Delivering Tailorability to the Tactical Level in the Age of AI
BLUF | Shadow IT is not a compliance problem. It is a design failure. The Intelligent Enterprise is where we need to go. Intelligent Transformation is how we get there. Solving tailorability at the tactical level is what we build along the way.

The opportunity to close the gap, delivering Tailorability (Image by J Eselgroth with Gen AI)
Have you ever started a task and realized the business system does not meet your needs? So you open a spreadsheet [or some other tool]. You craft a solution with the tools you have, not the tools you need.
Maybe it becomes an Access database. Maybe you sidestep corporate IT and purchase software because you needed to solve a problem yesterday. The official process moves so slowly that workarounds become the only path forward.
Does this sound familiar? This is not rebellion. It is survival.
Innovation Without Integration
Honorio Padrón III, captured the pattern perfectly in his recent LinkedIn article, The Real AI Bubble: “The result was innovation without integration.” He was describing the flood of AI investment that never connected to enterprise architecture. That line applies to the last decade of enterprise technology with uncomfortable precision.
We bought the platforms. We built the dashboards. According to Auvik Networks, 30-40% of enterprise IT spend still flows into Shadow IT. Zluri also reports that the average organization uses more than 270 SaaS tools. More than half were never approved.
You can call it noncompliance. I see it as unmet need.
I have written before about the 5Ps of Intelligent Transformation: People, Policy, Process, Partners, and Platforms. Shadow IT sends signals across all five. People improvise because platforms cannot flex. Processes fracture because policy cannot adapt. When you see Shadow IT, you are seeing the 5Ps under stress.

The 5Ps under stress (Image by J Eselgroth with Gen AI)
Then came generative AI. People hoped it would close the gap. Instead, it exposed it. MIT found that 95% of enterprise gen AI pilots delivered no measurable value. Not because the ideas were bad. Because the work was isolated. Innovation without integration, all over again.
The Architectural Pivot
Honorio raises this tension with the shift toward the Intelligent Enterprise. That destination is right. Reaching it requires Intelligent Transformation. This is an intentional journey that rebuilds architecture, capability, and culture together.
AI factories represent a critical milestone. Think of them as the physics layer of the enterprise finally consolidated. Data, identity, security, governance, compute. All in one coherent environment. They give intelligence a place to live, evolve, and scale.
But here is the part we do not talk about enough. AI factories may fix the backbone. But they do not fix the last mile.
Walk into a claims unit, a field office, a military unit, or a distribution center. Core platforms give you transactions. Dashboards give you trends. Real action sits in the exceptions. The judgment calls. The tiny workflow steps no product manager ever designed.
If Intelligent Transformation is the journey and the Intelligent Enterprise is the destination, then tailorability at the tactical level is what we build to complete the trip.
Safe Tailorability Changes Everything
Tailorability is the ability to deliver capability that stays malleable at the point of need. It resolves the tension between economies of scale and the reality that one size never fits all. Standardize the foundation. Adapt the experience. This applies to digital systems and physical operations alike.
Inside an AI factory, tailorability becomes safe. Not the free-for-all of Shadow IT. Not the rigidity of a monolithic system. Something in between.
Imagine a team lead who notices friction in a weekly process. Today, she can file a ticket and wait six months. Or she can solve it herself with an unauthorized tool. Inside an AI factory, she has a third option. She describes the friction in plain language. The environment generates a micro-app in minutes, not months.

Before and After delivering Tailorability to the tactical level (Image by J Eselgroth with Gen AI)
This is the shift from violinist to conductor. She sets intent and lets intelligent systems perform the heavy lift. Craftsmanship moves from execution to orchestration.
Because it runs inside the AI factory, it inherits everything the enterprise requires. Security. Data permissions. Audit trails. It feels like Shadow IT in speed. It behaves like enterprise IT in safety. That is the breakthrough.
When this works, people reduce the amount of tools through the side door, and maybe even stop altogether. They build inside the system. Every micro-app feeds back into the Business Body of Knowledge. Tribal knowledge becomes documented and learnable. The gap closes through a legitimate path, not forced compliance.
The Path Forward
You do not need a fully built AI factory to start. But remember the super-serum principle: AI amplifies what already exists. Sloppy processes scale sloppiness. Strong foundations scale excellence.
Start by mapping real workflows. Capture exceptions and judgment calls. Create a safe sandbox for tailorability. Standardize data, identity, and permissions. Pair technologists with operators. Measure what happens outside the system.
For decades, enterprises have cycled through the same pattern. Build a system. Watch people work around it. Crack down. Repeat. Each cycle hits the same effort hump. The steep climb before benefits appear.

Flattening the curve through Intelligent Transformation (Image by J Eselgroth with Gen AI)
Intelligent Transformation flattens that curve. Safe tailorability eliminates the friction that creates the second bump. Constraints become compounding returns instead of fixed trade-offs.
The path to the Intelligent Enterprise runs through the last mile. The last mile finally has a chance to keep up.
References
- Honorio Padrón III, “The Real AI Bubble: Inside Zero-Latency Decision™ Capitalism and the Extinction of Many of the Existing 80,000 AI Startups” https://www.linkedin.com/pulse/real-ai-bubble-inside-zero-latency-decision-many-80000-padr%C3%B3n-iii-tqo0e/
- Auvik Networks, “Shadow IT Stats” https://www.auvik.com/franklyit/blog/shadow-it-stats/
- Zluri, “Shadow IT Statistics: Key Facts to Learn in 2024” https://www.zluri.com/blog/shadow-it-statistics-key-facts-to-learn-in-2024/
- MIT (reported via AI Magazine), “Why 95% of Enterprise AI Investments Fail to Deliver” https://aimagazine.com/news/mit-why-95-of-enterprise-ai-investments-fail-to-deliver

