Design Thinking in an Turbulent World

Design Thinking - Entrepreneurship - Reagan Pollack

Design Thinking in an Turbulent World

Between 2016 and 2018 I attended Stanford University for a series of continuing educational courses on entrepreneurship and design thinking. My goal was to sharpen the tools in my tool belt, meet some incredibly gifted and motivated classmates, and hopefully walk away with a clearer understanding of how to tackle today’s most pressing entrepreneurial challenges — I got all of that and a whole lot more. 

At the time, the concept of Design Thinking was becoming the hottest buzzword around Silicon Valley, and I had to discover just why. In Design Thinking, we learned to remove ourselves from the eyes of running our business, and put ourselves in the shoes of the customer. Modeled around a series of frameworks, discovery strategies and implementation tools, we began unlocking unique insights that led us to innovative solutions to problems we didn’t even realize our customers were experiencing. For short, we called these ‘friction points’. 

Design thinking is a human-centered approach to innovation that draws from the designer’s toolkit to integrate the needs of people, the possibilities of technology, and the requirements for business success.


The Million Dollar question for me, was, “How would Design Thinking unlock new blue ocean opportunities for my company, and the startups that I advise?” 

In 2018, Harvard Business Review published an article entitled Why Design Thinking Works, and highlighted 7 key steps that the process follows to discover insights, unlock user friction, and re-imagine experiences to delight. As the article outlined:

In most organizations the application of design thinking involves seven activities. Each generates a clear output that the next activity converts to another output until the organization arrives at an implementable innovation. But at a deeper level, something else is happening—something that executives generally are not aware of. Though ostensibly geared to understanding and molding the experiences of customers, each design-thinking activity also reshapes the experiences of the innovators themselves in profound ways.

  1. Customer Discovery – understanding the users’ job(s) to be done. 
  2. Immersion – role playing to feel, see, think, touch, experience everything the customer feels
  3. Sense Making – mapping patterns into clusters, data points, and key takeaways (with Post-It® notes)
  4. Alignment – building team consensus around what is the correct problem to be solving.
  5. Ideationdivergence of ideas to explore the most outlier potential solutions to accomplish the goal(s).
  6. Articulationconvergence of ‘achievable’ ideas to explore a select few from the wide basket of possibilities.
  7. Prototyping – developing rudimentary, hypothesis-driven tests that yield actionable responses/results to prove (or disprove) the solution’s ability to reduce friction and solve pain.

‘A design process to design a process’ I thought to myself. I had always figured my old late-night ‘brainstorming’ sessions over a glass of wine seemed to always produce a few clever, creative ideas. While on paper, Design Thinking seemed a bit redundant, in reality, it was quite the opposite. 

With one of my e-commerce sites, I quickly decided to implement the methodology to see if it was all that it was cracked up to be – here’s what I found out. 

I decided to contact a dozen or so customers (some frequent shoppers and others infrequent), to gauge their feedback on the site’s user experience. 

I’d ask each customer a series of the same 5 questions: 

1. If we removed one thing from our store, what would be the one thing that would cause you to begin to shop elsewhere and never return?

2. When something goes wrong with your order, what is the most frustrating part? 

3. What would be the one thing we could do that would pleasantly surprise you on your next order?

4. Tell us about a time when you used the products you purchased from our site, where it helped you accomplish something, and how that helped you?

5. If we disappeared tomorrow, or were unable to deliver the items to you for a month, how might you get the results you are seeking? Would you buy from someone else, if so who? Do you have another innovative solution to solve your need in a pinch?

The answers poured in like I’ve never seen before – some in anecdotal irony, others with an undertone of dismay, but all shrouded with varying degrees of emotion that helped me feel what my customers journeys were.  

The goal of Design Thinking, I realized in that very moment, was to feel. It wasn’t to sell. It wasn’t to reply. It was to feel

That feeling changed my life as both an entrepreneur and a startup advisor forever. The ability to empathize with another person on a deeply profound level, put myself in their shoes as they try to solve the pain in their life, and to share in the hope that the product that they discovered serendipitously on my website might actually free them from that struggle, well, that was eye-opening.

My old way of brainstorming was missing the most important piece – the user’s emotion. 

With Design Thinking, I now had a way, a framework, a strategy to uncover that emotion, and re-design all of the touch points of my user’s experience with that in mind. 

Today, as a startup advisor, I implore founders to throw out the business plan, put away the spreadsheet and the slide deck, and use Design Thinking to drive their companies forward. In so doing, they achieve incredible user feedback, design more innovative solutions that deeply resonate with customers, and use their customers as the fuel for innovation.

In today’s uncertain times, we must re-discover the journey of our customers that we once thought we knew, as emotions globally have changed for the foreseeable future. What we once knew must now be re-experienced, and our businesses must be re-imagined to serve those needs moving forward. 


Photo by Hugo Rocha