3 Strategies for Wicked Problems

4 min read
Jan 28, 2022 2:55:00 PM

What Makes a Problem “Wicked?”

Covid-19 and its knock-on effects creates many complex problems for business leaders, compounded by mixed signals from the market, unaligned internal stakeholders, and the risks of uneven solution implementation. In the late 1960s, Horst Rittel, a professor at UC Berkeley, characterized these complex problems as “wicked problems,” that include high levels of ambiguity, incomplete information, cross-sector inputs/outputs, and an ill-defined grasp of the initial problem. This term is now a foundation of design thinking.

In their 1973 paper, Horst Rittel and Melvin Webber of UC Berkeley described, “a wicked problem as not only difficult to define, because the proposed solutions are worse than the symptoms and inherently unsolvable without a societal shift.”

Most likely, your business is not directly curing the Covid-19 virus, thus, you are dealing with the knock-on effects of the virus on your suppliers, supply chains, employees, and customers. Each stakeholder has unique needs and thus offers conflicting data for your team to process. Where to begin?

We suggest diverging, seeking new information from our users through one-on-one interviews debriefed via an empathy map. Separating what users say, versus what they do and what users think, versus what they feel is the first step. The benefit is twofold: first, by targeting these four buckets of information, your team does not validate their hypothesis, but listens with openness and second, contradictions will undoubtedly emerge and trigger opportunities for action.

“When a customer says they want a cheaper solution, this never means sacrificing quality. Thus, the opportunity may lie beyond your contribution to the total solution.”

Only after embracing the ambiguity of divergent thinking can we have confidence that our voice of the customer is deep enough to begin prototyping solutions. If your first attempt at solving a “wicked problem” involves a timeline greater than two weeks or a budget greater than $100, our experience says either you’re testing too broad of a hypothesis. Go back and prioritize your user’s needs. What is their “must have?” This should be the focus of your first prototype.

Wicked problems require patience, optimism, and, most importantly, empathy before understanding is even possible.

For businesses to continue to thrive, they must embrace a radical diversity of signals from the market to inform the problem space, actively employ empathy for users to synthesize this data and align internal stakeholders, and iteratively prototype these solutions in a minimum viable product (MVP) format to test solutions with your existing and potential customers. This is the essence of the design thinking process that guides teams through a mutual understanding of the wicked problem so the solution addresses the real need.

How to Approach Wicked Problems?

Start with Curiosity

I love training my two dogs. Although I have a result in mind, reaching that end is not a straight line. For example, one dog is food-motivated while the other is retrieve-motivated. Without first understanding each dog’s motivations, a one-size-fits-all approach will fail. The same is true for wicked problems. First, we “observe to understand," which uncovers the user's needs even if it takes us “off course” from the shortest path to a solution.

As design thinkers, we begin by asking, “why,” understanding the question and only then, we attempt to solve the “problem.”

Segment to Address Challenges

Creating a breakthrough solution to “disrupt” an industry is an outcome. Executives want the best outcome; yet, the solution starts with describing the problem. Showing empathy for our users helps in this segmentation process. Companies often segment via an inside-out approach, e.g., prioritizing product features, whereas design thinking embraces an outside-in approach that requires understanding our stakeholders’ needs, then designing backwards to our capabilities.

Listen with Empathy

The nuance in this phase is a willingness to accept user feedback even if it contradicts our earlier assumptions. Listening with empathy risks disrupting a company’s status quo; however, listening with the end in mind only reinforces the orthodoxies that got us into this situation. Practicing empathy creates unexpected connections that lead us to deeper insights.

3 Strategies for Tackling Wicked Problems

1. Seek “New” and “Unusual”

Discovery is the first phase of the design thinking process where we seek “new and unusual” information to better understand the opportunity space and our users. Tools of the trade include empathy maps, user journeys, and persona templates. Each requires us to diverge, build empathy, and understand the opportunity space from our customers’ perspective.

2. Operate Outside of Your “Circle of Competence”

As organizations grow, their needs become more specific, just look at your job postings on your website. These specific roles are necessary to optimizing existing business operations. However, each person’s “circle of competence,” reinforces convergent thinking and blocks out “new and unusual” information that challenges the status quo.

Innovative organizations empower employees at all levels to share observations and solutions from outside their “circle of competence” to facilitate bottom-up strategies to emerging opportunities.

3. Separate Facts from Assumptions

Wicked problems are made worse by applying orthodoxies. Yet we intuitively know these problems will not be solved by the same tools and processes that are complicit in creating them. First principle thinking separates facts from assumptions to uncover the core elements of the challenge. It enables us to reverse engineer complicated problems and analyze the complex interconnections of the multiple causes, consequences, and cross-functional stakeholders of the problem.

Design thinkers commonly apply the "five whys" method (which is a modern framing of the Socratic questioning method) to uncover the real reason behind a user’s action or behavior. Ultimately, the goal is to uncover the baseline assumption or orthodoxy, such as, “it’s the way we’ve always done things.”


Like a doctor first understanding the patient’s symptoms or a construction company preparing land for building, design thinking has applications across a wide range of industries to understand your users and their needs and identify opportunities to create change and accelerate growth. And, yours is likely included.

Tell us a long-held industry orthodoxy that you wish to challenge. We’ll help you reframe the opportunity space, ideate disruptive innovations, and prototype minimum viable products to explore new verticals and industries for your company’s future growth.


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