The Secret to Taming Your Messiest Problems (Part III in a series on Wicked Problems)

This is the final article in a three part series on Wicked Problems. If you missed Part I (the difference between Simple, Complex and Wicked problems), click here and for Part II click here.

So you’ve diagnosed your problem and have most likely come to the conclusion that at least a significant chunk of it is Wicked (or it wouldn’t be doing your head in). In all likelihood, your problem is probably a mixture of all three, with the Simple and Complex aspects ending up contaminated by the messiness of the Wicked ones, which is probably stopping you making progress on the parts that are actually solvable.

Which leads us to the million-dollar question. If Simple, Complex and Wicked problems all require completely different approaches in order for us to be effective in those spaces, then what are they?

What are the different approaches to be effective in those spaces?

Effective Approaches
Effective Approaches to Problem Types

Simple problems: Formulaic approach

Simple problems — where both the problem and solution are obvious from the start — suit a paint-by-numbers approach. So the question to ask when you face one is simply:

What’s the solution?

Simple problems tend to be context-free, so checklists and recipes or previously proved processes are perfect. Follow the bouncing ball. Not a lot of cunning required (though ingenuity in this space can yield surprising bonuses — just grab a bottle of wine and Google ‘simple life hacks’ and say goodbye to your weekend. Endlessly riveting.)

To get better returns, you can provide training (sheep-dip variety is fine ), define procedures and policies, and focus on improving performance (time and motion).

Complex problems: Systematic approach

Complex problems are still rational and objective, but are trickier. Because you are looking at an emergent and context-dependant clutch of interconnected parts, the approach you need in order to uncover them all and hit the jackpot is Systematic. Methodical. Thorough. Rigorous, even. And the question you are asking is:

How does it work?

In other words, what’s the system? How does everything connect? Because if you figure that out, all becomes clear. And this is where all our classic management and project management training in deductive reasoning and analysis comes into its own.

Because the problem is emergent, you’ll find yourself using a lot of mapping and pattern-matching tools as you strive to unearth root causes and create a new recipe. Discovery processes in quest of data points tend to be rigorous and exhaustive. The more data the better. Coverage is king. You’ll probably want to define the scope, determine the logistics, then pursue your chosen process in a deductive, logical and analytical manner, mining and refining the sea of information down to a few key options and a final best choice that you can design a concise or convoluted, critical path to execute on. A classic waterfall approach. And extremely effective in the right contexts.

Wicked problem: Creative approach

So how do you deal with a problem you can’t nail down enough to even define, that’s never been seen before (or at least, not like this), that has lots of messy stakeholder dynamics and keeps shifting every time you take a poke at it?

You have to get creative.

Formulas won’t work. Recipes don’t exist for what hasn’t been dealt with before. Rational processes can’t constrain non-rational contexts. And, as ever, you can’t legislate engagement. Enforce innovation. Mandate happiness. Not that people haven’t tried…

So what can you do?

If the question you ask in a Complex systematic approach is ‘How does it work?’ then the question you must ask over and over when playing in a Wicked space is: What does it mean?

It’s not what something is but what it leads to — what it signifies — that’s important.

In a Wicked space, it’s not what something is but what it leads to — what it signifies — that’s important. Which is one of the reasons that nothing is ever as it seems, and why people act so seemingly irrationally so much of the time.

Remember: Wicked problems are first and foremost subjective and personal. So if we’re working on a major project together, I guarantee that it’s going to mean something different to both of us. One of us might have a promotion riding on the project while the other just wants to work with someone they fancy, or do anything but their current day job. Whatever the motivation, it will determine how much investment we each put in and how we behave and make decisions in that space.

Taking a creative approach means, first and foremost, accepting that;

  • the issue can’t be solved,
  • we can only make it better or worse.
  • coming up with a positive outcome is going to take time.

How much time? Frustratingly, as long as it takes, and generally with no reference to the flowcharts, milestones and deadlines we have allocated to it. Which means we have to dance between them, doing as much as we can and getting the best result possible in the timeframes we have to work within, while recognising that the issue will keep mutating and unfolding to its own schedule. Which, in turn, means we have to keep our process flexible enough to accommodate that as we go.

Knowing the issue can’t be solved and that the space is ruled by subjectivity also means there’s no point in classifying things as right or wrong. The only question worth asking is: ‘Is it useful?’

A creative approach requires a playful mindset.

It requires that we play with ideas and possibilities and primarily with each other. That we experiment, that we make-to-learn, that we be flexible and opportunistic (much more on this later). And it requires that we bring our empathy, our intuition, our insight and our awareness to bear, even though these are often overlooked, discouraged and even derided in a Complex environment. Wicked is a subjective space. People first, front and centre. Emotions rule. Humans are post-rational beings, however rational we pride ourselves on being. Particularly when it matters to us. Everything is personal. Meaning is everything. And the more it matters to us, the more dysfunctional we tend to get as we seek certainty by trying to control the outcome.

Which is why one of the most important skills we need to have with a creative approach is the ability not just to tolerate but to gleefully swim in ambiguity. To be comfortable not knowing what things mean, to be happy to leave things open and unresolved, and to be able to create more ambiguity when situations close down too quickly.

So instead of trying to solve it, we focus on what we want to create, and why this matters.

Focus on what we want to create, and why this matters.

Because it’s a social space, with different perspectives and opinions driving it, we need to get clear on whom we’re creating the outcomes for, and whom we’re creating them with. Whom the stakeholders and collaborators are.

Then instead of analysing the crap out of everything, which will likely just have us spinning in circles drowning in TBU (true-but-useless) data, we have to act. We learn by doing, in order to see what works, what makes things better or worse. Which means that instead of coming up with a long-range plan to execute, we keep our eye on the goal and focus on what the next step is. Because every time we do something, every time we take action in a Wicked space, the whole thing changes.

So if we want to move from a Simple or Complex mode to being effective in a Wicked problem space, we have to fundamentally shift our orientation — and that can be pretty much a one-eighty degree flip.

Wicked Problem Approach

Intuitively, many people get this. However for whatever reason (habit, hard-wiring, training, stress, assumptions, comfort zone, external pressure, a desperate need for certainty and step-by-step models, whatever), the vast majority don’t actually do it. Even in the classes I teach, when we spend ages understanding and practising it — looking at the assumptions, the mindsets and behaviours we need to change or adapt — most instantly flip back to their default mode as soon as any stress intervenes. Which can often be just as soon as they aren’t that sure of themselves. So don’t underestimate how hard this can be, for you and for others you might be sharing the space with. Knowing is not doing or being. And it’s the doing and being bit that counts.

I do have a structured process for working in this space, one that provides the handrails we often need to look at a problem though a creative lens, but it is this fundamental shift in orientation that is key to making it work.

The good news is that however difficult it might be to switch, you will already doing it somewhere. The challenge is to recognise that and tap into it at will.

So where are you already doing it? What areas of your life do you automatically adopt this approach? Perhaps you play a musical instrument, or team sports. Make some form of art. Surf. It could be you’re a natural gardener or a creative cook. It might be playing with your kids or horsing about playing silly games just for the hell of it with your mates. Where do you truly play? Just for it’s own sake? Not just enjoy watching other people play, but actively do so yourself? What’s your creative outlet? Everyone has one.

Notice it, and notice how and who you are in that space. Notice how you respond to things. And then see how you might be able to bring a little of that into your problem space. How would you handle it if it were a tricky new piece of music you were learning? If you were preparing to catch a wave? Cater for surprise visitors? Go exploring in a new city? How would you approach it?

How would you create the outcome you want?

And now, how will you play?

This is an adapted 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 to be notified on the publishing date sign up here.

The next public course on Navigating Wicked Problems and Ambiguity at MGSM is on March 26-27, 2019. Check it out here.


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