Useful Books For Designers Who Work On Complex Problems

Chances are high that you are working on a challenging, complex product. Workplaces with deep organizational hierarchy, domain complexity, entrenched culture, legacy, and a wide array of conflicting priorities from opinionated stakeholders at every turn.

How do you thrive and survive in such environments? Well, there are no quick answers to that question, but there are a few books I would wholeheartedly recommend to get started. Let's take a look.

My Book Recommendations #

• How Big Things Get Done, by Bent Flyvbjerg & Dan Gardner. Fantastic research on why complex projects run late and over budget, why right-to-left thinking matters and how to minimize risks of failures and delays.
• Factfulness, by Hans Rosling. A fantastic book on how to better understand messy reality by learning where progress has happened, where challenges remain and how evidence can guide better decisions.
• The Phoenix Project, by Kim, Behr & Spafford. A fictional novel, but a truly insightful book on the importance of flow, bottlenecks and operations in a product/IT company.
• The Goal, by Eliyahu Goldratt. A legendary classic on improving a system by finding and fixing bottlenecks — for PMs and product or staff designers.
• Thinking in Systems, by Donella Meadows. Probably the clearest guide I could find about systems thinking, feedback loops and how to intervene at the right time, with the right pace at the right place.
• Algorithms to Live By, by Brian Christian & Tom Griffiths. An insightful deep-dive into how people make daily decisions, and how to deal with overwhelming choices.
• The Culture Map, by Erin Meyer. A wonderful book on how to communicate and work with truly global teams across cultures — from feedback and trust to collaboration and decision-making.
• Articulating Design Decisions, by Tom Greever. A very practical strategic book on how to communicate UX work effectively to senior management and people who need to approve your work.
• Narrative Economics, by Robert Shiller. A book focused on economy, but really about how ideas move markets. A great read on how contagious stories, not just data, drive decisions, events and spread impact over time.
• Envisioning Information, by Edward Tufte. A deep, dense classic on how to deal with complex data and how to display it to maximize clarity. A must-read for every data visualization work.

• The Great Mental Models, by Shane Parrish. How people think, grasp new areas, find patterns and understand the world. A lovely series about mental models and how people think.
• A Pattern Language, by Christopher Alexander. Actually a book about patterns in architecture, but also about how spaces are organized, and how to think of living and working systems.
• Org Design for Design Orgs, by Merholz & Skinner. How to build, structure and scale in-house design teams — on hiring, roles and operating models. Not a topic that's often covered.
• Thinking in Bets, by Annie Duke. Perhaps a bit of a cliché recommendation, but a lovely book on how to make better decisions under uncertainty, when you don't have enough evidence.
• The Missing Billionaires, by Haghani & White. To me, a fantastic book about risk management without being a risk management book. How to strategically approach risk and financial decisions over a long period of time.
• Bulletproof Problem Solving, by Conn & McLean. A classic 7-step framework for tackling complex, ambiguous problems — and how to embrace imperfectionism.
• Practical Charts, by Nick Desbarats. The only practical guide to charts that I found incredibly easy to understand. A must-read for data viz and dashboard design.
• The Laws of Simplicity, by John Maeda. A classic. A very short book that entirely changed how I think about design decades ago.

Wrapping Up #

The world desperately needs patient and passionate designers to improve the messy, complex and legacy-ridden systems that are so common and so frustrating in daily lives of millions of people.

You might feel stuck — in enterprise environments, education, healthcare and public services; yet that's exactly where your design work can make a tremendous impact for people who need it the most. It's at times a painful but extremely rewarding experience, as long as you bring along enough patience and care.