Beyond the Workshops: Three ways leaders can foster Design Thinking capabilities by Dani Chesson

Over the past two decades, Design Thinking has emerged as a practice that enables innovation, change, and complex problem solving. Many companies hoping to benefit from Design Thinking invest in training workshops to learn the Design Thinking way of working. While training workshops are an effective way to learn new skills, putting new skills to use requires taking the learning beyond the workshop. It is when organizations put new skills into practice that they start to see the benefits. So, how can you continue to foster Design Thinking capabilities after the workshops?


1. Share Your Failure Stories: When clients tell me that they need creative ideas and that they are looking for ways to innovate, my first question to them is, are you willing to fail? To innovate you must be willing to try something new which comes with the risk of failing. I have seen many companies, teams, individuals squander their full potential by maintaining the status quo because they unwilling to fail. This fear is justified in that most of our lives we are told to chase success and avoid failure.

However, if you do a bit of research on successful companies, business owners, entrepreneurs, you will discover that their early failures paved the way to their later success. If we want our teams to be creative and drive innovation, we have to start changing our mindset about failure. We have to start embracing failure as simply a step in the process. One way to do that is through stories, specifically by sharing your failure stories.

The spirit of sharing failure stories is to reframe how we talk about and see failure. It is important to remember that this is not a self-deprecating exercise where we bash ourselves for not getting something right. Instead, follow these steps:

  • Briefly describe what you tried to do and how it failed
  • How did you feel when you realized what you attempted to do was not going to work?
  • What did you learn about yourself, about the situation?
  • How did you move forward? What did you do next?

Notice that most of the steps above involve talking about how you responded, what you did next. Failure stories are about reframing our mental models, they are about focusing on the learning that comes from something that doesn’t go the way we expected.


2. Sketch It Out:About half a century’s worth of research shows the benefits of sketching in helping the brain navigate complexity. This is because our brains can process imagery at a faster pace than it can process words. Our memories, dreams, ideas are all strongly associated with imagery. Our ability to communicate visually starts way before we have developed verbal communication skills. The ability to create visuals in an innate ability we all have…don’t believe me? Put some crayons and some paper in front of a toddler and see what they do. Now, let’s get clear about something, I am not saying that we all have the ability to create museum quality drawings, but we do all have the ability to draw basic shapes and lines to communicate ideas.

Imagery is important to how we process information. Images help us visualize, recognize patterns, and flush out ideas.

Here are a few ways to put this innate skill to use:

  • At your next meeting use mind mapping to capture notes
  • Next time you are trying to explain an idea, draw a diagram
  • Replace lined notebooks and pads with unlined ones
  • Fill your workspaces with whiteboards


3. Encourage Empathy: The ability to understand and relate to other humans is becoming increasingly important in business today. Cross-functional teams, working across multiple disciplines, and operating on a global scale is the reality of most organizations today. Each of us comes to the table with our own lens, goals, and agendas. Empathy is the ability to see a situation from another person’s perspective. Our default is to approach a situation only through our own lens and this can be very limiting because we can only see what we know. Empathy allows us to broaden our view and see things from other points of view. How differently might we approach a conversation if we walk in with an understanding of how others at the table were seeing the situation?

Here is how you can encourage empathy in your teams:

  • Ask your team to consider a solution from the perspective of a different business function. For example, if you work in sales consider how a solution might look from an accounting perspective.
  • Have your team engage with your company as if they were a customer. For example, if you are a retail business have your team go through the shopping process as if they were a customer.


With a unique blend of design, business, and organizations development skills, Dr. Dani Chesson’s helps companies tackle complex challenges to reach their full potential. Dani is the creator of Chesson’s DESIGN THINKER PROFILE, Dani takes a Design Thinking approach to creating innovative yet pragmatic solutions to complex business challenges.

Throughout her career, Dani has taken a design perspective to help organizations create new products and services, adopt emerging technologies, and successfully implement large-scale transformational change. Prior to starting Chesson Consulting, Dani was a former Vice President at Bank of America where she led global teams in operationalizing innovation, managing change, and responding to regulatory requirements. She has also held leadership and consulting roles at Carlisle Gallagher Consulting, Sherpa, LLC, and HSBC.

Dani holds a Bachelor of Arts in Visual Communications with a focus in graphic design. She holds a Master of Science in Business Administration and a Master of Science in Organization Development from Queens University of Charlotte where her research focused on how designers approach their work. As part of her graduate work, Dani also completed a Certificate in Executive Coaching. She is also accredited in the DISC Value Index, a certified Six Sigma Green Belt, and a trained facilitator of the Immunity to Change process. Dani earned her Ph.D. in Leadership and Organizational Change from Antioch University where her research involved developing an assessment for measuring the capabilities of Design Thinkers and expanding the use of Design Thinking in organizations. Dani is a scholar-practitioner who brings insights from research into organizations and whose research is informed by her work with clients.