November 2025

Why most "digital transformation" fails (and what to do instead)

We've all seen the playbook. A company decides it needs to "transform." They hire a Big 4 consultancy, buy a suite of expensive enterprise software (Salesforce, ServiceNow, SAP), and appoint a Chief Digital Officer.

Two years and $10M later, what has changed?

Usually, very little. The tools are different, but the work is the same. People are still emailing spreadsheets back and forth, but now they also have to log into a slow web portal to "update the system of record."

The Map is Not the Territory

The fundamental error is optimizing the org chart instead of the work. Most transformations start by defining roles and departments. They assume that if you fix the structure, the work will follow.

But work flows horizontally, across silos. Value is created when a customer request moves from Sales to Engineering to Support. When you optimize vertically (within silos), you often break these horizontal flows.

Map Reality First

Before you buy software or reorganize, you must map how the business actually operates. Not the SOPs (Standard Operating Procedures), but the real paths.

  • Who actually talks to whom?
  • Where does data get re-entered manually?
  • What happens when the "happy path" fails?

Only when you make the invisible work visible can you begin to optimize it. Otherwise, you're just paving cow paths—digitizing chaos.

Need help mapping your reality?

I help organizations uncover their hidden workflows and build systems that actually fit.

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