An Executive’s guide to design investments: Design Thinking and Cynefin

I was reminded how good the Double Diamond is as a way for executives to think about their strategic investments in product development.

Double Diamond for Design Thinking

Good design practices build empathy in teams and increases their insight into people in a given product experience context. In turn, such insight helps make good investment decisions regarding where to impact customer satisfaction and create more business value. This is an important part of agile product development, in that it moves strategic investment beyond milestones and deliverables to what impact are we trying to make and what will that impact then create as an outcome, both for the organisation as well as for its consumers, users and stakeholders.

What is Design Thinking?

Design Thinking is the framework that underpins the Double Diamond. Its five phases, according to the Hasso-Plattner Institute of Design at Stanford, are as follows:

  • Empathise – with your users
  • Define – your users’ needs, their problem, and your insights
  • Ideate – by challenging assumptions and creating ideas for innovative solutions
  • Prototype – to start creating solutions
  • Test – solutions


Overall, the framework assess the facts, analyses them, and asks designers to then apply an appropriate, good design pattern or practice, to then test. According to Stewart (Management 2.0, 2002) “here it is possible to work rationally toward a decision, but doing so requires refined judgment and expertise’.

But, product development is complex

Agile, though, reminds us that product development is a complex endeavour. As such, we’ll only ever really know if a design truly meets a need is when people actually use it in a real life situation. Until then, it’s all just an educated guess.

The tendency of some executives is to do more design work upfront to give some comfort in the outcome. Unfortunately, the more we design upfront the longer we delay the delivery of value. The more we prototype the more time we spend eliciting feedback that is of lower quality than feedback on working software. The more time (and money) we spend on this kind of testing the lower our return on investment.

There’s a balance to be struck. But where do we draw that line? How much should we invest in design and research upfront to inform good product development?

Cynefin has some of that answer.

Look to Complexity Theory

Frameworks like Cynefin remind executives that making informed decisions requires an assessment of the context.

Simple environments allow us to collect requirements, design and deliver because the solution is obvious. Processes are used in simple environments because they always create the desired outcome.

Complicated environments require us to plan the risk out of an unknown solution. In other words, by getting experts to assess the situation, analyse what is known, interpret the findings, and then decide on the best response using “good practice”. This is what Design Thinking is designed to do.

Some leaders rely too heavily on external experts in complicated situations, while dismissing or overlooking creative solutions from other people. To overcome this, I often advise leaders to assemble a group of people from a wide variety of backgrounds, including business stakeholders, and use facilitation techniques like Liberating Structures to ensure everyone has equal voice.

Complex contexts are typically unpredictable and unknown until you run an experiment. That is, rather than trying qualify the context through research first, conducting business experiments in these situations is the best course of action. It requires, though, that executives accept that learning about how the real context responds to the experiment is part of the decision-making process.


Design Thinking is often treated like the proverbial hammer. Empathy in design is critical, as is good user research, but your choice of what actions to commission as a leader of product development should always depend on context.

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