How Can Design Thinking Enhance Solution Selling Skills

In a world increasingly shaped by AI, the ability to solve complex problems is more important than ever. That's why I've developed a four-day course and a separate workshop for creative problem-solving. My course and workshop are based on the design thinking model taught at the University of Virginia’s Darden School of Business. In an AI-driven world, we increasingly face 'wicked problems' – those complex, ill-defined challenges where traditional problem-solving methods fail, like adapting to rapid technological change and navigating ethical dilemmas and social changes.

Characteristics of Wicked Problems

Knowledge as the Foundation, Behaviour as the Change

With over two decades of enterprise software sales experience and numerous sales training courses, I realized that teaching design thinking tools can help account executives improve their solution-selling skills. While Darden’s design thinking model has proven to deliver enduring results, most sales training programs do little more than provide a short-lived morale boost. Within weeks, salespeople revert to their old habits, and onboarding new account reps from a different industry rarely helps them adjust and adapt their selling approach to the new space.

Earning my Advanced Certificate in Learning and Performance (ACLP) helped me understand why most sales training programs fail. The issue isn’t knowledge transfer—you can get that from a book, the company intranet, or a few online videos. The real challenge is sustaining behavioral change. Just as learning behavior and ability are shaped by ethnographic factors, buyer behavior varies based on context, role, challenges, and industry. Active learning is the arena where the alchemy of change happens.

Understanding Human Behavior

Change is hard—our brains naturally resist it because it takes a lot of work and a lot of energy. So, what design thinking tools can we integrate into solution selling to create lasting improvements in account executives' selling skills? These tools align with the five stages of design thinking: Empathize, Define, Ideate, Prototype, and Test. However, the Darden model refines this approach into a repeatable, teachable 15-step process based on the four key questions of design thinking: What Is, What If, What Wows, and What Works.

Similarities You Can Use

Solution selling shares many characteristics with design thinking. Like solution selling, design thinking requires qualifying the problem—can we succeed or win? Is the problem complex and poorly defined? Complex sales are often less structured than they seem. Understanding the boundaries of the project is key. Were you engaged with buyers before the RFP was released? The RFP defines the scope of the desired solution, much like design criteria in design thinking.

With a qualified lead or wicked problem identified and a clear scope, it's time to strategize and plan. In sales, this means executing according to the company's established sales motions. In design thinking, we follow the steps guided by the four key stages: What Is, What If, What Wows, and What Works.

The goal of the What Is stage is to uncover the reality of the current situation by answering what, why, who, when, and how. Wicked problems are often characterized by scarce relevant data, requiring a combination of quantitative insights from secondary research and qualitative insights from detailed ethnographic conversations. We use empathy tools to understand what’s behind someone’s say-do gap. Pay attention to what they say and trust what they do because the two don’t always line up.

The Say-Do Gap

Insights through Empathy

Key empathy-building tools include a structured conversation guide, direct observation, job-to-be-done analysis, user journey maps, and persona development. We use value chain and supply chain analysis to get a more holistic understanding of the problem. All this research can then be used to create an industry- and persona-based sales playbook that is more realistic.

As we transition to the What If stage, we use tools to distill insights from our research. BI and AI tools help identify patterns and correlations, guiding idea generation. The What If stage is where ideas are collected, sorted, and evaluated to build a portfolio of rough, ‘beta’ concepts. Through convergent thinking, only the most viable ideas advance to the What Wows stage, where we build prototypes and test them. In sales, the analog is vision and value creation, with demos serving as prototypes and slide decks supporting storytelling.

Role-playing is another shared tool between the two disciplines. In design thinking, it helps test hypotheses and refine prototypes. In sales, role-playing personas bring more focus to sales playbooks and conversation guides, making them more effective, repeatable, and scalable. It can also be used to model buyers' decision-making and negotiating styles so your team models ways to better manage those interactions. Role play is great because it provides a safe and supportive space for practicing skills and receiving constructive feedback.

Test for Experience and Sell It

Just as design thinking uses prototypes to test and refine solutions to see What Works, sales teams craft demos and slide decks tailored to each stakeholder's functional and emotional triggers. Testing a conversational demo with peers acting in "red team" roles helps practice objection-handling skills and assess whether the pitch wows. In design thinking, we ask testers to verbalize their thoughts while engaging with prototypes. We want to identify key emotional high and low points in the journey map of their job to be done. Why? Because we are emotional beings, not logical ones. Emotions, not logic, drive actions.

So, whether you’re driving innovation within your organization or selling solutions to high-value prospects, design thinking offers powerful tools that can enhance your sales teams effectiveness through active learning. I bring both the experience and methodologies to help you apply these principles for real, measurable results