The softer side of Design Thinking

Leslie looks into Design Thinking's softer side.

Fluffy pillows in the shape of the double diamond.

Why we are getting stuck.

With the recent conversations around International Women’s Day, I noticed quite a few posts on social media quoting: “empathy is a strength, not a weakness”. 

It feels as though society associates empathy with women. I’m not going to debate gender stereotypes, nature versus nurture, or the differences between emotional and cognitive empathy. Quite frankly, this is not the right conversation.

The conversation we need to be having, is the importance of empathy, creating self and social awareness to navigate these disruptive times.

Talking with design leaders around the globe and, in speaking with organisations here in Singapore, there is controversy over Design Thinking and its role in business transformation. I’ve been hearing: “we understand the value of Design Thinking and how to do it, but we are not seeing the results” or “we are getting stuck”.

Every organisation is considering how it continues to thrive and respond to change in these disruptive times – digital, political, health, and environmental disruption on a global scale. Design Thinking is one tool both business leaders and individuals can use to assess and respond with purpose. 

But for Design Thinking to be effective, we need to be effective at empathy, experimentation, and resilience.

We are seeing so much around the process, tools and techniques of Design Thinking, but Design Thinking is a philosophy, a mindset, and a way of being. With the right team, culture, and capabilities, it can help organisations frame and solve the right problems, as well as techniques that provide transformative solutions.

It includes these key ingredients:

My advice

Whilst most organisations understand all of this, they continue to get stuck. Typically, they’re held back by legacy business culture and the stories they tell themselves. We also see organisations wanting to embrace experimentation, however, with experimentation comes some expected level of failure. And it is failure that humans struggle with; no one wants to make mistakes in front of their peers, colleague, or boss. Therefore failure, and the required level of trust needed in organisations, is also holding us back. 

We see words like empathy, resilience and experimentation being thrown around, overused - often with little understanding of what they mean and how to actually ‘do’ empathy, resilience and failure.

The softer skills needed to undo this attitude


Empathy begins with self-awareness and social awareness. Self-awareness is key to ensuring you are aware of your own values, emotions and behaviours and how these may impact those around you. You may not realise, but your own actions and behaviours may be holding you back from understanding the situation and making better decisions. I’m not a psychologist or life coach, but I like to use two things to help me understand.

Those are:

1. What am I bringing to a meeting

2. Who am I bringing to a meeting 

In bringing these two things to my conscious awareness, I am able to adjust, to listen openly and capture the information I need to make good decisions. My colleague Lily shares an interesting take on this here, and I talk to it in of my UX India talk from last year. 


Broaden your range for greater stability so that you can respond to external forces with purpose and intent. When I speak of range, I refer to the knowledge, skills, tools and experience you will need to carry out a task or project. This may include your subject matter knowledge, design skills and tools, experience managing diverse project teams, facilitation and listening skills, and storytelling for example.

As a former sports scientist, athlete, and manager, I draw on the concept of expanding your ‘comfort zone’, and the ‘arousal theory’ by Yerkes-Dodson. Both theories have been criticised, however as a framework they are helpful to consider how far to push myself outside of my comfort zone without choking or not pushing myself enough and become complacent.


Experimentation helps us speed up product design and identify the best direction forward. It also comes with a level of expected failure. We humans do not like failure. Despite being born with curiosity and using play to learn, somehow this is conditioned out of us. We become afraid of making mistakes. We need to fundamentally shift company culture, to see failure and mistakes as learning, and moving forward with direction and intent.

Whilst organisations often find it easier to manage and lead transactional relationships, all organisations are made up of humans who want connections and acceptance. Therefore we need to build emotional safety and trust.

Summing up

Empathy, resilience, and trust are interwoven and crucial skills needed for organisations and individuals to thrive and respond in today’s world. When we think about building empathy, as well as resilience, and trust, we need to start by reflecting on our own behaviours, language, and actions and take responsibility for what we do and say.

In some ways, you could say the softer side of Design Thinking, empathy, also happens to be the much harder side.

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