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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

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 LinkedIn post, and I talk to it in this recording of my UX India talk from last year. 

Resilience

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

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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Design Thinking Insights - FAQs

The softer side of design thinking focuses on human qualities such as empathy, collaboration, communication, curiosity, and emotional intelligence. While design thinking often involves structured methods and frameworks, its success depends heavily on understanding people and fostering meaningful interactions. These human-centered elements help teams uncover deeper insights and develop solutions that genuinely address customer needs.

Empathy allows designers and organizations to understand people's experiences, motivations, challenges, and emotions. By seeing situations from the customer's perspective, teams can identify opportunities that may not be visible through data alone. This deeper understanding helps create products and services that feel more relevant, useful, and meaningful.

Design thinking benefits from diverse perspectives. Bringing together people from different disciplines and backgrounds helps teams generate richer ideas and consider multiple viewpoints. Collaborative environments encourage creativity, improve problem-solving, and increase organizational alignment around customer needs.

Yes. Emotional intelligence helps teams communicate effectively, build trust, navigate uncertainty, and understand human behavior. These capabilities are particularly valuable when addressing complex challenges that involve customer experiences and organizational change. As a result, emotional intelligence can strengthen innovation efforts and improve decision-making.

Listening enables organizations to understand what customers truly need rather than relying on assumptions. Through interviews, observation, and feedback, teams can uncover valuable insights that inform better solutions. Effective listening helps ensure that products and services are built around real user needs and expectations.

Organizations can encourage empathy, collaboration, active listening, and customer engagement throughout the design process. These practices help teams develop a deeper understanding of users and create solutions that deliver meaningful outcomes. Combining structured methods with human-centered behaviors often leads to stronger customer experiences and more innovative solutions.