Retiring technical debt can be a wicked problem

Last updated on July 16th, 2021 at 07:38 pm

Prototypes of President Trump’s “border wall.”

Prototypes of President Trump’s “border wall.” Building the wall is an example of a wicked problem. Building prototypes in short segments of the wall is a tame problem. But these are just prototypes of short segments of the wall. They aren’t prototypes of the project.

Prototypes of the wall itself don’t demonstrate the process for taking private property, or how to build construction access roads, or the effects on wildlife, or how the government of Mexico will respond, or how to repair the wall when drug gangs destroy sections of it in isolated regions, or even the effectiveness of the wall. Prototyping works well for tame problems. It helps us project how the finished project will perform, and how difficult completing the project will be. But for wicked problems, prototyping is of limited value. As Rittel observes, prototyping can make the problem worse.

Photo by Mani Albrecht, U.S. Customs and Border Protection Office of Public Affairs, Visual Communications Division.

The theory of wicked problems originated with Horst Rittel in the mid-1960s. He was addressing “that class of problems which are ill-formulated, where the information is confusing, where there are many decision makers and clients with conflicting values, and where the ramifications in the whole system are confusing.” [Churchman 1967] The term wicked isn’t a moral judgment. It suggests the mischievous streak in these problems. Many of them have the property that proposed solutions can lead to conditions even more problematic than the original situation. Is it just me, or are you also thinking, “Ah, technical debt”? In this post, I suggest that retiring technical debt can be a wicked problem. I’ll show how wickedness explains many of the difficulties we associate with retiring forms of technical debt that involve many stakeholders, assets, revenue streams, policies, or strategies.


Horst Rittel was a design theorist at the University of California at Berkeley. His interest in wicked problems came about because designers must deal with the interactions between architecture and politics. In today’s technology-dependent enterprises, analogous problems arise when we retire technical debt. When we do, we affect multiple sets of quasi-independent stakeholders.

Applicability to the technical debt problem

In the years since Rittel originated the wicked problem concept, others have extended it. These extensions have led some to regard the concept as inflated and less than useful. But extension or less-than-useful concepts rarely occurs, I take it as an indicator of worth. The focus of this post, then, is applying Rittel’s version of wicked problems to the problem of designing a complex technical debt retirement project.

The wicked problem concept has propagated mostly in the realm of public policy and social planning. Certainly wicked problems abound there. Poverty, crime control, and climate change are examples. But I know of no attempt to explore the wickedness of retiring technical debt in large enterprises, but have a look below and see what you think.

Rittel defines a problem as the discrepancy between the current state of affairs and the “state as it ought to be.” For the purposes of technical debt retirement planning, the state as it ought to be might at times be a bit ambitious. So I take the objective of a technical debt retirement project to be an attempt to resolve the discrepancy between the current state of affairs and some other state that’s more desirable. For the present purpose, then, the problem is designing a technical debt retirement project that converts the current state of an asset to a more desirable state that might still contain technical debt in some form. But in that new state, the asset is in a better configuration.

A note on super-wicked problems

Actually, there is a subset of wicked problems—super-wicked problems—that I think might include some technical debt retirement problems. I address them in the post “Retiring technical debt can be a super wicked problem.”

For now, though, let’s examine the properties of wicked problems. Let’s see how well they match up with the problem of designing technical debt retirement projects.

Attributes of wicked problems

Rittel’s summary of the attributes of wicked problems [Rittel 1973] convinced me that major technical debt retirement projects present wicked problems. Here are those attributes. In what follows, I use Rittel’s term tame problem to refer to a problem that isn’t wicked. (See also [Kreuter 2004])

1. [No Definitive Formulation] Wicked problems have no definitive formulation

For any given tame problem, it’s possible to state it in such a way that it provides the problem-solver all information necessary to solve it. That’s what definitive formulation means. For wicked problems, on the other hand, our understanding of the problem depends on the solution we’re considering. Each candidate solution might potentially require its own understanding of the problem.

When designing a technical debt retirement project, we must fully grasp the impact of the effort on all activities in the enterprise. Each proposed project plan has its own schedule and risk profile. Each proposed project plan affects enterprise activities in its own way. In principle, each candidate approach to the effort affects a different portfolio of enterprise assets in its own unique order. Because examining all possible candidate project plans is impractical, choosing a project plan by seeking an optimal set of effects is also impractical. By the time you’re ready to execute a given project plan, the data supporting your decision might be obsolete.

2. [No Stopping Rule] Wicked problems have no stopping rule

For any given tame problem, solutions have “stopping rules.” Stopping rules of solutions are signatures that indicate clearly that they are indeed solutions. For example, in a chess problem to be solved in N moves, N and checkmate provide a stopping rule. We know how to count to N and the position of checkmate is well defined.

Wicked problems have no stopping rule.

When planning a major technical debt retirement project, we must determine the attributes of the project. The attributes include a task breakdown, a sequence for performing the tasks, a resource array including both human and non-human resources, a risk plan including risk mitigations and risk responses, a revenue stream interruption schedule, and so on. For each such plan, we can estimate the direct and indirect costs to the enterprise. We can project the effects of the plan on market share for every affected product or service. Every plan has these attributes. When we compute them for a given candidate plan, the result doesn’t reveal that we’ve found “the solution.” We will have found only an estimate for that given solution. What we learn by doing this doesn’t reveal whether or not a “better” solution exists.

There is no indicator contained in any given candidate solution that tells us we can “stop” solving the problem. Most often, we just stop when we run out of time for finding solutions. In some cases, we stop when we find just one solution.

3. [Solutions Are Good/Bad] Solutions to wicked problems aren’t true-or-false, but good-or-bad

The criteria for finding solutions to tame problems are unambiguous. For example, if a candidate function satisfies a differential equation, it’s a solution to the equation. The volume of concrete required to pave a section of roadway is a single number, determined by computing the area of roadway and multiplying by the thickness of the roadbed, and subtracting the volume of any reinforcing steel.

The solutions to wicked problems have no such clarity. When evaluating a candidate project plan for retiring a technical debt, we can estimate its cost, the time required, interruptions in revenue streams, and the timing of resource requirements. But determining how “good” that is might be difficult. Much depends on what other demands there might be for those resources or funds. Much also depends on the political power of the people making those demands. No single number measures that.

4. [No Test of Solutions] There is no immediate ultimate test of a solution to a wicked problem

To test a candidate solution to a tame problem, the problem-solving team determines whether the solution meets the requirements set in the tame problem statement. The consequences of implementing the solution are all evident to the problem-solving team. The team has everything it needs to judge the success of the solution.

Not so with wicked problems. Any candidate solution to a wicked problem generates waves of consequences. As these waves propagate, some of the problem’s stakeholders might find the solution unsatisfactory. They’ll report their objections, possibly through politically powerful people or organizations. Because the consequences can be so diverse, the team can’t anticipate all of them. In some cases, the team might have difficulty understanding how the troubles that plague some stakeholders were actually related to the implemented solution. Some undesirable consequences can be far more harmful than any intended benefits are helpful. In other cases, the undesirable consequences might remain undiscovered until long after the solution is in use and operational.

When designing a technical debt retirement project, it’s necessary to determine everything that must be changed, what resources must be assembled to do the work, and what processes might be interrupted, when and for how long. Only rarely, if ever, can we determine all of that with certainty in advance. For that reason, determining that the design of the project is “correct” isn’t possible, except perhaps in the probabilistic sense. We never really know in advance that we’ve found a solution. Most of the time, after execution begins, we must make adjustments along the way, in real time.

5. [No Trial-and-error] Every solution to a wicked problem is a “one-shot operation”; because there is no opportunity to learn by trial-and-error, every attempt counts significantly

When solving tame problems, we can try candidate solutions without incurring significant penalties. That is, trying a solution might require some effort, and therefore incur a cost. But it doesn’t otherwise affect the ability to find other solutions. Wicked problems are different. Every attempt to “try” a solution leaves traces that can potentially make further solution attempts more difficult, costly, or risky than they would have been if we hadn’t tried that solution. These traces of past solution attempts might also impose constraints on future solutions. Those constraints can effectively transform the wicked problem into a different wicked problem. This property makes trial-and-error approaches undesirable and possibly infeasible. Indices of such undesirability are the half-lives of the traces of attempts to address the problem. A long half-life might mean that the problem solver has only one shot at addressing the problem.

When designing a technical debt retirement project, we sometimes try to “pilot” a potential approach to determine difficulty, costs, feasibility, political issues, or risk profiles. Even when we can revert the asset to its former state after a pilot is completed or suspended, the consequences for stakeholders and for stakeholder operations might not be reversible. When we next try another “pilot,” or perhaps a fully committed retirement project, these stakeholders might be significantly less willing to cooperate. Every attempted solution can thus leave political or financial traces like these, making future attempts riskier and more challenging.

6. [Solutions Are Not Describable] Wicked problems don’t have an enumerable (or an exhaustively describable) set of potential solutions, nor is there a well-described set of permissible operations that we can incorporate into the plan

In devising solutions to tame problems, one common approach entails first gathering the full set of possibilities. Next, we screen them according to a set of favorability criteria. Reducing the field of possibilities is a useful strategy for finding optimal or acceptable solutions to tame problems.

Wicked problems defy such strategies. Gathering the full set of possible solutions to a given wicked problem can be a wicked problem in itself. We cannot parameterize the set of possible solutions to a wicked problem. We cannot define a finite set of attributes that fully covers the solution space. For these reasons, we can never be certain that the set of candidate solutions is complete.

Candidate designs for technical debt retirement projects present this same quality. We have a dizzying array of choices. In what order should we retire different kinds of technical debts? In what order should we address the debts different assets bear? Can we “refinance” portions of the debt to intermediate forms [Zablah 2015]? What kinds of refactoring should we perform and when? Because options like these are neither denumerable nor parameterizable, we cannot know whether a given set of candidate project designs is complete.

7. [Essential Uniqueness] Every wicked problem is essentially unique

Among tame problems, we can define classes or categories of problems that share a solution method. That is, using the method associated with a given class, we can solve all problems in that class. For example, we can solve all second order linear differential equations with the same method.

Even though we can define classes of wicked problems whose members are in some sense similar, that similarity doesn’t enable us to find a unified solution strategy that works for every member of the class.

So it is with designing technical debt retirement projects. Certainly, the collection of all technical debt retirement projects is a class. But the problem of designing a given retirement project is essentially unique. What “works” for one project in one enterprise in one fiscal year probably won’t work for another project in another enterprise in another fiscal year. It might not even work for another project in that same enterprise in that same fiscal year. Elements of the solution for one project might be useful for another project. But even then, we might need to adapt them to the conditions of that next project.

This essential uniqueness property of technical debt retirement projects collides with a common pattern decision makers use when chartering major efforts. That pattern is reliance on consultants, employees, or contractors who “have demonstrated success and experience with this kind of work.” Because each technical debt retirement project is essentially unique, relying on a history of demonstrated success is a much less viable strategy than it would be with tame problems. Decision makers would do well to keep this in mind when they seek approaches, leaders, and staff for major technical debt retirement efforts: no major technical debt retirement project is like any other.

8. [Problems as Symptoms] We can regard every wicked problem as a symptom of another problem

With tame problems or wicked, we typically begin the search for solutions by inquiring as to the cause of the current condition. When we find the cause or causes, and remove them, we usually find a new problem underlying them. Thus, for wicked problems, what we regarded initially as the problem is thereby converted into a symptom of a newly recognized underlying problem. By repeating this process, we escalate the “level” of the problem we’re addressing. Higher-level problems do tend to be more difficult to resolve, but addressing symptoms, though easier, isn’t a path to ultimate resolution.

Rittel also observes that incremental approaches to resolving wicked problems can be self-defeating. The difficulty arises from the traces left behind by incrementalism, as described in the discussion of the unworkability of trial-and-error strategies. Rittel provides the example of the increase in difficulty of changing processes after we automate them.

To regard the wicked problem of designing a technical debt retirement project as a symptom of a higher-level wicked problem, we must be willing to regard as problems the very things that make the technical debt retirement project design effort a wicked problem. That is, the processes that lead to formation of technical debt, or that enhance its persistence, are themselves wicked problems. For example, one might inquire about how to change the enterprise culture so as to reduce the incidence of technical debt contagion. To undertake major technical debt retirement efforts without first determining what can be done to limit technical debt formation or persistence due to contagion or due to other processes, might be unwise.

9. [No Controlled Experiments] The existence of a discrepancy representing a wicked problem can be explained in numerous ways. The choice of explanation determines the nature of the problem’s resolution

When addressing tame problems, problem-solving teams can often perform controlled experiments. The general framework of these experiments is as follows. The team forms a hypothesis H as to the cause of the problem, conjecturing a solution. Then assuming H is correct, and given a set of conditions C, they deduce the consequences E that must follow. If any elements of E don’t occur, then H is incorrect. The process repeats until an H’ is found that provides all elements of E. H’ then provides the basis of a solution. Essentially, this is the scientific method.

With wicked problems, the method fails in numerous ways. Foremost among these failure modes is the inability to control C. That is, interventions that might be required to set C to be a desired C0 tend to be impossible. Moreover, even if we can establish C0, the experiments that determine whether E is observed tend to leave the traces discussed in Proposition 5 [No Trial-and-error]. Finally, the determining the presence or absence of the elements of E is usually subjective.

When planning enterprise-scale technical debt retirement projects, as with many projects of similar scale, we believe that we can benefit from running a pilot of our proposed plan, to determine its fitness. These trials are sometimes called “proof of concept” exercises. However, because we cannot control the conditions in which we execute the pilot, we cannot be confident that our interpretation of the results of the pilot will apply to the actual project. Moreover, a small-scale pilot cannot generate some of the effects we most want to observe because they occur only at full scale. These effects include staff shortages, resource contention, and revenue interruption incidents.

10. [100% Accountability] The planner (or designer) has no right to be wrong

In solving tame problems, solvers can experiment with proposed solutions. They make conjectures about what might work, and gather the results of trials to determine how to improve their conjectured solutions. There is no social or legal penalty for failed conjectures.

In solving wicked problems, experiments don’t exist. Any trial solution is a real solution, with real effects on stakeholders and later, real effects on the problem solvers themselves. Problem solvers are accountable for the undesirable consequences of each solution, whether it’s a trial or not.

In planning a technical debt retirement project, any attempt to gather data about how the approach would affect the enterprise could potentially have real, lasting, deleterious effects. The project bears the costs associated with these consequences, if not officially and financially, then politically. The politics of failure can lead to serious consequences for the problem solvers. Any approach that the team deploys, on any scale no matter how small, can potentially create financial problems for the enterprise, and political problems for anyone associated with the technical debt retirement project.

Last words

The fit between wicked problems and technical debt retirement project design looks pretty good to me. But the research on a subset of wicked problems—super wicked problems—is also intriguing. I’ll look at that in my next post. After that, we’ll be ready to examine which approaches to retiring technical debt take these matters into account.


[Churchman 1967] C. West Churchman. “Wicked problems,” Management Science 14:4, 1967, B-141–B-142

Available: here; Retrieved: October 16, 2018

Cited in:

[Kreuter 2004] Marshall W. Kreuter, Christopher De Rosa, Elizabeth H. Howze, and Grant T. Baldwin. “Understanding wicked problems: a key to advancing environmental health promotion.” Health Education and Behavior 31:4, 2004, 441-454.

Available: here; Retrieved: October 26, 2018

Cited in:

[Rittel 1973] Horst W. J. Rittel and Melvin M. Webber. “Dilemmas in a General Theory of Planning”, Policy Sciences 4, 1973, 155-169.

Available: here; Retrieved: October 16, 2018

Cited in:

[Zablah 2015] Raul Zablah and Christian Murphy. “Restructuring and Refinancing Technical Debt.” Proceedings of the IEEE 7th International Workshop on Managing Technical Debt (MTD). IEEE, 2015.

Available: here; Retrieved: February 13, 2016

Cited in:

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