Your Biggest Problem is Impossible to Solve — And That’s a Good Thing (PART I IN A SERIES ON WICKED PROBLEMS)

Navigating Wicked Problems

Think of a problem.

In fact, think of two. A professional one and a personal one. Problems that are of the gnarly-never-seem-to-go-quietly variety, regardless of how often you take a run at it.

Maybe you can’t get a micro-managing boss to give you enough space to do what you can do, or you need to get a couple of teams or divisions to play nicely in the sandpit together. Get buy-in for this week’s transformation program or pivot quickly in response to all the disruption in your market. Or maybe your sister-in-law’s feud with your spouse is tearing the family apart. Your psychopath of an ex is ruining your relationship with your kids. Your teenager’s floor-drobe is opening a portal to another universe. Any situation where you hear yourself saying “Why can’t they just xxxxx?!”.

Whatever it is, it’s giving you a headache and you’d like the mental and emotional real-estate back. Make sure both scenarios are ones you’re right in the middle of, that matter to you personally, and are not something abstract and “out there” that you’ve filed as “other people’s issues”.

Now think: What would it be worth to be much more effective in these areas?

Keep these problems in mind as we explore the landscape of the different types of problems and note which aspects of them fit where. And then wait for the sure-fire five step solution at the end.

Ha! You already tried that… (didn’t work, did it?)


There are three types of problems.

Simple, Complex, and Wicked.



Simple problems are easy to solve.

Complex problems resist solving.

And Wicked problems resist even defining.

Let’s start, as is the human default, with Simple problems.

Simple Problems

Simple problems are easy to solve.

As we’ve said, Simple problems are easy to solve. You know what the problem is, you know what the answer is. All you have to do is join the dots in a predictable, linear way. Simple problems are obvious. Straightforward. We can do them in our sleep, so we often delegate them to junior bods in the office and recalcitrant offspring at home.

Examples? Baking a cake. Restocking the stationery cupboard. Checking an order. Doing the laundry. Mowing the lawn.

We love Simple problems. They’re the ones we can add to and tick off our endless to-do lists as occupational therapy to make us feel functional when the world gets overwhelming. In fact we love them so much we optimistically try to turn everything into a Simple problem so we can feel like we’re in control. Even when it’s not and we’re not. (Like the “Simple” instruction to increase your revenue by 20% in the next six months. Tsk).

Complex Problems

Complex problems are trickier. They resist solving.

Complex problems are trickier. They resist solving. You probably won’t know exactly what either the problem or the answer is when you start out, but you will by the time you’ve solved it. So they are emergent. They are usually non-linear, have lots of interconnected moving parts, and a bunch of hidden root causes. They’re complicated. They’re puzzles.

So if Simple is baking a cake, Complex might be building a car. Or a skyscraper. Reorganising the kitchen. Or managing payroll. Like Simple problems, they are essentially objective. They are also frequently technical, mechanical or of an engineering flavour.

These are the problems we are trained to do from the classroom to the office, using skills like critical thinking, logic and rational deductive analysis. There is something hugely satisfying in solving or “cracking” them, in restoring order and being able to resoundingly close the book on them knowing that they are finished. Solved. Which may be why experts in this space are so highly valued. It’s theoretically where the money’s been for years.

Which brings us to Wicked. Out of the textbook and into the schoolyard. Off the spreadsheet and into the boardroom.

Wicked Problems

If Complex problems resist solving, Wicked problems resist even defining.

If Complex problems resist solving, Wicked problems resist even defining. In fact, accurately defining a Wicked problem is in itself a Wicked problem. They are characterised by ambiguity and chaos. The whole problem landscape keeps shifting. Root causes appear and disappear, and dealing with one aspect just gives birth to a hydra’s head of others. They don’t emerge so much as evolve, and they rarely do so predictably — except perhaps in hindsight.

Wicked problems tend to have a strong social aspect — lots of different stakeholders with lots of conflicting opinions. So they’re subjective. For me, the biggest clue that your problem might be Wicked is if it has anything to do with changing how people do things, what they think, feel or believe, or how they see themselves. Their sense of identity and who they are. And the more people in the mix, the more exponentially Wicked the problem is likely to be.

Oh, and if you think you’ve seen it before, you haven’t. Every time around the goldfish bowl is the first. Every Wicked problem is unique, and every approach has to be ad hoc. The gender diversity issue may have the same elements in different companies or even departments, but the problem itself will be different, and something that works well in one place will have very different results in another. An innovation may take one market by storm and be a flop everywhere else. And the dinner-movie-present-seduction routine that worked such a treat last last time may leave you dancing solo this time around.

There is no such thing as right or wrong, or good or bad in a Wicked space. Things are only useful or not useful, better or worse. Because it’s all relative, and full of subjectivity, chaos and ambiguity.

Above all, regardless of how rational and objective people pretend to be in this space, Wicked problems are PERSONAL.

Above all, regardless of how rational and objective people pretend to be in this space, Wicked problems are PERSONAL. To you and to everyone else dipping their toe in the problem space. And this more than anything is what makes them so messy to work with.

With a Wicked problem, context is everything, and the context is always shifting. Which is why the standard answer to questions in a Wicked space is that familiar and frustrating consultant-speak standby: “It depends”.

Examples? Well if a Simple problem is baking a cake, and a Complex problem is building a car, a Wicked problem might be raising a child. Or coming up with a breakthrough innovation. Losing 10kg. Getting more women into senior management. Merging companies or running a transformation program. Negotiating a divorce. Or (probably) the two problems you thought of earlier.

In business, you’ll find Wicked problems hunting in packs in areas like culture, change, innovation, leadership, engagement or communication. All of which feature regularly on CEO priority lists and all of which experience approximately 80% (70-96%) failure rates.

And the kicker?

You can’t solve them.

That’s right.

You cannot provably solve a wicked problem. You can’t crack the puzzle to get the One Right Answer that everyone will agree fixes everything and makes sure the problem never returns.

You cannot “solve” a Wicked problem. But you can create amazing outcomes.


Amazing outcomes. You can turn around a tanking company, save a failing marriage, create a new industry, vastly improve endemic social problems like child malnutrition, pull yourself or someone else out of depression or addiction, create ground-breaking new innovations, raise healthy happy children…

You just can’t “solve” them.

And that’s OK.

It’s OK because Wicked problems never disappear — they morph. And if all our success in these areas is based on a roughly 20% hit rate, then we don’t have to 100% solve them to add enormous value. We just need to shift the dial by a few percentage points. And then we have to be able to keep shifting it, adapting to them as they morph. Because as they morph they create new opportunities. Opportunities we can’t possibly anticipate and that we will miss by closing down the problem space.

So we don’t need to solve them. We need to make them better. And then make them better again. And again.

Download our Summary Chart here

So how do you work out what kind of problem you’re dealing with? And then how do you tackle them to create meaningful outcomes? To get the most value out of each opportunity? In fact, how do you go beyond just being able to manage the messes effectively, to being masterful in how you do it?

And instead of having it do your head in, how do you actively revel in the experience?

I’ll be dealing with those questions in Parts II and III of this series.

Until then, welcome to Wicked.

This is an excerpt from my upcoming book Navigating Wicked Problems & Ambiguity: A Guidebook to Taming The Unsolvable Messy Problems That Matter Most

If you want to get access to advance chapters, sneak peaks to some of the tools, and be notified on the publishing date sign up here.

Next public course on Navigating Wicked Problems and Ambiguity at MGSM is on December 4-5 2018. Check it out here.


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