Jory MacKay on October 29, 2024 What are wicked problems? How to tackle complex problems and projects
With factors including new stakeholders, technology systems, organizational politics, turbulent economics, and changing sponsor priorities, it’s easy to see why 41% of projects are classed as being highly complex.
But even the most complex projects pale in comparison to so-called ‘wicked problems’ — problems and projects with their own unique characteristics, interdependencies, and no definitive right or wrong answer.
As a leader, to avoid being part of the 70% of businesses that fail due to complexity, success relies on your ability to identify, analyze, and solve wicked problems.
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In this article, we’ll dive deep into wicked problems, including what they are, how to spot them, and a seven-step guide to solving even the most complex problems you’ll face at work.
What is a “wicked problem”? What makes them so dangerous?
Wicked problems are problems with many interdependent factors, characteristics, and challenges that make them seem impossible to solve.
While most commonly referred to when tackling social and societal issues, wicked problems also exist in the workplace — specifically surrounding topics such as culture, transformation, operational crises, and people management.
But what makes wicked problems so wicked?
Here are just some of the most common factors that make these problems so challenging to solve:
- Multiple interdependencies. Wicked problems have several interdependencies with other issues, sometimes even to other wicked problems. That means to fix them, you need to unpick a wide web of systems, processes, and people.
- No silver bullet. There’s no right or wrong way to fix a wicked problem, only options with varying levels of discomfort. This lack of a silver bullet means, no matter the outcome, the problem never truly goes away.
- Each one is unique. Each wicked problem is unique, meaning you cannot re-use a solution from a previously solved problem. This means leaders cannot draw on previous experiences. Instead, each requires a long and analytical process to solve.
- One-shot solution. Many wicked problems can only be solved with a one-shot solution, meaning it’s not always possible to test and learn different answers. This makes solving wicked problems risky, with no guarantee of success.
- They are infinite. The most challenging wicked problems can never be truly solved. When you apply one solution it goes on to create further issues. Essentially, as you cut one head off, two grow back.
A common wicked problem is cultural transformation. While a company may identify their culture needs fixing, actually changing it is extremely challenging.
This is because every company’s culture is unique, can change overnight, has multiple interdependent factors, has no right answer to fix it, and as the culture changes it breeds new challenges to overcome. Thus, the problem of culture is most definitely wicked.
How are wicked problems different from other issues?
We all face problems in our working lives, but how does a wicked problem truly stack up?
To understand what we’re dealing with, let’s compare simple, complicated, complex, and wicked problems side-by-side:
| Problem type | What it is | Example |
|---|---|---|
| Simple | Simple problems are those where we clearly understand the problem, the solution is easily developed, and there are no additional dependencies. | Developing an Android app item: With a clear understanding of the user’s needs and the Android technology, this is fairly simple to solve and deliver. |
| Complicated | Complicated problems are those where the problem is easy to understand and there are no dependencies – but the solution is complex. | Choosing a new payroll solution: The user’s needs are clear, but there are multiple technology options available, all with different pros and cons. |
| Complex | Complex problems are those where the problem is easy to understand, but the solution is complex and has multiple dependencies. | Updating an end-of-life, embedded technology system: The problem is defined, but the solutions are complex and will introduce knock on impacts to other systems. |
| Wicked | A wicked problem is where the problem itself is hard to define, the solution is complex and undefined, and there are multiple dependencies. | Overseeing a competitive digital transformation strategy: The problem is always evolving with new solutions emerging all the time. Each problem or solution is linked to multiple parts of the existing operation. |
While there are crossovers between simple, complicated, complex, and wicked problems, the level of analysis and care you need to take increases at each level. For example, developing quick, iterative solutions is risk-free for simple problems, but may cause further challenges as the complexity increases.
The most challenging wicked problems can never be truly solved.
6 questions to help determine if you’re dealing with a “wicked” problem
As a project or team leader, when a wicked problem crops up, you need to put your best team forward to tackle it. But while all problems seem scary at first, you would rather not waste the time and effort of your best people on a simple or complicated matter.
To help you quickly assess a wicked problem, here are some questions to ask yourself:
- Do you have clarity of the problem and its root cause?
- The cause is unclear, and the problem is difficult to fully articulate - 3 points
- The cause is unclear, but the problem is easy to describe - 2 points
- The cause and problem is understood and agreed - 0 points
- Have you come across a similar problem before?
- No - 3 points
- Yes - 0 points
- How many interdependencies does the problem have with other business areas?
- More than five - 3 points
- Between one and four - 2 points
- None - 0 points
- How well can you determine the consequences of the problem?
- Consequences are completely unknown - 3 points
- Some consequences are known - 2 points
- All consequences are known and understood - 0 points
- Is the best course of action clear?
- Actions and their effectiveness are impossible to predict - 3 points
- The effectiveness of an action can be assessed after implementing - 2 points
- The best action can be determined and is easy to implement - 0 points
- Once implemented, how easily can your solution be changed?
- The solution is impossible to change - 3 points
- The solution is difficult to change but could be done - 1 points
- The solution would be easy to change - 0 points
If you scored 12 or above: Your problem is more definitely wicked and needs maximum time and resources to try to solve it.
Anything under 12: You likely have a complex or complicated problem that, while it may seem challenging, should be able to be resolved comfortably.
How to tackle complex problems in the workplace
Even though wicked problems are the most complex, daunting, and mind-boggling of all, they’re not impossible to solve if you follow a logical process.
If you’re facing a wicked problem, here’s a seven-step guide to help you assess the situation, devise a plan, and take action!
1. Step back to see the entire problem
Because of their interdependencies, to assess the scale of wicked problems, you need to pull yourself out of the details to see the bigger picture. This will help you gather all the facts and think more strategically.
Steps you can take:
- Start workshopping. Getting together as a team is a great way to form a collective view of the problem at hand. Use mind-mapping and brainstorming techniques to get all of your thoughts out in the open.
- Create an information repository. In these stages, tools like Planio are great at helping the team pull that information into one place, either in a document repository, wiki, forum, or team chat. This information can then be shared with new team members, stakeholders, or external suppliers at the click of a button!
As a leader, success relies on your ability to identify, analyze, and solve wicked problems.
Real-life example:
John is managing a cultural transformation program for MotorSure, with the aim of improving the company culture based on feedback in the annual staff survey. The feedback is basic, but clearly shows people feel unsatisfied with the company.
To start, John gets the team together to brainstorm on all the contributing factors to company culture to assess the scale of the problem.
2. Get diverse internal stakeholder feedback
Wicked problems need input from people with a wide range of expertise. Once you’ve mapped the team’s view of the problem, reach out to subject-matter experts to get their thoughts and opinions, too.
Steps you can take:
- Ask targeted questions. Wicked problems have a habit of growing arms and legs. So, when you ask for stakeholder feedback, make sure it’s targeted around the information or expertise you require.
- Get real user feedback. If your wicked problem is IT systems orientated, try throwing in some user interviews to get a real-life perspective on how the problem is impacting those people day-to-day.
Real-life example:
Armed with some initial thoughts, John and the team reach out to critical stakeholders in HR, Comms, and Operations to gain expert opinion on the problems with MotorSure’s culture.
The input points to a number of contributing factors that could all be improved. John and the team reach out to a sample set of employees to gain deeper feedback on those factors and how they could be improved.
3. Spend longer than you normally would on external research
When solving wicked problems, it’s easy to get stuck in the trap of ‘the way we’ve always done it.’ To overcome this, get an outside view by investing additional time in external research, leaning on lessons learned in other organizations and the expertise of consultants, thought leaders, and regulators.
Steps you can take:
- Search for inspiration. Search online or on social media platforms such as LinkedIn for stories and articles from companies who have faced and overcome similar challenges – there might be a nugget of information you can draw on.
- Lean on experts. Wicked problems are highly complex and need the best brains to help solve them. Oftentimes, consultancies or think tanks have experience in helping companies solve complex problems, so don’t be afraid to spend some money on external support.
Real-life example:
John reaches out to Sparks, a workforce consultancy specializing in cultural transformation programs. They help John and the team run some workshops to think about the problem at hand from different angles, suggesting some root causes of the issue based on work they’ve completed with previous clients.
4. Revisit your principles and values to help guide your approach
Once you’ve defined the underlying issues of the wicked problem, it’s time to begin planning how you’re going to fix it. Before you do, take a moment to revisit your values, as they’ll help guide your approach.
Steps you can take:
- Align values and outcomes. As a team, take the time to reassess the values of your company and your project team to guide how you’ll make the change. For example, a customer-focused organization may choose a solution that limits any impact on customer operations. Whereas, a commercially focused organization may prioritize the cheapest solutions.
Real-life example:
John holds a workshop for the team to review MotorSure’s values and set principles for how the team will move forward. MotorSure are currently focused on establishing their brand in the market, so the team decides to focus on a solution that helps them solve the problem, while also driving positive PR and enhancing their reputation.
5. Build your tolerance for uncertainty and risk
Once you know the guiding principles of your solution, you need to draw out your red lines. This will help you set boundaries you cannot cross and give team members an element of control and certainty around where the solution can and can’t go.
Steps you can take:
- Set your risk appetite. This article from the Risk Leadership Network provides great tips to help you set your own risk threshold, including how to make effective and considered decisions while still driving fast performance.
- Get a plan in place. From there, you can begin to build out your own risk management plan. If you’re struggling, you can also tap into our guide on the 11 most common project risks and even get a free risk management template.
Real-life example:
As the size and the scale of the wicked problem come to life, John is worried that a future solution may have the ability to make the culture worse. To help, he works with his sponsors to determine a risk appetite, establishing the minimum and maximum impacts they’re happy to have on the business. He uses this to identify risks for the project, including a further drop in employee morale and potential impacts on company finances.
6. Solutionize and test with smaller “pilot projects”
Now that you’ve laid all the groundwork, it’s time to start developing and testing potential solutions. This is where you and the team will need to think outside the box to come up with a revolutionary idea to a wicked problem. Then, you’ll test the idea on a small scale to see if it has the desired outcomes.
Steps you can take:
- Validate ideas. Especially if you’re working in a product-led environment, once you’ve come up with an idea, you need to validate it. The Planio guide to product idea validation can help here, laying out a step-by-step approach to creating, validating and testing left field ideas.
- Build your confidence. If you’re struggling to get those creative juices flowing, it may be because you’re struggling with limiting beliefs. As a team, work through building your confidence to help you overcome those mental blocks.
Real-life example:
John’s project team comes up with three ideas to improve culture: focus-time Fridays, investing in more regular socials, and creating an employee voice forum.
They validate these ideas with Sparks, who provide some additional tweaks to add extra value. John and the team implement them within the Operations department and monitor feedback from employees.
7. Implement, review, and go again
Once you’ve tested a solution to a wicked problem on a small sample, it’s time to push on and launch more broadly. This is especially true for wicked problems with a one-shot solution, where you simply have to bite the bullet and trust that the solution will work!
Steps you can take:
- Go for it. Launches of any type are nerve wracking moments, but none more so than new product launches. Check out the Planio guide to product launches to help you get inspired by different ways to launch a new solution out to your target audience.
- Adapt and iterate. Like all things Agile project management, the solution may not be 100% on the first try. Keep in touch with stakeholders to gather feedback and look for ways to continually improve for your next implementation.
Real-life example:
After some initial success with the employee voice forum, John’s project team decides to launch the concept out to the wider business. It’s a success, giving employees a place to provide feedback and vote for additional changes.
But, the forum also provided a platform for new culture-damaging issues to emerge, meaning that, like most wicked problems, further solutions are needed to continue solving the evolving wicked problem!
Organization is a superpower when tackling wicked problems
Organizations are complex, and wicked problems only add fuel to the fire. Given their unique, ever-changing, and complicated nature, wicked problems require teams to think outside of the box, with no guarantee the solution they choose will actually work.
But the best way to solve a wicked problem? Structure!
Tools like Planio are great at helping project teams improve their organization, with features for tracking and managing tasks, actions, risks, communication and more! By getting your admin straight, it gives you more time and energy to focus on solving wicked problems and, ultimately, improving your chance of project success.
Try Planio with your own team – free for 30 days (no credit card required)
