Empathy, Perspective, & the Perils of Design Thinking Dates


I have experienced the design thinking process several times over the past few months and each time, the overwhelming feeling that I was left with was a sense of playful wonder and discovery. Design thinking is fun, lively, fast and in each of my experiences with the process thus far, it has a contagious childlike component of sheer excitement and possibility. But as my month of discovery is quickly coming to an end, I decided a little extra practice would be beneficial. So I decided to make use of the great resources over on the Stanford d.school website and take their 90 minute virtual crash course in design thinking. Wanting to really ‘live’ out design thinking in my everyday, I enlisted my boyfriend, Matt, to be my partner for the course and attempted to make a date of it.


Two Saturdays ago we gathered arts and crafts supplies and other oddments accumulated around our apartment, poured some wine and settled into the couch ready for a fabulous DT date. Except that it wasn’t fabulous. It wasn’t even fun. In fact it was unnerving, boring and left me in a bad mood. I had to sit on that observation for a while before being able to make some sense of these strange (given past experiences) feelings. And the conclusion I came to is that we know (and think we know) each other too well. Instead of really listening to each other and trying to draw out information that would reveal the true tension at the heart of the challenge for our partner, we were both filling in the blanks ourselves (those blanks we assumed were important) with what we knew and supposed about each other.


The d.school virtual crash course is based around redesigning the gift giving experience for your partner. You are asked to interview your partner about their last gift giving experience–enquire about the whole process, from deciding to buy a present to choosing which one to get, to giving one and receiving a thank you card. The aim of the challenge is to identify the core tensions at the heart of the gift giving experience for your partner and redesign the experience or relevant parts of it to align more organically with the needs, constraints, motivations and challenges of your partner.



We had both been present at the other’s last gift giving experience. I had helped Matt pick out an infant tummy turtle for one of his colleagues who had recently become a mother and he was with me when I ordered a wedding gift for my friend off of her Bloomingdale’s registry. That was the first problem. Since both of us had been present the last time the other bought someone a gift, we arrived at the interview with a lot of preconceptions from having been there and thinking we knew, if not the whole story, at least the facts. That was a key (and negative) departure from the design thinking process. By thinking we knew, maybe even better than our partner himself or herself, what the core tension at the heart of their gift giving experience was, we had left the emphatic, playful terrain of design thinking and entered the stifled, user unfriendly ‘focus group’ mentality. We had observed and engaged with the other person during their last gift giving experience and we naively assumed that this meant we understood what the experience felt like for the other person. We were not actually seeking deep, empathic understanding but rather ‘baiting’ each other with subjective questions that would lead the other to give answers we, as the interviewer, had already decided on.


The course is presented as a 90-minute video, where two IDEO designers lead a group of people through the design thinking process and encourage the viewers to do the same in real time. In all my previous experiences with Design Thinking, the organizers’ prompts to move on from one stage of the process to the next have always felt like an interruption. As though you are finally starting to get to what you were reaching for when bam! It’s time to move on to the next activity. Not so for our design thinking date. We were both done interviewing each other at least a minute before the four allotted for each of the partner’s interview were up. Instead of taking a step back and trying to evaluate why it was that the process felt so different this time around, I became frustrated, decreed the experience on the verge of failure and yelled at Matt to take this seriously. And just like that, with three little words, I obliterated the spirit of the design thinking process; I lost sight of the playfulness and empathy intrinsic to the process. Over the course of my few experiences with design thinking, I had come to identify a baseline ‘normal’ feeling for the process and as soon as my emotions deviated from the standard that I had established, I freaked out and felt like the entire process—rather than say, my interview questions—were all wrong. Part of that issue, I think, stems from the fact that we are rarely taught to think about the connection between feelings and processes. We are not taught to be attuned to our feelings over the course of a process and to identify and accept negative feelings when they arise; to see them as real time feedback—warning signs to step back from the immediacy of the project, determine their cause and address them as they arise.


I have spent some time trying to understand the underlying cause to the various points where we went wrong and I have come to the conclusion that it was a perspective issue, in the literal sense—we were too close: to each other and to the experience. There is a famous anecdote about looking at paintings: if you are too far away from a painting you miss all the brushstrokes and the magic of the details but if you are too close you miss the unity and flow of the entire piece. In experiencing life, as in art, one should strive for that middle ground, the perspective that captures both the brush strokes and the big picture. But that is much more easily said than done. We are programmed to think and live in contrasts and binaries. To give salience to our experiences we must parcel reality into digestible portions. There is no such thing as silence, yet it is something that we all agree exists and have experienced. Silence is a necessary byproduct of sound. For us to hear things, we must tune out others. And because evolutionary the new and unknown represented a very real threat (hello frenzied, blood thirsty dinosaurs), we tend to foreground the new and unusual at the expense of the familiar, which we take granted to such a degree that we often fail to notice it entirely.

The challenge then becomes about creating ways of seeing the familiar with new eyes and minds. How do we unroof the familiar? How do we instill discovery and wonder into our every day routine and interactions? This is no easy feat but a worthy pursuit. I am toying with the idea of committing to a rethinking…* the everyday challenge where I would experiment with one idea or activity each day that would help me experience the habitual, familiar and common sensical—all those things that form a ‘given’ part of my life and which I rarely notice—as if for the first time.

Our prototypes for the redesigning the gift giving experience design thinking challenge. I made Matt a Digital Gift Giving Assistant App that would not only track birthdays, anniversaries and other gift giving occasions, it would also help him generate gift ideas based on various variables (such as the recipients likes and dislikes, online wish-lists, character traits, etc.). Meanwhile, Matt made me a tiny reusable camera that can be inserted into a gift box and will notify me when a friend receives a present I have sent so that I can then see her reaction online where the camera is live streaming her opening her present.

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