Books that helped me become a better designer

There is obviously a wealth of shortform content online, but the longform nature of books allows for such greater depth of exploration. But that length can also be a waste of time if not done right. Luckily for you I’ve picked out a few that I think can help level up your game from a successful design practitioner into a great design thinker and leader.

These aren’t reviews or summaries per se, just a few thoughts on what made them useful for me, and what people or situations it may be useful for in the future.

Daniel Kahneman

Kahneman explains much of human behavior as a dialog between System 1 and System 2. System 1 represents our instincts and immediate (fast thinking) reactions, responses that have evolved over millennia. System 2 is our conscious and thoughtful behavior, our logic and reasoning (slow thinking). We think of ourselves as rational creatures, more System 2 than 1. However, not only is the inverse demonstrably true, our System 2 even serves to defend our automatic System 1 responses, rather than truly analyze them.

The bad news is that our fast-thinking instincts are full of bias and are generally easy to manipulate. What’s worse is that our slow-thinking mind often finds rational-sounding stories to justify biased conclusions.

The good news is that we can train System 2 to be more aware of these biases and learn to spot the difference between justifying a quick conclusion and truly analyzing a situation. Kahneman lays out the theories and research on how we create and enforce these biases and examples of how they may come up in our day to day life.

How I see this as a UX practitioner: as product designers (by which I mean anyone who is making a product, including managers and developers), we are imprinting a part of ourselves onto our “users” (human beings). If we create and release our products quickly and without much thought, then we are imprinting a very large and unfiltered part of ourselves (let’s call this Fast Work). If we slow down, do the research, collaborate across disciplines, release, analyze, and iterate based on quantitative and qualitative feedback, then our imprint is greatly diluted, though of course still present (Slow Work).

There is nothing wrong with Fast work, just as we cannot live without our Fast Thinking System 1. But just as Kahneman suggests we be more conscious of the pitfalls of this mode of thinking, I believe we must also understand the risk of doing Fast Work, especially at scale. No amount of experience, intuition or intelligence can replace the value of Slow Work.

Jaime Levy

I love this book. It’s geared somewhat closer to early to mid-level practitioners, but I think holds universal value as a clear articulation of the value and practice of UX in the context of business. Early in the book, she mentions that it is sadly common how often UX practitioners are isolated from business strategy, making it challenging to form a cohesive system that works for both users and for the organization.

Levy provides a framework for practitioners to dig deep into the questions of “why” and “what” well before digging into the “how”, the typical domain of designers. The four tenets she proposes are:

I believe most UX professionals are well practiced in the last tenet, familiar with the third, and probably aware of, though not involved in, the first. The difference between the first and second tenet wasn’t clear to me at first, but she explains it like this: Business Strategy is how the idea will eventually generate revenue by serving customers and is exemplified by the Business Model Canvas. Value Innovation is figuring out what exactly it is that your product does for customers that they previously could not do, and how it provides these services at lower costs than the products customers were familiar with.

I think the book downplays the impact of brand and emotion on people’s decision-making, but Levy uses the language of modern businesses, and if UX professionals want to better communicate with their business-minded stakeholders, then we must learn that language. I look back to this book when I am starting on a new product or product strategy, working with someone new, or looking for ways to better communicate with stakeholders.

Abby Covert

I listened to Abby Covert speak at an event in New York a while ago and was so impressed with her and her book that I bought it on the spot. The book is an informal, light, and short collection of different ways to communicate information and flows. While the examples are weighted towards people who work in service or product design, I actually think Covert’s breakdowns are approachable enough that basically anyone who has to put presentations together at work may benefit from reading it.

For example, below are 3 small doodles interspersed with her text as quick examples of communicating a journey, a structure, and a system.

Covert goes well beyond diagrams. She tackles content strategy, taxonomy, research methods, and analysis. Perhaps my favorite is how she pre and endcaps the book, discussing intent, realities, constraints, and adjusting. If you work in at all complex organization, the following passage may ring true:

If you can’t tell, this is one of my favorites. I believe that it’s simple and clear tone makes it a valuable read even for experts who may have all these tools under their belt, but may not necessarily be able to explain them to non-experts.

David Deutsch

Deutsch spends some time defining science and progress beyond the practices of experimentation and observation. Well developed and executed experimentation may help us evaluate the strength of an explanation, but less rigorous ones may actually reinforce bad explanations by providing “evidence” that we are quick to absorb. A good explanation reaches well beyond our own experience and intuition, and the better it is the more universally it holds true.

Science without explanations — reporting numbers and variations without attributing any possible causes, is “science in form only.” The more unexpected the numbers, the more exciting the results. But without an explanation, this form of “bad philosophy” allows no room for growth, failure, even true discussion. But good philosophy and science with good explanations allow others to continue the conversation, to stretch or break it to the limits of our current ability. The formulation of these explanations and our willingness to test, amend, accept, or replace them is the beginning of infinity.

There is a lot to this book, but I’d suggest that everyone working in tech would benefit from a critical analysis of our own forms of testing and knowledge production. I’d come back to refresh my understanding of quantum computing and to find a sense of optimism in the pace of technological achievements and understanding.

Rochelle King, Elizabeth Churchill, Caitlin Tan

This book was integral to getting started on my path to understanding the role of UX in data-focused organizations. If you’re not deeply familiar with statistics and the best practices of AB testing, it is easy for me to recommend this book. I’ve written about my learnings from this book, and how I took it into my own design practice while working at Paperless Post.

If there’s one thing I would communicate in brief, it’s the distinction between being data-driven and data-informed. Letting yourself be data-driven gives you a scientific process and a quantitative decision-making framework, but it quickly boils down to minor iterations and tweaks. Data-informed design, on the other hand, sacrifices some of that rigidity and pure statistics in order to allow for other kinds of inputs and broader explorations. The authors show us the statistical best practices to bring into design thinking, and how to communicate with our more data-driven colleagues.

I’d come back again to this book to refresh my understanding of statistical principles, and to reference whenever I need to talk to designers about working with data.

Johanna Drucker

One of the more academic books in my list, this is not an easy read for those not steeped in the language of semiotics and media theory. Like most practitioners I know, I have only a tenuous grasp on some of this language, which made reading this book a challenge. However, I still found value in Drucker’s humanist analysis of “informational visualizations” — her term for what most practitioners might call UI.

The first chapter is dedicated to a history of visual representations of data, which makes this book valuable in and of itself. For example, she provides some examples of the development of plotting data on a grid, from a 10th Century diagram of planetary movement to Descartes’ analytical geometry. I only wish the imagery was larger and of higher quality, as those provided are too small to serve as much more than thumbnails.

Her primary concern is that of interpretation. Visualizations (UI), especially contemporary interactive ones, are distributed as presentations of data, devoid of any subjectivity or opinions. But they are, in fact, interpretations that make countless decisions on what to show, when, and how. While the subjectivity itself is nothing new, the ubiquity and power of the tools are at a scale not previously known to man.

Think about Google Maps. How does it calculate your routes? Pick the best one? Why do some businesses show and hide as you move the map? We rely on the application’s decisions daily, but there is no way to learn its mechanisms. Though not mentioned in the book, star ratings would be equally fascinating to dissect in Drucker’s language of interpretation, meaning, and obfuscation.

There are some ironies to this book, including a lack of any digital presence. Its author wishes for more access to the underlying systems to better understand tools’ interpretations. It is published as part of Harvard’s metaLab, a studio/lab dedicated to exploring the digital humanities. A print-only publication written in language accessible only to academics does not feel in the right spirit, though I believe the intentions of the author are true and I am glad for her contribution.

David C Evans

It feels as though this book has flown under the radar compared to other more popular books about psychology and design, like Designing with the Mind in Mind and 100 Things Every Designer Needs to Know about Design. Similar to Designing with the Mind in Mind, Evans uses established psychological theories as a foundation to discuss design best practices.

The key difference between those books and this one is its focus on design in the context of business, and not simply task comprehension and completion. I have to admit that at times I found the book shocking in its directness of how to utilize weaknesses in human behavior for the purposes of monetization. For example, it barely acknowledges any ethical considerations while reviewing the success of ads that mimic almost exactly organic content, instead leaving the resulting increase in clicks as the barometer of morality. I don’t believe that this is an inherently evil practice, but I would hope that his thinking is more nuanced than “more clicks = good.”

But that said, I strongly recommend this book for any designer working within a business, and especially ones working within an e-commerce or ads-based model. The main reason I propose designers should read this is that Evans is simply using the language of modern business, psychology, and product management. Those who receive formal design training learn about psychology as well, but usually in the form of visual Gestalt principles, or possibly theories about short and long term memory and multitasking if they study UX or usability. But the direct connection to some of these same principles and digital monetization is left to marketers and business students.

I believe this puts designers, and users, at a disadvantage. Maybe we feel uncomfortable implementing a feature that feels disingenuous, but we lack the language to discuss it from either a business or psychological perspective. And perhaps most unfortunately, we are reduced in our ability to provide alternatives that could be more positive to both the user experience and the business.

In the end, I will follow Evans’ lead and leave the complex subject of ethics out of this. Learn how your colleagues and employers think. Learn what they learned. Understand their point of view. Then, if they present a direction you disagree with, you will have the tools to have a balanced and meaningful conversation. You may not be able to set the organization’s line of right and wrong, but you will be an informed part of the conversation.

Erika Hall

A short, simple summary of some basic UX research principles. Its main argument is that ‘research’ is really just critical thinking by another name and that projects of any size benefit from its practice. Some of the main challenges standing in our way aren’t necessarily time or resources, since some research does not require much of these at all. Rather it is our own human foibles that are usually holding us back:

Politics — your boss or the board has chosen a direction, strategy or approach. Who are you to question it? Do you feel comfortable sharing differing results?

Insecurity — I’m a designer with years of experience. Shouldn’t I know what is the best approach? Why do you need a survey and usability test?

Laziness — To be blunt, it is easier to work with the above currents, rather than against them. Solutions from above or those available on blogs or popular websites represent easy outs.

I still reference this book at times for short and informative reasoning on what kind of research is appropriate for what kind of problems. This should for sure be on every UX Designer’s shelf, and even for professional researchers it can help provide language to communicate with your peers

Robert Hoekman Jr

Hoekman has a range of platitudes that speak to leadership within organizations generally, and to UX practitioners specifically. He also provides some helpful definitions for terms that we use and misuse every day. Some I noted:

“UX is the application of psychology to the design of technology.” (I liked thinking about how this could translate to other disciplines. Is Product Management the application of business to technology?)

“Process is crap.”

“The result of design is communication.”

One of the things that stuck with me is the range of competency we can experience in a skill.

Unconscious Incompetence -> Conscious Incompetence -> Conscious Competence -> Mastery

He attributes this to Harry Max, one of his UX leader peers. We start off not knowing what is good or bad, then developing enough taste to realize our own flaws. We then understand how, with conscious thought, to create good work until the point when we are skilled and experienced enough to create good work with barely any conscious thought given to the practice.

This book felt like a collection of well written Medium articles on a subject that not enough UX professionals write about — how to be real leaders within an organization.

Mike Monteiro

I’ve been following Monteiro since the beginning of my design career, when a peer showed me this YouTube clip of him and his Lawyer explaining when it’s time say “fuck you, pay me” to a client.

In those years his language and drive has not softened, but the target of some of his ire has. At first his tone felt like that of a tough dad, pushing designers to take the business side of our jobs more seriously. But his writing now has a darker edge, and I feel he has become angry at the world that, by his own admission, he has helped create. Whether as an agent of business or a tool of it, he believes designers (including anyone creating software — UXers, developers, product managers, etc) have created a technological ecosystem that is destroying our politics, our social structures, and our world.

He lays the biggest share of blame at Facebook and Twitter for knowingly creating systems that allow and profit from nazi and white supremacy rhetoric. Uber and Airbnb get swipes as well, less for their product and more for their disregard for local institutions and even their own employees. He mentions no specific names but briefly complains about ads that overly mimic site content and draw us in with targeted click bait headlines.

The press has taken a darker view of “big tech” recently, but often the ire is aimed at overzealous investors, hyper-ambitious founder/CEOs, or mysteriously powerful software engineers. Designers may occasionally get some flack for their role in crafting addictive experiences. Monteiro thinks we don’t get enough of that flack. We may say that it’s a CEO or Product Manager coming up with a product or feature, and it’s our job to turn that feature into reality, and we’re just doing our job. But it’s that logic that got us into this mess, says Monteiro. Our only hope is if our job also includes the ability, and willingness, to stand against features and business models that we believe has serious ethical and legal ramifications. No more excuses.

He has a few proposals, including unionizing and standardized certification for designers. I actually believe in some form of both the above, and hope that the certification part is inevitable. However, I disagree with him that these will solve the problem. Licensed and unionized professionals still need jobs, and that licensing may include an ethics review, but it doesn’t provide glasses to see through the fog of corporate strategy and the effects of seemingly small meeting room decisions.

The problem is way more complex than Monteiro gives it credit. But addressing the problem at all is so rare, that I think this is still an important book. Thank you, Mike.

Here’s a short list of more books that have helped shape my practice, I simply haven’t written about them yet:

This list is limited, largely by recency. I include more books on my website, though I haven’t written about all of them yet. I plan on revisiting this every now and then to add any books that stand out for me. Please let me know in the comments if there are any must-haves I should add!