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The Lorenz Attractor of Chaos Theory

The Social Dilemma is a Wicked Problem

& How to Address Wicked Problems

There’s been a lot of buzz about the documentary “The Social Dilemma” that was released on Netflix last year. It’s been a great catalyst for starting much needed critical discussions on ever more urgent social issues.

When participating in these discussions it’s not uncommon to hear the following solutions or some variation of them being proposed:

  • The Hermit Approach — We just need to get off social media
  • The Social Pressure Approach — We just need to convince the tech companies to be more ethical
  • The Regulatory Approach — We just need more laws and government oversight
  • The Silicon Valley Approach — I’ve figured out the tech solution which will solve all our problems — people just need to listen to me
  • The Egalitarian Approach —We just need to eradicate bias and be more inclusive, etc.
  • The Education Approach — We just need to teach everyone to be more aware of what is going on

None of these ideas are bad, but none are particularly good either. It’s not that these ideas don’t have merit, it’s that none of them meaningfully solve the dilemmas of social media, the attention economy and surveillance capitalism.

For instance, we won’t be able to convince everyone to stop using social media as presented in the Hermit Approach. Social media a normalized and useful way in which communities stay connected in today’s world. Asking people to stop using social media today is the equivalent of asking people to stop using electricity.

The Social Pressure Approach may work for some time, but given that tech companies have already shown their willingness to act unethically, there is no guarantee that given the right circumstances and mixed with the right incentives and enough impetus, they won’t go back to their unethical ways.

The Regulatory Approach has merit, but regulation is always late to the party and typically only succeeds in establishing a game of cat and mouse where regulation is created and the tech giants figure out the loop holes.

The Silicon Valley Approach is suspect since the very problems that we are dealing with now, stem directly from the technology that was supposed to solve all of humanity’s problems.

The Egalitarian Approach is unlikely to completely solve the issues as humans are inherently biased and will remain so into the foreseeable future. Proposing to eradicate bias is equivalent to eradicate the diversity of our various skin tones.

The Education Approach is an important element for sure, as we must first learn to be aware of what is going on before we can actively and successfully address problems. However, simply knowing what is going on is no longer enough. Bad actors in tech have become so skilled at using our brain’s cognitive biases and illusions against us that even when we know what the problem is, we still cannot stop our automatic responses. It is equivalent to trying to avoid thinking about pink elephants when someone explicitly forbids us to think about pink elephants — of course all we are now thinking about is pink elephants.

The reason these proffered solutions are incomplete is actually quite simple — we are dealing with what is known as a wicked problem and wicked problems don’t have clear, singular, and simple solutions.

In fact a key characteristic of a wicked problem is that it is almost always an unsolvable problem. An easily understood wicked problem is crime. We can and certainly should fight crime and an individual crime can be “solved” in that a culprit can be found and be brought to justice by the law, but we cannot solve the issue of crime, nor will crime ever be completely eradicated.

A subclass of crime is the illegal drug trade, efforts against which, in the US, have been labeled as “The War on Drugs.” This is a terribly unfortunate misnomer as wars have an end —the fight against illicit drug trafficking does not have any meaningful end. The illegal drug trade will never be completely eradicated as long as there is misery, joy, entrepreneurial spirit, boredom, etc. and it is folly to frame efforts against the illegal drug trade as if it is a war that can be won and ended.

Now the idea of social media being a wicked problem leads to a critical question:

How then should we approach addressing a wicked problem?

There is a brilliant paper published by Keith Grint titled “Wicked Problems & Clumsy Solutions: The Role of Leadership” that aptly portrays the scope and breadth of the nature of wicked problems. The paper is quite dense and in all honesty took me a while to read through during which time I took copious notes. I have linked to the paper above so you can read it for yourself, however the following is my endeavor to convey a summation of the overarching ideas presented in the paper skimming past some of the reasoning and examples that are presented.

How then do we typically approach problems?

The approach primarily depends on the type of problem encountered.

When encountering a problem that requires change, we typically do not undertake any or all kinds of change. We typically only undertake particular or specific kinds of change.

In short, general, pre-established solutions to wicked problems fail because:

“no org changes are the same as other org changes.”

Stated in reverse, all organizational change is different from any other organizational change.

What typically happens is we apply the standardized approach methods used to address tame problems to similarly address wicked problems. Wicked problems by definition, however, are inherently different than any other problem ever encountered.

If wicked problems were the same as other problems than pre-established methods for approaching problems would have already solved the wicked problem.

The fact that wicked problems remain wicked is the evidence that using standard, established methods for tackling and resolving wicked problems is not adequate and will not suffice.

Therefore, wicked problems necessitate that completely new and possibly radical tactics are pursued in the course of addressing them. Tactics that allow for the pursuit of any and all types of change — not just particular types of change that are already known and have already been established.

When we approach addressing a wicked problem from a “let’s try what we know works” angle instead of a ”“let’s try anything” angle — we limit ourselves to addressing the problem only via existing methods.

This limited approach implies that the answer already exists which in turn begs the question:

If a method or tactic to solve the problem already exists, why hasn’t the problem been solved?

Clearly we must first ascertain what type of problem we are dealing with and if we find that it is a wicked problem, we must expand our methods for addressing the problem from a “let’s try what we know works” to a “let’s try anything” approach.

Now to tackle a wicked problem optimally, requires us to consider an additional question:

Which leadership role is optimal for addressing which type of problem, and in particular, which style is optimal for addressing a wicked problem?

There are three primary roles that deal with problem solving:

Managers, Leaders, and Commanders.

Managers deal with problems in the realm of “deja vu” or “seen this before” and are best suited to addressing tame problems systematically according to a priori knowledge.

Leaders deal with problems in the realm of “ vu jade” or “never seen this before” and are best suited to addressing wicked problems by having the wisdom and experience to know that before they can take any action they must first ask:

What is the question or questions we should be asking to address this wicked problem?

Wicked problems which require Leaders in order to optimally address them typically:

  • have longer time periods
  • need more strategic perspectives
  • require solving something novel/atypical/unusual

Now if we accept the differences in the definitions of the roles of Managers and Leaders we can say that:

  • The act of managing requires utilizing the similar methods to routinely solve similar problems. Essentially managers use a predefined list of actions taken to solve a problem the last time it emerged, thereby resolving similar problems over and over again.
  • The act of leading requires reducing the anxiety of others who face the unknown by facilitating the construction of an innovative response to a novel problem, rather than utilizing documented processes that have already been successfully applied to problems encountered previously.

In effect, a wicked problem is a problem where the answer to the problem does not already exist — it needs to be found and that can only be done by tackling the problem from an all angles approach.

The more approaches we take to a problem, the more likely we are to stumble upon a solution to the problem that works, but this requires something that resembles creative chaos or creative anarchy.

Management is rooted in certainty and only requires tackling previously encountered problems with previously established and successful methods and attack vectors.

Leadership is rooted in uncertainty and requires tackling new and novel problems that have NOT been previously encountered with new and unorthodox methods and attack vectors.

Now a tame problem may certainly be considered complicated but it is always solvable through a set of unilinear actions. Additionally the problem is very likely to have occurred before. With these types of problems there is a limited degree of uncertainty and thus it is best associated with management.

Tame problems are akin to puzzles — simply apply a scientific approach properly and the best solution will naturally emerge.

The (scientific) manager’s role, therefore, is to provide the appropriate processes — the veritable standard operating procedure (SOP) — to solve the problem.

Wicked problems, on the other hand, are complex, rather than just complicated — that is, the problem cannot be removed from its environment, solved, and returned back without affecting the original environment.

Moreover, there is no clear relationship between cause and effect. Such problems are often intractable.

For instance — “we cannot provide everything for everybody; at some point we need to make a political decision about who gets what and on what criteria.
This kind of inherently contested arena is typical of a wicked problem and while we often turn a collective blind eye to such issues we cannot avoid making a decision at some point.”

To be clear, the categorization of problems as either tame, wicked or sometimes even critical is completely subjective (as opposed to objective). The type of problem encountered generally depends on perspective — where you are “positioned” relative to the problem and what you know.

These perspectives lead many to inappropriately address a wicked problem as a tame problem, which in turn leads to the misconception that the problem has a simple solution.

At this point it is crucial to remember, as mentioned previously, that for wicked problems there is no end nor complete and elegant solution to the problem.

Thus in tackling a wicked problem we must recognize, admit, and accept that we can never completely solve a wicked problem.

No doubt this is a difficult pill to swallow. One can justifiably ask:

So what’s the use of addressing an unsolvable, wicked problem?

This is a fatalist response to life and if you’re reading this, you are clearly not a fatalist. The question then becomes as redundant as asking, “what’s the use of addressing crime?” Most agree that addressing crime is a worthwhile endeavor for the good of humanity.

Although, yes it is true that we cannot solve a wicked problem, we can still assert our will, our right to dignity and our sovereignty upon the problem, which in turn can lead to improving circumstances for the whole of humanity. Facing wicked problems head on instead of avoiding them or misunderstanding them is our best chance at achieving an optimal outcome for the human race.

So although leadership can be thought of as a continuous exercise of uncertainty, conventionally, we associate leadership with precisely the opposite, that is:

  • the ability to solve problems
  • the ability to act decisively
  • to know what to do in any situation

But wicked problems typically embody the inverse of this — we cannot solve wicked problems and we need to be very wary of acting decisively, precisely because we cannot know what to do when a wicked problem is encountered.

If we knew what to do with the problem, it would be a tame problem. Yet the pressure to act decisively, often leads us to try to solve a wicked problem as if it was a tame problem.

When we try to solve wicked problems as tame problems, the typical result is that other problems emerge that compound the original wicked problem.

Only collective engagement can hope to address wicked problems.

Wicked problems must therefore typically be addressed collectively — as a group or community rather than on an individual basis such as an entrepreneur might.

Tame problems might be solved individually in the sense that an individual is likely to know how to deal with it — e.g. an entrepreneur.

But since wicked problems are defined by the absence of an answer on the part of the leader, then it behooves the individual leader to engage the collective in an attempt to come to terms with the wicked problem.

In other words, wicked problems require the transfer of authority from an individual to the collective because only collective engagement can hope to successfully address a wicked problem.

Uncertainty implies that leadership is not a science but an art — the art of engaging a community in facing up to complex problems.

The leader’s role with a wicked problem, therefore, is to ask the right questions rather than provide the right answers because the answers may not be self-evident and will require a collaborative process to make any kind of progress.

Now to review, there are three types of roles that deal with problem solving:

The role of a commander is to find the appropriate answer in a crisis.
The role of a manager is to find the appropriate process to a tame problem.
The role of a leader is to find the appropriate question to a wicked problem.

The social construction of a problem legitimizes the deployment of a particular form of authority, whether it be commander, manager or leader.

It is often the case that the same individual or group with authority will switch between the commander, manager and leader roles as they perceive — and constitute — the problem as either critical, tame or wicked, or even as a single problem that shifts across these boundaries.

Indeed, this shifting of roles by the decision maker (often perceived as ‘inconsistency’ by a decision maker’s opponents) is crucial to success as the situation, or at least our perception of it, changes.

Leadership remains the most difficult of the approaches and the one that many decision-makers will avoid at all costs because it implies that:
1. The leader does not have the answer
2. That the leader’s role is to make the followers face up to their responsibilities (often an unpopular task)
3. That the ‘answer’ to the problem is going to take a long time to construct and that it will only ever be a ‘more appropriate solution’ rather than ‘the best solution’
4. That it will require constant effort to maintain.

It is far easier, then, to opt for and prefer either a managerial style solution where a tried and true process is engaged or a commander style solution where “the answer” is enforced upon followers (some of whom may prefer to be shown ‘the answer’ anyway).

Success (in addressing a problem) is rooted in persuading followers that the problematic situation is either one of a critical, tame or wicked nature
and that therefore the appropriate authority form is either commander, manager or leader in which the role of the decision-maker is to either provide the answer, organize the process or ask the question, respectively.

One particular skill that all three leadership roles require is the ability of re-framing problems, in other words seeing the problem differently so as to rethink how it might be addressed differently.

The more decision-makers constitute the problem as a wicked problem and interpret their power as essentially normative, the more difficult their task becomes, especially with cultures that associate leadership with the effective and efficient resolution of problems.

A wicked problem requires long term and collaborative leadership processes with no easy solutions, and where everyone must participate and share the responsibility of solving the problem.

Wicked problems are wicked precisely because they reside at the cross-section of the contrary cultures of individualism, hierarchy, and egalitarianism, thus we need all types of cultures to solve wicked problems.

Rather as the Rock, Paper, Scissors game works, no single (elegant) option is sufficient for gaining the upper hand against all other options, but all of them together have something to offer.

This individual weakness of each elegant (single mode) solution and the mutual requirement for support leads us to the final aspect of addressing wicked problems:

Clumsy Solutions —

Single mode (elegant) solutions can only ever address elements of wicked problems, but do not attack the wicked problem entirely as a whole entity.

We need to eschew the elegance of the architect’s approach to problems (start with a clean piece of paper and design the perfect building anew)
and adopt the approach of the Bricoleur (the do-it-yourself craft-worker).

As Kant said:

“Out of the crooked timber of humanity, no straight thing was ever made.”

Put another way, to get some purchase on wicked problems we need to start by accepting that imperfection and making do with what is available is not simply the best way forward but the only way forward.

We should avoid alienating significant constituencies — but note that progress does not depend upon consensus — consensus would be too elegant and take too long.

We need to start by asking:

What do we all (or at least most of us) agree on?

We also need to assume that no-one has the solution in isolation and that the problem is a system not an individual problem and not a problem caused by or solved by a single aspect of the system.

We need to take the bricoleur’s (tinkerer or iterator) line and start from where we are.

The best we can hope for is a non-linear, “crooked” response to stitch together an inelegant or clumsy solution combining all three modes of understanding (individualist, hierachical, egalitarian) and making use of the fatalists acquiescence to go along with the changing flow of public opinion and action.

A clumsy solution space actually requires all three frameworks attacking the problem simultaneously:

  • Individualists — e.g. technical innovations
  • Egalitarians — e.g. community, concensus, inclusivity
  • Hierachists — stronger global regulation, laws, policies, standards, etc.

The attempt to tame a wicked problem through a scientific or rational solution is to treat the problem as if you were an architect facing a tame problem rather than a bricoleur facing a wicked problem.

The quest for elegant (scientific) solutions is part of the problem not the solution.

Wicked problems are inherently political in nature not scientific or ‘rational’ and any useful progress is likely to be only via a clumsy negotiation of the common ground.

For this our bricoleur actually needs to acquire Aristotle’s Phronesis (a.k.a. mindfulness, prudence, practical virtue/wisdom) — the wisdom to acknowledge that the situation is not like any other, combined with the experience to recognize that such wicked problems require a qualitatively different approach from either tame or critical problems.

Socrates proposes that thinking with Phronēsis represents virtue.
This view equates Phronēsis with virtue, making all virtuousness a form of Phronēsis. Being good, is to be an intelligent or reasonable person with intelligent and reasonable thoughts.

Phronēsis allows a person to have moral or ethical strength.

Socrates explains how Phronēsis, a quality synonymous with moral understanding, is the most important attribute to learn, although it cannot be taught and is instead gained through the development of the understanding of one’s own self.

A critical component of a necessarily clumsy solution is to combine elements of all three cultural types: the individualist, the egalitarian and the hierarchist, into a (clumsy) solution-space and within each of these types are techniques that, when combined, might just pry the wicked problem open enough to make some progress with it.

Since every wicked problem is slightly different from all others, and since we cannot know the answer initially (otherwise it either a tame or critical problem), there is no guaranteed method available. The skill of the bricoleur is in trying new things out, setting loose experiments to see what works and what doesn’t, and all this requires an initial acceptance that you — our great esteemed leaderdo not have the answer.

Bricoleurs make progress by stitching together whatever is at hand, whatever needs to be stitched together, to ensure practical success.

This is not the clean world of analytic models and rational plans for progress to perfection. This is the world where wise leaders are opportunistic, ad hoc, devious, creative and original.

Thus the clumsy solution is an interweaving of:
- Positive Deviance not negative Acquiescence
- Constructive Dissent not Destructive Consent
- Negative Capability

- Collective IQ not Individual Genius
- Empathy not Egotism
- Community of Fate not Fatalist Community

- Questions not Answers
- Relationships not Structures
- Reflection not Reaction

Incrementalism is a common, though not universal, obvious feature and useful method of policy-making, as well as personal decision making.

The first step for the hierarchist is to acknowledge that the leader’s role has to switch from providing the answers to asking the questions. Such questions demonstrate that the problem facing the organization is not of the common-garden variety — this is something different that needs a different response. In other words the leader should initiate a different narrative that prepares the population for collective responsibility.

The reason that this role sits within the Hierarchists’ camp is that only the hierarchical leader has the authority to reverse his or her contribution from one of answers to one of questions (aka the General).

The job of a leader is not to know the answer but to categorize the problems and if they are wicked or look like they have the possibility of being or becoming wicked, then it is incumbent upon the leader to ask the appropriate questions.

Linked to this switch in approaches of the leader from expert to investigator is the related requirement that hierarchists are most suited for — relationships not structures.

Research on social networks and systems theory makes it clear that organizational structures are empty vessels until populated by the relationships that make them work.

In other words, a ‘university’ building without students or teachers is not a university.

This usually occurs because we mistake the structure for the relationships that make the structure work (i.e. we focus on building digital platform as all that is needed for community, whereas what we need to focus on is the community).

Indeed, it is probably true that good relationships can transcend a poor structure but not the other way around.

Finally, power is not something you can possess. If power was a possession we would be unable to explain why mutinies occur in that most coercive of hierarchies, the military at war. If soldiers refuse to obey (and accept that the consequences may be dire) then generals are necessarily resistible in principle.

This means that change cannot be ordered from above by leaders who pull the right levers of power in the right sequence because power is a relationship.

Change depends upon the relationships between leaders and followers.

In effect it is followers that make or break change strategies not leaders alone because organizations are systems not machines. If followers choose not to obey — or to comply in such a way that little progress is made — then the greatest strategy in the world is likely to fail.

Now in uncertainty, (the modus typicam of wicked problems) we often conflate ‘doing nothing’ with ‘reflection’ but they are not the same thing. The former implies indecisiveness, indolence and weakness, while the latter implies a proactive philosophical assessment of the situation.

Often enough, “being decisive” can actually be reduced to mere reaction, being driven by somebody else’s agenda or by the insecurity of an ambiguous situation. The hierarchical leader can manage this best by the construction of a narrative explanation.

Negative Capability is the ability to remain comfortable with uncertainty and wicked problems are inherently uncertain and ambiguous. The real skill is not in removing the uncertainty but in managing to remain effective despite uncertainty.

The ability to tolerate anxiety but to ensure it does not become excessive (leading to panic) or denied (leading to inaction) generates different sense-making actions.

The quest for the certainty of an elegant solution is sometimes a mechanism for displacing the anxiety of ambiguity that is an inherent condition of wicked problems.

The difficulty for a leader facing a wicked problem and seeking to use elements of the hierarchist and the egalitarian in a clumsy approach is not of securing consent but in securing dissent.

Wicked problems demand the collective responses typical of systems not individuals. It is the community that must take responsibility and not displace responsibility upon the leader.

There is more to this than being brave enough to do something and willing to take the risk that it will not be easy; it is about recognizing the importance of building SOCIAL CAPITAL to develop an identity that generates a Community of Fate rather than a Community of Fatalism.

The identity must be collective, but the responsibility must be individually shared for wicked problems to be addressed.

The high proportion of organizational change failures can probably be attributed to the assumption that all kinds of changes are susceptible to the established change methods when, in fact, change is often radically different.

Phronesis relates to the skill of what we now call “apperception,” that is, the ability to relate new experiences to previous experiences, in other words to recognize patterns in situations that facilitate understanding and resolution.

By definition, this is something that we can only acquire through experience but experience alone is insufficient to ensure apperception because some level of Reflective Learning needs to have occurred if patterns are to be discovered and understood.

In effect, apperception is the ability to frame or re-frame situations.

In the great words of Laurence J. Peter:

“Some problems are so complex that you have to be highly intelligent and well informed just to be undecided about them.”

As a reminder and disclaimer this is NOT my own original work. This is a summation and interpretation of Keith Grint’s phenomenal essay “Wicked Problems & Clumsy Solutions: The Role of Leadership” that has forever altered my perspective on how to approach the social dilemma.

I hope it does the same for you.




A collaborative publication to present, discuss, frame & define the critical issues threatening humanity in our increasingly surveillance capitalist world.

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Human Being, b. circa 1990 ~ planet Terra, Via Lactea Galaxia

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