Published on | Prototyping: From UX to Front End — Medium Ashish Goel

7 books that helped deepen my design practice

If you’ve read or looked for books on design thinking, you have surely comes across some of the usual suspects. Books like Change by Design, The Design of Everyday Things, Creative Confidence and more. These are excellent books and do a great job of giving you an overview of the design thinking landscape — the impact design thinking can have, success stories, research studies, key concepts and ways of applying it to your life and work.

However, when I was a teaching fellow at the Stanford d.school, I often needed to go deeper. How exactly does one go from interviews to insights? Why is it enough to just talk to 5-6 people to frame your design problem? Why the particular phrase “How might we…” to set up a brainstorm? Why does the sensemaking phase feel so draining? and so on. I had to deepen my own understanding of the tools and concepts I was trying to teach.

Luckily, one of the great joys of being in academia was that reading was part of my job. Here’s a list of books that I discovered during my time as a student, teacher and beyond that helped answer some of these questions and deepened my understanding of design thinking.

Creative Behavior Guidebook

Sidney J. Parnes • 1967

If you have experience with design thinking, you must have come across the notion of ‘deferred judgement’, one of the rules of brainstorming. The idea is to delay evaluating ideas in a brainstorm — even if they are impractical or obvious. Why defer judgement? One reason I’d heard is that it separates idea generation from idea selection. Or, that it creates a supportive environment — by not shutting each other down, you increase the quantity of ideas. This concept is easy to understand, but it is very hard to internalize and it took me some practice to do so.

Ever the skeptic though, I like finding better reasons for a rule. Here’s one that Creative Behavior Guidebook offers:

Deferred judgement does not actually increase the generation of creative ideas but rather increases the *willingness of a person to report ideas* that he ordinarily might devalue in his own mind.

This is a much more cogent rationale, and one that makes it easier to start practicing deferment of judgement. Before becoming a better group brainstormer, become a good individual brainstormer. I am often critical of my ideas — so giving myself the permission to puke out five bad ideas before a good one is liberating.

Here’s a figure from the book describing the trade-off between “complacency” and “perfectionism”:

Parnes writes,

The low end of the curve might be called “complacency” — willingness to accept common associations and habit-bound solutions. The upper end might be called “perfectionism” — unwillingness to let go of an idea because it is not the ultimate idea. Willingness to operate in the middle portion of the curve probably represents the happy compromise between staying “too tight” and staying “too loose” and probably represents the area of maximum creative accomplishment.

Design thinking is often linked with innovation. But how do you know when what you’ve come up with is innovative enough? As Parnes writes, finding the happy compromise between staying “too tight” and “too loose” represents the area of “maximum creative accomplishment”.

I’ll do one more snippet, and then I promise I will move on to the next book. Here’s Parnes talking about “Method vs Purpose”

Some new practitioners of design thinking get too attached to the process or the tools. They get in a state of ‘blind conformity’ and lose sight of the what the intent or purpose of a step or method is. The above excerpt is an excellent reminder to stay nimble in how you use the design thinking process.

This book also comes with a full course on teaching creative behavior, laid out in exquisite detail. There are quotes you might put on a flipchart, materials, in-class exercises with suggested times for each exercise and much more.

Unfortunately, this book seems out of print. Here a link to a PDF of the first chapter. Also a WorldCat link to libraries that hold this book.

Design Thinking

Nigel Cross • 2011

Another book I highly recommend is Nigel Cross’ ‘Design Thinking’. I wish this book had a different title because the phrase design thinking has become a tad too attached to the process diagram.

What Cross talks about is actually much more fundamental than the Process. Here’s his approach to this book

“My approach to trying to understand how designers think and work is research-based: I look for and report evidence that comes from observation, experiment, analysis and reflection. My aim is to reveal and articulate the apparently mysterious (and sometimes deliberately mystified) cognitive and creative abilities of designers, that are common across many design domains.”

By studying designers across fields like car design, product design and architecture — he has found common patterns and problem solving approaches which remain implicit in the process-centric approach. Here are a few excerpts:

On the nature of design thinking:

Lionel March preferred to call designing ‘productive reasoning’ because the designer has to produce a composition, or product. Unlike conventional logic, a design solution cannot be derived directly from the problem, but can only be matched to it. Unlike the scientist, who searches for many cases to substantiate a rule, and then one case to falsify it, the designer can be gratified in being able to produce just one satisfactory case that gives an appropriate result.

About prototyping not just being a step in the process, but a necessary tool for thinking:

Designing, it seems, is difficult to conduct by purely internal mental processes; the designer needs to interact with an external representation.

Or, on reframing, how the initial problem statement often changes:

Designing utilises aspects of emergence; relevant features emerge in tentative solution concepts, and can be recognised as having properties that suggest how the developing solution-concept might be matched to the also developing problem-concept.

One of my favorite bits is his analysis of Philippe Starck’s Alessi Juicer. Cross writes, “The renowned (perhaps even notorious) French designer Philippe Starck is known to suggest that design ideas seem to come to him quite magically. It is possible to unravel even Philippe Starck’s mystical account of the conception of his Juicy Salif lemon squeezer into a much less mysterious explanation”

On the left, “Juicy Salif”. On the right, a sketch Starck did at a restaurant after he had gotten the design brief.

Let us set aside for a moment on whether or not the Alessi juicer is “good” design, or if making a new juicer is a problem worth tackling through design thinking. But in deconstructing how Starck thinks through this design, one thing that Cross notices is,

“Starck, in developing the concept, was doing what many designers do, which is to draw upon a repertoire of precedents, of remembered images and recollections of other objects that helped him to give a more coherent, practicable and attractive form to the concept. Starck drew for inspiration not only on the squid but also on his boyhood interests in sci-fi comics and spaceship imagery.”

The current canon on design thinking focuses on the user, and rightly so. But it does not fully capture the role of the designer itself, and how much one’s experiences, influences and history can affect what you make.

A great short read to get started with Nigel Cross’ work is the paper ‘Designerly Ways of Knowing’.

Notes on the Synthesis of Form

Christopher Alexander • 1964

In Notes on the Synthesis of Form, Christopher Alexander explores a mathematical approach to tackle complex design problems.

He does this in the following sequence. First is a framework to think about any design problem. This part is the closest to design thinking. The second compares design in pre-industrial societies, which he calls unconscious design to industrial-era design which he calls conscious design. The third part lays down a mathematical approach that involves listing all the constraints (or forces) of a design problem and then creating abstract diagrams that can then be used to design the actual form.

I personally found the part on listing forces and creating diagrams exceedingly obtuse, which calls for a second read. But the first part — his framework for thinking about design problems is a refreshing and analogous take on design thinking.

It gave me a brand new vocabulary to talk about design. For example, he writes:

Every design problem begins with an effort to achieve fitness between two entities: the form and its context. The form is the solution to the problem; the context defines the problem. When we speak of design, the real object of discussion is not the form alone, but the ensemble comprising the form and the context.

This notion that “the real object of discussion is the ensemble comprising the form and context” gets to the heart of how the product or prototype is less important than what experience or behaviour it facilitates for its particular context of use. Alexander also writes:

We must also recognize that no one division of the ensemble into form and context is unique. Fitness across any one such division is just one instance of the ensemble’s internal coherence. Many other divisions of the ensemble will be equally significant. Indeed , in the great majority of actual cases, it is necessary for the designer to consider several different divisions of an ensemble, superimposed, at the same time.

Alexander uses the example of a kettle to demonstrate this. If you were designing a kettle, you could draw a boundary between the kettle and the rest of the ensemble, because the kettle itself is a clearly defined kind of object. Alternatively you may claim that it is not the kettle which needs to be redesigned, but the method of heating kettles. In this case the kettle becomes part of the context, while the stove perhaps is form. Or, perhaps you might say that a kettle is the wrong way to heat domestic drinking water anyway, and be involved in the redesign of the entire house, and push the context back to those things outside the house form.

The process of empathy often helps identify which boundary is worth designing for.

I’ve written a longer post on this book here that explains these ideas better.

Exposing the Magic of Design

Jon Kolko • 2010

In my second year at graduate school, I worked on a year long design thinking project. Until then I had only worked on projects that lasted a fraction of a quarter. Now our team was going to spend a full quarter just doing design research (or needfinding). Our team chose redesigning long distance communication as our theme. We spoke to lots of people, did several observation sessions and built many sacrificial prototypes. But the process felt nebulous and de-energizing. Which of the stories we had heard was worth pursuing? Were any of our insights interesting? When were we supposed to start designing?

You may have experienced similar angst, especially after the interviewing and observation phase of the design process. The mass of qualitative data can feel daunting to navigate, especially when you are seeking non-obvious insights and trying to uncover latent needs. This mode needs a lot of simmering and sensemaking.

It was then that I ran into Damien Newman who said “Oh, you should read Exposing the Magic of Design, it is the only book on design synthesis”. I had never heard the phrase ‘design synthesis’ before. Luckily the book turned out to be exactly what I needed to understand where we were in our design process. If you’ve ever found yourself stuck on the “Define” phase of the design thinking process, this book should help.

Here’s a quote from the book:

Add complex content and often scarce time, and you are forced into an immediate conundrum: You must make sense of the data by immersing yourself in it, but the immersion takes time — and the more time spent inspecting the data, the less time can be spent actually designing .

Besides serving to allay my fears of are-we-doing-too-much-needfinding, there are several ideas in the book that I found really helpful. First was Kolko’s overarching framework of data, information, knowledge and wisdom and how these are separated by chasms that you have to leap over.

Another bit I really liked was his qualification of design research as an activity with decidedly different intentions than other kinds of research, whether it is scientific research or marketing research.

The subjectivity of the design process indicates that the ability to replicate findings — a critical aspect of a scientific method or process — is not a relevant part of design. One quite capable designer may synthesize gathered data with a certain result, whereas another equally capable designer may synthesize the same data with a wildly different result.

Here’s another table comparing design research with marketing research:

Note the differences from the third row onwards. Design synthesis attempts to *understand culture* in an effort to *inspire design*

I frame it as follows: Scientific research is the pursuit of truth (or what is), design research is the pursuit of inspiration (what might be).

Finally, the third part I love is the methods section. The methods are no different from what you find in any design thinking toolkit, but Kolko uses names that I presume come from their social or behavioral science origins. Capturing quotes on post-its on a wall? It’s called “memoing”. Grouping and categorizing for themes? It’s called “affinity diagramming”. I always enjoy finding alternative names for the familiar — it allows you to see something with fresh eyes.

Out on the Wire: Storytelling Secrets of the New Masters of Radio

Jessica Abel • 2015

I didn’t expect to include Out on the Wire by Jessica Abel on this list. In this book, Abel speaks to the creators of podcasts like Radiolab, Snap Judgment, Planet Money and others to show how they create great radio.

Yet, I was amazed by how much in this book has direct analogs to design thinking.

My buddy Seamus Harte once described the empathize mode of design thinking to me as storyfinding. Perhaps it’s no surprise that radio, a medium that is all about stories has the most evolved set of methods for storyfinding.

Some examples below:

Point of view madlibs

Folks familiar with design thinking would have come across a “point of view madlib”. It is used as a way to go from interviews and observations to an actionable and generative design challenge. It looks something like this:

A “Point of View” mad-lib. You can practice a variation of this through the d.school’s virtual crash course

Seems like it is no different in the radio world…

Yup, just how it goes after talking to users.

In Abel’s book, many radio creators use something called the topic sentence to articulate why the story is meaningful and worth producing.

Two examples of the ‘Topic Sentence’ from Transom Workshop and Planet Money.

Here’s the kicker though: by talking to several radio creators, Abel is able to highlight how this mad-lib is just a tool. A producer from Radiolab says “Those sentences give you high-percentage gambles on stories that have all the extra goodness in them. But the truly awesome stuff that happens with any story is not in the pitch…it emerges.”

Soren Wheeler from Radiolab

Prototyping and pain

Another part this book captures well is how design feels. This is where the graphic narrative shines — it would be hard to show that through words alone. One such emotional challenge is showing your prototype to a user or sharing your ideas within your design team. Hearing that something you worked on is not good enough is a hard truth to accept, and can be a big a blow to your ego.

The prototype-equivalent in the radio world is an Edit. It’s where a producer plays or reads a draft of the story and the rest of the crew critiques it. Abel notes that in her earlier graphic narrative on radio, she wrote “Just play it for people. Get their feedback”. Here she gets deeper, and notes that “it’s just way way more important and more demanding, than that”.

It’s like Testing your prototype!

In the chapter on Edits one can truly see the emotional challenges one radio producer has to go through.

Just the way “go talk to some users” is subpar advice for empathy, “show it users and get their feedback” is also terrible advice for testing. Overcoming the hesitation in showing unfinished work, dealing with the feelings of failure — all this is not easy, and this book makes that visible.

‘Most people will be polite in your edits. But there is not a lot of “I thought this moment was really beautiful”’. ‘You just have to develop a thicker skin’

Yup, you have to develop a thick skin. Here’s Ira Glass himself talking about how it feels.

“Don’t you know who I am? I produce this show!”

In case you didn’t read the strip, he says:

Sometimes people will give you notes on your piece, and you really disagree with the notes…I totally have a part of me which just like, I know what I’m doing. I’m really good at this. I hired all of you. And you work for me. I’m like, Don’t you know who I am? I produce this show!

I am not proud of these feelings. And I totally know that I’m completely in the wrong. There’s no question. I’m 100% in the wrong. They’re right and I’m wrong. It’s encountering your own failure.

This can get amplified when you move into a leadership role. No matter how experienced you get, being able to encounter your own failure is a muscle that you have to keep building as a designer.

Sketching User Experiences

Bill Buxton • 2007

Yes I am including a book on “UX” on this list! Why? Because this is the only book on prototyping that I’ve read that captures the ethos of prototyping as taught at the d.school.

Prototype is an overused word, and usually implies clay models or hacked-together contraptions. In the design thinking canon, it has an expanded definition. It isn’t about prototyping the product, but the experience. We often use phrases like “sacrificial prototype” or “low-fidelity prototype” to describe the kind of prototyping that is generative and exploratory. Buxton captures this well in his book, except he calls it “sketching”.

Tom-ay-to To-mah-to? What Buxton calls a ‘sketch’ is what ‘prototyping’ refers to in design thinking practice.

Here’s him writing about what the aim of sketching is:

What we are creating is less a product than a “context for experience.” Another way of saying this is that it is not the physical entity or what is in the box (the material product) that is the true outcome of the design. Rather, it is the behavioural, experiential, and emotional responses that come about as a result of its existence and its use in the real world.

This is exactly what testing is supposed to help us uncover — the behavioral, experiential and emotional responses that came about as a result of the existence of the designed artefact or prototype and its use in the real world.

The second part of the book has some methods for “sketching” — while most of the examples are from the world of interaction design, they can be easily applied to prototyping products, services and systems.

The Universal Traveler

Don Koberg and Jim Bagnall • 1974

One of the first classes I did in graduate school was a quarter long introduction to design thinking through multiple design projects. I thought I had the basics covered. So imagine my surprise, when in one of my other classes, Professor Bill Burnett put up the process hexagons and said there is a step before ‘empathize’. The zeroth step. That step is to ‘accept’.

I was struggling with one of my projects and this seemed to be the missing element. I was doing the project, but I hadn’t really given myself to it. I was going through the motions.

To accept is to give in to a problem or a challenge, to accept that it is you who is going to be working on the problem at hand. To not find easy excuses. I found this idea powerful. So when it came around to me being in the role of a teacher, I wanted to teach ‘accept’ to my students. I was wondering if there was a book that touched upon the theme. The amazing Scott Doorley recommended ‘The Universal Traveler’.

What did I find? Well, first, the design process:

Many articulations of the process. S0me quotes “Procedural stages need not follow one another linearly, like coaches of a train”, “The problem-solver is rarely relieved from dealing with all stages of accepting, analyzing, defining, ideating, deciding, acting and evaluating throughout the process”.

And then here’s what the book has to say on the topic of acceptance:

To ACCEPT is to make something part of your life…to open yourself to it…to assume involvement. Acceptance is a voluntary agreement to adapt yourself and your needs at least in part or for a trial period, to something else. In short, ACCEPTANCE IS AN ACT OF SELF-GIVING. As such, it makes sense to consider carefully what you can feasibly accept or must practically reject in life. Getting in over your head or never getting involved are the extreme fringes of poor acceptance management.

It is the lack or presence of acceptance that can determine how you behave when you hit a roadblock. I once had to lead a corporate team through an on-site design thinking project. They engaged with the fun parts, but when things got hard, they always had a seemingly valid excuse. They had not really accepted the challenge.

The Universal Traveler adds:

The most profound choice in life is to either accept things as they exist or the accept the responsibility of changing them.

It is also one of David Kelley’s recommended books.

How could you note include <insert-amazing-book-here>?

The hardest part about making a list is what to omit. How do I avoid the you-forgot-to-include-the-best-design-book-ever problem?

Even from my own limited reading universe, there are several amazing books and articles that I did not include here.

How did I select these? I used the the good ol’ point-of-view framework to decide include and what not to include.

The books I have listed above are the ones that I feel are very close or analogous to the design thinking canon as taught at the Stanford d.school. However, they are either written at a much earlier time, or written by people who are not a part of that community. In not being from that milieu they bring new ways of looking at the same topics.

Oh, and I’ll also leave this quote here from The Universal Traveler…

from The Universal Traveler

Design Thinking — after the appetisers was originally published in prototypr on Medium, where people are continuing the conversation by highlighting and responding to this story.

Design Thinking — after the appetisers

Cool stuff, every week

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