using digital technologies. His message is direct: act now, or risk irrelevance.


Key Concepts

1. The Four Technology Pillars

  • Cloud Computing – On-demand computing infrastructure enabling scalability and speed
  • Big Data – Massive, diverse datasets that can be analyzed in real-time
  • Artificial Intelligence (AI) – Predictive, adaptive algorithms that learn from data
  • Internet of Things (IoT) – Billions of connected devices generating actionable data

2. A Mass Extinction Event for Legacy Businesses

  • Over half of Fortune 500 companies have disappeared since 2000
  • Disruption is hitting all industries—not just tech
  • Traditional business models are no longer sustainable

3. Digital Transformation Is a Strategic Reinvention

  • Not about marginal gains—requires full-scale operating model redesign
  • Core focus on operational efficiency, customer experience, and new value creation

4. Data as the Foundation for AI

  • Success with AI requires clean, integrated, and governed enterprise data
  • Enterprises must break down data silos and standardize architecture

5. Speed and Scale as Differentiators

  • Companies must move fast, think big, and deliver value quickly
  • Long, drawn-out transformations are no longer viable

6. Real-World Case Studies

  • Enel – Predictive maintenance across its global energy grid
  • Royal Dutch Shell – AI for well safety, energy trading, and asset optimization
  • U.S. Department of Defense – AI and IoT for battlefield awareness

Implementation Recommendations

1. Modernize Your Tech Stack

  • Shift from legacy systems to modern, elastic cloud infrastructure

2. Centralize and Unify Data

  • Build a data integration layer across all business units
  • Ensure governance and real-time accessibility

3. Deploy High-Value AI Use Cases First

  • Focus on predictive maintenance, customer churn, fraud detection, etc.

4. Adopt Agile and DevOps at Scale

  • Encourage continuous delivery and rapid iterations

5. Re-skill and Upskill the Workforce

  • Provide training in AI, data science, and cloud technologies

6. Build a Cross-Functional Operating Model

  • Blend business, IT, and data science in unified delivery teams

7. Create a Transformation Office

  • Establish a dedicated team with budget, authority, and board-level visibility

Siebel’s 10-Point CEO Action Plan

  1. Declare Digital Transformation a Strategic Priority
  2. Establish a Digital Transformation Office (DTO)
  3. Unify Enterprise Data Architecture
  4. Identify High-Impact Use Cases
  5. Deploy Agile Methodologies
  6. Form Cross-Functional Teams
  7. Invest in AI and IoT Capabilities
  8. Lead Cultural Change from the Top
  9. Develop Digital Talent and Skills
  10. Track Progress and Iterate Continuously

Final Thoughts

Digital Transformation by Thomas Siebel is a must-read for executives seeking to lead their organizations through an era of exponential change. The convergence of cloud, big data, AI, and IoT isn’t just a tech revolution—it’s a business survival imperative. With practical insights, a strong strategic framework, and a CEO-focused action plan, this book is a blueprint for industrial-scale reinvention.

Highly recommended for leaders ready to move from intention to impact.

Harnessing Curiosity for Digital Transformation Success

In a world shaped by accelerating change, new technologies, and shifting customer expectations, digital transformation is no longer optional—it’s a strategic imperative. But technology alone doesn’t drive transformation. The real differentiator lies in human capabilities—and among these, curiosity stands out as a key enabler of successful change.

Curiosity: The Human Advantage in a Digital World

Curiosity isn’t just about asking questions. It’s the active pursuit of new knowledge, perspectives, and possibilities. It fuels learning, drives innovation, and enables people to adapt quickly in fast-moving environments.

As Deloitte puts it in their research on digital fluency, “Curiosity is the catalyst that allows people to keep pace with technology—and lead with it.”

For transformation leaders, this has direct implications:

  • Curious individuals are more likely to experiment, learn, and improve.
  • Curious teams are better at breaking silos, seeking input, and iterating solutions.
  • Curious cultures are more resilient, adaptive, and open to what’s next.

Research That Connects Curiosity to Transformation Success

The Business Case for Curiosity – Harvard Business Review (Francesca Gino, 2018)

  • Curious employees are more engaged, collaborative, and better at decision-making.
  • Organizations that foster curiosity experience higher innovation and reduced groupthink.
  • Read the article →

The Mindsets of Transformation Leaders – McKinsey & Company

  • Highlights intellectual curiosity as a hallmark of successful transformation leaders.
  • Curious leaders are more willing to challenge assumptions, adapt strategy, and engage stakeholders.
  • Read the article →

Human + Machine: Reimagining Work in the Age of AI – IBM Institute for Business Value

  • Emphasizes that in the AI era, human skills like curiosity are vital complements to automation.
  • Curious individuals are better at interpreting data, asking better questions, and guiding AI to impactful outcomes.
  • Explore Human + Machine →

The Curiosity Gap: What Holds Teams Back

Despite its value, many organisations unintentionally stifle curiosity:

  • Rigid hierarchies discourage questioning.
  • Execution pressure leaves no room for reflection.
  • Fear of failure shuts down experimentation.
  • Overreliance on expertise limits fresh thinking.

These are culture issues, not people issues. Leaders play a pivotal role in changing this dynamic.

How Leaders Can Foster Curiosity

Transformation leaders can amplify curiosity in practical, powerful ways:

  • Ask more than tell: Use open-ended questions to spark exploration.
  • Normalize experimentation: Frame pilots and prototypes as learning opportunities.
  • Listen actively: Signal that new ideas and diverse perspectives are valued.
  • Reward growth: Recognize not just performance, but how people learn and adapt.
  • Lead with humility: Show you’re learning too—and invite others on the journey.

Final Word

Digital transformation is ultimately a human transformation. And curiosity is the mindset that keeps humans relevant, engaged, and future-ready.

It’s what helps a data analyst spot an emerging trend, a product manager test a radical new idea, and a CEO rethink a decades-old business model. It’s also what allows us to partner more effectively with AI—asking the right questions, interpreting signals, and imagining better solutions.

As you lead your organisation through transformation, don’t just invest in platforms and capabilities. Invest in curiosity. It’s the spark that turns potential into progress.

Master Impactful Communication in Digital Transformation

Why Communication Is the Lifeblood of Transformation Communication is more than a soft skill—it’s a strategic lever. Miscommunication or a lack of timely information can erode trust, stall progress, and sow confusion. According to McKinsey, 70% of transformation programs fail, and poor communication is often a silent contributor. Impactful communication aligns stakeholders, drives engagement, mitigates resistance, and reinforces progress. It is how leadership earns trust, how teams stay focused, and how change becomes real.

1. Why Communicate: Purpose, Alignment, and Momentum At every stage of a transformation, communication serves a purpose:

  • Clarify Purpose: Explain the “why” of the transformation—the vision, strategic drivers, and burning platform.
  • Create Alignment: Ensure all stakeholders understand their role in the broader narrative.
  • Build Momentum: Regular communication reinforces progress and sustains engagement.

Example: Continuously link messages to how the topic supports the overall strategy and purpose of the transformation.

2. What to Communicate: The Three Strategic Narratives

  • Purpose: Why are we doing this? Lay out the rationale, desired future state, and expected benefits.
  • Progress: What’s happening now? Share timelines, milestones, and any course corrections.
  • Proof: What’s working? Highlight quick wins, user stories, and lessons learned. Success stories inspire belief.

Example: A transformation dashboard updated monthly with progress visuals and a rotating spotlight on team success stories creates transparency and boosts morale.

3. How to Communicate: Channels, Formats, and Tone

  • Stakeholder-Focused: Tailor content to audience needs. Executives need strategic updates, while frontline teams need clarity on operational impacts.
  • Formats: Mix videos, infographics, text updates, and live events. Use storytelling, visuals, and humor where appropriate.
  • Tools: Combine traditional (emails, town halls) with digital (Yammer, Teams, digital signage).

Example: A short animated video used to explain a new agile model across the company generates more engagement than a 10-page slide deck.

4. Where to Communicate: Choosing the Right Channels

  • Channels: Leverage both formal (newsletters, intranet) and informal (team meetings, social platforms).
  • Internal and External: Don’t forget partners, customers, and external stakeholders when relevant.
  • Beyond Standard: Use unconventional methods like pop-up booths, floor ambassadors, or interactive kiosks.

Example: Place screens in break rooms with FAQs and video testimonials from users. Often, employees read external communication (e.g. LinkedIn) more attentively than internal channels.

5. Who Should Communicate: Roles and Responsibilities

  • Leadership: Sets the tone and provides credibility.
  • Program Teams: Share updates and own the transformation story.
  • End Users: Involve them in co-creation and let their stories become advocacy.
  • Champions/Change Agents: Act as trusted messengers within the organization.

Example: (Team) Leaders deliver tailored talking points to their teams after town halls to reinforce key messages locally.

6. When to Communicate: Cadence with Purpose

  • Routine Rhythm: Weekly newsletters, monthly video messages, quarterly town halls.
  • Event-Driven: Go-live updates, milestone achievements, leadership transitions.
  • Embedded Moments: Integrate into standups, one-on-ones, and performance reviews.

Example: A transformation team sends a short Friday note every week with “Top 3 things to know” – brief, consistent, and effective.

7. Making Communication Two-Way

  • Feedback Loops: Open Q&A forums, feedback forms, sentiment pulse checks.
  • Listening Mechanisms: Focus groups, digital suggestion boxes, skip-level meetings.
  • Empower Managers: Train and support them to act as translators and listeners.

Example: Run quarterly listening sessions where employees can anonymously submit and vote on questions.

8. Measuring Communication Effectiveness

  • Quantitative Metrics: Email open rates, intranet views, video play completion, attendance.
  • Qualitative Feedback: Employee surveys, pulse checks, sentiment analysis.
  • Behavioral Indicators: Are stakeholders taking desired actions (e.g., using a new tool, adopting a new process)?

Example: Use employee surveys to check communication effectiveness. Include questions on whether the why, who, what, where, and when of the transformation are well understood.

Conclusion: From Messaging to Meaning

Impactful communication is not just about delivering information—it’s about shaping perception, building trust, and enabling action. It’s a leadership discipline that requires intent, empathy, and agility. In digital transformations, where uncertainty is the norm, communication becomes the connective tissue that keeps strategy and execution aligned. For senior leaders, investing in communication is not optional—it’s foundational to transformation success.

How Continuous Improvement (PDCA and Kaizen) drives Adoption and Value in Digital Transformation

Why Continuous Improvement Matters in Digital Transformation

Many digital transformations falter after implementation. Technologies go live, but the full value often remains unrealized. One key reason? A lack of embedded, ongoing improvement practices.

Continuous Improvement Cycles—specifically PDCA (Plan–Do–Check–Act) and Kaizen—provide the discipline required to keep improving after deployment. They shift the mindset from “project completion” to continuous value optimization, embedding a culture that learns, adapts, and evolves.

The impact is well-documented:

💡 According to McKinsey & Company (2021), organizations that embed continuous improvement into their digital transformations are 2.5 times more likely to report successful outcomes than those focused solely on implementation.

📊 A Deloitte study (2022) found that 78% of organizations that sustained their digital transformation benefits had formalized continuous improvement processes, compared to just 31% of those that didn’t.

Real transformation success isn’t just about launching change—it’s about sustaining and evolving it continuously.


PDCA: A Structured Learning Loop for the Digital Age

The PDCA cycle, originally developed by W. Edwards Deming, remains foundational in continuous improvement. In today’s digital environment, it has been enhanced with real-time data, agile delivery, and user-centered design.

1. Plan

Define the opportunity and craft a value-aligned, testable intervention.

  • Traditional: Diagnose the current state, set improvement goals, design the change.
  • Digital Evolution: Use analytics to identify friction points, apply design thinking to understand user needs, and define digital KPIs aligned with business outcomes. Prioritize minimal viable changes over complex upfront plans.

2. Do

Test the change in a low-risk environment and gather real-world feedback.

  • Traditional: Pilot changes, document execution, and support implementation.
  • Digital Evolution: Use feature flags for controlled rollouts, run A/B tests, automate behavioral data capture, and deploy rapidly to shorten time-to-feedback.

3. Check

Assess impact and extract learnings.

  • Traditional: Compare actual results to expectations, conduct retrospectives, identify lessons.
  • Digital Evolution: Monitor via real-time dashboards, use automated testing, apply UX research, and leverage predictive analytics to detect patterns.

4. Act

Scale what works—or iterate again.

  • Traditional: Standardize successful practices, communicate changes, revisit unresolved issues.
  • Digital Evolution: Automate through CI/CD pipelines, codify learnings into playbooks, build communities of practice, and use retrospectives to institutionalize learning.

✅ When PDCA is adapted with digital enablers, it becomes a strategic engine for transformation value realization—not just an operational tool.


Kaizen: Creating a Culture of Relentless Improvement

Where PDCA offers structure, Kaizen—meaning “change for better”—injects continuous improvement with energy, ownership, and culture. Originating from Japanese manufacturing excellence, it is a philosophy that emphasizes daily, incremental progress driven by everyone in the organization.

Core Principles of Kaizen

  1. Continuous, Incremental Improvement
    • Small, low-cost changes compound into significant long-term impact.
    • Especially valuable in digital contexts, where feedback loops are fast and ongoing.
  2. Process Focus
    • Kaizen targets flawed processes, not people.
    • Teams are encouraged to map and improve end-to-end workflows—not just surface-level symptoms.

💡 Insight: In many digital failures, technology isn’t the issue—process design is. Kaizen helps uncover complexity and inefficiencies that digital tools alone can’t solve.

  1. Elimination of Waste (Muda)
    • Waste is any activity that doesn’t add customer value. Kaizen uses the TIMWOODS framework to identify eight key forms of waste:
TypeDigital Example
TransportRedundant data transfers between systems
InventoryUnused data, reports, or stored digital assets
MotionExcessive navigation in systems or interfaces
WaitingDelayed approvals, system lags
OverproductionFeatures or reports no one uses
OverprocessingManual re-checks due to low trust in automation
DefectsRework from bugs, data errors
Skills (Underuse)Not tapping into employee creativity and insight
  1. 🧭 Transformation Tip: Process mining and automation can help eliminate waste—but without a Kaizen mindset, digital solutions may just replicate analog inefficiencies.
  2. Employee Involvement and Ownership
    • Those closest to the work are best positioned to improve it.
    • Kaizen encourages bottom-up contributions, while leaders provide the tools, time, and recognition.

🟢 Example: A logistics firm equipped teams with tablets to log small improvement ideas. In six months, they implemented over 200 enhancements—resulting in a 12% productivity lift.

  1. Standardization of Improvements
    • Once something works better, it becomes the new standard.
    • This locks in gains while setting the stage for the next cycle of improvements.

“Without standards, there can be no improvement. For improvement to happen, changes must be made.”
Masaaki Imai, father of Kaizen


Making It Stick: Enablers of Success

To embed continuous improvement in your transformation:

  • Leadership Commitment – Role-model curiosity and support learning-by-doing.
  • Digital Enablers – Use analytics, process mining, and feedback loops to identify what to improve.
  • Training & Empowerment – Equip teams to run their own improvement cycles.
  • Recognition – Celebrate both the small wins and the mindset behind them.

From One-Off to Ongoing

Transformation is not a finish line—it’s a journey of continuous alignment and adaptation. PDCA and Kaizen offer practical, proven ways to embed improvement into the DNA of your organization, ensuring digital capabilities evolve with business needs.

Organizations that adopt these cycles at scale don’t just implement change—they sustain it, extend it, and accelerate its value.

AI and Digital Transformation Insights from the GDS CIO Summit

Last week, I had the pleasure and privilege of attending and speaking at the GDS CIO Summit – Noordwijk | March 12-13 2025, where I joined around 150 senior leaders from the tech industry. Over two days, we explored some of the most pressing topics shaping our industry today and those that will define the near future. It came as no surprise that 84% of CIOs consider AI a top priority, yet many are still figuring out how to effectively integrate it into their business strategies.

From Vision to Value – IT as a Competitive Advantage

The summit opened with a fantastic panel discussion featuring Angelika Trawinska van Bolhuis ( Dyson), Claudio FINOL (Fyffes), and Cameron van Orman (Planview). A key theme that emerged: IT is no longer just an enabler but a core driver of business strategy—capable of creating either competitive advantage or disadvantage.

Organizations are shifting from project-based ROI thinking to a product and business value-driven approach, requiring agile, dynamic planning and tools like Planview to align IT initiatives with evolving business priorities.

AI’s Growing Impact – The Need for Real-Time Insights

AI was a dominant theme throughout the event, and Kai Waehner (Confluent) led a deep dive into how real-time data fuels AI success. Many infrastructures aren’t designed for this shift, but event-driven architectures and data streaming are emerging as critical enablers.

One standout insight: 2025 is poised to be the year of “Agentic AI”—where autonomous AI agents collaborate in real time to optimize operations. Businesses that prepare for this transformation now will gain a significant competitive edge.

The Future of Work – Productivity, Transparency & AI Integration

How can organizations improve productivity and alignment? Sven Peters (Atlassian) shared fascinating insights into modern Systems of Work. High-performing teams don’t operate in silos; they align around OKRs (Objectives & Key Results) with full transparency.

At Atlassian, they have a simple but highly effective approach: ✅ Weekly 280-character updates to keep work visible ✅ Monthly check-ins to assess progress ✅ Quarterly reviews to refine objectives

AI is deeply embedded in this process, assisting teams in defining OKRs and structuring projects in a smarter way.

AI Regulations, Security & Workforce Evolution

The regulatory landscape around AI is evolving rapidly, particularly in Europe, and Ulrika Billström (OpenText) provided a compelling look at how companies must adapt. AI orchestrators are emerging, capable of managing multiple AI agents to drive large-scale innovation.

A key trend: Instead of moving data to AI, AI is now being deployed closer to where the data resides, fundamentally changing how organizations structure their AI ecosystems.

Day 2 – Real-Time Data & Trust

I had the honor of opening Day 2 alongside Ellen Aartsen ( KPN ), Joshan Meenowa (The KraftHeinz Company), and Ben Thompson ( GDS Group) in a discussion on how data fuels real-time decision-making.

A key question we tackled: How “real-time” does data actually need to be? While not every use case requires real-time data, all use cases require trusted data. Transparency, governance, and reducing reliance on alternative, non-trusted data sources are key to success.

AI Lifecycle Challenges – Managing Rapid Evolution

Kevin K. ( Airia – Enterprise AI Simplified ) shed light on a major challenge: the rapid pace of AI development. With 6,000–8,000 new AI models being created every week, companies struggle to keep up.

The solution? AI orchestration layers—which sit between the data, source systems, and AI models—are becoming essential to manage AI lifecycles efficiently and ensure tangible ROI.

The CIO’s Role is Evolving – Business Leadership is Key

In an insightful discussion with Alan Guthrie ( Calderys) and Alexander Press (Sanofi), we explored how the role of the CIO is undergoing a fundamental shift.

Today’s CIOs must: ✔ Operate at strategic, tactical, and operational levels ✔ Set clear technology guardrails while fostering innovation ✔ Shift IT functions toward product-driven organizations

Technology leadership alone is no longer enough—CIOs must now be business leaders.

Maximizing Tech Investments – Understanding TCO & ROI

To close the summit, @ManishNirmal ( Vimeo) provided a valuable session on how to assess the true Total Cost of Ownership (TCO). Hidden costs—such as training, migration, and operational impact—often make or break the business case for tech investments.

His recommendation? Use frameworks like MEDDIC (Metrics, Economic Buyer, Decision Criteria, Identify Pain, Champion) to map tech solutions based on real business value.

One of the most memorable takeaways: Crawl before you walk, walk before you run—but standing still is not an option.


Final Thoughts

The GDS CIO Summit was a fantastic opportunity to exchange insights with industry leaders and explore where AI and digital transformation are headed. A huge thank you to the GDS Group, especially Sophie Charnaud for her support, and all the brilliant speakers and participants for making it such an insightful event!

Balancing between Balcony and Dance Floor – Tip for Leadership in Digital Transformation

The “Balcony and Dance Floor” metaphor, introduced by Ronald Heifetz and Marty Linsky, offers a powerful framework for balancing hands-on leadership with strategic oversight. Leaders must be immersed in execution (the dance floor) while also stepping back to gain a broader perspective (the balcony). Striking this balance is crucial for digital transformation success.

Understanding the Metaphor in a Digital Transformation Context

  • The Dance Floor: This represents the daily execution of digital initiatives—overseeing system rollouts, engaging with teams, managing stakeholder concerns, and addressing immediate roadblocks. Leaders who remain solely on the dance floor risk being overwhelmed by operational challenges, losing sight of strategic priorities.
  • The Balcony: This vantage point provides the necessary space to assess overall progress, identify patterns, and anticipate challenges. A balcony perspective allows leaders to ensure that digital initiatives align with long-term business goals, rather than being reactive to short-term operational issues.

Applying the Concept to Digital Transformation Leadership

  1. Maintaining Strategic Alignment: Leaders must continuously step onto the balcony to ensure digital transformation initiatives align with broader business objectives. Without this, transformation efforts may become disjointed or lose executive sponsorship.
  2. Balancing Execution with Reflection: While hands-on engagement is necessary to drive momentum, leaders should also create time for reflection, whether through strategic reviews, executive meetings, or external benchmarking.
  3. Empowering Teams While Providing Vision: Leaders should guide digital transformation by setting a clear vision from the balcony but allow teams to execute with autonomy on the dance floor. This approach fosters innovation while maintaining alignment with the strategic roadmap.
  4. Leveraging Data and Insights: Digital transformation generates vast amounts of data. Leaders must use this data to inform their balcony perspective, identifying trends and adjusting strategies as necessary.
  5. Ensuring Adaptability: Transformation initiatives rarely go as planned. A leader’s ability to move between the dance floor and balcony ensures they can adjust strategies dynamically, responding to challenges without losing sight of the ultimate goal.

The Leadership Imperative

Effective digital transformation leaders seamlessly transition between execution and strategic reflection. Those who remain only on the dance floor risk micromanagement and burnout, while those who stay only on the balcony may become disconnected from execution realities. By mastering this balance, leaders can guide their organizations through digital transformation with clarity, resilience, and adaptability.

In an era of rapid technological evolution, adopting the “Balcony and Dance Floor” approach is more than a leadership technique—it is a necessity for driving sustainable digital change.

Harnessing Lessons Learned for Digital Transformation Success

Introduction

Digital transformation is a complex, multi-phase journey that requires continuous learning and adaptation. Organizations that systematically capture and apply lessons learned improve their chances of success, avoid recurring mistakes, and optimize future initiatives. However, many businesses either fail to document insights effectively or struggle to integrate them into future projects. This article explores the importance of lessons learned, effective approaches, implementation strategies, key challenges, and a step-by-step framework to ensure digital transformation efforts benefit from past experiences.

1. Why Lessons Learned Matter in Digital Transformation

Lessons learned play a crucial role in refining digital transformation efforts. Key benefits include:

  • Preventing Repeated Mistakes – Avoiding common pitfalls saves time, money, and resources.
  • Enhancing Decision-Making – Informed decisions based on past experiences lead to better outcomes.
  • Optimizing Processes – Continuous improvement ensures that digital initiatives become more efficient over time.
  • Strengthening Governance – Ensuring that digital transformation governance evolves based on real-world insights.
  • Fostering a Learning Culture – Encouraging teams to reflect on successes and failures promotes organizational agility.

By embedding a structured approach to lessons learned, companies can accelerate their digital transformation efforts and increase long-term success.

2. Approaches to Capturing Lessons Learned

Various methodologies exist for systematically gathering insights from digital transformation initiatives. Some of the most effective approaches include:

A. After-Action Review (AAR)

Originally developed by the U.S. Army, the AAR method uses a structured reflection process:

  1. What was supposed to happen?
  2. What actually happened?
  3. What went well and why?
  4. What can be improved and how?

B. Agile Retrospectives

Agile methodologies integrate lessons learned through retrospectives at the end of each sprint. Common questions include:

  • What worked well?
  • What didn’t go well?
  • What can we improve?
  • What are the action items for the next sprint?

C. Post-Implementation Review (PIR)

A PIR is conducted after a major project phase or the entire transformation effort. It assesses:

  • Whether objectives were met.
  • What worked and what didn’t.
  • How to apply insights to future transformations.

D. Lessons Learned Workshops

Interactive sessions where key stakeholders share insights using structured formats like:

  • Start, Stop, Continue review.
  • Root Cause Analysis (Fishbone Diagrams).
  • Timeline Review with Thematic Grouping of Issues.

E. Knowledge Repositories for Continuous Learning

Organizations can store and share lessons learned using:

  • Digital transformation playbooks.
  • Internal knowledge management systems (e.g., Confluence, SharePoint).
  • AI-driven repositories for searchability.

3. Applying Lessons Learned in Digital Transformation

Capturing lessons is only valuable if they are applied effectively. Here’s how organizations can ensure insights drive real change:

A. Integrate Lessons into Governance Structures

  • Assign a Lessons Learned Owner or a Transformation Office to track insights.
  • Make lessons learned a standard agenda item in executive steering committees.
  • Embed lessons into organizational decision-making and process improvements.

B. Apply Lessons at Different Levels

  1. Sprint/Phase Level – Immediate adjustments based on sprint retrospectives.
  2. Program/Portfolio Level – Aggregate insights to refine digital strategies.
  3. Enterprise Level – Consolidate transformation-wide lessons into strategic planning.

C. Communicate Lessons Effectively

Lessons must reach the right audience to be impactful:

AudienceCommunication Approach
ExecutivesSummary reports, dashboard insights
Project TeamsWorkshops, sprint reviews, playbooks
Entire OrganizationNewsletters, town halls, digital knowledge hubs

D. Overcoming Common Challenges

ChallengeSolution
Teams don’t document lessonsUse structured templates and automated tools
Lessons aren’t appliedAssign accountability and track implementation
Resistance to discussing failuresFoster a blame-free culture focused on improvement
Insights are scattered across silosCentralize in a knowledge management system

4. Step-by-Step Framework for Implementing Lessons Learned

Step 1: Capture Lessons at Key Milestones

  • Conduct lessons learned sessions at the end of sprints, phases, and projects.
  • Use structured templates and tools to document insights.

Step 2: Analyze and Prioritize Insights

  • Categorize lessons into successes, challenges, opportunities, and recommendations.
  • Use analytical tools like Root Cause Analysis to extract meaningful trends.
  • Prioritize lessons based on strategic impact.

Step 3: Integrate Lessons into Future Projects

  • Update digital transformation playbooks and methodologies.
  • Include lessons learned in risk management frameworks.
  • Modify Standard Operating Procedures (SOPs) based on past experiences.

Step 4: Communicate Lessons Across the Organization

  • Tailor communication methods for different audiences (executives, teams, entire organization).
  • Use multiple channels: internal portals, newsletters, videos, and town halls.
  • Establish a continuous feedback loop for ongoing knowledge sharing.

Step 5: Institutionalize Lessons for Long-Term Impact

  • Develop a centralized knowledge repository for easy retrieval of past lessons.
  • Create a Lessons Learned Playbook to guide future teams, e.g. with Do’s and Don’ts
  • Measure impact through KPIs such as reduced project failures, increased efficiency, and improved adoption rates.

5. Final Thoughts

Applying lessons learned in digital transformation is essential for continuous improvement and long-term success. By embedding a structured process into governance, decision-making, and cultural practices, organizations can avoid repeating mistakes, optimize their digital initiatives, and drive better outcomes.

Successful digital transformations are not just about implementing new technologies—they are about learning, adapting, and evolving. Organizations that prioritize lessons learned as a strategic capability will lead the way in digital excellence.

Unlocking Value in Digital Transformation with VDT & BRM

The Importance of Value Driver Trees and Benefit Realization Management in Digital Transformation

Digital transformation is not just about implementing new technologies—it is about generating real, measurable business value. Too often, organizations invest in digital initiatives without a clear understanding of how these efforts contribute to strategic goals, leading to wasted resources and unfulfilled expectations. I could have put this tool as well in the Strategy to Plan section, since you will need these insights already when setting up a transformation. Due to it’s focus on Sustainable Value Creation you find it here.

To ensure digital transformation delivers tangible benefits, organizations need structured approaches that tie initiatives to business value. Value Driver Trees (VDT) provide a visual and analytical way to break down how value is created, while Benefit Realization Management (BRM) ensures that transformation initiatives deliver the expected outcomes. By integrating these two approaches, organizations can bridge the gap between strategy and execution, ensuring every initiative contributes to meaningful business impact.

This article explores these frameworks, their interaction, and provides a step-by-step guide for implementing them effectively in digital transformation initiatives.


Understanding the Approaches

1. Value Driver Tree (VDT)

A Value Driver Tree (VDT) is a structured framework that breaks down an organization’s high-level business objectives into actionable and measurable components. It helps leaders identify the key levers that drive financial and operational performance.

Example: VDT for Retail e-Commerce Growth

Goal: Increase e-Commerce Revenue

👉 Sales Volume Growth
 🔹 Improve Website Conversion Rate
 🔹 Increase Traffic via Digital Marketing
👉 Average Order Value Increase
 🔹 Personalized Product Recommendations
 🔹 Bundled Pricing Strategy
👉 Customer Retention Improvement
 🔹 Loyalty Program Enhancements
 🔹 Improved Customer Support Response Time

This hierarchical breakdown helps organizations prioritize initiatives that have the most impact on revenue growth. Below one more example from the web on how to look at Value Drivers/KPIs.


2. Benefit Realization Management (BRM) – PMI Approach

PMI’s Benefit Realization Management (BRM) framework provides a structured approach to ensure that projects and programs deliver measurable benefits that align with strategic objectives. It consists of three key phases:

  1. Benefit Identification: Define expected benefits, align them with strategic goals, and establish key performance indicators (KPIs).
  2. Benefit Execution: Monitor benefits realization through governance and stakeholder engagement during project execution.
  3. Benefit Sustainment: Ensure ongoing measurement and reinforcement of benefits post-project completion.

Example: BRM in an ERP Implementation

Objective: Improve Operational Efficiency Through an ERP System
👉 Benefit: Reduced Order Processing Time
 🔹 Initiative: Automate manual order entry processes
 🔹 KPI: Reduce order processing time from 48 hours to 12 hours
👉 Benefit: Lower IT Costs
 🔹 Initiative: Consolidate legacy systems into a unified ERP platform
 🔹 KPI: Reduce IT maintenance costs by 30%

By applying BRM, organizations can ensure that digital transformation projects remain focused on delivering real business benefits rather than just implementing technology for technology’s sake.


How VDT and BRM Interact

VDT and BRM complement each other by linking high-level business value drivers with structured benefit realization processes. Here’s how they work together:

  1. VDT Identifies Key Business Drivers → Helps organizations understand where value comes from.
  2. BRM Ensures Benefits Are Tracked and Realized → Ensures projects are aligned with value drivers and measured effectively.
  3. VDT Provides a Data-Driven Basis for Prioritization → Helps select the most impactful initiatives.
  4. BRM Embeds Value Tracking into Governance → Ensures sustained realization of benefits post-implementation.

By integrating VDT and BRM, organizations can establish a clear, data-driven transformation roadmap and ensure continuous value creation.


Implementation Plan

Step 1: Develop a Value Driver Tree

  • Identify overarching business objectives (e.g., revenue growth, cost reduction, customer experience enhancement).
  • Break them down into measurable value drivers and initiatives.
  • Assign KPIs to each driver to establish clear tracking mechanisms.

Step 2: Align BRM to the Value Driver Tree

  • Define benefits based on value drivers.
  • Create a Benefits Dependency Network mapping initiatives to expected benefits.
  • Assign accountability for benefit realization.

Step 3: Establish Governance and Measurement

  • Integrate benefit tracking into program governance.
  • Set up regular benefit reviews (e.g., quarterly assessments).
  • Adjust strategies if expected benefits are not materializing.

Example: Applying VDT and BRM in a Digital Transformation Initiative

Scenario: A Bank’s Digital Banking Transformation

Step 1: Develop a Value Driver Tree

Goal: Enhance Digital Banking Experience
👉 Increase Mobile App Adoption
 🔹 Simplify Onboarding Process
 🔹 Improve User Interface & Experience
👉 Reduce Customer Support Costs
 🔹 Introduce AI-powered Chatbots
 🔹 Automate Fraud Detection Alerts

Step 2: Align BRM to VDT

BenefitKPIInitiativeMeasurement
Higher Mobile Adoption% of active usersUX RedesignMonthly user growth rate
Lower Support CostsReduction in live callsAI Chatbot DeploymentCall volume trend
Increased SecurityFraud incident reductionAI-driven fraud detectionFraud report metrics

Step 3: Governance & Tracking

  • Regular executive reviews track realized vs. projected benefits.
  • Adjustments made based on data insights and customer feedback.

Conclusion: Driving Digital Transformation Success with VDT and BRM

Successful digital transformation requires more than just implementing technology—it demands a structured approach to ensure value realization. By leveraging Value Driver Trees (VDT) and Benefit Realization Management (BRM) together, organizations can:

✅ Clearly define how transformation initiatives contribute to business objectives.
✅ Prioritize efforts based on quantifiable value impact.
✅ Continuously track and adjust for sustained benefit realization.

To drive real business outcomes, organizations should integrate these frameworks into their transformation governance, ensuring a clear line of sight from strategic objectives to measurable benefits.

Call to Action

If your organization is embarking on a digital transformation journey, start by building your Value Driver Tree and structuring a Benefit Realization Framework. Need help applying these methods? Let’s discuss how to tailor them to your organization’s needs.

Enhance Project Success with Pre-Mortem Techniques

A pre-mortem is a proactive risk management exercise that helps teams anticipate potential failures before they occur. Unlike traditional risk assessments, which often focus on known risks, a pre-mortem encourages teams to imagine a scenario where the initiative has already failed and work backward to identify the causes. This method:

  • Uncovers hidden risks that might otherwise be overlooked.
  • Encourages open and candid discussions within teams.
  • Enhances risk mitigation strategies early in the process.
  • Strengthens team alignment and shared accountability for success.

What Are the Outcomes of a Pre-Mortem?

When executed effectively, a pre-mortem delivers several valuable outcomes:

  • A comprehensive list of potential failure points.
  • A prioritized risk register with mitigation actions.
  • Stronger team cohesion and ownership over the initiative’s success.
  • Improved decision-making, ensuring proactive rather than reactive responses to risks.

How to Execute a Pre-Mortem

Follow these structured steps to conduct an effective pre-mortem:

  1. Set the Stage: Gather the key stakeholders, including project sponsors, team leads, and operational experts. Ensure a psychologically safe environment where candid discussions are encouraged.
  2. Define the Scenario: Present the hypothetical situation: “It is six months (or an appropriate timeframe) in the future, and the project has completely failed. What went wrong?”
  3. Brainstorm Failure Points: Each participant individually lists reasons for failure, considering strategic, operational, and technical factors.
  4. Share and Categorize: Consolidate and group similar failure points into themes (e.g., governance issues, resource constraints, external disruptions).
  5. Prioritize Risks: Use voting, ranking, or a risk assessment matrix to determine which failure points are the most critical.
  6. Develop Mitigation Actions: For each high-priority risk, define preventive measures and contingency plans.
  7. Integrate into Governance: Assign ownership for risk monitoring and integrate these insights into ongoing project reviews.

When and With Whom Should You Conduct a Pre-Mortem?

  • When: Ideally, before finalizing the transformation strategy or at key milestones in major initiatives (e.g., post-planning, before execution phases, during major pivots).
  • With Whom: A cross-functional group including executives, project managers, functional leads, risk officers, and frontline implementers.

By embedding the pre-mortem approach into your transformation governance, you significantly improve the likelihood of success by proactively identifying and addressing risks before they materialize.

This technique not only improves project outcomes but also builds stronger teams through enhanced communication and psychological safety.

Effective Risk Management in Digital Transformation

1. Introduction

Organizational transformations represent some of the most complex undertakings in business. According to research by McKinsey & Company (2019), nearly 70% of transformations fail to achieve their stated objectives, with inadequate risk management frequently cited as a contributing factor.

Effective risk management requires a structured approach where risks are identified, assessed, and mitigated at the appropriate levels:

  • Portfolio Risks – Strategic risks impacting the entire transformation, requiring executive oversight. Examples include: resource allocation, organizational capacity for change, external (market/regulatory) and financial sustainability risks.
  • Program Risks – Cross-project risks affecting multiple initiatives, managed at the program level. Examples include: interdependencies/resource conflicts between projects, timeline/milestone risks, development, technical integration, adoption, and benefit realization risks.
  • Project Risks – Operational and execution risks handled by project teams. Examples include: scope/requirements, schedule, budget, resource, quality, performance, team capability/capacity, and stakeholder acceptance risks.

A clear governance structure ensures that risks are escalated to the right level—whether the Executive Steering Committee, Program Leadership, or Project Management—for timely decision-making and intervention.

2. Risk Management in Transformation Governance

To embed risk management into transformation governance effectively, organizations must:

  • Define risk ownership at different levels (executive, program, project).
  • Establish governance bodies with clear escalation mechanisms.
  • Integrate risk reviews into decision-making forums.
  • Ensure risk reporting is transparent, structured, and aligned with transformation objectives.

3. Risk Assessment & Mapping Tools

Several proven tools can help organizations systematically assess and map risks:

  1. Risk Matrix (Probability vs. Impact): Prioritizes risks based on likelihood and severity.
  2. Risk Breakdown Structure (RBS): Categorizes risks by type (strategic, organizational, operational, financial, technical, change management, etc.).
  3. Bow-Tie Analysis: For high-priority risks, visualizes potential causes, consequences, and controls for a given risk.
  4. Monte Carlo Simulations: Provides probabilistic forecasting for risk impact on budgets and timelines.
  5. SWIFT (Structured What-If Technique): Facilitates structured brainstorming on potential risks.

Each of these tools helps organizations gain visibility into risks and prepare for effective mitigation.

4. Mitigation Planning & Execution

Risk mitigation involves defining structured responses based on the nature and severity of risks:

  • Avoid: Eliminating the risk by altering the transformation approach.
  • Mitigate: Reducing the impact or probability through proactive measures.
  • Transfer: Shifting the risk to a third party (e.g., insurance, outsourcing).
  • Accept: Acknowledging the risk with contingency plans in place.

A Risk Register should be maintained to track risks, owners, mitigation actions, timelines, resources, and follow-ups. Additionally, mitigation progress should be reviewed in governance forums to ensure accountability and timely interventions.

5. A Step-by-Step Guide to Implementing Risk Management

  1. Risk Management Framework: Agree on the objectives, structure, policies, and procedures.
  2. Risk Identification: Engage stakeholders and put mechanisms in place across all levels to surface risks early.
  3. Risk Assessment: Use structured tools to break risks down, categorize them, and evaluate the likelihood and impact.
  4. Risk Prioritization: Align risk priorities with transformation goals and organizational risk appetite.
  5. Mitigation Strategy Development: Define risk responses (avoid, transfer, mitigate, accept) and allocate necessary resources.
  6. Governance & Oversight: Integrate risk reviews into transformation governance structures, with dedicated risk review sessions.
  7. Ongoing Monitoring & Communication: Establish reporting mechanisms, including risk trend reporting, and continuous improvement processes.

6. Example – Global Financial Services Transformation

A major financial institution undertaking a digital transformation employed a three-tiered risk management approach:

Portfolio Level (Executive Steering Committee)
The ESC focused on strategic risks including regulatory compliance, competitive disruption, and organizational capacity for change. They established quarterly “risk deep dives” where each transformation workstream presented their top risks and mitigation strategies. The ESC maintained a portfolio-level risk contingency reserve, allocating funds to address emerging risks based on severity and alignment with strategic priorities.

Program Level (Transformation Office)
The Transformation Office implemented a “Risk Guild” comprising risk owners from each workstream who met bi-weekly to identify cross-program dependencies and risks. They employed a sophisticated risk visualization dashboard that highlighted interdependencies between workstreams and potential cascading impacts. The office also maintained a centralized risk register with automated escalation of risks that exceeded defined thresholds.

Project Level (Agile Teams)
Individual teams incorporated risk identification into their sprint planning and retrospectives, with “risk spikes” allocated to investigate high-priority uncertainties. Teams used “risk-adjusted story points” to account for implementation uncertainties in their capacity planning. A “see something, say something” culture encouraged anyone to raise potential risks through a simple digital form.

The results were impressive: while industry benchmarks suggested that 70% of financial services transformations fail to meet objectives, this institution achieved 85% of its targeted benefits within the planned timeframe.

7. Common Pitfalls and How to Avoid Them

Risk Management as Compliance Exercise

  • Problem: Risk management becomes a bureaucratic checkbox exercise rather than a decision-making tool.
  • Solution: Focus on decision-relevance by integrating risk discussions directly into key decision points. Emphasize how risk information has influenced specific decisions. Use concrete, specific risk descriptions rather than generic categories.

Overemphasis on Documentation

  • Problem: Teams spend more time documenting risks than managing them.
  • Solution: Simplify documentation requirements, focusing on action-oriented information. Implement user-friendly tools that minimize administrative burden. Establish “one source of truth” rather than duplicative risk registers.

Failure to Close the Loop

  • Problem: Identified risks have mitigation plans, but no one follows up on implementation.
  • Solution: Implement clear accountability for mitigation actions with regular status reviews. Treat high-priority risk mitigations as projects with defined deliverables, timelines, and resources. Celebrate successful risk mitigation.

Risk Isolation

  • Problem: Risk management operates in isolation from other management processes.
  • Solution: Integrate risk considerations into strategic planning, resource allocation, and performance management. Use consistent language and frameworks across processes. Ensure risk owners participate in relevant decision forums.

Static Approach

  • Problem: Risk register becomes a static document that doesn’t evolve with changing circumstances.
  • Solution: Implement regular risk refresh cycles. Establish triggers for out-of-cycle risk reviews based on internal or external events. Create mechanisms to identify and assess emerging risks.

8. Conclusion

Risk management in organizational transformation is not a peripheral activity but a central governance function that enables informed decision-making and increases the likelihood of success. By implementing a multi-layered approach that addresses portfolio, program, and project risks, organizations can navigate the inherent uncertainties of transformation with greater confidence.

The tools, frameworks, and step-by-step guide outlined in this article provide a roadmap for implementing robust risk management practices. However, the most important factor is creating a risk-aware culture where identifying and managing risks becomes part of everyone’s responsibility.