How to Identify a Wicked Problem in Strategy and Decision-Making

There is often a moment, early in a project or initiative, when something feels slightly off. What initially appears to be a clear problem begins to shift—and what you may be facing is not a standard issue, but a wicked problem.

The problem appears clear enough at first. It can be described, scoped, and assigned. There is a sense that, with the right analysis and coordination, a solution can be found and implemented.

And yet, as the work progresses, the situation becomes harder to hold in place.

New aspects emerge that were not visible at the outset. Stakeholders begin to disagree not only over what should be done, but also over what the problem actually is. Attempts to move forward seem to generate new complications rather than resolve existing ones.

At that point, it is tempting to conclude that the problem has not yet been properly defined, or that more information is needed before a decision can be made.

Sometimes that is true.

But there are also situations in which the difficulty does not lie in incomplete analysis, but in the nature of the problem itself.

When the problem does not stay the same

In more familiar situations, problems tend to be stable. They may be complex, but they can be described in a way that holds over time. As understanding improves, the problem definition becomes sharper, and the path toward a solution becomes clearer.

Wicked problems behave differently.

They do not remain fixed while you are working on them. As you intervene, the situation changes. Elements that seemed peripheral become central, while earlier assumptions lose their relevance. The act of trying to solve the problem becomes part of what reshapes it.

This makes it difficult to say, at any given moment, that the problem has been fully understood.

When agreement is part of the problem

Another signal is the role of stakeholders.

In many projects, disagreement exists but can be resolved through discussion, evidence, or authority. Over time, a shared understanding emerges, even if not everyone fully agrees.

In wicked problems, disagreement is not simply a temporary obstacle. It reflects underlying differences in perspectives, interests, and values that cannot be easily reconciled.

Different actors are, in effect, working with different versions of the problem.

As a result, what counts as a “good” outcome is itself contested. Progress for one group may be seen as a setback by another.

When solutions do not resolve the issue

In more bounded situations, a solution leads to a sense of closure. Once implemented, the problem is either eliminated or, at a minimum, substantially reduced.

Wicked problems do not offer this kind of endpoint.

Interventions tend to produce effects that extend beyond the original scope of the problem. Some of these effects may only become visible over time. Others may create new issues that require attention in their own right.

The problem does not disappear; it evolves.

This makes it difficult to say when the work is “done.”

A wicked problem is a problem that cannot be clearly defined, has no single solution, and changes as you attempt to address it.

A comparison that often remains implicit

At this point, it can be useful to make a distinction that is often present but not explicitly articulated.

In more familiar (tame) problems:

• The problem can be defined in a stable way

• Stakeholders can, in principle, agree on what the problem is

• Solutions can be evaluated against clear criteria

• There is a recognizable point at which the problem is considered resolved

In wicked problems:

• The problem changes as you work on it

• Stakeholders hold fundamentally different views of what the problem is

• Criteria for success are contested and may shift over time

• There is no clear endpoint, only better or worse ways of responding

The difficulty is not that wicked problems are rare, but that they are often approached as if they were tame.

Why this distinction matters

If a wicked problem is treated as if it were a more stable, solvable one, a number of familiar patterns tend to appear.

Effort is spent on arriving at a definitive problem definition, even as the situation continues to shift. Plans are developed on the assumption that the key variables can be identified and controlled. When outcomes diverge from expectations, the explanation is often sought in execution rather than in the underlying assumptions about the problem.

This can lead to cycles of reanalysis and rework, without a corresponding increase in traction.

Recognizing that a problem is wicked does not make it easier in any immediate sense. It does, however, change what makes sense to do.

What follows from recognizing a wicked problem

If the problem cannot be fully defined in advance, then the aim is no longer to arrive at a complete and stable formulation before acting.

If stakeholders do not share a single view of the problem, then alignment becomes an ongoing process rather than a one-time step.

If interventions reshape the situation, then each move needs to be understood not only in terms of its intended effects, but also in terms of how it may change the conditions for subsequent action.

In this light, progress is less about solving the problem and more about shaping its development in a way that remains workable.

Learnings

Recognizing a wicked problem does not provide a solution, but it does suggest a different way of proceeding.

• If the problem does not stay stable, then waiting for a definitive formulation may delay action without increasing clarity.

• If stakeholders hold different, persistent views of the problem, then disagreement needs to be worked with rather than eliminated.

• If interventions change the situation, then each step should be treated as both an action and a source of new information.

• If there is no clear endpoint, then success is better understood as maintaining direction and coherence over time, rather than achieving closure.

This shifts the task from solving a problem to managing an evolving situation—one in which understanding and action develop together.

Further Reading

• The situation itself does not behave in a stable way