Design Thinking Learning vs. Doing: Stories and Lessons from the Front Lines


When I teach design thinking in a training environment, my goal is to expose people to how design thinking works conceptually and generate excitement about how the mindsets can help them work more collaboratively and effectively. But in the real world, the pressures of solving problems, the ambiguity of the process and the challenging nature of group work can make it more frustrating than practicing in a learning environment.

Each problem is unique and comes with different variables that impact how you apply design thinking. The process gives you a set of tools and a framework for thinking, but doesn’t tell you how to address your specific challenge. That comes from intuition built through experience.

I’ve put together a collection of stories and lessons I’ve gained through my own practice of design thinking over the years. Hopefully, they can provide insight into what it is like to use design thinking day to day, as well as tips for overcoming some of the harder parts of design thinking in the real world.

Research seems easy, but is actually really hard.

Research in practice can be tricky to get right. Asking deeply personal questions of strangers and suspending personal biases takes skills developed through experience. Research also takes rigorous preparation. In the classroom, we focus on jumping into conversations with others to quickly learn about conducting an interview. While this gets the lesson across, it overlooks the real work required to generate quality research outputs.

Preparing the Research Plan:

Setting up quality research starts with a brainstorm of questions related to the topic you’re exploring. Always start with the question, “what are we trying to learn from this research?” Brainstorming things you already know about the topic, as a way of highlighting gaps in knowledge and opportunities for further exploration, is also productive at this point.

A couple years back, I was leading a project related to exploring unmet needs in financial advising. We weren’t the first to explore the topic and there was already a wealth of knowledge from past project teams. So we started there. We combed through old research, created a simple framework to organize the insights that had already been generated and let that process reveal the gaps we needed to research further. Only then did we design our research plan with the questions we wanted to ask and the people we needed talk to.

The process of rigorous planning may seem in contradiction to the bias towards action we encourage in design thinking training, but it’s critical to conducting quality research. It sets the stage for the questions you ask, the people you talk to and the research methods you use. One resource I consult at the beginning of the Examine phase is Universal Methods of Design. It’s full of research methods beyond the empathy interview and can help inspire the types of question you could ask.

Unpacking the Data:

The other overlooked part of research is the unglamorous work of unpacking the data gathered, before synthesizing it into insights. When you’re deep in qualitative research, it’s critical to unpack the research as you go, while it’s fresh. This is no easy task, but you’ll thank yourself later for making the time investment. Plan to spend as much time unpacking as conducting the actual research. Having all the data clearly written on Post-its, with photos of each person you spoke to, will help your team get on the same page about what was learned and allow everyone to analyze the data together.

Insights require a leap of faith.

Synthesizing research into quality insights is a process wrought with ambiguity and frustrating moments of circular discussion. That’s because a good insight gets to something that’s not obvious, through a combination of gut instincts, nuanced observations and leaps of faith. If done well, you’ll come to a differentiated understanding of the problem. If done poorly, you could end up with a bland and broad problem statement that you could have written on day one of the process.

People get stuck in synthesis when they focus on making their insight universally true. But an insight is just a hypothesis—an educated guess about what the problem is and what is true for your customer. Because it is an educated guess, it’s better to be provocative and inspiring than socially acceptable.

The nuance involved in generating insights is hard to explain in theory, so I’ll share an example from a project I led on a homepage design. Our brief: Explore how people use the homepage of their bank. What we heard from almost every user we spoke to is that they only use their bank’s homepage to log into their account. If we synthesized solely based on what we actually heard customer say, we would have ended up with an insight like, “Users don’t care about the bank’s homepage. They see it as just the first step to getting what they want: their account information.”

So what? We already knew that at the beginning of the project—without talking to anyone—which meant we couldn’t stop there with our synthesis of what we had learned. We needed new perspective about the problem and that didn’t position us to solve for anything. The easy part is identifying what is going on, the hard part is explaining why people feel and behave a certain way. Instead, we tapped into our gut instincts and beliefs about how people behave, and asked tougher questions like:

  • Why do people feel differently logging into Facebook than to their bank?
  • What makes Instagram so engaging and how do people feel when browsing the app?
  • What beliefs exist about banking that influence people’s perception of the homepage?
  • How do people get distracted online?

These questions forced us to peel back the layers of the stories we heard to make assumptions about how people think and what drives behavior. Filling in those gaps yielded a set of insights and design principles about the browsing process, as well as inspiration—from people scrolling through their social media feed—that we could use to redesign our homepage.

When I teach the Understand Phase, we usually spend 15-30 minutes on a quick needfinding activity to move from a set of stories to a reframed problem. In reality, this process took my team over a month and was the most challenging part of our project. We were designing our point of view about what we’d learned. This work can be grueling and exhausting—it takes trial and error, patience and perseverance. But, there is tremendous satisfaction in breaking through the fog of ambiguity to arrive at an insight with such clarity.

The brainstorm is just the first step.

Ideation represents a shift in the design thinking process, moving from problem identification to solution exploration. In ideation, the common mistake is not being specific enough. It is much easier to describe a desired outcome than it is to articulate a specific way to achieve that outcome.

I recently had a team in a workshop trying to make the workplace more collaborative. They were energized by their idea: “people should know the moods of other people in their office so they know how to approach them for collaboration.” I asked them how they’d actually make that happen and the group paused. They didn’t have an actual idea, they just had a desired outcome: people knowing each other’s moods.

Discussion continued and each person had a different picture of the solution for achieving the outcome. But, because they hadn’t been specific, they actually had no idea what their solution was. Eventually, the team landed on a simple flag system that allowed people to display a mood flag at their desk, signalling to others how (or if) they should approach them.

Was it a good idea? That’s not the point. The point is they articulated a specific way to achieve the outcome they were describing. There are also hundreds of other ways to achieve the same outcome and the purpose of ideation is to uncover those.

Ideation doesn’t stop with the initial brainstorm of ideas. That’s just the first step. The real work is sifting through all the ideas (and desired outcomes) generated and refining them to be concrete, testable ideas.

The idea dashboard is a really helpful tool at this phase. Even when you think you have the idea right, there are probably other ways it could be executed. The dashboard helps explore many possible ways an idea could come to life before determining how to prototype it.

A prototype is nothing without a hypothesis.

When we teach the Experiment Phase, the emphasis is on putting unfinished ideas out in the world for the sake of learning and getting feedback. However, there is an important nuance to prototype testing that will determine how successful it is. Just like in science class, experimentation should always be designed to test a hypothesis.

I remember teaching a workshop to senior executives and one team had come up with an app that would encourage weight loss and healthy behavior through setting goals and taking bets about whether or not people would reach those goals. Their first prototype of the idea was a series of screen mockups of the user flow. Sure, that might be a fine prototype if you were trying to test how someone moved through your app experience and if they knew which buttons to click. But that wasn’t the question they needed to answer.

They needed to validate whether betting for or against someone would influence behavior and create motivation. Did their paper screens test that? No. So instead, my co-facilitator encouraged them to recreate an experience that answered the question: can we motivate someone to complete a goal by having others bet for and against them?

Before I knew it, they challenged me to do 50 push ups in under two minutes and people around the room were placing bets with real money. I had a growing and engaged audience and the pressure to perform was on. For the record, I completed the challenge and a few people lost some money.

That little experiment taught them so much more about their idea than showing someone fake screens of an app and asking what they thought. They were able to see the dynamics of peer pressure and betting, and they understood how I actually felt, not how they imagined I’d feel. They saw the experience play out for real and they validated their hypothesis.

While making something is a really important part of prototyping, if the thing you’re making doesn’t help you prove or disprove a hypothesis, it doesn’t serve much value. The goal is to derisk the unknowns of your idea through testing and feedback, so be methodical about how you design both the prototype and the test to ensure each iteration is helping you answer a critical question.

The success of your idea depends on the story you tell.

In the classroom, storytelling is the fun end to a long day where everyone shares their idea, usually in form of a skit. But I don’t want the silly and fun nature of storytelling in the classroom to diminish the importance of strong storytelling in the real world. Will you perform a skit in real life? Maybe? I hope so, actually. But the point is to find a compelling way to convey your message to others so that it engages, inspires and motivates.

A couple months ago I had to give a presentation on how artificial intelligence could impact the workforce as it automates knowledge-based work. I started to put together a typical PowerPoint presentation outlining some research I’d done on AI trends and it hit me: what better way to tell the story of AI automating our jobs than to have AI automate this presentation? So rather than give the presentation myself, I built an automatic presentation narrated by a Siri-like voice. I hacked it together using auto-advancing slides and a script I’d written and recorded using the text-to-speech feature on my computer. The result was my audience got to experience what it could be like if AI actually takes our jobs. No one paid attention to the information on my slides because they were so fascinated with the experience of a self-presenting artificial intelligence PowerPoint.

That’s just one example of how to take the power of storytelling to move past conveying information to creating a moving experience. When the default is powerpoint slides, think about how to break the mold and draw your audience in. Because. at the end of the day, if you can’t captivate your audience, it doesn’t really matter how great your idea or message is—they won’t hear it.


People spend their entire careers building expertise in design thinking. While the tools and mindsets are often easy to try out yourself, don’t get discouraged by the fact that this work is hard and it takes time to build confidence, intuition and fluency. Like anything worth doing, you can’t become an expert overnight. But consistently applying the mindsets and methods to understand what works for you is the best way to master the art of design thinking.



This week’s blog post is from Lead Trainer Reilly Carpenter. Reilly has a background in marketing and branding and is now a Design Strategist for Capital One. In his current role, his focus has been championing internal education and adoption of design thinking into his organization’s culture as well as leading large-scale design thinking projects. Reilly is your go-to guy for questions on securing buy-in and implementing design thinking projects. You can ask him all about it at an upcoming Design Thinking Bootcamp.



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