Understanding Before Transformation

There is a number that everyone in this field can recite. Seventy percent of transformations fail.

It appears in nearly every article, every pitch deck, every board memo written to justify a new initiative or explain an old one. It is quoted so often that it has stopped being a finding and started being furniture.

It is also, when you go looking for it, almost impossible to source. Trace the number back and it dissolves into something more like folklore than research: a strict definition of success from one consulting firm, a wider “fell short of ambition” band from another, an opening-line assertion from a third with no study named beneath it, all echoing an older claim about change programs that a peer-reviewed review found had no empirical basis at all. The most-cited statistic in the transformation industry turns out to be a figure no one has cleanly measured.

I open here not to dispute that transformations struggle. They do; the failures are real, and anyone who has lived inside one does not need a percentage to believe it. I open here because the number is a perfect small example of the thing this entire essay is about. An organization can spend thirty years, billions of dollars, and the better part of its collective attention operating on a shared belief that no one ever actually examined.

The more interesting question was never the failure rate. It was the shape of the failures. And when you look closely at what actually goes wrong, the failures rarely look like what the word “transformation” leads you to expect. They do not, mostly, look like execution failures — teams that couldn’t build, tools that didn’t work, plans that weren’t followed. They look like something quieter and stranger. They look like organizations that changed the form of something they had never clearly seen.

What Transformation Forgot It Means

Transformation means a change of form. That is the whole of the word. Trans-, across; -form, shape. To transform something is to move it from one shape to another.

Somewhere in the last two decades the word was hollowed out and refilled. Now it means buying software. It means reorganizing. It means a program with a name and a budget and a steering committee. These are real activities and some of them are even necessary, but none of them is transformation, and treating them as though they were is the root of an expensive confusion.

Here is the confusion, stated plainly. You cannot change the form of a thing you cannot see.

A sculptor who cannot see the block cannot shape it. A surgeon who cannot see the anatomy cannot operate. And an organization that cannot see its own current form — how work actually moves through it, where value is actually created, what its people actually believe, where the friction actually lives — cannot transform that form, no matter how much it spends trying. It can only disturb it, and hope.

Most transformation initiatives skip directly to the disturbance. They begin with a target state, a future shape, a vision of what the organization should become. This feels like the responsible place to start, and it is exactly one step too late. Before you can responsibly describe what an organization should become, you have to be able to describe, accurately and in shared terms, what it currently is. That second thing is far harder than the first, and almost no one budgets for it, because it does not feel like progress. It feels like delay.

But it isn’t delay. It’s the survey you take before you build on a site, and everything skipped in the survey gets paid for later, once the foundation is already poured and the cost of moving it is real.

The Fragmentation Problem

Why is seeing the current form so hard? The instinctive answer is that organizations lack information, and the instinctive fix is to gather more of it. Both are wrong. Organizations are not starving for information. They are drowning in it. What they lack is a shared picture.

Consider a single initiative and the people around the table.

One person sees the process — the sequence of steps, the handoffs, the way the work is supposed to flow. Another sees the system — the platforms, the integrations, the data, the technical constraints. Another sees the risk — what is exposed, what is regulated, what could fail an audit. Another sees the customer — or the student, or the patient, or the citizen — and what the change will mean for them. Another sees the budget, and the quarter, and what has already been promised to whom.

Every one of these views is accurate. Every one is the product of real expertise and real attention. And not one of them is complete. The person who sees the process cannot see the risk. The person who sees the budget cannot see the customer’s experience of the thing being budgeted. Each is looking at the same organization and seeing a different organization, because each is standing in a different place, and the organization looks different from every place you can stand in it.

This isn’t a failure of intelligence; it’s the structural cost of how complex organizations are built. We create depth by dividing labor, and the division buys that depth by spending wholeness. A specialist sees further into her own domain precisely because she has stopped watching everyone else’s. So the fragmentation isn’t a flaw that crept in. It’s a byproduct of the very thing that makes the organization capable in the first place — the price specialization quietly charges for depth.

Which means the fragmented picture is the default condition, and the shared picture is the achievement — something that has to be deliberately built, because nothing about the ordinary operation of an organization builds it for you. Left alone, the pictures drift further apart, not closer together. Everyone becomes more expert, more confident, and more separately certain, and the gap between their certainties grows silently until something forces it into the open.

Where Misunderstanding Becomes Visible

Usually, the thing that forces it into the open is the technology.

This is why transformation failures so reliably get blamed on the system, the vendor, the integration, the platform. That is where the failure becomes visible — in the release that slips, the integration that won’t reconcile, the go-live that reveals two teams meant different things by the same word. It is genuinely tempting, in that moment, to conclude that the technology was the problem.

The technology was not the problem. The technology was the mirror.

Software is unforgiving in a way that conversation is not. Two people can leave a meeting with the same words and different meanings and never discover the difference, because language is elastic and human agreement is easy to fake, even to ourselves. But when those two meanings are encoded into a system — when one team’s definition of the customer has to actually connect to another team’s definition, in a database, in production — the elasticity runs out. The system demands that the two pictures become one, and if they were never reconciled upstream, they cannot be reconciled now, and the whole thing seizes.

The misunderstanding was there all along. It was there in week one, sitting quietly inside an agreement everyone thought they had. The technology did not create it. The technology found it, at the most expensive possible moment, and presented the invoice.

This is what we mean when we say that technology is where misunderstanding becomes visible — not where transformation begins. The most sophisticated platform in the world cannot supply an understanding the organization never had. It can only expose its absence, precisely, in front of everyone, after the money is spent.

The Sequence

There is an order to how an organization moves from raw material to real change, and most of the trouble comes from trying to skip the middle of it.

Information becomes knowledge. Knowledge becomes understanding. Understanding becomes alignment. Alignment makes confident decisions possible. Confident decisions make transformation possible.

Each link in that chain is load-bearing, and each is a different kind of thing.

Information is what the organization has in abundance — data, documents, dashboards, reports. It is inert on its own. Having it is not the same as knowing anything.

Knowledge is information that a person has actually absorbed and can use. But knowledge, crucially, lives inside individuals. Each specialist holds their own, and the sum of everyone’s separate knowledge is not the same as a shared understanding. It is exactly the fragmented picture described above.

Understanding is the step almost everyone skips, because it is the only one that cannot be done alone. Understanding, in the sense that matters here, is not a private mental state. It is a shared one — the point at which different people can look at the same complexity and see the same thing clearly enough to reason about it together. It has to be constructed, deliberately, out of the separate knowledge in the room. Nothing produces it automatically.

Alignment is what becomes possible once understanding is shared: not agreement enforced from above, but agreement that holds, because it rests on a picture everyone can actually see. Alignment without understanding is just compliance, and compliance reverses itself the moment no one is watching.

Decision made on that foundation holds. Decision made without it gets re-litigated in four weeks, wearing the costume of a new problem.

And only then, at the far end of a chain most organizations try to leap across in a single bound, does transformation become something you can actually steer rather than merely survive.

The pattern in failed initiatives is almost always the same. They have information and they have decisions. They are simply missing the understanding and the alignment that were supposed to connect them — and so the decisions sit on nothing, and quietly slide.

Understanding Is Built, Not Assumed

If there is one idea beneath all of this, it is this: understanding is an asset, not an assumption.

Organizations treat shared understanding as a precondition that already exists — as something you can presume walking into a room, the way you presume everyone speaks the same language. It is not. It is something you build, with real effort, out of the fragmented and separately-held knowledge of the people who do the work. And because it is built, it can also be lost: it degrades as people leave, as reorganizations scramble the picture, as time passes and the map stops matching the terrain.

Treating understanding as an asset changes what you do. Assets are produced deliberately. Assets are maintained. Assets can be measured, and their absence can be measured too — which is what the idea of Understanding Debt is for: the accumulated, compounding cost an organization pays for every decision it makes before the understanding beneath it is actually shared. You do not have to take my word that the cost is real. It is sitting in your own rework logs, your reversed decisions, your proliferating alignment meetings, waiting to be read.

Building understanding as an asset is not a mood or a value. It is a discipline, with a method — a way of working that organizes discovery, analysis, facilitation, design, and delivery around a single center of gravity, which is helping an organization see itself clearly enough to act. The method does not replace good Agile practice or good business analysis or good product discovery. It gives those practices a purpose they too often lose in the machinery: not to produce documentation, but to produce shared sight.

That’s the work, and it isn’t requirements or software or artifacts. It’s helping intelligent people who are each looking at a different organization discover that it’s the same organization — and finally see it together.

A Pattern Across Twenty-Five Years

I did not arrive at this thesis by theorizing about it. I arrived at it by doing the same work, without knowing it was the same work, for a very long time.

The path ran through more than two decades and six vantage points. It began in analysis, translating between what people asked for and what they meant. It deepened through operations, where the elegant picture meets the actual friction of the day. It expanded through architecture, where you learn that systems are just organizational assumptions rendered permanent. It sharpened through product leadership, where you must decide, repeatedly and under pressure, what actually matters. It matured through transformation consulting across financial services, higher education, and enterprise platforms, where the stakes and the scale grew but the underlying pattern did not.

For years I thought I was changing jobs. Different roles, different systems, different industries, different titles on the door. It took an embarrassingly long time to notice that beneath all of it, I had been asking one question the entire time, in every role, regardless of what the role was called:

How does an organization come to understand itself well enough to change?

Everything I now believe is downstream of finally seeing that the question was always the same. The frameworks, the method, the studio — none of it is a departure from that work. Organizational sensemaking is the name for it.

The Survey

No one has ever admired a survey.

You cannot see it in the finished building. It is not in the photographs. It was not at the ribbon-cutting, and nobody has ever stood in front of a structure and remarked on the remarkable understanding of the ground beneath it. The survey disappears the moment the foundation covers it, and it is the reason the foundation holds.

We fund what we can see. Transformation is the visible part — the program with a name, the platform going live, the growth someone can point to in a quarterly review. Understanding is the survey: unglamorous, invisible in the finished thing, and impossible to photograph. So it gets compressed, and then skipped, and then everyone is surprised when what was built on top of it will not stand.

Transformation does not fail for lack of talent. The people are almost always good. It does not fail for lack of tools; the tools have never been better. It fails because organizations try to change a form they have never clearly seen — because they fund the building and skip the survey, and hope the sequence can be skipped along with it.

It cannot. Understanding is not a courtesy that precedes the real work. It is the real work — the part that happens before anything visible can bear weight. Everything worth building in an organization rests on whether its people can finally see the same thing clearly enough to act on it together.

That is what this practice is for: to survey the ground before the building. To help organizations understand themselves well enough to transform with confidence.

Everything else is a consequence.

Understanding Before Transformation is the founding thesis of a studio for organizational sensemaking. It is grounded in established Agile, business analysis, product discovery, facilitation, and systems-thinking practice.