Planning is killing your transformation—here's how to get it rolling

Uncertainty is the problem

Every year, organizations spend massive amounts of time and resources on transformation initiatives designed to change how they work, think, and operate. They create detailed implementation plans, establish new performance metrics, and launch comprehensive training programs. These approaches are methodical, well-resourced, and systematic.

They also routinely fail to produce lasting change.

McKinsey popularized statistics showing that roughly 70% of organizational transformations fail. Similar numbers from other consulting firms and from academic research have shaped how we think about change: as inherently difficult and likely to disappoint. Even transformations that initially appear successful often collapse when employees revert to old behaviors months later.

The more interesting question is what the minority that succeeds actually does. A metaanalysis of 200 transformation case studies found a striking pattern: they don't follow the prescribed sequence of any established change model. They adapt their approach continuously as they learn what actually works.

This points to something fundamental: when it comes to the complex challenges of organizational transformation, picking a framework, making a plan, and sticking to it is not the way to go. That type of linear planning is built for a different kind of problem.

The natural reaction: grasp for certainty

Transformations change the foundation of how an organization operates. They involve multiple, if not all, aspects of the organization, cutting through departments, tiers, roles, and geography. A transformation aims to develop new core capabilities, fundamentally changing the way value is created and the key behaviors of the people who create it.

Transformation is, by nature, uncertain. There are no silver bullets, best practices, or industry standards that will guarantee impact. This uncertainty is deeply uncomfortable for most organizations and management teams, so they reach for the tools they know best.

In an attempt to escape that unease, most organizations treat transformation as a design, planning, and execution problem. They define requirements, create detailed plans, execute them systematically, and measure progress against the original specifications and objectives. Well-intentioned transformation teams and leaders instinctively reach for rigorous planning methods in a challenge that doesn't yield to those tools.

The misdiagnosis: a complex problem treated as a complicated one

In complexity, the more you plan, the more you distance yourself from reality. As facts and statistics accumulate, slide decks grow, and Gantt charts develop, a false sense of certainty clouds your mind. All those ambitious solutions to important problems are—however well-intended—assumptions. The more perfect your plan becomes, the more you want it to work, and the less open you will be to testing those assumptions against the harsh reality.

But, over time, reality pushes back and assumptions don't hold. Not everyone is on board, perspectives shift, and the needle isn't moving as you expected. Before you know it, you're in a state of even more confusion than before all that rigorous work began.

Now, what do you do? You're at a road crossing, choosing between two equally bad options.

Either you halt the transformation in everything but name—keep analyzing, designing, and planning, but don't change anything because the perfect route forward hasn't revealed itself. You're stuck in analysis paralysis.

Or you push forward, grabbing the first available solution and rolling it out with brute force—at least you're doing something, and assertiveness is a trait that is celebrated in many organizations. You're jumping to conclusions.

But there is another way.

Organizations that succeed with transformation understand that it is a complex undertaking and treat it accordingly. Not by control, planning, or focusing solely on the assertive execution of activities, but by pointing out a clear direction, testing what works in reality, and learning continuously to act and navigate in uncertainty.

You’re used to treating transformations as a complicated problem, which you solve by analyzing, designing, planing and executing. But you need to start treating them as a complex problem instead, which you can only solve by trying, learning, deciding and adapting as you go.

Before we go on, the distinction between complicated and complex used here draws on Snowden's Cynefin framework. In short: a complicated problem can be solved by analysis and expertise. A complex problem must be navigated by experimentation and learning. The latter requires a different way of thinking.

Confidence through learning, not planning

In the traditional, linear approach to transformation, confidence comes from thoroughness and comprehensiveness. The analysis needs to provide enough information to guide the design. The design needs to include everything that should be implemented. And the implementation plan needs to cover all steps until completion.

All the important decisions are made at the beginning—when learning from reality hasn't even begun.

In complex, uncertain situations, the best point in time to make an important decision is at the last responsible moment: as late as possible to maximize learning, but not so late that it creates unnecessary risk. The same logic applies to transformations: every decision made before it was necessary means you wasted the learning you could have gained in the meantime.

Done right, each decision made is clearer than the one before it as the transformation progresses and we learn from changes in reality.

Change reality first, then draw the map

Have you ever seen an organization where the map—processes, routines, role descriptions, learning programs, and posters of values in the entry hall—really matched reality? Probably not. And that's not strange. The modern organization is far too complex, dynamic, and fast-changing to be captured in documents.

What's ironic is that organizations keep attempting to change reality, the actual terrain of work, by making updates to the map. The thinking goes: "We're not performing, the system must be broken. Let's update it, and we'll perform again!" But if the map can't keep up with reality, how on earth should reality adapt to … documents?

Instead, you need to dive straight into the messy reality of work, figure out what sticks and what doesn't, and let people do things differently. When reality has moved, update the map so others can find their way to the new reality, too. That's continuous change in practice.

Validate, validate, validate!

In complexity, cause and effect can only be understood in retrospect—there are simply too many interacting variables to predict which action will produce which outcome. Thus, all decisions are based on assumptions, not facts.

"What's the real problem?" "What's a good solution?" "Will that solution work in our reality?" "Will it work across the organization?" You can never know for sure; you need to validate (validate, validate!) all your assumptions all the time.

This mindset turns classic logic on its head. In a linear world, execution is everything. "We're on this train now, it hasn't arrived until every car is at the end station. Let's make it so!" Everyone wants—no, needs—the change initiative to succeed. Their job might depend on it. So they do what they can to prove that the decisions they made are correct.

In uncertainty, that approach is dangerous. When assumptions are not validated yet pushed all the way to the end station—that's how projects fail, resources are wasted, change fatigue is born, and unnecessary complexity is built into our organizations. The sooner we figure out we're solving the wrong problems, the better. It saves us time, resources, and human creativity, and we can direct all that towards solving the right problems instead.

But for change to be continuous, it needs to get rolling in the first place. So, how do you find the confidence to start when you don't have all the answers up front? That's the point of our sandpaper*, Planning is killing your transformation, of which you've now read the first two chapters.

Three strategic decisions will get your transformation rolling

If you want to read the rest of this paper, where we share a transformation strategy with three key decisions that will move you from planning in your imagination to transforming in reality, you can download Planning is killing your transformation here.

*A sandpaper is a white paper, but with a bit more Friktion.