Written by Annabelle O’Donnell, Managing Consultant & Design Thinking Lead

Over the past decade, my work has spanned international business strategy, innovation, diplomacy, organisational change and, more recently, leadership development. Throughout much of that career, design thinking has been a core part of my practice.

I first learnt design thinking as a way to solve complex problems: start with people, understand their experience, surface assumptions, test ideas and learn as you go.

At the time, I thought I was learning an innovation methodology. Looking back, I was also learning a different way of thinking about people, change and uncertainty.

That feels especially relevant now. Leaders are driving AI transformation and preparing for futures that are still emerging. In that environment, the ability to adapt, experiment and innovate is becoming a matter of survival.

Organisations do not become adaptable because a strategy says they should. They become adaptable through how people relate to each other, make decisions, respond to uncertainty and learn. Leadership is the biggest determinant of whether those behaviours take hold, because leaders create the conditions that either enable adaptability or constrain it.

The more time I spend working with leaders and teams, the more connections I see between leadership development and design thinking. A design mindset can help leaders become more human-centred, question their assumptions, experiment with their behaviour and learn from how that behaviour is experienced by others.

Leadership is experienced, not intended

A moment from a leadership session recently stayed with me. A General Manager was sharing her vision with their executive team, and afterwards we asked them to reflect back what they had heard from her. Their answers were surprisingly different. The leader realised that only around half of what she thought she had communicated had landed in the way she intended.

It exposed a gap leaders can often miss: the difference between intention and how someone experiences you. A leader may intend to give someone autonomy - but that person experiences a lack of direction. A leader may think they are creating urgency - while the team experiences anxiety. A message may have been communicated several times without creating clarity or being understood.

Leadership is about creating the conditions for other people to perform at their best. You can intend to create trust, clarity or psychological safety, but it is the way those conditions are experienced that shapes what people do.

In design thinking, we ask: what is the experience we are creating for the person on the other side? The same question is useful in leadership: how are people experiencing your leadership?

Bringing the ‘user’ into leadership development

Leadership development asks leaders to reflect on themselves: What are my strengths? What do I need to work on? What kind of leader do I want to be? Design thinking adds another useful lens: who is experiencing my leadership, and what is that experience like for them?

There is no generic ‘employee’. They could be a new graduate deciding whether it is safe to speak up, the high performer who wants more autonomy, the first-time manager looking for clarity, or the person working remotely who feels one step removed from decisions. There will also be customers experiencing the consequences of how that team is led.

In design thinking, tools like personas, stakeholder mapping and empathy interviews help us get closer to the people we are designing for. The same tools can make the people experiencing a leader’s behaviour more present in their development.

Who is affected by the way this leader leads? What matters to them? What pressure are they under? What might they need? What is being assumed about them that has not been tested?

“I need to communicate better” can then become a more useful question: what does clarity need to feel like for this person, in this context, from this leader?

That brings leadership development closer to the people experiencing it.

What do you know, and what are you assuming?

Leaders make assumptions constantly: why someone is resisting change, what motivates them, what a customer needs, whether the team understands the strategy.

Design thinking gives us a practical way to make those assumptions visible while separating what we know from what we think we know.

What evidence do we have? What are we assuming? How could we find out?

That distinction matters. A leader who interprets someone as resistant may respond very differently from one who discovers that the person is confused, unconvinced or missing information.

Making assumptions visible creates space to get curious, gather better information and make a more conscious choice.

A workshop is the catalyst, but experimentation turns insight into behaviour change

No product leader or service designer would run a workshop, take whatever came out of the room and launch it as the finished product.

A design thinking workshop helps teams understand the problem, generate ideas and create prototypes. The real work comes next: testing those ideas, gathering feedback, learning what works and refining the approach.

Leadership development is no different. A workshop creates insight, surfaces assumptions and gives leaders the opportunity to learn and practise. But insight alone does not change behaviour. Leaders need to take what they have learned back into their day-to-day work, try something different, notice the impact, ask for feedback and adjust.

Think of a high-performance athlete working with the best physio in the world. The physio can provide expertise, feedback and the right exercises, but they cannot do the exercises for the athlete. Leaders also need to practise in the messy reality and day-to-day flow of their work.

Rather than leaving a program with “I need to delegate more”, turn that intention into an experiment. Delegate something differently with one person. Notice what happens. Ask how they experienced it. What worked? What didn’t? Adjust and try again.

Overtime, those small experiments can become new habits, and everyday leadership moments become opportunities to keep learning and developing.

Four practices, not four answers

This connects closely with LIW’s 4 Practices: Be Present. Stay Curious. Make Conscious Choices. Keep Experimenting.

They are called practices because leaders strengthen them by using them. Being present helps them notice what is happening. Staying curious helps them question assumptions. Making conscious choices helps them respond with intent rather than habit. Experimenting helps them learn from what happens next.

The mindset is very similar to design thinking. A meeting can be where a leader tries a different behaviour, a difficult conversation can be an opportunity to test an assumption, and a one-to-one can be where a leader asks how their leadership is landing.

Development becomes part of the work, rather than something confined to a program.

Building organisations that can adapt

AI, changing customer expectations, new technology, workforce shifts and continuous transformation mean organisations cannot know exactly what is coming next. They need to be able to learn and adapt as they go.

That requires leaders who are comfortable being curious when they do not have all the answers, challenge their own assumptions, seek out the experience of people affected by their decisions, make it safe to test ideas and learn when something goes wrong.

These behaviours shape how people work and how quickly an organisation can respond when something changes.

Design thinking helps us understand people, surface assumptions, experiment and learn. Leadership shapes whether those things can happen inside an organisation.

Developing leaders this way can build an organisation’s capacity to sense, learn and adapt.

The practical questions are: Who is experiencing your leadership? How are they experiencing it? What are you assuming that you have not tested? What could you try differently, and what could you learn from what happens next?

What next? Book a meeting with me to discuss how we can apply design thinking to leadership in your organization and follow me on LinkedIn for thought-leadership and updates.

Further reading