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Wicked Problems In Technology Projects

Updated: Feb 27



A speedometer with the engine warning light in.

Wicked problems are said to be non-linear and hard to define, and the solution depends on the context. Due to their complexity, wicked problems are subjective and often go unsolved. Attempts can be made at more pressing aspects of the problem, but the root itself is incredibly difficult to resolve.


They exist in all fields, from politics to education and technology projects. Classic examples of wicked problems in business can range from effective team management to full digital service transformation.


Wicked technology projects are especially hard to solve because the solutions are dependent on more than the technology; not only are there innumerable technology options, but the people and processes that use the technology are also factors in whether the project is successful. When we get into the complexities of the human factor and how many individuals operate, any existing problems are magnified exponentially.


How to identify a wicked technology project


Here are some ways wicked problems appear in technology projects:


1. The problem doesn't have an objectively 'right' solution.


There is no 'best' answer that everyone agrees on, as there are infinite potential solutions to the problem. The project team doesn't understand the full scope of the problem, which means stakeholders don’t know what to prioritize (or even if they should be working on it at all). There isn’t an inherent step-by-step to follow.


We often see wicked problems in legacy replacement projects where the intent is to replace one outdated piece of technology. Legacy systems are notoriously under-documented, and the knowledge of their functionality lives in multiple people's heads. Even if one service appears to be understood, there’s no telling what downstream systems are affected by different scenarios.


One objectively ‘right’ solution for one part of a legacy system can be catastrophic for another.


2. The solution is a 'moving target,' changing continuously in response to the stakeholders' immediate needs.


Business is always operational, so it’s likely the problem is evolving, which makes it hard to know the true nature of the problem. And at the same time, new problems are coming up.


Wicked problems have no fixed definition but evolve according to the situation and context in which they arise. They often involve multiple stakeholders with different goals and perspectives on what should be done, especially in the short term.


The hardest part of the moving target is keeping up with the solutions put in place in the meantime. From workaround processes to extra support staff, getting things to just work can also create new requirements and confuse the true nature of the problem.


3. There are many stakeholders, and they often have contradictory requirements.


Regarding technology projects, the biggest challenges can arise when many stakeholders have conflicting requirements. Legacy systems were built to meet everyone’s needs so everyone has a seat at the table and everyone’s needs are the highest priority.


Here are some examples:


Technical stakeholders want high-quality code that works as expected. They want fewer bugs in their software delivery pipeline and less time spent fixing them after delivery. This means they want short development cycles where they can deliver working software every few weeks or months instead of waiting until every feature has been designed and tested before they start coding.


Business stakeholders want new features as soon as possible. This does line up with the technical team’s requirement for short development cycles, but getting to that point will take longer due to a lack of understanding of the system as a whole.


4. New information continuously changes our understanding of the problem.


It can be difficult to understand the systems involved when there are no clear boundaries around the problem. It's not just one thing that needs to be changed; it's many things that need to change in concert.


As an extension to including all relevant taxes applicable to the services rendered in accordance with applicable tax laws since legacy systems are rarely fully documented, “new” information will always come up. As the project team attempts to resolve issues that have come up, the project scope will continue to change in ways you won’t expect while tending to the issues that have come up.


5. There are many possible solutions, but no one knows enough about the problem to know which one will be right.


Once the project's direction is set, there will still be decisions about implementing various parts of the solution.


This point encompasses all 4 of the previous points; when the complexity of the systems is not understood, the scope of the problems can’t be defined. Each individual problem has no stopping point - it can only get “good enough.” Instead of accepting this, project teams may spend more time perfecting solutions that only need to be good enough.


How do we find solutions to wicked problems?


The complexity of wicked problems means that there is no one right answer and simple solutions are likely to fail if they do not address enough aspects of the problem.


Technology projects are called "wicked" when they are not amenable to standard solutions or their problems are not soluble in any known way. Any standard, effective problems solving techniques can resolve surface problems, yet the overall problem is unique.


Every good idea needs to be tested. The more options you have for solutions, the more likely you’ll be to solve wicked problems at hand without creating more!


Technology projects are hard; wicked problems are harder


Most, if not all, organizations tackle wicked problems at some point.

To improve the chances of success with technology projects, it's important to consider the following:


  • Understand what makes your project unique — This can help you set realistic expectations about what's feasible within your time frame and budget without compromising your overall vision;

  • Understand the risks – Knowing the risk profile and having the plan to mitigate will guide decisions around what solutions to follow through with;

  • Understand its complexity — This will help you avoid getting bogged down in unnecessary details that could distract from your main goal;

  • Understand its impact — Make sure everyone involved understands how their contributions will affect the larger scope of work.


The best way to deal with wicked problems is to focus on the process of solving them rather than fixating on a specific solution. Because so many stakeholders have conflicting requirements, it's impossible to make everyone happy.

"We cannot solve problems with the same thinking that went into creating them." – Albert Einstein

If you think you’ve got a wicked technology problem on your hands, it’s important to get a second set of eyes.

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