Fixing Transformation Failure: Why I’m Building CapabiliSense

Digital transformation is broken. For over a decade, the industry has accepted a catastrophic standard of failure. According to data from McKinsey and BCG, roughly 70% to 95% of digital transformation initiatives fail to achieve their stated goals.

That statistic isn’t just a number; it represents billions of dollars incinerated in wasted cloud spend, abandoned platforms, and burnt-out engineering teams. I am building CapabiliSense because we cannot fix this problem with the same tools that created it.

We don’t have a technology problem. We have a sensing problem. Organizations are flying blind, attempting to navigate dynamic, complex terrain using static maps drawn by consultants six months ago. CapabiliSense is designed to be the “GPS” for this journey—an AI-driven, evidence-based engine that replaces subjective opinions with objective capability data.

The Billion-Dollar Blind Spot

I haven’t come to this conclusion lightly. Over a 30-year career spanning roles at major tech giants like AWS and Airbus, I have sat in hundreds of boardrooms. I have watched brilliant leaders make disastrous decisions, not because they lacked intelligence, but because they lacked visibility.

The standard operating procedure for transformation is archaic. You hire a consultancy. They deploy a team of bright analysts who spend weeks interviewing your staff. They ask questions like, “How mature is your DevOps practice?” or “Is your data governance compliant?”

This process produces what I call the “Illusion of Clarity.” You get a beautifully formatted 200-page PDF assessing your organization’s maturity. But the moment that PDF is exported, it is obsolete. The market has moved, your code has changed, and your staff has rotated. You are making strategic bets on “dead” data.

The Problem: “Assessment Fatigue” and Subjectivity

The “old way” fails because it relies on human testimony rather than empirical evidence. When a consultant asks a generic question, the answer is rarely raw truth. It is filtered through politics, fear, and career preservation.

A middle manager worried about their budget will rarely admit their department is failing. A team utilizing “shadow IT” won’t disclose it in a survey. We end up with a sanitized version of reality.

This leads to Assessment Fatigue. Teams get tired of answering the same questions from different consultants every quarter. They copy-paste previous answers. The data quality degrades. Meanwhile, the actual evidence of your organization’s capability—your Jira tickets, your Confluence pages, your architecture diagrams, your strategy docs—sits unread in siloed repositories.

This is the gap CapabiliSense fills. We need to stop asking people if they are compliant and start looking at the evidence to see if they are.

The Solution: From Static Reports to Dynamic Sensing

CapabiliSense is an apolitical dashboard for organizational maturity. It is not just a tool; it is a shift in methodology. We are moving from “asking” to “sensing.”

The core mechanism is simple yet radical:

1. Ingestion: Instead of interviews, the AI ingests unstructured text and documentation already existing within the enterprise.
2. Analysis: It evaluates this raw data against established maturity models.
3. Scoring: It provides a capability score based on proof, not claims.

If your strategy document says you prioritize “Cloud First,” but your architectural diagrams show 90% on-premise legacy dependencies, CapabiliSense flags the disconnect. It doesn’t care about hurting feelings. It cares about alignment.

This approach solves the speed issue immediately. What used to take a team of five consultants three months can now be baselined in days. More importantly, it solves the bias issue. <a href=”https://en.wikipedia.org/wiki/Large_language_model” target=”_blank”>Large Language Models (LLMs)</a> do not have office politics. They do not fear losing their job if they report a red flag.

Building in Public: The “Good, The Bad, and The AI-gly”

I believe in radical transparency, so let’s talk about the reality of building this. We are leveraging Generative AI, specifically advanced LLMs, to perform this analysis. This allows us to process vast amounts of unstructured data that was previously “dark” to analytics.

However, building an enterprise-grade AI tool is not as simple as wrapping a ChatGPT prompt. The challenge—and where we are spending 80% of our engineering effort—is on Contextual Grounding.

In a B2B context, “hallucination” is unacceptable. If the AI claims a security gap exists, it must cite the specific document and paragraph that serves as evidence. Trust is the product here. We are building guardrails that force the AI to “show its work.” If it can’t find the evidence, it must say “I don’t know,” rather than inventing a plausible answer.

This is the difference between a cool demo and a viable enterprise product. We are optimizing for precision over creativity.

The Future: Agentifying Consulting

We are standing on the precipice of a massive shift in the professional services industry. The era of the “static consultant” is ending. We are entering the era of Agentic Consulting.

Does this mean consultants are obsolete? Absolutely not. But their role must evolve.

In the future I envision, consultants will no longer bill hours for data collection and basic assessment. That work is drudgery. It is slow, expensive, and error-prone. CapabiliSense handles that layer.

This frees up the human experts to do what they are actually good at: high-level strategy, cultural change management, and decision-making. The AI provides the map; the human drives the car.

Why This Matters Now

The pace of technological change is accelerating. The lifespan of a competitive advantage is shrinking. Organizations that rely on quarterly or annual assessments to check their “digital health” will simply be too slow to survive.

You wouldn’t drive across a new continent with a hand-drawn map from 1990. You would use a GPS that updates in real-time when you miss a turn.

That is what I am building. CapabiliSense is the GPS for your transformation journey. It is designed to cut through the noise, bypass the politics, and show you exactly where you stand.

We are building this to lower that 70% failure rate to negligible numbers. It is time to stop guessing, stop hoping, and start sensing.

If you are tired of transformation initiatives that stall and static reports that gather dust, I invite you to follow this journey.