Point of View

Leadership Is a Wicked Problem

January 2020

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 Point of View

About the Research

Research Approach
The authors developed this point of view using several sources of information:

• Their own experiences providing research and advice to board members, C-level executives, operational
supervisors, employees, and managers, among others, at large enterprises and mid-sized businesses since the
mid-1990s

• AchieveForum’s leadership development programs and reinforcement tools, created and delivered over nearly
50 years

• AchieveForum’s research archives

• Primary research that included interviews with talent development professionals and other leaders at large,
mid-size, and small organizations

Authors
Sam Marquez, research manager, has extensive experience designing, implementing, and analyzing research
across multiple sectors of the learning and development field. Sam also has been involved in most parts of the L&D
pipeline—from course design to classroom implementation. Before joining AchieveForum, Sam worked as a research
and analytics consultant. He has a B.A. (Philosophy) from Birmingham-Southern College and is currently a graduate
student in Georgia Tech’s Master of Science in Analytics program.

Scott Bohannon, CEO, has provided guidance to boards of directors, C-level executives, and leaders of every major
function at top global companies. Before joining AchieveForum, Scott was CEO of Info-Tech Research Group and
McLean & Co. in Canada. Prior to that, Scott was president of nsight2day. From 1999 to 2011, Scott was general
manager and executive committee member at the Corporate Executive Board, where he also oversaw the firm’s
European research department. He also was an attorney at Sidley Austin and an instructor at the University of
Virginia. Scott is a chairman of the board of directors for The Goyen Foundation. He has a B.A. (Public Policy) from
Centre College as well as an M.A. (Economics), J.D. (Law), and Ph.D. (Economics) from the University of Virginia.

© 2020 AchieveForum, A Korn Ferry Company 2

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Executive Summary
In 1967, Charles West Churchman, philosopher and systems scientist, coined the term “wicked problems.” Today,
we describe challenges like climate change and poverty as “wicked” because they are very difficult or impossible to
solve. Our research has shown that employees today routinely confront wicked problems in the course of their daily
work, although on a smaller scale. In particular, deciding how to lead is a wicked problem because: 1) complexity
and the pace of change make the conditions unique; 2) multiple stakeholders usually have different perspectives on
the problem; 3) it is difficult or impossible to define a correct answer; 4) the current leadership decision affects other
concurrent and future leadership decisions; and 5) how we decide to lead changes the environment, so the same
decision in the future won’t necessarily produce the same result.

It’s usually impossible to know the best way to lead in a given situation, even after the fact. We can’t rely on rules or
formulas when deciding how to lead. Reasonable people will disagree, for example, on whether to rely on prescription,
authority, influence, empowerment, or motivation to get colleagues to adopt a new process. It’s a judgement call.

So, how do you manage the wickedness of deciding how to lead decisively and effectively in such an uncertain world?

Peter McIntyre, the wartime painter and author, said, “Confidence comes not from always being right but from not
fearing to be wrong.” A decisive leader in the digital age shouldn’t act with confidence because they believe they are
right, but rather because they anticipate being wrong and adapting.

Based on our research and experiences with our clients, here are three steps you can take to lead decisively and
effectively:

1. Use rules, formulas, decision tools, and job aids with great care. They may provide some insight, but only to a
limited degree because they usually assume stable and predictable circumstances (despite using words such as
situational, uncertain, and agile). Use them to expand and sharpen your thinking, not direct it.

2. Set tripwires for revisiting your leadership decision. Identify in advance what evidence you might observe if your
leadership decision (as opposed to other related decisions) isn’t working out well. Treat those indicators as signals
for revisiting your decision.

3. Treat trust as an asset. The emotional and competence-based trust people place in you dramatically affects
your ability to lead people over time. Regularly assess how your leadership decisions undermine or foster trust
with different individuals and groups, recognizing that a single decision may build trust with some and reduce it
with others. The affect of a leadership decision today on the trust others place in us for the future is often more
important than the outcome of that leadership decision.

There is a significant opportunity to leverage research into effective decision making in complex environments to
develop new leadership tools. Some of those ideas are introduced in this piece, but aren’t explored in depth.

Effective leadership is an ongoing process, not an action. It usually starts not with dogma or exhaustive analysis, but
with a reasonable guess about how to successfully enlist others in accomplishing your objective, actively searching for
evidence that you need to adapt your approach, and then gracefully adjusting as necessary.

© 2020 AchieveForum, A Korn Ferry Company 3

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What’s the Problem?

Historically, we have treated leadership behaviors as linear processes—a series of steps to be taken that, when
followed correctly, will lead to the right outcome more times than not. For a long time, this worked. Many business
systems may have been complicated, but they followed patterns with enough stability and predictability that we
could define best practices which would create good outcomes. As a result, our goal in leadership development has
traditionally been to find the right “formula” for the current situation, business model, or interaction.

We can see this conceptualization of leadership reflected in the way we teach and
support leaders. We talk about leadership models and tactics distilled from great Less than 1 in 3
managers feel that
leaders in history and present them as a formula that, if followed, will produce
good results. We also provide support in the form of toolkits, decision trees, and
checklists—all tools which represent leadership as a sort of linear, deterministic they have become
process that can be taken a step at a time. more effective at
Over the last 60 years, this model has become less and less effective. In fact,
managing as a
a 2016 Study by HBR found that less than 1 in 3 managers feel that they have result of leadership
become more effective managers as a result of leadership development programs.1 development
What’s going on? programs.
Business has transformed in the modern era. Systems that used to be siloed are now
connected and interdependent, supply chains are woven through diverse, global ecosystems, and job functions that
might have been the responsibility of a single expert now involve diverse, multidisciplinary teams. Fundamentally this
represents a shift from complicated systems to complex systems.

A complicated system is like the engine in a car—it consists of many moving parts, but ultimately acts in a
predictable manner that can be modeled. This makes it easy to forecast how a particular engine might perform under
a number of different conditions. By contrast, a complex system is like the weather. Some limited parts of it can be
modeled, but the long-term forecast (say, one month out) is essentially unknowable.

To be clear, it’s not that it’s hard to model the weather a month in advance, it’s that it is impossible. This is due in part
to the system’s high sensitivity to small changes in initial conditions, as well as its fundamental interconnectedness
to other complex systems. Think of the old adage about a butterfly flapping its wings in Italy causing a hurricane
across the ocean.

The implication is that leadership has become a much less straightforward proposition (if it ever was one). As the
business environment has become more complex, leadership has increasingly become a “wicked problem”—a term
usually applied to complex, messy challenges frequently found in the social sciences. Decision trees and checklists
are ineffective because by the time the leader tries to apply them, the environmental context and the underlying
model they’re trying to apply may no longer be relevant. As a result, our current approach to leadership development
is ineffective because it assumes a level of linearity, stability, and predictability that simply doesn’t exist in the
modern workplace.

© 2020 AchieveForum, A Korn Ferry Company 4

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Why Is It Hard?
The Bureau of Sugar Experiment Stations introduced cane toads to Australia from Hawaii in 1935 in an attempt to
control the native grey-backed cane beetle.2 The cane beetle feeds on sugar cane, a major source of income for the
country. Pesticides do not work on the cane beetles, so The Bureau of Sugar Experiment Stations hoped that the
toads would eat the beetles, controlling the pests.3

Unfortunately, they discovered that the cane toads can’t jump high enough to reach the beetles on the upper stalks
of the cane plants. To make matters worse, the toads quickly took over native amphibian habitats through the spread
of foreign disease and the fact that predators like tiger snakes and dingoes can’t eat the poisonous toads.

Attempts to control the cane toads have proven unsuccessful. For example, trapping often captures unintended
native species, and the toads quickly move to repopulate areas once cleared.4 One proposed solution would insert
a gene into female toads that only allows to produce male offspring, limiting reproduction rates. Such a genetic
approach is highly speculative, however, and has never been tried on a large scale. Today, over 200 million cane
toads continue to threaten native habitats and species.

The challenge of dealing with invasive species is a great example of a wicked problem. Such problems tend to be
large in scale, deeply interconnected with other systems and processes, and involve complex causes and effects.
As a result, wicked problems are slippery, defying our attempts to resolve them and often generating unintended
consequences even if we do manage to address the original challenge.

Wicked Problems 101

Horst Rittel and Melvin Webber, two professors of design and urban planning at the University of California at
Berkeley, developed the notion of “wicked problems” in their 1973 paper Dilemmas in a General Theory of Planning5.
They used the term to describe large-scale, complex social issues such as homelessness or poverty which resist
traditional, linear approaches to analysis and problem-solving.

Rittel and Webber identified the following ten characteristics of wicked problems:

There is no definitive formulation of the problem. The problem can be formulated in multiple ways,
1
depending on the perspectives of stakeholders involved.

Wicked problems have no stopping rule. Since you cannot clearly define a wicked problem, it is impossible
2 to say when you have “solved it.”

Solutions to wicked problems are not true/false but good/bad. A math problem has a definitive, correct
3 answer: 2 + 2 = 4. By contrast, there is no “right” answer to a wicked problem. We must assess whether the
solution is good enough, often in the face of various trade-offs.

There is no definitive test for the solution of a wicked problem. Changes to a complex system have
4 ripple effects that are unpredictable and hard to trace. As a result, we can’t accurately define or measure all
of the effects of our solution.

Every solution to a wicked problem is a “one-shot” operation. Any implemented solution changes the
5
system irreversibly, meaning we cannot learn through repeated trial-and-error.

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Wicked problems do not have a fully definable set of solutions. Wicked problems bleed into other wicked
6 problems, meaning that where one problem begins and ends is a matter of judgment. Where we decide to
draw the line determines what the “solution set” looks like.

Every problem is essentially unique. Despite similarities between a current problem and previous one(s),
7 there is always at least one defining characteristic which is of overriding importance.

Every wicked problem can be considered to be a symptom of another problem. As part of complex,
8 interconnected systems, wicked problems do not have easily defined root causes. For example, crime levels
can be seen as connected to poverty or poor education, which are themselves connected to other complex
issues.

A wicked problem can be framed in many ways, each of which changes the nature of the potential
9 solution. The frame we use to analyze a problem changes the set of potential solutions we come up with.
Take poverty: two potential views are poverty as an economic problem which is rooted in labor market
issues, or poverty can be viewed as an issue of educational access where low-income communities don’t
have the knowledge resources they need. Depending on our perspective, we will propose very different
solutions.

The architects of the solution are held liable for the consequences they generate. With wicked
10 problems, we often find that there is high risk of generating widespread, unintended consequences. Given
that these consequences often touch the social sphere, there is frequently expectation that those in charge
bear some sort of ethical responsibility.

It’s not hard to see why the above characteristics make wicked problems difficult to handle. Multiple ways to view a
problem means that stakeholders might not even agree on what the problem is, let alone how to solve it. Complex
outcomes mean that our solutions can end up having unexpected consequences, sometimes worse than the problem
we originally tried to solve.

Now, it is important to note that not all problems are wicked problems—many are tame. A “tame problem” is one for
which the traditional, linear problem-solving process is sufficient to produce a workable solution in an acceptable
time frame6. A tame problem:

A tame problem:

1. Has a well-defined and stable problem statement

2. Has a definite stopping point (i.e., it is clear when the solution is reached)

3. Has a solution which can be objectively evaluated as right or wrong

4. Belongs to a class of similar problems which are all solved in the same similar way

5. Has solutions which can be easily tried and abandoned

6. Comes with a limited set of alternative solutions

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Tameness or wickedness of a problem is not binary, but rather a matter of degree. Many problems have some
amount of wickedness; the important thing is to notice when wickedness becomes the defining characteristic of the
problem. This occurs as more and more of the “wicked characteristics” become present.

Most problems we encounter in daily work are more tame than wicked. Getting a correct piece of information from
someone, setting up a meeting, or writing a report are all tame problems which have definable processes and
solutions.

Wickedness can present itself on a smaller scale than the societal or organizational level—individuals and teams
experience it too. On the individual level, modern work has changed significantly in terms of complexity and
uncertainty. Many “knowledge workers” must learn to navigate complex systems in order to be effective.

For example, the marketer who has to develop a new campaign is certainly wrestling with a wicked problem:

• Uniqueness: Each marketing campaign is meant to address current market demands, with the current product
set, aligned with the current company goals.

• “One-shot”: Each campaign will impact the target market in an irreversible way, making trial-and-error learning
extremely difficult.

• Multiple frames: One can frame a particular campaign in multiple different ways, each of which can be valid
depending on how they choose to model the important characteristics of the market.

To be sure, there is certainly a difference in significance when we shift from the societal level to the individual. Rarely
do our individual challenges rise to the level of impact that say, climate change, presents. But if the problem an
individual faces at work has wicked characteristics, then they can’t approach solving it like a tame problem (and it
probably creates a lot more anxiety for the individual as well).

Similarly, wickedness presents itself at the team level. When multiple people are involved, we see the challenges
of different possible perspectives and solutions come to the fore. Multiple team members can have different, but
equally valid, ways of framing the problem. Furthermore, given that solutions to wicked problems can only be varying
degrees of ‘“good enough,” team members can disagree on what “good enough” entails for a particular project.

Leadership Is a Wicked Problem

Deciding how to lead usually looks more wicked than tame. To see why, let’s focus on a subset of Rittel and
Webber’s characteristics that are particularly relevant in organizational contexts:

• Uniqueness: Given the complexity and pace of change in the modern environment, as well as the need to
frequently work with other individuals, most leadership moments are to some degree unique.

• Multiplicity of perspectives: It is the rule, rather than the exception, that multiple stakeholders have different
perspectives/understandings of the problem, especially in complex systems with many possible frames of
reference.

• Every solution is a “one-off”: Most leadership decisions will shape the organizational environment irreversibly,
thus removing our ability to easily test and refine our leadership behaviors.

• Lack of a definitive “correct” answer: Given that there are multiple, valid frames of reference from which
to view a wicked problem, there is no way to define which one is “correct.” Changing frames changes the
potential solutions, meaning that there is no single “correct” answer.

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• Interconnectedness: Leadership decisions are never siloed. Whether it’s related to personnel, product, or
strategy, a leadership call is going to have impact that ripples outward and affects other systems. This means
that we can never know or predict the full extent of the impact our leadership behaviors have.

To be fair, leadership has always been wicked for those at the top of the organizational chart. For executives, the
wickedness outlined previously is nothing new, although it has become more pronounced. Activities such as defining
corporate strategy, negotiating mergers and acquisitions, and leading the organizations through disruptive change
have always been wicked. For the executive level, what is new is not the complexity of the problems, but rather
the pace. What used to happen once or twice a year, is now occurring quarterly or even faster, usually under more
ambiguous conditions as well.

Today, employees at every organizational level make leadership decisions. Innovation at the individual level is
now a key ingredient for success, contrary to during the manufacturing age when innovation primarily occurred
at the organizational level. Today’s workers must demonstrate artistry and innovation all while abiding by certain
critical standards and regulations. Adding to the complexity of the greater variety of types of work, the digital age
accelerates what work needs to be done. Businesses see competitive advantages in speed, but this quicker pace
poses new challenges and increases the wickedness of problems.

Managers tend to experience wickedness as greater difficulty in defining goals and allocating resources effectively
for their teams. Deadlines and project goals constantly shift with the business landscape, making it harder to give
effective direction. Resource allocation has become a more complex problem, as the requirements of employees and
various systems they use are constantly changing—indeed, requirements often differ across multiple projects for a
single employee.

Front-line employees have shifted from managing tasks to managing systems. Throughout much of the early 20th
century, a worker was responsible for a limited set of tasks, each of which was well-defined and well-behaved. This
has changed radically. The modern worker deals with a number of systems, which must be made to interact and
communicate with each other effectively. They also deal with many more stakeholders, and the stakeholders they
collaborate with are often different across projects, and even across different stages of the same project.

Taken together these shifts in the nature of work, increased pace of change, and heightened complexity and
ambiguity mean that employees at all levels need to make more leadership decisions, more frequently. Even if we
could write a playbook for the modern work environment, it would quickly become outdated. As a result, employees
must cultivate and rely on good judgment more than ever before.

Butterfly Effects
The link between leadership decisions and their impacts are frequently unclear or overlooked. The effects of
leadership decisions are often ascribed to managerial choices, or simply the outcomes of the tasks involved. This
effect can be further exacerbated when the lag between decision and outcome is substantial.

For example, let’s say we’re working against a tight deadline and choose an unpleasant, if effective, coercive method
for getting our team to meet the deadline. While it may not be immediately obvious, small decisions can have subtle
effects that compound over time to become significant. The disruption in trust and rapport we’ve created in the team
dynamics can present itself further down the line—perhaps as a small amount of reluctance or resistance that comes
up every time a similar situation occurs. This small resistance, compounded over time, becomes a significant source
of drag on the effectiveness of the team.

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404 Error: Feedback Not Found

Feedback is fundamental to learning. It provides us with the inputs necessary to know what is or isn’t working, so
we can then make the appropriate adjustments. When we view leadership through the lens of wicked problems, it
becomes clearer why development of good leaders is so difficult: we lack access to clear, reliable feedback.

These are structural issues driven by the fundamental characteristics of “wickedness” inherent to leadership:

• The uniqueness of every leadership challenge makes it difficult to isolate important variables across different
situations. Even when we think we’ve identified critical factors, there could be a hidden change in the structure
of the problem that is actually at play. Even when situations are superficially similar, there could be critical
differences below the surface that we don’t recognize.

• Leadership challenges can be framed from multiple perspectives—each of which can be legitimate in its own
right. The feedback signals we look for are going to be highly dependent on how the problem is framed. We
can look at a particular problem from multiple frames of reference, but ultimately we must choose one to collect
information. However, the next time we encounter a problem of a similar class, we might choose another frame.
For example, let’s say the first time we encounter a situation we frame it as a skill deficit problem. We choose
a particular type of solution. The next time we might frame it as a compliance problem. We approach it with a
different solution. We have used two different frames for what are similar problems. The challenge with changing
frames of reference like this is that we can’t compare results between the two instances.

• Another critical challenge is the fundamental interconnectedness of the environments where leadership
decisions are being made. Even if we have a relatively reliable framework for analyzing a particular set of
leadership decisions, small changes in connected systems can fundamentally alter the environment we’re
working in. This can lead to upended assumptions and changes in the behavior of systems, meaning that our
analytical framework may no longer apply, or lessons from previous experiences aren’t applicable in the same
way.

As a result, we don’t have access to the sorts of trial-and-error methods we are used to in many other fields of
learning. For many areas of life, systems are predictable enough that we can practice our skills over and over as we
gradually develop mastery. The stability of the system helps us isolate the critical parts of the process, and get a sense
for how the adjustments we make (reliably) alter the process we’re engaged in. With leadership, we don’t have this
opportunity. It is not likely that you’ll have the chance to run a feedback session with an employee, and then get to
rewind time to try a different technique to see what goes differently.

Case in Point

When I first joined AchieveForum (now a Korn Ferry company) as CEO in 2017, we faced significant financial
challenges. Besides making decisions about which changes to pursue, I also had to decide how I would lead,
especially with regard to transparency. Our people didn’t trust senior management, so I decide to open up our
leadership meetings to everyone in the firm, as well as to share that our financial performance over the ensuing
months would determine the size of any layoffs required to ensure our survival. That leadership decision did
foster a lot of trust and I believe helped influence a higher level of performance. But reasonable people disagreed with
my leadership approach. They worried it would cause our best people to search for jobs and also create paralyzing
fear. Because we had a good outcome, I could easily conclude that I was right and they were wrong, but I have to
recognize that their approach might have produced an even better outcome.

- Scott Bohannon

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Why Don’t Our Solutions Work Well?

Traditionally, L&D has treated leadership decisions as tame problems that only require knowledge transfer and
rules-based systems. But as we’ve outlined above, leadership relies on other people, defies clean defined lines, and
conditions can change quite rapidly. This places leadership high on the wickedness spectrum. It resists reduction to
formulas or standardized processes. Consequently, it’s not enough to describe leadership conditions as tumultuous.
We have to abandon the techniques, rules, and heuristics that de facto assume a level of stability, linearity, and
predictability that simply does not exist in most leadership contexts. Complex problems require complex solutions.

Boxed In
Currently, most approaches to leadership development are similar to skill development across other sectors of L&D.
Common solution sets include some combination of:

Classroom Informational Job aids, Training support Coaching

learning or tool kits reference in the form of
e-learning sheets, refresher
videos decision- courses and
making tools on-the-job
training

For many types of work, these methods are effective. As long as the environment/task is relatively stable and
predictable, then the above techniques work well for training. We can take the task, distill it into its component
pieces, and teach them in a setting that recreates the environment where the skill will be implemented. Practitioners
learn the methods through trial-and-error, and once they’ve got the system down, they can reliably implement it back
in the workplace.

This doesn’t work for leadership. The heterogeneity of leadership moments means that any methodology devised for
resolving a particular leadership problem will, by definition, have at least some of its critical assumptions violated any
time someone tries to apply it. Those in leadership development seem to understand this, at least intuitively. It is not
uncommon to see “leadership frameworks” riddled with caveats and edge-case scenarios because it is realized that,
in vivo, leadership is rarely neat enough to be captured by a decision tree or matrix.

Ultimately, we end up with two potential types of decision aids: 1) a decision model that is thorough enough to
be somewhat accurate, but as a result is too complex to actually be usable or 2) a decision model that is abstract
enough that one can actually remember it during a leadership moment, but the abstraction is achieved by making
the model so vague as to be useless. In either case, the decision-framework approach seems ill-suited for wicked
problems.

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Let’s look at an analogy. On one end of the spectrum, there are the highly in-depth toolkits and models. These are
rather like buying a new toaster oven, but the instructions are 40 pages long and include detailed descriptions of how
the electrons flow from your wall socket, through the heating coils, and the physical processes these heating coils
use to generate heat. The instructions may be technically correct, but they’re certainly not useful when you’re just
trying to re-heat a slice of pizza. Chances are you’re more likely to dread opening the instructions, than find them a
useful resource.

At the other end of the spectrum there is high-level advice such as, “always aim to build trust” or “lead through
influence.” This is like opening your brand-new toaster oven to find that it only has a single button labeled ‘heat food’
on it. Sure, the toaster might work somewhat for a wide range of foods, but you’re missing a level of complexity
needed to get desirable outcomes (i.e., handle different heating ranges). High-level leadership models are much like
the one-button toaster—broad enough to capture a wide range of scenarios, but lacking in the detail to help leaders
get a good outcome.

No Room for Judgment

The reductive approach to leadership execution has wider implications. It carries with it an unspoken attempt to
remove judgment from the leadership process. Substituting rules for judgment fails for a number of reasons:

• Rules foster a false sense of security and stability. We have the sense that as long as we apply the rules
consistently, then we can eliminate (or at least significantly reduce) any uncertainty or risk inherent to the
system. In well-behaved systems this might be true, but risk in complex systems is much less predictable.

• The likelihood biases will affect our decision increases. Utilizing the same ruleset repeatedly locks us
into a particular way of viewing and solving a problem. This, in turn, reduces our sensitivity to changes in the
environment that could signal the need for a different approach.

• Our post hoc assumptions are that application of the rules is the correct approach. Each rule is based on
a set of assumptions about the environment where it is being applied. If we aren’t careful to consider whether
or not those assumptions are currently true, then the rule can easily be misapplied.

• Determining how best to lead usually happens in an uncertain context, resulting in a force-fitting of
rules that reduces our leadership effectiveness. This causes us to “lead backwards” by trying to force the
environment to fit our models, rather than continuously re-evaluating our models as the environment shifts.

Judgment is necessary because we don’t have enough information about the system to apply a set of rules until we
actually interact with the system. Of course, interacting with a complex system changes the system itself, meaning
the rules change along with it. As a result, there is no comprehensive set of rules that we can actually determine
ahead of time. So, human judgment always has to be involved in the solution.

When All You Have Is a Hammer …

Broadly speaking, leaders aren’t taught how to approach wicked problems. In formal education, they are
generally given problems that have been stripped of their “wickedness.” They are sterilized to look like something
well-behaved that fits neatly into an analytical framework. Leaders learn the framework, apply it to the problems, and
celebrate their (supposed) mastery after learning the system. While this works quite well for neat, stable problems
like you might find in an introductory algebra class, the real world is rarely so well organized.

Even in the sciences, where a need for experimentation and iteration is foundational to the enterprise, truly innovative
experimentation often isn’t found until at least the graduate level. Most undergraduate work is limited to recreating

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and internalizing the canonical experiments and methods for the chosen field. For example, most introductory
physics textbooks have projectile motion problems that include the statement, “For the purposes of this problem,
ignore the effects of air resistance.” In the real world, air resistance can’t be ignored.

Another challenge with most leadership frameworks is that they suffer from survivorship bias. Often case studies will
pick surviving/successful companies, distill their methodology, and present it as a recipe for success. The problem is
this approach leaves out all of the companies who did exactly the same thing and failed. To compound the issue, in a
case study there is often a sample size of 1, so it’s hard to say whether the outcomes measured are simply a result of
luck or circumstance. As a result, we often don’t have any idea what the true success rate for a particular leadership
tactic looks like.

Taken together, the above factors lead to employees who are not well-versed in how to approach wicked problems.
Almost all of our formal education and professional training assumes a relatively high level of stability and predict-
ability (or create it artificially) such that the methods we teach are often not well-suited for handling wickedness. This
is changing somewhat with Agile and Lean methodologies becoming more popular, but such developments have not
yet been broadly integrated into leadership development.

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Where Do We Go from Here?

Before the advent of sophisticated computers and radar systems, ranging shots were used by naval warships to
calibrate the firing of their artillery. The distance and direction of a piece of gunnery on any given day could be
affected by numerous factors like latitude, powder temperature, atmospheric conditions, and barrel temperature.
This meant it was almost certain that the first few shots would miss. Thus, the goal for these early shots wasn’t
necessarily to hit the enemy, but rather to hone-in on how a piece of artillery was performing as quickly as possible.

The context of leadership presents an equally complex set of causes and effects. On a given day, the team is
subject to the effects of individual personalities, business conditions, interpersonal dynamics, and whether the
coffee machine was working this morning. Accordingly, it’s nearly impossible to predict what today’s most effective
leadership behaviors will be. We need to be prepared to make some “ranging shots” to learn as quickly as possible
what today’s leadership environment requires.

Treat Leadership Decisions as Ranging Shots

Most people receive little formal training in the development and application of good judgment. Ultimately, the
success of the leadership process hinges on the exercise of effective judgment calls—choosing the right lens for
the problem, choosing the appropriate decision among competing possibilities, and choosing the right analytical
framework for interpreting and understanding the data collected by the leader are a few examples.

The last few decades have seen massive advances in the science of decision-making, from Kahneman and
Tversky’s behavioral economics revolution to new advances in neuroimaging technology that help us deepen our
understanding of brain mechanics. These are more than just interesting findings. They are crucial to the core function
of leadership: application of judgment. Below are just a few areas where leadership development can do more to aid
leaders:

• Developing people’s ability to apply good judgment:

- Teach probabilistic thinking as a fundamental problem-solving skill
- Cultivate forecasting skills
- Design processes to optimize group brainstorming/ideation
- Develop methods for de-biasing analysis of information and decision-making
- Teach leaders to continually seek disconfirming information
- Make a habit of scheduling/requiring time for deep thought
- Assist leaders in creating habits for good “decisional hygiene”
• Developing and implementing systems that account for common cognitive blind spots
• Teaching people how to understand ecological/systems thinking in addition to hierarchical organizational
frameworks

This is just an introductory list. It is fully expected that it will grow and change as our understanding of human
behavior continues to deepen and as we build our empirical dataset as we begin to approach leadership decisions
as wicked problems.

The most important point here is to recognize that human judgment is the core of leadership. Traditional tools such
as rulesets, decision trees, and job aids do have use in the leadership sphere, but we must take great care that
they are used in service of judgment, rather than as a substitute for it. The best use for such tools is to expand and
broaden our thinking to help us orient ourselves toward practices of good judgment as outlined above. Too often we
fall prey to letting the tool do the thinking for us.

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Act Like a Meteorologist

We can look to meteorologists for inspiration on modeling chaotic, complex systems. Accurate weather forecasting
relies on modeling complex systems of humidity, temperature, air pressure, wind, and a number of other factors
that all interact and constantly change. Despite the challenge involved, meteorologists have steadily improved their
forecasting predictions—3- and 10-day forecasts have been improving by about a day per decade, meaning a today’s
6-day forecast is as accurate as a 5-day forecast 10 years ago.

How did they do it? By making lots and lots of predictions, and routinely checking the accuracy of those predictions.
By analyzing their predictions post hoc, meteorologists are able to tweak faulty assumptions and recognize errors in
the model. Fundamentally it’s an extension of the classic scientific method we learned in grade school.

The twist is that a chaotic system places severe limits on the range of predictions we can make, both in terms of
breadth and temporal range. This Is due to the fact that in complex systems small changes in initial conditions can
cause large, downstream divergences. Complex systems experience a level of sensitivity to small changes that many
linear systems do not.

In terms of the weather, this means that we can’t, say, predict the weather in Monaco based on conditions in London.
There are too many tiny variances that add up over such a large distance. Similarly, the farther out we try to forecast,
the more time there is for small changes to accumulate. In fact, meteorologists theorize that the limit for predictions
about hurricanes and winter storms is about two weeks. Anything more distant in the future simply has too much
uncertainty to say.

Much like building an effective weather model, the exercise of effective leadership requires an iterative, dynamic
approach. We must learn to treat leadership decisions as ranging shots. We accept that our information is likely
incomplete and, rather than trying to get it “right,” we focus on learning quickly and efficiently. From this perspective,
a leadership decision represents an opportunity to test our assumptions and learn from how the environment actually
reacts. Once we’ve collected some data, we tweak and try again.

When we frame leadership as a continuous experiment, it becomes a process that is fundamentally about exploration
and flexibility, rather than choosing and applying standardized models. If there is a rule for leadership development,
it is that there are no rules—at least none universal in scope. This leads us to consider a new paradigm for effective
leadership:

• Leadership decisions are hypotheses about how to resolve leadership puzzles. Based on the best
currently-available information, the leader crafts a number of different potential hypotheses, and ultimately
chooses the one that seems most promising.
• Execution of the leadership decision is essentially an experiment. The leader seeks to improve their mental model
of leadership in the relevant context. They can never finalize the model, but they can continuously update it.
• Analysis of the data is unlikely to tell the leader a ground-level truth, but it can help them develop better
hypotheses and devise better tests of how well the hypothesis performs.
We can’t assume that our first decision on how to lead will work well, so we should actively look for how to adapt as
quickly as possible. This gives leadership development professionals a new set of teaching goals than what we are
used to. Namely:

• How do you help leaders make a choice when the “best” approach is usually unknowable?
• How do you help leaders make choices that maximize learning while minimizing the risk involved?
• How can we teach leaders to become better “satisficers” (i.e., shift from seeking the optimal solution to the
solution that is good enough to start and learn from)?
• How do we help leaders plan their decisions knowing that the system will change when they implement them?
Rather than reacting to the dynamism in the system, leaders must be taught how to proactively account for it.

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For leaders themselves, the exploratory paradigm suggests at least one critical habit we can implement—building
tripwires into their process that will alert them to shifting conditions. Given that leaders can expect at least some of
their initial assumptions to be off the mark, they can consider ahead of time what signals in their environment might
alert them to that fact. These are the tripwires to look out for. When the wire is “tripped” the leader can take that as
a sign that they need to reflect on their original decision and potentially update it given new information. The need to
learn and update the model is thus built directly into the leadership process.

Treat Trust as an Asset

In the factory environment trust was embedded in the system and processes. You didn’t necessarily have to trust
your fellow employees, so long as you could trust that the system within which you all operated was robust and
dependable. Given the stability of the environment, this was a reasonable approach. Many well-known companies
were built on the dependability and trustworthiness of their systems.

The modern era has shifted that trust away from systems and back into people. Systems in complex environments
are much less resilient since it is often impossible to predict when or how conditions might change. As a result,
resilience is derived from the human operators who reintroduce adaptability to the process rather than the systems
themselves.

As a result, trust is more important than ever for leaders as they have to be able to lead their people through
continuous change. When a leader needs to go “off script,” test a new idea, or challenge an assumption, the
team has to be able to trust that the leader can carry them through the disruption effectively (and as noted above,
“effectively” here means having openness to learn and flexibility to adapt).

Leaders should consider that trust has two forms: competency-based trust and emotional-based trust. The
former, which has been the traditional focus of trust-building, requires personal competence or the ability to garner
competent resources. Emotional trust is about perceived honesty and benevolence.

Ultimately leaders need to be able to recognize and build both. There will be times when the leader is operating
outside of their sphere of competency and must rely on their reserve of emotional trust. There will also be times
where the depth of relationship necessary for emotional trust is not yet present, and so the leader must lean on other
sources (such as competency) to garner the trust required.

The challenge is that trust building occurs within a complex system of human relationships that can often be in
tension with one another. You can’t simply maximize trust across all relevant stakeholders. Sometimes doing the
right thing in the long run will damage trust in the short run (e.g., cutting personnel when the business is at risk of
bankruptcy).

In VUCA environments, we inevitably see more breaches of trust, by which we mean outcomes outside the bounds
of expectations. When emotional trust is high, people tend to ascribe the breach to competence, making it easier
for things to return to normal quickly (especially where there is transparency around steps being taken to address
the out-of-bounds outcome). When emotional trust is low, the unexpected outcome is ascribed to a lack of honesty/
benevolence, which tends to make things deteriorate further, rather than recover. In other words, high trust teams are
more resilient and can move more quickly and confidently.

Ultimately this adds another layer to the calculus of leadership. Leaders must regularly assess how their decisions
will increase or decrease trust with different individuals and groups, recognizing that sometimes building trust with
some might mean reducing it elsewhere. This is a continuous, long-term project, not least because the effects are
both subtle and cumulative. We don’t always see the effects of undermined trust immediately; they can present
downfield at emotional junctions.

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Conclusion
Leadership is a wicked problem, which means that teaching people to lead better will require a set of solutions
better tailored to handling complexity. Historically, we have leaned far too heavily on methods designed for managing
simple and complicated systems, which is why we’ve seen leaders continue to struggle despite historic levels of
investment in training and development. Tools such as job aids and information sheets fall short because they
assume a level of continuity in the system that doesn’t exist. Future generations of tools must be dynamic and
adaptable, just like the problems they are meant to help address.

For development professionals, this requires a significant shift in mindset. We must resist the urge to remove
judgment from leadership in favor of formulas. The complex nature of modern business systems, combined with the
speed at which they change, makes it impractical (if not impossible) to create stable, accurate models which leaders
can rely upon. As a result, we need to help leaders accept the level of uncertainty inherent to the system and give
them new tools for handling it.

First, this means resisting the urge to “systematize” leadership. Frameworks and tools can be useful, but only when
they support the exercise of judgment rather than replace it. Ultimately, leadership decisions are inherently wicked.
This means that the exercise of judgment will always be required to navigate them effectively.

Second, to more effectively embed the exercise of judgment into leadership will require a reframing of the process
itself. Too often we’ve taught leadership as choosing which model is right for the situation and then applying it. Often
there is no effective model for a wicked problem—hence the wickedness.

Accordingly, leaders must recognize that leadership is less about “getting it right” than it is “getting better.”
Leadership is a dynamic, iterative process. We can never know that we’ve gotten the “best” (or “worst”) answer,
but by continually testing and revising our leadership methods we can be confident that we’re moving in the right
direction.

Finally, we must place increased emphasis on trust as a critical leadership asset. Machines, systems, and tools are
fundamentally ill-equipped to deal with the complexity of wicked problems. Human beings are necessary to bring the
adaptability and judgment required to navigate wickedness and, with the rise of wickedness in the workplace, this
means a greater reliance on our fellow employees.

Our research has led us to conclude that trust is fundamental to the effective functioning of teams in wicked
environments. This means that leaders will have to learn, and continuously monitor, the health of the trust among
themselves and their team members for it is only in high-trust environments that people are willing to take the risky,
but necessary, experimental approach to tackling wicked problems.

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References
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Turvey, Nigel. “Everyone agreed: Cane
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agreed-cane-toads-would-be-a-winner-for-
australia-19881.
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org/wpf/wickedproblems.pdf
At AchieveForum, we empower people to lead
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June 13, 2015. https://www.psychologytoday. From in-person instruction to digitally enabled
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Klesman, Alison. “How Weather know-how.
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