Surviving the Experience of Working on a Wicked Problem

The views expressed are those of the author and do not necessarily reflect the views of ASPA as an organization.

By Tanya Settles
June 26, 2026

Recently, I walked away from a public meeting convinced that I had failed.

The process started well enough. Participants engaged thoughtfully. New ideas were beginning to emerge. Then the conversation unraveled. Frustration escalated into anger as deeper systemic tensions surfaced. Perspectives collided. There was even some name-calling. By the end of the meeting, I found myself wondering whether I had led my client down the right path.

After two days of introspection and questioning everything, I realized I might have been asking myself the wrong questions. This wasn’t about whether the meeting was a success. The real question was how governments and communities persevere when confronting problems that are inherently unsolvable. Like all problems of this nature, there are no clear definitions, straightforward solutions or easy measures of success.

The sting of failure and disappointment never feels good, but I did learn three important lessons.

Lesson 1: Expect Resistance

Resistance is not necessarily evidence that the process is broken or that the problem is hopeless. Resistance may be evidence that the problem is truly wicked. In governance, we tend to assume that resistance means poor communication, stakeholders don’t understand the true nature of the problem or the process needs refinement. Admittedly, sometimes these things are true. But dig a little deeper and you see more.

Wicked problems involve competing values, interests and definitions of success. The more complex the problem, the more open to interpretation success or a solution becomes. When multiple stakeholders who are passionate about the issue or deeply entrenched in their perspectives come together, resistance should not surprise us. It should be expected.

If everyone agrees on the problem and its solution, the issue probably isn’t wicked. The problem is that resistance often feels like failure.

Lesson 2: Don’t Confuse Discomfort with Failure

Public servants often judge success too quickly. We look for immediate wins or evidence that something useful occurred. We tend to leave difficult meetings thinking, “That went badly,” “Nothing was accomplished” and, of course, “We should never do that again.”

But what if, just below the surface, the meeting revealed something important?

Once I peeled away my own reaction and explored what was really said, I found hints of fear that the problem was so complex it might never be solved. Hidden distrust surfaced, barriers became visible and concerns emerged that were previously unspoken. There was anger and, while some of it was directed toward people in the room, much of it was aimed at stakeholders who were not present. Once I set aside my own bruised ego, I heard something different: the legitimate fear of people who were directly affected by the problem itself.

Adaptive leadership often creates discomfort because it forces people to confront competing values and difficult tradeoffs. Wicked problems nearly always require adaptive work, and discomfort is a sign that the real issues have finally entered the room. But learning is valuable only if we decide to do something with it.

Lesson 3: Resist the Urge to Retreat

After a difficult experience, there’s a strong desire to return to familiar approaches, narrow participation, avoid experimentation and reduce risk. I’ll admit that during my two days of post-meeting introspection, I considered all of these alternatives. My first reaction was to return to a process that felt safer and more predictable.

Then I realized retreat can masquerade as prudence.

It is tempting to return to familiar processes that generate less conflict. But wicked problems rarely yield to familiar approaches.

The fact that an experiment produced discomfort doesn’t always mean it failed. It may reveal something important. While there is value in reducing discomfort, especially for the people experiencing the most direct impacts of the problem, avoiding conflict entirely does not lend itself to durable solutions.

Solutions are found when we learn and adapt.

The opposite of retreat is not persistence. It is adaptation.

Scholars Brian Head and John Alford argue that wicked problems are best addressed through collaboration, adaptation and incremental progress rather than definitive solutions. This means a willingness to engage in adaptive leadership, experiment, learn from failure as much as success and resolve to try again. Not every intervention succeeds, but every attempt should generate learning. When stakeholders with diverse perspectives and experiences convene with a shared purpose, even if they can’t fully define the problem, there is opportunity.

Surviving the Wicked Problem

After a difficult experience, we all face a choice. One option is to give up and abandon hope. The other is adaptation.

In complex and uncertain environments, progress rarely comes from getting everything right the first time. Instead, progress emerges through experimentation, reflection and adjustment and, yes, sometimes failure.

The goal is not perfection. The goal is to learn enough from each attempt to make the next one better.

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Author: Tanya Settles is the CEO of Paradigm Public Affairs, LLC. Tanya’s areas of work include relationship building between local governments and communities, restorative justice and policy and program dynamics, strategy and evaluation. Tanya can be reached at [email protected]. The opinions in this column and any mistakes are hers alone.

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