Wicked Leadership

Miljan Bajic
19 min readJan 21, 2020

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Lead Yourself and Others Through Wicked Problems of Volatile Change

Miljan Bajic

Why Wicked Problems Matter

Back in 1993, when I was a boy growing up during the civil war in Bosnia, electricity would go out all the time due to bombardments in the city of Sarajevo. My mom would tell my sister and me to go to bed very early. In order to fall asleep, I found myself staring at the large decorative roman numeral wall clock.

I found clocks fascinating, they seemed like magical devices with tiny little pieces all working together to tell time. But as soon as I would start falling asleep, the sound of a tank or a gunshot woke me up. I would focus my attention on watching the clock in order to fall back asleep. Even to this day, when I pause and look at a clock, I feel a soft breeze of comfort, the same comfort that helped me fall asleep in the middle of a war.

Wars Are Complex, Clocks Are Complicated

During the civil war, I didn’t understand the difference between complicated and complex systems. I used them interchangeably. As I would learn later, there is a big difference between complex and complicated.

The distinction between complicated and complex can help us appreciate the challenges organizations and people face today. A complicated system is where the parts can be separated and dealt with in a linear and logical way. On the other hand, a complex system is one oin which we can’t get a firm handle on. Complex systems are emergent and don’t have the same degree of order, control, or predictability.

Clocks, guns, and tanks are all complicated systems: however, the civil war was complex. Ias it involved people with different beliefs and value systems, engaged in combat that is always dynamic and emerging. In complicated systems such as a clock, tank or an airplane, there is no emergent behavior that can arise from interactions among all of its parts.

A simple example of emergent behaviors is the way a school of fish moves. Hundreds of thousands of fish move as a single group, turning or diving to avoid obstacles or predators, moving as if one lead fish were directing their actions. But there is no leader; those behaviors emerge spontaneously from the various instincts of each fish combined with their interactions with each other and their environment.

While our organizations are much more complex than a school of fish, the same principles apply. People in an organization behave based on their values, beliefs, interactions, organizational structures, policies, and the environment. Emergent behaviors are there whether we notice them or not. We lead and manage organizations as if they were complicated when they are complex.

My Son Is Complex

Living systems are complex and behave in nonlinear ways that are difficult to predict. Machines are complicated systems and behave in more predictable ways. Computers and machines can handle complicated problems better than humans. But they are not so well suited for complexity.

Hence, a machine may out-perform humans at complicated board games, such as chess; but this does not guarantee that a computer will be successful at complex tasks, such as leading and empathizing.

When I think about complexity, I think of my two-year-old son when he gets upset. Sometimes picking him up and hugging him will soothe him, and sometimes it will make him cry. Why? The variables that go into his reaction are myriad, hence the complexity of his system. As opposed to the complicated tank, if we pull on the left lever, it will always turn to the left.

Organizations Are Complex

Organizations must deal with both the complex and complicated systems. Some levels of complexity in organizations have always existed. But over the last three decades, it’s gone from something that could be sensed in large organizations and cities to somethingalmost everything we deal with daily. The most profound difference is the level of complexity people have to cope with. We’ve seen startups quickly innovate and become global players and established organizations longing for the old days of market dominance and stability. The technology evolution and the radical changes in our world have led to a more interconnected, interdependent, and faster-paced world.

Organizations have made a lot of progress in managing complicated systems, even large ones; we’ve done this by studying breakdowns and adjusting accordingly. The most significant difference between complicated and complex systems is that complicated systems are predictable and don’t have emergent properties. In a complex system like organizations, things like processes, dependencies, and diversity of people are continually changing. Three properties determine the complexity of an organization. The first, agents, the number of interacting parts, such as employees, customers, stakeholders, processes, and technology. The second, links, relates to how connected people, processes, and technology are. The third, diversity, has to do with the variance of people, processes, and technology. The more agents, links, and diversity we have, the higher the complexity of the organization. What that means for organizations is that any decision can have unexpected, lasting effects. Complex systems such as most organizations today are dynamic and operate in patterned ways but whose interactions are continually changing.

The challenge that a lot of organizations face is that they’re designed as complicated systems. A complicated system assumes expert and rational leaders, top-down planning, smooth implementation of policies, and a clock-like organization that runs smoothly. Work is specified and delegated to particular units. This approach works if we’re in a complicated environment. In complex environments, this approach doesn’t work, hence the challenges that organizations are facing today. The lifespan of organizations has dropped significantly over the last three decades. Complexity in organizations keeps increasing and our approaches are not keeping up. While we can manage a complicated system, we can only manage our reactions to a complex system. The fact that both the complicated and the complex occur concurrently often confuses the people in the organizational system and this can lead to an unhealthy tension. It’s this confusion that often gets us into trouble. Leaders need to recognize these different dynamics and apply the appropriate approach to a given circumstance.

Leaders need to tailor their leadership approach to fit the complexity of the circumstances they face and adjust their strategy. It’s not one size fits all. Leading in complex situations requires fundamentally different leadership and cognitive capacities. In the complicated space, leaders have at least the hope of certainty, whereas, in the complex, they do not, and pretending they do will consistently lead to “solutions” that will soon become tomorrow’s problems.

Meet Wicked Problems

Some problems are so complex, entangled, and multifaceted that we cannot approach them alone. They change and morph as quickly as our ability to understand them. They are most commonly known as wicked problems, and we need a new way to approach them. Urban planner Horst Rittel used the term wicked problems in the 1960s to describe problems that spring from many diverse sources. Rittel observed that there are a set of problems that cannot be resolved with traditional analytical approaches. He described wicked problems as emergent, evolving, shifting, and often without one right answer.

The COVID-19 pandemic can be best described as a “wicked problem”. Wicked problems are complex by nature and ones where the relationship between cause and effect can only be recognizedconsidered in hindsight. The challenge for leaders in making sense of a complex, contradictory, paradoxical, or ambiguous problem has been made even more difficult by advances in technology, big data, globalization, and cultural change.

While many leaders are skillful in managing or even solving some problems, they often find themselves confused, perplexed, and frustrated. Most of this angst comes from the fact that while leaders are expected to solve problems, few of their biggest problems get solved. The principal reason for this is that leaders are unaware that the biggest problems they struggle with cannot be solved but only worked on. Wicked problems are so complex that we have to be highly cognitively aware and well informed to recognize their complexity.

Consider the very wicked problem of running a country. The problem is wicked because no one can agree upon a single solution. Solving the ethnic and religious divide in the Balkans where I was born is a wicked problem. The war in Bosnia and Herzegovina began in 1992 and was marked by various phases, alliance shifts, and blurred lines between victims, observers, and perpetrators. Widely considered the most devastating conflict in Europe since World War II, the international community’s delayed response was itself historic.The NATO peacekeepers ignored the region’s complex history and tried to solve it as though it had an identifiable solution. It didn’t work; it never did.

There is no doubt that our world is perplexing, our times are fast-moving, and our choices are many. Finding an appropriate path or paths is a daunting yet vital challenge confronting us as individuals, as organizations, communities, and as a civilization. While there is a tendency to see all problems as solvable, not all problems can be solved. Many organizations deploy an analyze and control approach to their problems and leadership. This model of leadership impedes creativity and decision-making during times of change and uncertainty. Unlike with complicated problems, the wickedness of wicked problems isn’t a degree of sheer difficulty, but rather, completely different types of problems. There are no right solutions for wicked problems. They evolve and shift. Wicked problems can’t be solved, only influenced towards evolving outcomes and impacts.

Not All Problems Can Be Solved

During the civil war, I felt that once that day started, it never ended. I would run to the only place in the world that always made me feel safe: my grandmother’s home. She tried her best to comfort me, but nothing seemed to work.

As I sat on the foot of her bed, staring at a picture of my Dad on her dresser, I started crying. Earlier that day, shells killed my cousin and three other people standing in line for food relief. There and then, I vowed to myself that I would end the violence when I grew up.

I didn’t understand then what I know now. Not all problems can be solved.

The civil war in Bosnia lasted for four years and claimed more than 200,000 lives. Decades later, the same problems persist. The problems in the Balkans are transborder and closely intertwined and can’t be solved with the current mindset, culture, systems, and actions.

Serving as a coach to executive leaders, I see many organizations operate like they are in war zones. The stress and the problems that they’re facing can not be solved with the same mindset that created them. There are problems that have solutions, and there are problems that can only get better or worse.

Wicked Problems Need Wicked Leadership

Not too long ago, I was in a meeting with the leaders of a large publicly-traded company as they wrestled with implementing a change initiative in their organization.

The group’s goal sounded simple, moving from silos into integrated cross-functional teams. The conversation soon became heated. There was a clear link between silos and improving business outcomes, but they couldn’t agree on their primary challenges to innovation. They realized that the organizational structure they had in place, arranged by functional silos, was they were structured by are not helping them respond quickly enough to the customer needs.

The conversation soon turned to a discussion of best solutions, how to fix the command and control culture, decouple monolithic IT systems, improve organizational architecture and policies, adopt new practices, and evolve leadership mindsets and beliefs.

“Remember, this is a wicked problem,” I said. “The challenges of organizational change are complex and so entrenched that there is no single solution.”

The room filled with silence and all eyes turned towards me. One of the leaders moved his chair closer to mine and whispered, “Our traditional transformation approaches aren’t working; in truth, they never have.”

Organizations Face Wicked Problems

Like countries, organizations face wicked problems relating to increasing competition, accelerating change, and increasing complexity. Successful organizations are developing new leadership capabilities to deal with these kinds of problems. I call these capabilities “wicked leadership capabilities.” For wicked problems, we need wicked leadership. Pick any leadership challenge, and it boils down to a problem-solving issue, nothing more. Leadership is a wicked problem.

Wicked leadership is a collective form of leadership — a concerted effort of many people working together at different places in the system and different levels. Even though many leaders are dealing with wicked problems, they try to solve and treat them as if they were complicated problems. It’s a mindset shift of how we look at our organizations and problems. If we want to build an organization that lasts, treating the issues as though they are tame problems is not an option. It’s what keeps some companies stressed and overworked, and others innovating, taking risks, and making ethical, heart-driven decisions that pay off in the long term.

Organizational changes and transformations are wicked problems, too. Every new executive brings their team and their ideas for solutions. One person’s solution becomes another’s failure. Learning to deal with wicked problems is essential to the art of leadership. The first step to dealing with wicked problems in organizations is recognizing that they exist. Many leaders prefer to pretend that all complexity can be removed with enough time and expertise and that those who disagree are wrong.

Embracing the Ambiguity Of Wicked Problems

Philosopher and former artificial intelligence researcher David Chapman argues that the things we experience in life and organizations always have a mixture of predictable patterns and unstructured ambiguity.

Although we always experience both, it’s a common human reaction to reject the ambiguity. Wicked problems undermine this view because they can’t be solved in a way in which everyone will agree. However, we can take a wicked problem like running a large company, protecting the environment or becoming successful, and try to transform it into a complicated problem, such as enacting control, eliminating emissions, or earning a lot of money.

Such transformations risk sweeping away some of the original problems. Ignoring ambiguity doesn’t eliminate wicked problems; it merely ignores their complexity.

In classic and traditional leadership models, where centralized leadership has existed, the ideal has been to get and keep control. Because organizational challenges usually have simple solutions, organizations won’t benefit from a traditional leadership approach. Uncertainty and ambiguity are the way of the world today, so we must break from the norm and learn to deal with uncertainty rather than attempt to remove it. A leadership accountability is to cultivate a climate that enables people to unleash their potential in this volatile environment. We can’t wait for a hero to come along and fix things. Leading in a complex environment is going to take all of us, bringing what we can, and playing our part. This means that we need to expand our awareness. We need leadership at all levels.

Leadership At All Levels

I will forever remember that night of May 29, 1991. My dad and I watched the underdog Red Star Belgrade accomplish the unbelievable by defeating the heavily favored Olympique Marseille of France for the UEFA Champions League soccer crown. It was also my first lesson in collective leadership. This team took ownership of their collective results as they self-organized and self-led their way to success.

Held every year, winning the UEFA Champions’ league is almost as important as winning the FIFA World Cup. This win was forever written in the soccer history books as the single most triumphant moment of a nation sitting on the cusp of extinction. It also was just a little over a year after this win that war started, and my father was taken to the concentration camp.

Red Star’s team was made up of representatives of five of Yugoslavia’s six republics. An obscure group of players who managed to beat the odds in a formidable manner and grab a European crown right in front of the noses of a soccer goliath at that time. It was an epic endeavor.

But how do you inspire a group of people, such as the Red Star Belgrade soccer team, to play for a bigger game and to think outside of their individual gain? It comes down to sharing a higher purpose and fostering leadership at all levels.

This team put their personal aspirations aside and took ownership of their collective results. This sort of team effort can, and should, be applied in complex organizations. Like complex organizations, a game sport like soccer is a complex, dynamic system. The profound changes necessary to accelerate progress against an organization’s most intractable problems require catalyzation and co-creation of collective leadership.

Time To Rethink Leadership

We need to rethink leadership for a complex context. Because leadership and context are inseparable, and our context has changed dramatically. Many refer to this context as VUCA (Volatile, Uncertain, Complex and Ambiguous) — an acronym borrowed from the US Army to describe extreme conditions in Afghanistan and Iraq. Leading effectively in this new world requires a very different mindset and cognitive capabilities. Most complex challenges can only be solved by those directly affected by them.

Leadership in complex environments requires everyone to take responsibility for the success of their team, organization, and society, not just for their areas. It means that leadership is distributed, rather than being centered on a few individuals in formal positions of authority. That is, everyone can generate ideas and make decisions from a place of ownership.

This creates an environment of aligned autonomy around self-expression, self-organization, self-management, and full accountability for results. Evidence shows us that leadership at all levels not only wins championships, but it also creates resilient organizations that are better fit to deal with complex environments.

My experience working with executives from a number of Fortune 500 companies has only confirmed these findings. These organizations all have the same goals: to innovate, to thrive, and to build towards something better. The ones that accomplish these goals are the ones with leadership at all levels.

People are purpose-driven and choose to align with leaders who strive to empathize with others and make a difference. This is exactly what drove the Red Star soccer team. They weren’t just playing for a championship; they played a tournament that could unite a country when it desperately needed to be united.

Symbolically enough, the country’s civil war and the subsequent break up were symbolized by an unbelievable soccer story, which at the same time also stood for the best things former Yugoslavia and it’s six republics should be remembered by.

Wicked Leadership And Ambiguity

In wicked leadership, we must embrace this idea of leading with a lack of control. and ambiguity, no matter how uncomfortable it might be. To enable people to contribute to what is valued by the organization, they have to be part of that organization’s leadership, not removed from it.

Therefore, wicked problems don’t require leadership as we know it today. We need to fundamentally change our thinking paradigm and approach things in context-appropriate ways. We need leadership space that is constructed and occupied by many empowered people, in the space formerly occupied by a small group of people at the top of the organization.

For wicked problems, the leadership space needs to be occupied by unguided deliberation, conversation, and mutuality among organizational members. This means disempowering traditional leadership and embracing collective leadership at all levels. The outcome of wicked leadership is that we start to understand leadership as a non-excludable collective good, owned, exhibited, and drawn on by all.

Wicked leadership is contextual, norm-based, principled, inclusive, accountable, multi-dimensional, transformational, collaborative, and self-applied. The wicked leadership model is based on personal growth and relationships. It’s about inviting and permission-giving. We have to give people permission to change their pattern of behavior and step into the leadership role. In their book Leading from the Emerging Future, Otto Scharmer and Katrin Kaufer describe three “openings” needed to transform organizations. Opening the mind and challenging our assumptions is the first opening. Opening the heart to be vulnerable and to hear truly is another. The third opening is the letting go of pre-set goals and agendas to see what is needed and possible. These three openings tend to be blind spots for most of us. We have to let go of our rigid assumptions and agendas so we can see that transforming organizations is ultimately about transforming mindset and relationships among people who shape the organizational culture.

Wicked Leadership Framework

The way we view organizations is changing, and a new perspective is emerging. This movement is fueled by growing distrust and cynicism in how we view organizations. There is an increased realization of the limitations of organizational systems, practices, cultures, and leadership mindsets, which are not up to the task.

In the complex adapt-or-die environment of the current business world, leaders are often called upon to act against their instincts. They need to know when it is okay to invite others to collaborate and share authority and when it is better to do things alone, and when to use the collective intelligence of the group and when to follow their direction.

A deep understanding of context, the ability to embrace complexity and paradoxes, and a willingness to change leadership behaviors are necessary for leaders who want to make their organizations thrive in a time of increasing uncertainty.

To deal with wicked problems, leaders need to take a holistic approach to their leadership and organizational development. The Wicked Leadership Framework is a meta-framework that identifies the relationship between and among various forms of knowledge and experience in an organizational setting for complex adaptive systems.

Grounded in the work of Ken Wilber and those who have influenced his work, such as Clare Graves, Abraham Maslow, Don Back, Chris Cowan, and Susanne Cook-Greuter the Wicked Leadership Framework can help leaders identify the appropriate intervention strategy for different levels of complexity. The Wicked Leadership Framework is a map, and it is important not to confuse this framework for reality with reality itself.

There are four core dynamics or lenses of this framework that enable leaders to unlock and facilitate individual and organizational evolution. The four lenses constitute an integral leadership approach that integrates our mindset, systems, actions, and culture. It recognizes that people create the future in their daily conversations, decisions, and actions that are, in turn, shaped by their mindsets, assumptions, and biases.

The four lenses operate in a continuum between the poles of the not easy to observe (left side) and the visible aspects (right side), as well as individual (top) or collective (bottom) aspects. The left-hand lenses have a people orientation and are hard to observe. The right-hand quadrants have a more visible environment orientation. They can be observed, are empirical and measurable — they are the visible organization. Think of Actions and Systems as something that’s in front of you. Mindset and Culture are things that are behind you. We focus on what’s in front of us.

If I want to describe an organization, I would use both less visible and more visible perspectives. For the visible side of the organization, I can look at its organizational architecture, policies, and strategy (bottom-right). I could also observe employee behavior, practices, and habits (top-right). However, I cannot see what people are thinking, feeling, and the values they live by (top-left). I also can’t easily observe invisible norms, relationships, and shared values amongst the employees that make up the organization’s culture (bottom-left). The culture is intangible and resides within the mind and relationships of the organization’s individuals.

We can look at any organization from these four lenses. The four lenses are closely intertwined and can help us map every bit of organizational knowledge and experience into a holistic view. We have to look at an organization through all of these lenses in order to describe it adequately. It always has the systems and structures, culture and relationships, practices and behaviors, and individuals who have thoughts, feelings, and values. Evolution in organizations takes place throughout all four lenses.

A wicked problem in any of these areas will reverberate through all four lenses because every wicked problem has these four facets. Our mindset lens (upper-left) zooms into our interior experience, intentions, motivations, ethics, emotions, and mindset. The culture (lower-left) lens helps us see our organization’s culture that’s composed of the shared values and beliefs of our peers.

The systems (lower-right) lens zooms into the various contexts in which our organization exists, including its systems, structures, customers, and the wider environment. And the actions (upper-right) lens looks at the actions, habits, and behaviors. This includes the way our awareness is expressed in terms of our habits, actions, and behaviors.

Let us say that an organization doesn’t have an equal pay system (lower-right). That will reflect in low morale for people that feel that is unjust (upper-left), and that feeling, thinking, and lack of motivation will be apparent in their actions and behaviors (upper-right), leading to a culture of low employee engagement (lower-left). Thus, a dysfunction that shows up most prominently in one lens is also present in the other three lenses.

Let’s look at each lens in more detail:

Mindset Lens. The top left lens represents individual needs, values, mindsets, beliefs, emotions, self-awareness, cognition, worldviews, and attitude. These are things that are invisible and subjective from other people’s point of view. We can’t observe individual mindsets, thinking, and emotions, but we can infer it from behaviors and practices in the top right quadrant. For example, nobody can see what I’m thinking, feeling, or what my values are. But they can see what I’m doing and how I’m behaving.

Actions Lens. In the top right lens, our behaviors, practices, habits, skills, performance, and observable actions will be visible and highly influenced by our mindset lens. The actions lens helps us make sense of how we use our actions to satisfy our needs. For instance, if my mindset and values are very ego-centric, those will manifest through my actions towards satisfying my needs and controlling my environment to achieve those needs.

Systems Lens. In the bottom right lens, this is the big picture, and it shows how things fit and work together in an organization as a bigger system. As a group, we use our collective thinking, feeling, values, behavior, and actions to implement organizational systems such as architecture, structure, governance, policies, processes, strategy, and technologies, as well as metrics to measure our organization’s performance across these systems.

Culture Lens. Our shared values, shared history, invisible norms, relationships, ethics, stories, meanings, and group dynamics exist in the bottom left quadrant. Culture emerges from the other three lenses, and, in return, this lens reinforces them. In other words, our culture is a reflection and manifestation of our mindset, actions, and systems.

By considering all four lenses, we acquire a holistic view of the current reality of how our organization functions. These four lenses each reflect organizational reality in their own unique and valuable way. The right side of the quadrant that includes actions and systems focuses on competency and functions. The left side of the quadrant that includes mindset and culture focuses on capacity. What we see through these lenses will depend on the platform that we use. We need to increase our cognitive capacity (top-left) to improve our competence (top-right). If we want to be better able to deal with wicked problems, we need to evolve our mindset lens. Our mindset drives how our actions and organizational systems manifest.

Mindset, actions, and systems are what determine our culture. And culture always wins.

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