The #1 Reason Your Design Thinking Program Isn’t Working and What You Can Do About It

Thinking Outside of the Box Paradigm Shit Cartoon

Design thinking is touted to help solve the business problems that existing or BAU processes can’t deal with. Problems like;

  • becoming more innovative,
  • becoming more customer centric,
  • running a successful transformation program,
  • breaking down organisational silos,
  • building “One Team” by engaging your workforce, or perhaps
  • trying to convince a bunch of usually pissed-off stakeholders to play nicely in the sandpit together so you can get stuff done.

You know, the problems with the most value and the most riding on their success.

Sounds like a silver bullet, doesn’t it? Hence the popularity. And when it does work, it’s an incredibly effective approach.

But it doesn’t always work — despite often massive effort and investment. Organisations might roll out design thinking programs and build sexy new innovation labs and still only end up with slight upticks in innovation or stakeholder engagement or customer plaudits. And the million dollar question then is, “Why?”

There are obviously a plethora of reasons for this, but there is one key culprit that usually underpins all of them. And that is:

They don’t understand the context they’re trying to use Design Thinking in.

In other words, they don’t understand the fundamental nature and drivers of the problem space they’re working in. And this is critical. Why? Because even if they “know” the problem is different (hence using a new toolkit), if they don’t understand why and how it’s different — what makes it tick — they’ll just use the new toolkit in the old way and get indifferent results.

So what are the different types of problem spaces or contexts? How do they work? What do we need to do to be successful in them? And where do we tend to go wrong?


3 Different Kinds of Problem

There are 3 different kinds of problem.

Simple (easy to solve, just follow the checklist— baking a cake, restocking the stationery cupboard),

Complex (the more logical, engineering type of problem we’re used to solving with lots of analysis and a systematic, rigorous approach, such as doing payroll or building a car), and

Wicked. Wicked problems are the messy ones like transformations, culture change programs, innovation, or creating new enterprise systems. These are the ones that we have started using design thinking (and other approaches like agile software development) for.

Wicked problems usually involve the following;

  • Coming up with a completely new outcome (innovation, change program),
  • Lots of stakeholders with different agendas and opinions (change, culture),
  • They rely on people doing or seeing things differently (culture, engagement, innovation, change), and
  • Are characterised by having a lot of ambiguity and a somewhat chaotic playing field that keeps changing (transformation / change, strategy).

While Simple and Complex problems are fairly objective, regardless of their level of complexity, Wicked problems are primarily subjective. Stakeholders tend to have different views and agendas and motivations, which makes projects personal and behaviour unpredictable.

While you can surface and map all the elements in Simple and Complex problems, the elements in Wicked problems keep changing, along with what they mean. So your project’s greatest supporter last week may totally disappear this week should their priorities change or they figure out that your project is going to hijack a bunch of their resources.

And while you can solve Simple and Complex problems (then apply that process to repeat the outcome), a Wicked problem cannot be solved.

You heard it. You cannot “solve” a Wicked problem. You cannot find the “One Right Answer” and get it to the point where everyone agrees it’s “done” and you can put it in a box on a shelf and archive it. Of course, you can create fabulous outcomes. You can turn companies around, launch ground-breaking innovations, create new markets, totally change your systems and processes… But you can’t “solve” them.

Wicked problems are not more complicated Complex problems. They are a completely different beast. In fact, the drivers sitting under Wicked problems are a complete inversion of those sitting under Complex problems. Which means the aspects that are key to being successful in a Complex space will not translate to a Wicked space. In fact, the mindset, principles, assumptions and approaches you need to succeed in a Wicked space are often the exact opposite of those that work in a Complex space.

This is one of the reasons why when done well, design thinking can prove to be quite disruptive — it’s more like creating culture change than just implementing a new methodology.

To work this way your whole orientation has to shift. And unless you understand this dynamic, it doesn’t matter how good your methodology and tools are — you’re going to get a truly mediocre result. You might even make the situation worse.

It’s like thinking that if we understand the root cause of someone’s depression we can rationalise them out of it. Won’t work. Or like assuming that we can systematise culture — we can’t. Nor can we legislate engagement, or mandate that an innovation be successful any more than we can insist our children be creative geniuses, or demand that someone be happy. Transformation, like marriage, isn’t an event — it’s a process. You don’t “solve” or “install” it at the altar like a new air-con system.

We know this. But we act as if we can, even when we have the right tools. It’s like expecting a surfboard to operate like a motorbike.

No wonder it doesn’t work.

So where does it tend to go wrong? And what can we do about it?

Here are 5 major traps I repeatedly see organisations fall in to when they don’t understand the context or nature of the problem, and some suggestions on how to counteract them.


  1. They expect the process and outcome to resemble a Complex problem, so they can’t see that they’re off-track from the start.
  2. They don’t frame the problem properly, so can’t get the most value out of the opportunity and usually don’t end up with a sustainable outcome
  3. They then deploy creative tools like design thinking with the wrong mindset and assume these processes can be treated like a production process instead of the messy, iterative, cyclical creative processes they actually are.
  4. They assume that anyone who’s done a design thinking course is capable of actually using that approach, even if they are under stress and when it really matters.
  5. They use Complex metrics to measure Wicked outcomes.

To elaborate…

Trap #1.

They expect the process and outcome to resemble a Complex problem, so they can’t see that they’re off-track from the start.

They assume the problem is logical and rational and can be solved instead of just made better, and that once we map it, it will stay consistent. They therefore assume They can ‘execute’ a process or plan instead of having to constantly collaborate to iterate and adapt. When this doesn’t work, they start blaming, bullying or re-scoping to somehow get it back under control.

DO: Get familiar with the dynamics of Wicked problems and your problem space in particular, and what being effective in this space entails. (If scouring google for this doesn’t suffice, I have a series of articles and a new book on this coming up, or you can come to my course Navigating Wicked Problems and Ambiguity at MGSM)

Trap #2

They don’t frame the problem properly, so they don’t get the most value out of the opportunity and they usually don’t end up with a sustainable outcome.

They assume they know what the problem is and are so desperate to start “doing” that they don’t spend enough time working out the most fruitful area to focus on and how to best engage people with it. Doing this well can take time. Days not hours.

DO: Focus on what you want to create (your ideal outcome) rather than what you want to get rid of (the presenting problem). Don’t bake the solution in as if you already know what it is and just need to execute it. Do focus on the outcome (how you want the world to be different) rather than the output or artefact. Do involve the people you’re working with and those who will benefit from it. And do be prepared to change it if needed. Download the 7 Steps to Better Problem Framing PDF

Trap #3

They then deploy creative tools like design thinking with the wrong mindset and assume these processes can be treated like a production process instead of the messy, iterative, cyclical creative processes they actually are, full of feedback loops and constant learning and adaptation.

I’ve noticed that even when the approach is done well once, it tends to get instantly hardened into “this is the Right Way to do design thinking here” and followed like a formula from thereon in. In this case design thinking is often seen like a creative condiment that gets sprinkled over existing processes in this space, which is akin to putting lipstick on a pig. (Oh, and proudly declaring that they want to “think outside of the box” without realising that starting with a cliche does the exact opposite is a perfect example of this.)

DO: Expect it to stay messy longer. Discovery can take over 80% of the total timeline. More even, since we’re learning all the way through. Do focus on learning and adapting as you go. Make sure you get a lot of feedback throughout — this is no place for black box “ta da!” solutions.

Trap #4

They assume that anyone who’s done a design thinking course is capable of effectively using that approach, even if they are under stress and when it really matters.

Even the naturals find this hard. Because to do it well means to completely change your habits of mind and the way you usually do things. This is hard enough at the best of times (as anyone who’s tried to start a new fitness regime will know) and is near-on impossible under stress and when nobody else really gets what you’re doing and wants it to be like it always was, when the leaders and managers aren’t leading by example, and when nobody’s rewarding the behaviours you need to practice (and may actually be rewarding the opposite).

DO: Make sure management understands what is involved. Do give newbies projects that matter but aren’t mission-critical to cut their teeth on, and have them coached and mentored through it. Encourage play (more on this in an upcoming article) — try new tools out with friendlies and be OK when they stuff up. Just learn and get better.

Trap #5

They use Complex metrics to measure Wicked outcomes.

For example, they tell salespeople to build relationships and focus on using design thinking to understand big picture business problems but reward them on short term incentivised sales. Hell, they even use the same awful business jargon in this space to make it sound less fluffy. Result? It becomes a tick-box exercise at best. After all, they have to pay the mortgage.

DO: Get clear on what aspects and behaviours of design thinking are most important in your organisation, and find a way to acknowledge, emphasise and reward them. Is it questioning? Problem finding? Collaborating? Understanding the customer? Experimenting and iterating?

Any of these sound familiar? No wonder so of the many organisations using design thinking get lacklustre results from such a great approach.

And it all gets back to this one, major problem:

That they don’t understand the context they’re trying to use design thinking in. They don’t understand the nature of the problem space they’re playing in. Which means they don’t understand what makes design thinking such a fundamentally different approach to standard processes.

And because they don’t understand what makes it different, they don’t know how to use it to get the results they brought it in for.

But when we do? We can create magic.

For further insights into some of the principles of Design Thinking and some other tools and skills my invitation is to watch some of my videos and download my free eBook — Stick It! Mo’s pro’s guide to getting more out of classic Design Thinking tools here

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