The first common thread to identify about my personal favorites is their orientation to designing products primarily for software users. There are only a few exceptions in this list.
Understanding the origins of user experience design will deepen your appreciation for the calling designers have in the world. There is a significant sequence of historical events surrounding Don Norman's life that every designer needs to be aware of. This is the man who coined the term 'User Experience' and invented the title while doing just that for none other than Steve Jobs at Apple. Before that, Don Norman's design of airplane control panels literally saved lives. Later he cofounded the Nielsen Norman Group, which publishes some of the most authoritative literature on design.
Don Norman's credentials aside, this book is maybe unsurpassed in decoding the extremely complicated variables and constraints that lead to simple design that pervades the world we now know. While design is largely de-intellectualized among the way most people - and even many designers - think of it, Norman does a fantastic job introducing the science and cognitive psychology behind great design. Read this book and you will never view your surroundings in the man made world the same way.
The way you communicate about design will level up after reading this book. UX is one of the most amorphous fields to most people. Design literature feels all over the place in the beginning. There is mountains of information of all creative varieties, all aspects of product architecture, all kinds of companies, and all types of design contexts. To be a good designer you're supposed to be able to know how it fits together, but if you're reading several books about design and you can't even confidently define what user experience design is or what a user experience designer does (!), you may feel a serious case of imposter syndrome. There is no better book I know of to go from having a brain looking like a hoarder's closet after an earthquake to a perfectionist's organized work bringing the mental serenity that goes viral on Pinterest. From here you'll always know where what information goes where in your head, how to dissect the design work of a product, and how people of different design disciplines fit together.
This book is the operation manual for designers for any standard design project. It doesn't just give you the must-knows of software design, but also how to facilitate design in a team environment (which is, in reality, half the job of a designer). If you are an aspiring designer looking to land your first job asap or someone who does not have a lot of design experience and you need quick help for a standard web or app design project, referencing this book is your step 1. You can venture into other books later to expand your design tool assortment, deepen your understanding of psychology and design principles, and lead design in a team.
After lack of experience launching a product, the second major factor I know contributing to novice designers' overconfidence in their design assumptions is ignorance of human factors. You just can't skip the education of cognitive psychology if you intend to design products that people love.
Human-centered design requires factoring principles of cognitive psychology. Similar to the way Don't Make Me Think will give you the principles of software usability to get you most of your way there in implementation, Thinking, Fast and Slow will get you far in understanding the human processes happening in the context of your design. I don't think there is a book that will help you understand the mechanics of thinking as well this book. Daniel Kahneman did not specifically write this book for designers. In fact, his psychology work is of such consequence that it earned him a Nobel Prize in Economics.
This book is a very accessible collection of psychology research that is highly-consequential to design work. It's very well organized, aesthetically pleasing, and separated into easy chunks you can easily process over a time. It's a great book to pick up for 5 minute increments. Doing so over time will effectively build your intuition for great design.
For anyone designing products for learning, this is the cognitive psychology book needing to make its way into your queue of books to read soon. If education were designed around the science of learning, it would basically not resemble the schooling structures we have. This book is one I, personally, cannot exclude from this list. That is because of my life's calling to turn education on its head - first at home and then in whatever possible way I can for the world.
We live in a world that is getting immersed in information at an exponential rate. Organizations and individuals are producing information for more contexts via more channels for more purposes than anyone could possibly wrap their mind around. There are, however, governing principles to designing information architectures for easier navigation and understanding that will remain constant in the face of constant change. Information architecture is the most invisible, yet very real, subfield of user experience design. "That's some sick information architecture!" said no one ever.
Everyone works in environments with politics, confusing standards, nonsense procedures, and/or complex sectors of the economy. Making sense of virtually any context takes a lot of work. If you're like most people, you can just learn how things are done and unquestion it. If you're interested in making sense of things, though, and maybe facilitate improvements for everyone's benefit, then this is your user-friendly field guide to information architecture.
This book is the most authoritative on the general subject that I know of. If you are interested in designing information products, this is a must read.
Making human / product interactions feel natural requires the anticipation and design of every thought and feeling through the user journey. That requires a lot of iteration, but more important than sheer trial and error is mastering the tried and true principles.
While UX design is not UX without user research (or other context-specific parts of the process), there are still rules to usability and conventions that can get you most of the way there in the implementation phase of your software design. This book outlines those more effectively and concisely for web and mobile design better than any that I know.
Few designers feel a need to publish another book on interaction design because of this book. This book breaks down every part of the process and every part of product architecture for designers to effectively build a product that is designed for the thoughts and behaviors of a user. When followed well, this book will guide you to create a product equivalent of an expert interviewer. It understands you and orients itself around your behavior to deliver what you want.
For any product whose strategy is at least in part to motivate the user, this book will help you identify ways of doing it. If you like designing for motivation, this book is a must read.
A widely-understood red flag in the UX world concerning designer credibility is having high confidence in one's solutions before seeing validation. In reality, you just never know how good your design work is until you have tested it. This is problematic at an individual level - someone could spend a hundred hours of work and rework that a good designer could accomplish in ten hours. This is catastrophic, though, on an organizational level. Companies waste thousands of man hours and millions of dollars all the time due to assumption-based design. The key to effective testing is designing the right kind of tests. These books will get you there.
In most design contexts, thick academic books on user research in general or specific facets of it will be overkill. Here is a great, authoritative, well organized 100+ pager with the sections you will need to reference for effective planning and on-the-go self-checking.
It's more common to work with people who understand web analytics, statistics, and marketing. So companies usually have their analytics measurement set sufficiently well. What is much rarer is having someone around to surface the blind spots and strategic insights through interviews that require more sophisticated execution than simple interactions. This book will effectively fill that gap for the action-oriented learner.
From the books on my favorites list it's pretty clear I focus on the functional problem solving aspects of human-centered design. There is one visual design book, though, that has helped me go a long way on my designs.
In the spirit of needing to master the rules before you can break them, this is a great book that is widely-regard as defining the basics with authority. I think about the principles I learned in this book and in the way Robin Williams taught them every time I evaluate or touch a visual design. It's a great go-to resource when defining your company's design system.
As products and services everywhere are increasingly expected to offer the great experiences tech giants offer, the world of design is, too. Companies have to keep up with best design management practices to stay relevant. It's becoming more and more the case that your design operations determine your successful implementation. Design leadership and promotion of design culture are becoming key to companies' success.
If you're not yet in a position to call yourself a 'UX Designer' but have enough sense to know your team has a gaping blind spots and headed toward more trouble than they know, here is your go to book. It will give you a research and design tool kit designed specifically for that purpose - to win teammate support and turn things around one thing at a time. This was the exact scenario I found myself in at Daplie, which helped me become CPO and work on a product that was eventually acquired by Clear Foundation.
Google Ventures designed this collection and sequence of tools to jump start companies who need to surface their highest priority challenges and hone in on the most important one to fix that same week. While the team exercise makes no promises of solutions, it does very effectively facilitate the creation and testing of a team's best shot very quickly.
When scope of design requires many designers and the implementation of those designs is carried out by multiple departments you have to take a few steps back and orchestrate. Someone needs to take over UX Writing, utilizing multiple forms of documentation, and presentations to key individuals. This book gave me the frame of mind and the actionable guidance to get this done to industry-standard when I never had before.
When experiences are being delivered that consist of physical and digital touch points by multiple departments of an organization, the user's experience is defined by the entirety of it. Ensuring seamlessness, consistency, and a brand-defined experience throughout requires cross-departmental coordination and the design of many mediums, evidencing to the user throughout that your company cares about them and its processes oriented around them. This book is a compilation of Service Design professionals' best takes on all aspects of this.