Soviet worker w flag

This Is Why Wicked Problems Require Radical Solutions

A long time ago in a galaxy not so far away…

Shell Oil, the Catholic Church and the Communist Party represented an organizational reality that was fairly predictable – one where executives, priests and party chiefs could set objectives and manage in a way to get them achieved. If it’s planned, it’ll happen.  Or so it appeared…

A few years later experts agreed that the future could still be predicted.  What an organization now needed was a system for “operationalizing the strategies which companies already have”.  Hence, the birth of strategic planning.

Fast forward to the present-day VUCA world and a 5-year plan is about as useful as a Soviet-era food stamp.  Incidentally, if you happened to grow up during the Cold War, this is MUST-SEE TV:

Thanks to relentless change and disruption circa 2018. what’s an organization to do when long-term planning is as important as ever, but a more short-term “agile” approach is needed?  Out with the old, in with the new, right?

Not so fast…

The more complex reality is that plans must still be made regarding a company’s use of resources, in addition to other critical matters.  Some might be short-term, but not all.  Think about it, if your organization didn’t plan, where would you sit?  Park?  Eat?  You get the picture.

What happens when an organization’s traditional planning approach looks too slow, rigid or bureaucratic?  I mean, why spend the time and energy on planning when you’re not even going to follow the plan.  Isn’t an organization utilizing centralized long-term strategic planning the polar opposite of one driven by teams deciding their own priorities and resource allocation on a short-basis basis?

Word of caution:  if your organization decides to scrap all traditional planning methods in favor of a new shinier method, it’s headed for trouble…

And so it is with wicked problems.  That is, problematic situations where no right approach or known solution exists.  In fact, the root cause might be unknown; it may appear unsolvable.

However, there is a way to manage or balance polarities that exist within a wicked problem.  But not without a radical approach.


Can you think of a wicked problem?  Are you going through an individual, group or organizational change right now where you see only obstacles ahead?  Or another situation that seems unsolvable?

Remember how Albert Einstein defined insanity – doing the same thing over and over and expecting different results.

Therefore, it goes to reason that if you want to manage or resolve a wicked problem, you’ve got to approach it in a different way.

One different, more radical approach would be to identify with the opposing perspective.  For example, if you see a change as bad for you and/or your people, the opposing perspective would be to view it as a potential opportunity, i.e. good.

If this triggers your skeptical voice, I’d say: “what have you got to lose – you’ve tried (or at least thought of) everything else”.  Secondly, I’d ask you to consider that many things couldn’t exist without their opposite.  They help define each other.  Dark & light, hot & cold, old & young – a few of the big ones.   You could argue that life is made up of polarities.  You couldn’t see yourself as “good” if you didn’t have a concept of “bad”, right?

A more radical thinker might suggest that the part of yourself you call bad allows you to be good.  Or at least allows you to be you – in all your polarities.

Stay with me.

If your cat hunts and kills a bird, you might scold it for its bad behavior.  And when it comes to you later and rubs its face against your leg, you might praise it for its good behavior.  However, both behaviors make up what it is.  A cat.

If only it were as simple for us humans.  However, I believe that if we learn to see ourselves in all our good and bad thoughts and behaviors, we’re on the way to being who we are.  What is.

On the subject of change, some people might even hold up The Paradoxical Theory of Change that says:  when an individual or group stops trying to become what it is not and fully acknowledge what it is, change can occur.

Imagine if your outdoor cat wanted to become a nice cat so it decided to stop its malicious habit of killing innocent animals.  What would happen to it while you were away on holiday?  Not a pretty picture.

Fritz Perls, the founder of gestalt therapy, wrote that when an individual or entire organization aligns itself with one pole, “the polarity itself can become, without anybody’s realizing it, a generator of conflict”.

Think about that for a second.

Can you imagine if your organization decided to make all project teams self-organizing, without a clear project leader?  Not to say it couldn’t work, but I’ve never seen it.


When groups and organizations grow, they naturally become more complex.  And with complexity, planning becomes more essential than ever.  Complexity also brings with it complex, wicked problems.

As established, a wicked problem can appear unsolvable.  The truth is, some situations are unsolvable, or at least irreversible (e.g. email for postal workers).  However, they can be managed.  Balance can be restored.  But before that can happen, they need to be seen, understood and reframed.

A first step to managing a wicked problem is to look at how you perceive the problem.

Drawing from ancient Western and Eastern wisdom in The Obstacle Is the Way, Ryan Holiday sees this as the first, critical step to solving a problem.

Building on the paradoxical Zen Proverb, Holiday believes that we are ultimately responsible for both the creation and solution of our obstacles. Therefore, how you perceive it is everything.  Furthermore, labeling something as good or bad happens inside of you – you assign meaning to things.  The good or bad isn’t there until you prescribe it.

I’ve experienced enough challenging situations to know that it’s not always possible to stay totally objective, especially when emotions are involved.  However, the way I think about it and how I approach it is within my control.  Back to control shortly…

Some might approach a problem with either/or thinking.  A or B.  However, wicked problems must be approached with both/and thinking.  Therefore, simply choosing option A or option B won’t work.  You might need a combination of A and B.  And don’t forget C-Z.

The complexity of a wicked problem often stems not just from competing priorities but also from competing realities.  Therefore, the way people see its competing aspects is highly relevant.

Underlining Perls’ warning about preferencing one polarity over another,  The Cleveland Consulting Group (CCG) writes:

“The significance of the polarity can be gauged by the degree to which each party rejects (disowns) or worse, discredits the validity of, the opposing reality. Rejecting or refusing serious discussion of one pole in a polarity diminishes the organization’s flexibility in responding to wicked problems…”

In my experience, many organizations aren’t even aware of this dynamic.  And I’ve experienced them across multiple continents.

With a view to preventing this toxic tendency, here’s a 2-step approach for effective Polarity Management:

  1. Recognize what is.

By recognizing a complex issue as a polarity to manage rather than as a problem to be solved, you open “the door to the possibility of resolution”, according to CCG.   Furthermore, awareness allows competing people to “become allies in the common search for a positive outcome, rather than uneasy opponents maintaining the split”.

This clearly points to the need for diversity not just of race and gender, but also diversity of thought.

Most importantly, you must be willing to suspend your belief that anyone who holds a different opinion is the opponent.  Think about it – when one position is absolutely right and the other absolutely wrong, is resolution even possible?

  1. Acknowledge the interdependence.

The next step to effectively managing a polarity is to accept that opposing forces of the polarity depend on each other.  In fact, “true polarities are never really resolved; they can only be managed or balanced…each pole and its apparent opposite depend on one another”.

Taking the HBR example of centralized long-term planning on one side and dispersed short-term planning on the other, you see how it could be dangerous for an organization to choose either one or the other.

This example clearly illustrates how both/and is far superior to either/or.  I’m sure you’d agree that in order to compete and survive in the VUCA business environment, both planning approaches are necessary for healthy organizational functioning.

Ultimately, an organization has to find its sweet spot somewhere in the middle.  To manage the planning polarities, HBR recommends a synthesized agile planning approach.

Starting to think in terms of managing polarities “allows an organization to move comfortably from one approach to the other, or to combine the two.”  However, CCG continues, it’s important to keep in mind that “the sense that we are in control is illusory”.

Highlighting this illusion, Holiday believes that a key to a solution lies in recognizing what is under our control and what is not.  This also requires that you are aware of what is right now – not how you think it should be or wish it were.

When facing an obstacle, a key first step is to assess what factors are within your control, and ignore anything outside of it.  You can’t change those anyway.

Bottom line:  before you can solve a problem, you have to see it for what it is.

Remember, the possibility for change emerges when an individual or group stops trying to become what it isn’t and acknowledges what it is.

Building on the ideas of a few Greek philosophers, Holiday stresses the need for objectivity.  And when pure objectivity à la the Stoics isn’t possible, a step toward it can still help you acknowledge what is.  Which in turn makes you ready to act.

And if you’re able to stand outside a complex, problematic situation, you can identify with the opposing point of view.  By doing this, you’ve taken a huge step to approaching the problem in a different, radical way.

Fresh possibilities can emerge and you’re on your way to a new what is.



To do agile planning right, here are two of the four characteristics HBR suggests:

  • Frameworks and tools able to deal with a future that will be different
  • The ability to cope with more frequent and dynamic changes

Moreover, to achieve organizational planning agility, a process is needed that meets these two “paramount requirements”:

  • A process able to coordinate and align with agile teams
  • A process that makes use of both limitless hard data and human judgment

Here is an approach called Relational Organisational Gestalt (ROG) which provides those synthesizing frameworks and facilitates such a process:

Like Holiday’s approach, ROG incorporates the ancient wisdom of East and West. And like Perls and CCG, it embraces the Paradoxical Theory of Change (Beisser 1970).  Best of all, it fosters the practice of dialogue and relational support as a catalyst for real and emergent change.

Like an experienced climber hitting an unexpected obstacle on a difficult climb, you’re likely to encounter a wicked problem on your assent.  And if you want to get past it and keep moving toward the summit, it will certainly require a different, more radical approach.


How do you approach wicked problems?

P.S. Here’s a solution-focused, action-oriented coaching approach that can help you and/or your group manage your wicked problem.  Drop me a note and let’s start a dialogue today.

    • Hi Greg – could you just give me an OK if you received this reply from me. Am trying to optimize my comments form. Thx!

  • Great article Tim.
    Now, more than ever, I would think that finding an open minded, intuitive aproach to tackling thorny strategic and organizational problems is essential to the success and ongoing survival of any enterprise.
    The easy polarized bureaucratic dogmas of the past just don’t cut it in our hyper competitive world.
    The Soviets found that one out the hard way.

      • Well, talk about a great example of hide bound decision making. How to respond to the tragedy of the nuclear meltdown in Chernobyl in 86? Ignore it!! Don’t even tell the people in the adjacent town and let the Swedes inform the world when they notice radiation levels going through the roof.
        Nice bit of decision making there comrades.
        The beginning of the end of their whole enterprise?

  • Thanks for the map, Sven! And for your comment. BTW, do you use that map/ppt with clients?

  • Hi Tim,

    thanks for the article. I think many organizations are or will be confronted with more and more “either/or thinking” as they try new ways of working in order to cope with new challenges.
    Hence, I see it as our work as consultants to point to this “either/or thinking” and help organizations to move to “as well as – thinking”.
    Here’s a link to the Polarity Map model with which you can move from either or to as well as.

    Best regards

    • Thanks, Steve. Good to know you’re carrying the ROG torch in your field of practice.

  • Thanks for your comment, Marie-Anne. And thanks for creating the ROG beacon to guide me.

  • Love what you write Tim, wicked problems require us to stay open to emergence, uncertainty and mostly support ourselves and organisations in that space – that is very radical indeed for most organisations. Thank you for situating ROG as one of the ways that support us to be with this uncertainty.