Building Bears and Building Empathy in Undercover Boss

Photo by congerdesign at

Do you know those kids who are always asking questions? “Why is the sky blue?” “Why do dogs bark?” “Why do we get hiccups?” Why, why, why. This behavior may seem annoying or disruptive, but it’s actually important for creativity, and critical thinking. There’s even a career for those of us who were never discouraged from this curious approach to life: user experience (UX) designer. UX designers are always asking questions, learning, and trying to understand everything they can. This is particularly important during the first step of the design thinking process—empathizing.

Design thinking puts users and their needs at the center of the design process, so in order to create a successful design, you need to learn everything you can about your users, even things they may not know about themselves. The empathizing stage is when you do this. During this time, UX designers will interview, survey, and observe users in order to understand and empathize with them. Some UX designers will even become users themselves to feel what it’s like to be in their shoes.

This is the aim of empathy, to understand what it is like to be someone else. Only by using empathy as a UX designer can you recognize people’s needs and design products, services, or experiences that work for them.

Undercover Boss

Photo copyright CBS

The reality show Undercover Boss is an example of how UX designers gain empathy for users. On the show, corporate leaders disguise themselves and work alongside employees responsible for the day-to-day operations of their companies.

Through this experience, leaders not only receive more honest insights about what is and is not working in their companies than a formal report or employee survey would provide, but the process of empathizing with their workforce often personally inspires them to change in some way.

The show’s structure exhibits how multiple people can have different experiences even within the same company. This is the reason UX designers want to gain insight into every type of user in the ecosystem of a product or service. Listening only to the perspectives of members of the C-suite or only to employees on the store floor doesn’t create a comprehensive understanding of the problems a design will need to solve.

undercover Boss: An Example of Empathizing

Build-A-Bear Workshop storefront
Photo copyright USA Today

Season 8, Episode 1 of Undercover Boss features Build-A-Bear Workshop, a global retail chain where customers create their own stuffed toys. The company’s President and CEO, Sharon Price John, goes undercover inside the company as Jessie, who employees are told is a contestant on a different reality show.

Sharon has worked primarily in toy and children-focused companies and developed a reputation for fixing businesses and turning around struggling brands, a reason she believes she was hired by Build-A-Bear in 2013 after the company suffered 4 years of decline. Sharon wants to go undercover to see how a new store model she developed called the Discovery store is doing.

In the episode, Sharon works first at a newly remodeled Discovery store in Northridge, CA where she learns to host an in-store birthday party with Leney, a teenage store employee. Then she travels to an older model store in Whitehall, PA where she learns the bear building process and how to run the store registers from employee Nick.

Next, she works with warehouse employee Solomon at the company’s distribution center in Columbus, OH before finishing up in Alpharetta, GA where Assistant Store Manager Kendall trains her on how to interact with and help customers.

Through these experiences, Sharon learns her Discovery store model may need some adjusting to get the right customer experience and that the company is not providing its employees with all the guidance and resources they might need to do their jobs well. For example, details like how many stitches a bear needs when being sewn up are not present in training materials.

From Kendall, she hears that not all new employees find the company’s new training manual that Sharon created to be easy to learn from either. Kendall has created a Cliff Notes version of the manual herself in order to better help on-board the dozens of employees she trains.

During the experience, the employees also share their personal stories with Sharon, stories that involve medical challenges, family separations, and exhaustion. Sharon particularly connects with Kendall, a mother of 4 with a fiancé in the Air Force who is often away from home. Kendall is so busy she barely has time to sleep. Manicures are the only time and money she spends on herself regularly. Sharon relates to Kendall because they are both working mothers and both lost their own mothers to cancer.

Despite these tough personal challenges, Sharon is met with employees who come to work every day happy and enthusiastic about their jobs. She sees that the warmth and openness of her employees is what generates the positive spirit of the company. By being their passionate and caring selves, they create memorable experiences for customers and a supportive work environment.

Sharon being interviewed about how the undercover experience affected her.

This inspires Sharon to change her leadership style. Like many other female leaders, she says she’s always held back showing parts of herself in the professional world in order to succeed. She realizes on Undercover Boss, though, that for Build-A-Bear to be successful it needs her to be her true self and show her joyful, enthusiastic, and emotional sides the way her employees do. She is thankful, to the point of tears on camera, to have her employees teach her this lesson and decides to pay them back.

When Sharon reveals her identity to Kendall at the end of the episode, Kendall fears she is in trouble for making her own training manual. Sharon, though, shows appreciation for her recognition of the problem and her effort to fix it. She asks Kendall to help create a quick reference version of the manual to be used company-wide, work for which she will compensate Kendall.

Sharon also empathizes with how Kendall sacrifices to work hard and care for her family. Sharon thanks Kendall for her dedication and selflessness by giving her manicures for a year, $10,000 for her wedding, and $40,000 in a college fund for her kids.

Empathy Mapping Undercover Boss

On the show, bosses only spend 1 day at each worksite and I was only able to view about 10 minutes of footage from each site when watching this episode. However, I was able to gain enough user insight about Sharon and Kendall to create empathy maps for each of them.

As I discussed in a previous post, empathy maps are a great visual way to organize and reflect on the user information you gather through empathizing activities, like exhibited in Undercover Boss. They can help you to identify holes in your user research and be used as references throughout the design process to make sure decisions are being based on user insights instead of personal bias or assumptions.

My empathy maps for Sharon and Kendall consist of 6 sections: Think and Feel, Hear, See, Say and Do, Pain, and Gain. Just from watching the episode, I was able to fill each section with 3 to 4 insights about each person.


On my empathy maps, Sharon and Kendall turned out to be pretty similar despite being in very different roles within the company. They are both dedicated and hard-working women who try to balance their professional lives with their families.

Both also have a deep care and love for Build-A-Bear and the culture of fun and family that the company stands for. They agree that success for the company looks like every customer getting a personalized and memorable experience that has them leaving with a smile on their face. However, because of this shared drive to help others and fix problems, whether it be at work or for loved ones, they are both prone to putting themselves and their feelings last.

Since the show focuses on the boss, though, I had a much easier time filling out an empathy map for Sharon because I had 40 minutes of footage to learn about her from compared to less than 10 minutes for Kendall.

Optimally in a real user research scenario, I would have more time, but the constraint did force me to focus on every little detail for Kendall more: when she smiled, if she hesitated to talk, did her eyes tear up a little. It was good practice for dealing with users who might provide me very little to work with either in time or responses. But scheduling enough time to talk to or observe users in the empathizing stage of design thinking is optimal for getting information and accurate insights.

After completing Kendall’s map, I felt like the editing and focus bias of the show was somewhat to blame for which areas I struggled with. I had an easy time filling in Kendall’s Pains because the show wanted to highlight footage of that in order to show what Sharon was learning and to heighten the drama. Kendall’s Gains though were much harder to identify than Sharon’s.

Sharon was directly interviewed on camera about her reflections and learnings from the experience and I was able to almost directly quote how this experience benefitted her. Kendall wasn’t interviewed, except through Sharon. Because of this, I can see how observations are valuable to the empathizing process, but frustrating because observers can’t control what information they receive from observations.

The guided nature of interviews, though, is helpful to allow for follow up or focus on specific, higher priority information. All user information is valuable, but some is more helpful than others.

If I’d found myself struggling to fill this section on a real project, I would have stopped and done a follow-up interview with Kendall to focus specifically on how working at Build-A-Bear benefits her. Unfortunately, I can’t do that with a tv episode so, I pushed through to come up with more Gains for Kendall in the form of hopes and dreams. I’m not as confident in them being as accurate as I am Sharon’s Gains since I felt I had to extrapolate from my limited knowledge of Kendall more than I felt comfortable with.

I also struggled to keep myself from worrying about different sections having related content. The point of the empathy map exercise is not to be precise, but I was concerned about whether I was paying too close attention to certain information since it popped up in multiple sections and ignoring other possible information as a result. I found, for example, that many things Sharon and Kendall felt were relevant to the Think and Feel section, but also to the Pain and Gain sections. It seems logical that these may be closely related, though, considering how much emotion affects whether we decide an experience is good or bad.

Everything Matters

The most important realization I had filling out empathy maps was how focused a UX designer has to be to notice every detail when observing or interviewing a user. I had the benefit of camera angles and editors that focused on the most emotional and important things about Sharon and Kendall for me. I also had the benefit of a rewind button to make sure I wasn’t missing something. But in a real situation, I would need to be attentive enough to notice someone biting their nails or averting their gaze while also paying attention to what they were saying.

It’s hard to do 2 things at once. There’s a reason patting your head and rubbing your belly at the same time is a challenge. To have a full and robust empathy map from which to understand your user requires recording data related to all 6 different categories.

A user could provide you information related to any of these 6 categories at any time and you must be open and receptive to that or you may miss a key insight. You can’t just listen to what is being said when you interview a user or only watch a user’s behavior when doing an observation.

Empathizing requires you take note of what someone is doing, saying, seeing, and hearing at the same moment. Collectively, all of this information is what makes up their experience—exactly what you are tasked with understanding as a UX designer.


Battarbee, K., Suri, J.F., & Howard, S.G. Empathy on the edge. IDEO. Retrieved from

Curiosity is the wick in the candle of learning. Penn State Extension. Retrieved from

Gibbons, S. (2018, January 14). Empathy mapping: the first step in design thinking. Nielsen Normal Group. Retrieved from

Kelley, T. & Kelley, D. (2013, November 8). Why designers need empathy. Slate. Retrieved from

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