Design Thinking

Most organisations are very good at solving problems.

They are far less consistent at solving the right ones.

Teams deliver features. Systems go live. Investment is approved. Yet customer behaviour does not change in the way leaders expected. Adoption is slower than planned. Benefits are harder to realise.

For CIOs and technology leaders, this gap is costly. It ties up capital, capacity, and credibility.

Design Thinking matters because it directly addresses this failure mode. It is not about better delivery. It is about better discovery.

Why Design Thinking Matters at an Executive Level

Design Thinking is a philosophical lens, not a delivery framework.

It is most valuable when leaders are operating in uncertain, human-centred problem spaces—where needs are unclear, solutions are not obvious, and analysis alone will not produce the right answer.

For CIOs seeking to operate strategically, Design Thinking supports three critical executive needs.

Discovering value before scaling effort

Design Thinking focuses attention on unmet needs and desired behaviour change. It helps leaders answer a foundational question early:

What problem is actually worth solving?

This is particularly important in new products, digital experiences, and service redesign, where assumptions are plentiful and evidence is limited.

Handling complexity deliberately

Design Thinking is well suited to complex domains, where cause and effect are only clear in hindsight. In these situations, learning must precede certainty.

Rather than relying on upfront planning, Design Thinking encourages experimentation and feedback. This aligns closely with the complex domain described in Cynefin, and with early-stage capabilities in Wardley Mapping.

Anchoring technology to outcomes

By grounding work in empathy and discovery, Design Thinking keeps teams focused on outcomes rather than output. Success is measured by changed behaviour and value realised, not features delivered.

For CIOs, this helps ensure technology investment is directed toward meaningful business impact.

The Five Stages in Practice

Design Thinking is commonly described through five stages. They are not linear and are often revisited as learning emerges.

Empathise

The goal is to understand the human need behind the problem.

This requires observing users, listening without judgement, and resisting the urge to validate existing assumptions. Leaders who skip this step usually do so because the problem feels “obvious”. It rarely is.

Define

Insights are distilled into a user-centred need or opportunity statement, expressed from the user’s perspective.

For example:

  • Enable customers to resolve post-purchase issues without contacting support
    rather than
  • Reduce call centre costs by 5%

This distinction matters. One invites solution discovery. The other prescribes an outcome without understanding behaviour.

Ideate

Teams generate multiple potential solutions, without filtering too early.

The purpose is range, not precision. Diversity of ideas increases the chance of uncovering a better approach than the first, most obvious answer.

Prototype

Ideas are turned into cheap, low-risk representations.

Prototypes are not products. They exist to test assumptions quickly and visibly. Feedback at this stage is far more valuable than refinement.

Test

Promising prototypes are exposed to a broader set of users.

Testing often reveals that the problem needs to be reframed, or that a different solution is more effective. Iteration is expected, not treated as failure.

These stages are often summarised using the Double Diamond, which separates problem discovery from solution development and reinforces the importance of divergence before convergence.

Two Practical Examples

Example 1: Redesigning a customer self-service experience

A business wants to reduce support costs by improving self-service.

Without Design Thinking, the solution is often predefined: a new portal, chatbot, or knowledge base.

Using Design Thinking, the team starts with empathy. They observe how customers actually try to solve issues. They discover frustration is not caused by lack of information, but by unclear status and poor handover between channels.

The solution shifts from “build better self-service” to “make progress and ownership visible”. The resulting design is simpler, cheaper, and more effective.

The outcome improves because the problem was redefined.

Example 2: Improving onboarding without defaulting to automation

A CIO is asked to reduce onboarding time for new employees.

The initial assumption is that the process is inefficient and needs better tooling. The proposed solution is a more automated onboarding workflow.

Using Design Thinking, the team observes new starters and interviews managers and support teams. They discover delays are not caused by systems, but by uncertainty around expectations and ownership.

The need is reframed from “reduce onboarding time” to “give new starters clarity and confidence in their first weeks.”

The resulting changes are simple:

  • clearer role expectations
  • defined points of contact
  • scheduled manager check-ins

System changes are minimal.
Time-to-productivity improves because behaviour changes, not because another platform is introduced.

Practical Takeaways for Leaders

Design Thinking works best when treated as a leadership discipline, not a team activity.

Practically:

  • Define objectives in terms of behaviour change, not systems or features
  • Delay commitment until assumptions are tested
  • Encourage cheap experiments before expensive delivery
  • Protect time for discovery, especially early
  • Measure success through adoption, satisfaction, and outcomes

The goal is not creativity for its own sake. It is clarity before scale.

How This Fits the Series

Design Thinking is the first philosophy in the series because it addresses the earliest and most expensive risk: solving the wrong problem.

Strategic leadership requires good judgement. Cynefin helps leaders recognise context. Design Thinking provides a disciplined way to explore uncertainty before committing to delivery.

Frameworks and tools follow. Discovery must come first.

References and Further Reading

Brown, T. (2008). Design Thinking. Harvard Business Review.
https://hbr.org/2008/06/design-thinking

Martin, R. L. (2009). The Design of Business. Harvard Business Press.
Explores how design thinking supports innovation and value creation at an executive level.

Ries, E. (2011). The Lean Startup. Crown Business.
Practical reading on experimentation and learning as a leadership discipline.