Last updated on November 2nd, 2018 at 07:44 am

In a recent post I explored conditions that tend to make designing a project to retire technical debt a wicked problem. And in another post I noted some conditions that tend to make designing a project to retire technical debt a super wicked problem. But not all technical debt retirement project design efforts are wicked problems, and “wickedness” can occur in degrees. Designing these projects can be a tame problem, especially if we target the technical debt for retirement early in its existence. In this post I’ll explore degrees of wickedness in retiring technical debt, and propose a framework for dealing with technical debt retirement project design problems that are less-than-totally wicked.

#### The degree of wickedness of a problem

As a quick review, here are the attributes of a wicked problem as Rittel and Webber see them [Rittel 1973], rephrased for brevity:

- There is no clear problem statement
- There’s no way to tell when you’ve “solved” it
- Solutions aren’t right/wrong, but good/bad
- There’s no ultimate test of a solution
- You can’t learn by trial-and-error
- There’s no way to describe the set of possible solutions
- Every problem is unique
- Every problem can be seen as a symptom of another problem
- How you explain the problem determines what solutions you investigate
- The planner (or designer) is accountable for the consequences of trying a solution

Rittel and Webber held that wicked problems possessed all of these characteristics, but Kreuter, et al., take a different view, which I find compelling [Kreuter 2004]. Their view is that wicked problems and tame problems lie at opposite ends of a spectrum. A problem that satisfies all ten of the criteria would lie at the wicked end of the spectrum; one that satisfies none would lie at the tame end.

A close examination of Rittel’s and Webber’s ten criteria reveals that they aren’t black-and-white; that we can regard each one as occurring in various degrees. For example, consider Criterion 1: “There is no clear problem statement,” which Rittel and Webber express as, “There is no definitive formulation of a wicked problem.” Burge and co-author McCall, who was a student of Rittel, offer this interpretation [Burge 2015]:

Here by the term *formulation* Rittel means the set of all the information need [sic] to understand and to solve the problem. By *definitive* he means *exhaustive*.

The original language of Rittel and Webber, with the interpretation of Burge and McCall, is indeed black-and-white. But one can easily imagine problems that satisfy this criterion to varying degrees. That is, one problem formulation might have *almost* everything one might need to understand and solve the problem, while another might have *almost none* of what one might need. In some of these cases, the problem solver might be able to make reasonable assumptions to fill in any gaps and then make some progress towards a solution. Or the formulation as given might be incomplete, but by working on a solution despite these lacunae, the missing information might reveal itself, or might arrive as a result of other research. For these reasons, I find it possible to regard the degree to which a problem satisfies Criterion 1 as residing on a continuum. And I expect one can make analogous arguments for all ten criteria.

This “continuum hypothesis” doesn’t conflict with the definition of a wicked problem. Wickedness still requires that all ten criteria be satisfied absolutely. But the position where a problem resides on the Tame/Wicked spectrum can be determined, conceptually, by the degree to which the problem fits the ten criteria of Rittel and Webber. In other words, as we address the problem of designing a technical debt retirement project, we can contemplate and consider the degree of wickedness of the problem; not merely that a problem is wicked or it isn’t.

The degree of a problem’s wickedness provides useful guidance. Specifically, if a problem clearly satisfies nine of the ten criteria, but not the tenth, according to Rittel and Webber, it would not be categorized as a wicked problem. Because it might be extraordinarily difficult to resolve, we would do well to treat it as wicked with respect to the nine criteria it satisfies. We would use that information to guide our decisions about where we apply resources, and what kind of resources we apply. The model of wicked problems provided by Rittel and Webber would be useful, even though the problem itself might not meet their definition in the strictest sense.

And so we’re led to the concept of the dimensionality of wickedness.

#### The dimensionality of wickedness

If we regard the ten criteria of Rittel and Webber as dimensions in a ten-dimensional space, then our “wickedness spectrum” becomes much richer. Maybe too rich, in the sense that its complexity presents difficulty when we try to think about it. But the concept of the dimensionality of wickedness can be useful, if we consider each dimension as having a degree of wickedness. This enables us to choose problem-solving techniques that work well for wicked problems that owe their wickedness to specific dimensions. That is the approach taken by Kreuter, et al. [Kreuter 2004]

This suggests a framework for designing (or re-designing) technical debt retirement projects:

- Deal separately (and first) with any parts of the technical debt retirement project design problem that are tame
- Determine the importance of each one of a set of “indicators of wickedness”
- Use that information to determine which of the ten criteria of Rittel and Webber are most relevant to this particular technical debt retirement project design problem
- Apply established approaches that account for the relevant criteria to formulate a project design

This program is too much for a single post. But I can make a start in my next post with descriptions of the indicators of wickedness, including an examination of the implications of each of these indicators relative to the presence of each of the ten criteria of Rittel and Webber. The next step will be to suggest techniques for technical debt retirement project design problems that meet, to some degree, the criteria of Rittel and Webber.

Buckle up.

### References

[Burge 2015] Janet E. Burge and Raymond McCall. “Diagnosing Wicked Problems,” Design Computing and Cognition 14, 2015, 313-326.

Available: here; Retrieved: October 25, 2018

[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

[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

- Glossary and Terminology
- Retiring technical debt can be a wicked problem
- Degrees of wickedness
- Indicators of wickedness
- Retiring technical debt from irreplaceable assets
- Legacy TDR decisions

### Other posts in this thread

- Managing technical debt
- Leverage points for technical debt management
- Undercounting nonexistent debt items
- Crowdsourcing debt identification
- Demodularization can help control technical debt
- Legacy debt incurred intentionally
- Metrics for technical debt management: the basics
- Accounting for technical debt
- Three cognitive biases
- The resilience error and technical debt
- Synergy between the reification error and confirmation bias
- Retiring technical debt can be a wicked problem
- Retiring technical debt can be a super wicked problem
- Degrees of wickedness