Selling Design Thinking to Management: What worked for us

Getting executives on board with design thinking can be an exercise in patience. 

Think of it as teaching a class. How would you explain to a classroom full of five year olds what design thinking is and how it can help them get more chocolate? More importantly, why this method over something else?

For starters, we like using this Venn Diagram to explain how Design Thinking fits into the larger picture of innovation in an organizations. It’s vital for management to see that you’re thinking bigger picture. 

As you narrow down to details, it’s helpful to break down the mystic barrier of Design Thinking into practical steps. There is no shortage of beautiful visuals out for you to use (here's an example). The process has its variations, but the general framework is fairly constant. 

That takes care of the what & how. 

The lynchpin is the why. Why do they need to pay attention to this method over their current mode of problem solving? In other words, what’s the benefit? 

Here are a few benefits of design thinking we've seen resonate: 

  • increase in revenue over time as products & services ideas are deeply rooted in customers’ actual (vs. speculative) needs

  • reduction in costs over time as validated product ideas are likelier to be more profitable

  • cross-functional ideation as a key component of the method brings about better ideas, eliminating homogenous group-think

  • application beyond R&D; any team can use this process to solve business (and even life) challenges and/or as team-building sessions.

  • Design Thinking improves organizational innovation outcomes by producing higher quality solutions

  • Design Thinking improves innovation outcomes by reducing the risk/visibility of failure

  • Design Thinking improves outcomes by improving the likelihood of implementation

  • Design Thinking impacts innovation outcomes by improving adaptability

  • Design Thinking impacts innovation outcomes by the creation of local capability sets

  • Design Thinking and co-creation isn’t a fad, but rather a new way for all problem solvers to put the user at the center of a problem to develop solutions from the outside in rather than the inside out.

We’ve also found it helpful to keep a regular schedule of updates flowing up the ladder for continuous buy-in. Updating executives on progress, letting them listen or view recorded user sessions is one of the most effective ways to get support. 

Selling Design Thinking to Management

“Design Thinking’ what? I can’t draw.” 

If you’ve ever tried explaining design thinking to executives, you’ve probably heard some version of this. 

Drawing abilities aside, in some ways “design thinking” is a misnomer. Although the method was born in the design world, it has long ago ceased to be the “designers” domain. And, while a lot of the tools embedded in the design thinking process come from the design world, the process itself is fundamentally a way to develop products and services in a customer-centric way. 

Yet, Here’s what usually happens today: an executive says, “wouldn’t be interesting if……?” His direct reports rummage through reams of data in expensive industry reports, or some such quantitative data source. They come back with a nice powerpoint presentation about why the idea will work (or not). Decisions get made.

Where’s the customer in all this? 

The outcome of applying design thinking has been proven through different case studies from various company sizes and industries such as Apple, Microsoft, IBM, IKEA, AirBnB, Starbucks, and others. Design thinking supplements existing quantitative methods with a qualitative approach of focused on identifying customer needs. Design thinking practitioners use data from customer conversations & observations to create validated products & services that fulfill today’s needs, anticipate future needs, and delight every day. 

No expensive industry reports required. 

Design Thinking IRL: The education initiative

You’ve probably heard that our education system may or may not prepare future leaders, mainly because it may or may not prepare our kids for real life. This is an unsettling thought, not only to parents, but also to businesses who will hire these students to solve organizational problems in the future.

Our education system, including the curriculum and school environment setup, has been EXACTLY the same (with only minor tweaks) for at least 50 years, if not more. But, the world has moved on, and so has problem solving in the real world. Yet, we don’t teach our kids how to problem solve with constraints, imperfect information, and focus on the people having the problem in the first place. More importantly, we don’t teach them to fail and learn.

And yet, some brave educators do. We’ve encountered several k-12 educators who are teaching the Design Thinking philosophy, methodology, & tools to their students. One of these brave souls is Rich Wiener, who leads the Ramsey High School Design Thinking class.

We spoke to Rich not long ago about his experience teaching Design Thinking to high school students, and how his class is preparing them for life outside the classroom.


DTL: How do you define design thinking? Why is it important? 

RW: I define design thinking as a process for creative problem solving. What’s particularly characteristic of design thinking is its emphasis on human-centered design and empathy. It’s oriented around understanding the user, empathizing with the user, and designing around the user’s needs. 

DTL: How did you first encounter design thinking as a methodology?

RW: I was drawn to it in 2013 because of an interview with David Kelley [of IDEO]. It particularly impacted me at the time because I was working on a project to define what it means to have 21st century skills in education.

I wanted to understand what the learning experience needs to be for preparing kids for this complex society. [Design Thinking] struck me as a possible solution to foster certain skills - creativity, innovation, complex/messy problem solving - that’s a real weakness in the K-12 school.

I’m also always concerned about the overemphasis on memorization of content, routine thinking, and socialization that educational institutions tend to emphasize. Design Thinking looked like a possible approach to setting up the conditions from an educational perspective that are necessary to promote 21st century skills.

DTL: How are you practicing Design Thinking in K-12? 

RW: After becoming more familiar with the methodology, we posed the question: what would happen if we dropped the Stanford D. School graduate course in design thinking into a high school?

We didn’t know how it would go, just given the students’ developmental level. There was also a question of: do we know enough about the dynamics of design thinking as instructors? It took about two years to train the teachers by sending them through various Design Thinking programs.

DTL: What is the structure of your K-12 Design Thinking program?

RW: So far, we’ve been through five sessions, with different real-world partnerships for each class.

We spend the first half of the semester training the students in Design Thinking, through a whole bunch of hands-on, practical exercises. And, then, they are partnered with a company for about three months to solve a real-life challenge using the Design Thinking methodology and tools to produce innovative solutions. 

DTL: Are there particular facets of design thinking that have helped your students most? 

RW: Fostering the mindset of creative confidence, or being comfortable with being uncomfortable. It teaches them to be fearless in putting their ideas out there for others to build on. 

Another one is failing forward, or being comfortable with making mistakes. In a K-12 system, this is really problematic. Students are programed to not want to fail in pursuit of that A-grade. That’s contrary, of course, to real creative, innovative thinking.

Design Thinking really forces the kids to experience what it feels like when you’re trying to produce new ideas, or see new relationships in the real world. This is really what creativity is all about.

DTL: How do you measure the impact of your design thinking program on your students?

RW: At the end of the day, our benchmark is: has their mindset shifted to embrace the unknown and accept failure as a learning experience?

We are constantly thinking about: can a student face failure and learn from it? Can a student tolerate the ambiguity of working through a really complicated problem with a real company? Can they handle not knowing where they’re going, afraid they’re not going to come up with an answer for that company, and not really understanding the problem along the way?

As you know, in design thinking, they’re going to have to reframe that problem based on customer needs. It's a really hard, yet extremely important thing.

DTL: Can you share some of the feedback you get from the students around their experience?

RW: We’ll often have students say to us that one of their biggest learnings was to be OK with uncomfortable ambiguity (as is often the case with problems in the real world).

Also, we have kids who say, “I’ve learned not to be held back by what I think is possible.” In the beginning the kids always look at a problem and they think, “I feel like quitting this class. I’ve been here two weeks, there’s no way we’re going to be able to solve this.” And then they learn, in the end, that they shouldn’t be held back by what they consider to be "possible”.

To me, that’s the kind of learning outcome I’m looking for.

DTL: How do you measure the impact of Design Thinking on the businesses you partner with?

RW: Ultimately, using Design Thinking, did the kids produce ideas/innovations that help the company or social organization solve their problem? In the end, we’re designers trying to solve a real problem.

With our K-12 program, I’ve received letters from these partnerships saying, “We didn’t have really high expectations of working with high school students, and we were very surprised that the team was able to produce great ideas using this approach." And, in a couple of cases, the kids actually solved some practical problems for these companies.

It makes me laugh as someone who has come to learn and believe in Design Thinking. When we start out in the practical portion of the course, you kind of hope that going through the Design Thinking steps you actually come up with good innovations. But, you’re always wondering in the beginning “Is it going to happen?”

DTL: As seasoned professionals, we wonder the same thing. Every time.

RW: Right?! We need a little magic and consistency. There’s a certain reality to this. A lot of failures and a lot of mediocre ideas have come up. But, there’s always been this collection of new, fresh ideas and insights that have produced this positive feedback for us. 

DTL: Collaborative design is a big part of Design Thinking. How does it play out in K-12?  

RW: In the K-12 system, there’s a difference between working in groups and real collaboration (or what we call "radical collaboration" in Design Thinking). To us, collaborating means you want your team member to succeed. Having that team member succeed is more important than worrying about, “Are my ideas good?” and, “Am I going to succeed?”  

So once we get that dynamic going, everybody feels a responsibility to help each other be their best creative designer. That’s when we have real collaboration.

In the end, the kids tell us that “Oh, we never had an experience like that. We never knew how to truly collaborate because we were basically playing out very linear tasks teachers give us, and these assignments have nothing to do with collaboration.”

DTL: Wow. So what are some examples of real-life projects the kids worked on? 

RW: Our students are often solving problems relevant to them. Schools tend to be so superficial, and the context is so content-memorization oriented that we really don’t confront or challenge our students enough with these authentic problems. In the K-12 system, we have really done a poor job of instituting these kind of programs.

One example would be solving for inclusion for LGBTQ+ in athletics. That was a really challenging, emotional topic. As the kids did their empathy interviews, they found a lot of diversity around people's beliefs around LGBTQ+.

With empathetic interviewing practice, the kids found that you have to establish a kind of belief system in your innovation process to cultivate that creative confidence, but also that you have a personal belief system that you need to constantly keep in mind. 

High school kids are very smart and insightful, and much less programmed than adults. The key is to unlock their ability to reflect on themselves and to understand insights associated with what they’re experiencing.

DTL: How has utilizing design thinking helped you in your own career? 

RW: On the professional side, educators are always looking for a vehicle that will be effective in developing cognitive and emotional growth. We also want the kids to feel social responsibility, and know how to take action. Most importantly, we want them to find a pathway to self-actualization.

That sounds kind of philosophical, but it’s really what it’s about. It’s about finding your voice and that pathway to who you are. So the point is, we’re always looking for these these instructional vehicles. Design Thinking, for me, is a really powerful pathway that I’ve come to embrace because I can see it’s made a difference in the students’ lives.

There are lots of models promoting high levels of cognition and creativity and innovation. But, Design Thinking is bringing out a level of understanding and insight that’s exactly what we’re looking for when we’re looking to promote “21st century higher level skills.”

DTL: How has utilizing design thinking helped you in your personal life? 

RW: Just like the kids, I’ve internalized the design thinking mindset as way to tolerate and embrace ambiguity. I use it in my own life as I deal with my own children when we run across complicated, messy problems.

For example, my daughter fell off track as a junior in high school with the SATs, final exams, boyfriend problems, etc., and she had this nervous breakdown recently. It’s a emotionally pretty intense for a parent.

So I find myself thinking, “Ok, how do you design yourself through this? How do you tolerate this ambiguity right now? How do I work with her and not be afraid that I might make the wrong decision?”

Whether professionally or personally, the Design Thinking mindset permeates my ability to be an effective parent, teacher, college professor and friend.


It’s always refreshing to take a step back from our day-to-day business consulting to see how Design Thinking is used in a different environment. Rich, and others, are getting real with what their students need to succeed in the real world. So should everyone else.

Design Thinking is not the only method of problem solving, but it’s a process to explore as an alternative to what’s currently in the school system. We are here to help. If you want to explore Design Thinking in your educational institution, let’s chat.

How are you teaching the kids to problem solve?

One Failure at a Time

Have you ever really, truly failed at something? What I mean to ask is, have you ever tried something hoping to get a result that you never even came close to attaining? How did you deal with this failure? Did you decide to let it define you, or did you choose to redefine it?

Recently, we've come up against one or two of these types of failures in our efforts to bring Design Thinking to a wider audience. We started to let this define our work, but then managed to catch ourselves. 

Instead of going down a path of fear, we decided upon a path of knowledge. We took a long, hard, and, most importantly, honest look at our failures. This honest view point (i.e. Admitting to ourselves that "We did not come close to succeeding here.) allowed us to ask WHY we failed, then alter our plans to try again.

It's a simple concept in theory, but one of those that can be extremely difficult to put into practice. Once we did put it into practice, however, that is when the successes started to unfold.

One failure at a time. Step by step. 

What If You Pushed Aside Doubt?

The ethos "There is no such thing as failure" is not new, but when was the last time you, or your team, actually practiced it?

Sure, embracing it too tightly can mean business demise, but what if you held on to the concept just a little?

What if the next time you had an ideation or design session you didn't allow doubt or potentiality of failure into the room just for that hour or so? What would you find?

Maybe nothing, or maybe something really amazing. [1, 2]

Why not try and find out?

1. Tsaousides, T. (2017, December 17). Why Fear of Failure Can Keep You Stuck. Retrieved from

2. Kalb, I. (2013, June 1). Could Fear of Failure Limit Your Success. Retrieved from

Don't Forget to Fail

Many a business person has been inspired by the story of Spanx founder, Sara Blakely [1]. After-all, she IS a self-made billionaire whose passion and perseverance have chiseled out one of the most successful businesses of our time. Who could deny being inspired by that?

Personally, I know many friends and colleagues who have worked to learn from and mimic her actions in an effort to foster their own business success (myself included). However, after reading a recent interview with Ms. Blakely [2], I realized there was one foundational milestone that many of us have been overlooking in this quest.


In the interview, Sara Blakely tells us that, "When I was growing up my father would ask me, 'What have you failed at this week?' His lesson was that trying was just as important as the outcome. Not trying something was failure."

The effect of this practice? Blakely tells us "It allowed me to be freer in trying things in life and to embrace failure as part of a growing process."; a mindset that allowed her to try to make a business out of pantyhose with the legs cut off, instead of stopping before she got started due to a fear of failure. 

I believe it is this mindset which is the cornerstone to all the other steps along her journey, yet so many of us overlook it. Instead, we define failure as an unfavorable outcome to some event, and look to avoid it at all costs.

Our main method of avoidance? Not trying at all.

The irony is that this avoidance tactic is not only not helpful, but it is the surest way to stifle any innovation.

1.  Wikipedia. Sara Blakely. Retrieved from

2. Schreiber, G. Sara Blakely: The Spanx Billionaire Who Thrived On Failure. Retrieved from

Using Design Thinking to Improve Brainstorming

A few weeks ago, I came upon an article from my alma mater, entitled ‘Thirty Ideas Are Better Than One’. Given that Design Thinking and idea generation was on my brain, I had to know more.

I began reading and when I got to the line, "30 ideas are always better than one", I paused. I asked myself, “Are more ideas really always better”? I thought back to the many brainstorm sessions I'd been in. Most of them generated amazing ideas in large quantities, but many of those ideas were lost along the way. 

As I considered the results of these sessions, I realized the answer to my question was "More ideas are usually better, but knowing how to prioritize and validate those ideas is where the real magic happens". Allow me to explain further. 

"Brainstorming" is a term most of us know and love. It’s an older term, “popularized by Alex Faickney Obsborn in the 1953 book Applied Imagination”. [1] Given that it’s a fairly inexpensive and effective way to generate cross-functional ideas (if you have the right players in the game, of course), teams like the one referenced in the article often utilize the exercise.

There is no doubt that brainstorming is a solid method for idea generation. It's a technique heavily utilized by most if not all of the major players in the innovation and design industry [2], and it's something we employ often at Design Think Labs. 

Despite knowing that brainstorming can help teams produce more ideas and fast, it’s important to realize that doing so is only half the battle. Many times teams go into brainstorming sessions and come up with a slew of ideas only to have the work get lost when the team leaves the room. 


There are two key reasons. Either the problem statement was not clearly identified at the beginning of the session leading to unfocused, ineffective ideas [3], or the ideas themselves are good but so numerous that teams have no idea where to begin. In this second case, the team freezes. Instead of chopping away at making the ideas a reality, they choose to look elsewhere for innovation. [4, 5]

One method for combating these problems is to call in Design Thinking. The Design Thinking process isn’t revolutionary, nor is it inaccessible. In fact, user-centered design practitioners have been utilizing it since the industry's inception. However, the method isn’t only for design practitioners, and once it's learned can be used time and again to solve problems like these. 

Using the method solves the brainstorming problems in several ways. 

First, when using Design Thinking as a framing of and extension to brainstorming, one's brainstorming efforts are inherently fusing the human point of view with what is technologically feasible and economically viable. [6, 7]

Brainstorming when your teams’ brains are primed in this way, means the ideas you produce, even those that seem way “out there”, are anchored at the intersections of user needs, business needs, and technical possibilities. Sure, the ideas may and should push the boundaries in these three regards, but because they are rooted at this meeting point, they’re sure to have a level of context necessary to at the very least add value and understanding to your outcome.

To take this point further, we know that Design Thinking allows a team to define the right problem, ask the right questions, and, when ideas are created, to choose the best answers. [8] Knowing this we can confidently say that framing any idea generating brainstorming session with Design Thinking will sit your team and the ideas your team generates at the golden intersection necessary for innovation. [9]

After you've used Design Thinking to solve the issue of ineffective idea generation through brainstorming, you'll need to know what to DO with all the new, effective ideas. Thinking like a designer solves this as well. Inherent in the Design Thinking process is a framework for selecting the best ideas to test, then testing those ideas quickly to see which ones hold promise. [10]

By framing brainstorming which so easily allows us to generate ideas, with the Design Thinking methodology which inherently ties our foci to the intersection of user needs, business needs, and technical feasibility, the problems which surface far too often as a result of brainstorming, cess. This means at the end of the sessions the team is left with a slew of effective ideas and a roadmap defining what to DO with those ideas. 

It's true. Thinking like a designer takes your brainstorms to a whole new level.

So I ask you this: Are more ideas always better than one?

I think by now you know the answer. 

1. Wikipedia. Brainstorming. Retrieved from

2. IDEO. Effective Brainstorming Techniques. Retrieved from

3. Perspective on problem definition - "It is important to spend time agreeing on the problem to be solved. A whole round of divergence and convergence on the problem statement can be done before giving people a chance to suggest solutions." - Markman, A. (2017, May 18). Your Team Is Brainstorming All Wrong. Retrieved from

4. "Without that rigor, organizations miss opportunities, waste resources, and end up pursuing innovation initiatives that aren’t aligned with their strategies." - Spradlin, D. (2012, September). Are You Solving the Right Problem?. Retrieved from

5. "The paradox of choice isn’t just for shoppers" - Wikipedia. The Paradox of Choice. Retrieved from

6. “which IDEO calls design thinking, brings together what is desirable from a human point of view with what is technologically feasible and economically viable.” - IDEO. Design Thinking. Retrieved from

7. “a method of meeting people’s needs and desires in a technologically feasible and strategically viable way." - Brown, T. (2008, June). Design Thinking. Retried from 

8. “Within these steps, problems can be framed, the right questions can be asked, more ideas can be created, and the best answers can be chosen." - Cohen, R. (2014, March 31). Design Thinking: A Unified Framework For Innovation. Retrieve from

9. Bole, K. (2012, December 4). Design Science: UCSF Project Applies Innovative Thinking to Research. Retrieved from

10. “There are some problems that are not solvable. You might not find a technology that’s going to solve a particular problem, but what you want to do is discover that quickly. So, the design thinking methodology doesn’t necessarily generate better ideas than competing methodologies. It’s just that this methodology allows you to test your ideas quickly to see which ones hold promise.” - Fyffe, S. & Lee, K. (2016, January 19). How Design Thinking Improves the Creative Process. Retrieved from

Choosing a Great Design Thinking Partner

So you’re looking for someone to guide you and your team through the Design Thinking process. There are thousands of consultants out there, offering various takes on the process and personal spins for a range of budgets. How do you choose?

You can go the traditional route: budget first, align dollars available with a vendor, and pray it works out. 

For others who want to hire a true design thinking partner, here are a few key things to consider: 

  • A Flexible Approach. Design Thinking is a loose construct. It’s a general framework to get from idea to customer validation, with many steps in between. Any design thinking practitioner who follows the process by the book doesn’t have enough field experience to know otherwise. Look for people who are flexible and comfortable in deviating from the “proscribed” textbook steps. They are the ones who will catch you when you inevitably fail at something. 
  • Customized, 360-Thinking. Yes, the design thinking process steps will be similar, but every business is different. There are a lot of designers out there unable to think in business terms. Yet, you’re hiring them to help you come up with solutions for your business. Look for practitioners who understand your business and team needs. People who can process what design thinking as a method means for your team, business, and industry. They’re the ones who’ll be able to customize the process to you.
  • Full Process Approach. Design Thinking can’t be done in a vacuum, and it can’t be done in a 1-day “workshop.” Sure, you can learn the basics in a 90 min class. If you’d like to do that, here’s a link. It’s free. For teams who want to use design thinking to solve real-world business problems, look for practitioners who offer longer training timelines. Think about it. A core advantage of design thinking as a method is to better understand your customers needs so you can design better solutions. To understand your customer needs, your team needs to get out of your office to connect with these customers. For that you need time. A month is minimum when it comes to really learning the design thinking method through practice. Customize your budget to that. 
  • Listening Skills. The experts you’re hiring are “experts.” Be careful of those who believe their own hype. True design thinking practitioners know that this is a growth process; you’re always learning new things and making the best decisions given present facts. The good ones know to listen to your needs, and adapt the process based on what they hear. Remember, it’s a malleable process as long as you give it enough time to take root. 
  • Real-World Experience. As with any academic theory, Design Thinking sounds like an easy, smooth process to sail through. It’s hardly ever lives up to that in the real-world. Things often go wrong, interviews can’t be scheduled, prototypes break down, ideation sessions veer into crazy debates, and so on. Lots of things can go wrong. Experienced practitioners who have not only taught the method to others, but have actually practiced it themselves in a business context can steer the design thinking ship to calmer waters. 
  • Great communicators. As surprising as this may be, a lot of design thinking practitioners are not great communicators. They may be great designers themselves, yet have trouble concisely explaining abstract concepts to non-designers. As trainers for your team, they need to be able to communicate not only the “how,” but also the “why” of design thinking. Furthermore, at some point, you’ll need to sell (or re-sell) your progress to upper management. It really helps to have your design thinking guides there with you to offer support either behind-the-scenes, or in the room alongside you. 

As you’re looking for vendors keep the above checklist in mind, and adjust your budget accordingly. It’s easy to get lost in snazzy bios and shiny past-client lists as you sift through available options. Don’t lose sight of what really matters. You’re looking for a partner, someone to guide and support you and your team through the process and catch you when you fall through the cracks.