Where to Start with Scott Berkun
Scott Berkun is a bestselling author, speaker, and former program manager at Microsoft, where he worked on Internet Explorer from versions 1.0 through 5.0. After leaving Microsoft, he became a full-time writer and speaker, drawing on his technology industry experience to write books that cut through conventional wisdom with humor and honesty. His books include Confessions of a Public Speaker (2009), The Myths of Innovation, Making Things Happen, and The Year Without Pants, which documented his time working at WordPress.com. Berkun’s writing stands out for its candor. He is as willing to share his failures as his successes, which gives his advice a credibility that polished business books often lack. His work has appeared in The Washington Post, The New York Times, Wired, Forbes, and The Wall Street Journal. He has been a regular commentator on NPR, MSNBC, and CNBC.
Start here
Confessions of a Public Speaker
Scott Berkun · 222 pages · 2009 · Easy
Themes: public speaking, stage fright, humor, real-world experience, presentation tips
Berkun’s most personal and entertaining book, built on fifteen years of professional speaking experience. Rather than offering a polished system, he shares the unvarnished reality of what it takes to stand in front of people and say something worth hearing. The book covers preparation, handling nerves, reading a room, and recovering from disaster, all told through stories that are as funny as they are instructive.
Why Start Here
This is the book that best captures Berkun’s voice and philosophy. His honest, self-deprecating style makes public speaking feel approachable rather than intimidating. You get the real story of what professional speaking looks like, including the bad microphones, the hostile audiences, and the moments when your mind goes completely blank. The practical advice is woven into these stories rather than presented as abstract rules, which makes it stick.
What to Expect
A quick, entertaining read at 222 pages with short, focused chapters. Berkun’s writing is conversational and often very funny. This is not a step-by-step system but a collection of hard-won insights that help you develop your own approach to speaking. Best read alongside a more structured guide for a complete picture of both the art and the craft of public speaking.
Alternatives
Scott Berkun · 408 pages · 2008 · Easy
Berkun’s definitive guide to project management, drawing on his nine years as a program manager at Microsoft where he worked on Internet Explorer and Windows. Rather than prescribing a single methodology, the book focuses on the thinking and judgment that makes any approach work: defining problems clearly, making realistic schedules, handling crises, and leading teams without losing your mind.
Why This One
Making Things Happen is the project management book that treats the discipline as a human challenge rather than a process challenge. Berkun covers everything from writing specifications to managing political dynamics, all grounded in specific stories from his experience. The chapter on “How Not to Annoy People” alone is worth the price of admission.
What to Expect
A thorough book at 408 pages, structured so each chapter stands alone. The writing has Berkun’s trademark honesty and humor. This is not a book of templates and checklists, though it has practical advice on every page. It is a book about developing the judgment to know what to do when the templates fail. Originally published as The Art of Project Management, then revised and retitled.
Scott Berkun · 258 pages · 2013 · Easy
Scott Berkun spent a year working as a team lead at Automattic, the company behind WordPress.com, and this book documents that experience. At the time, Automattic had around 120 employees in dozens of countries, working entirely remotely with no office, minimal email, and a culture built on trust and autonomy. Berkun gives readers an insider view of what a fully distributed company looks like in practice, writing with the same honesty and humor that defines all his work.
Why This One
Where Confessions of a Public Speaker captures Berkun at his most personal, The Year Without Pants shows him at his most observant. He embeds himself in a radically different company culture and reports back without either cheerleading or dismissing the experiment. The result is one of the best books ever written about remote work, precisely because it was written by someone who approached the experience with curiosity rather than an agenda.
The book is especially valuable for managers making the transition to distributed work. Berkun navigates questions that matter in practice: how to evaluate work when you cannot see people at their desks, how to build relationships through text, and how to maintain momentum on projects when your team is asynchronous. His background at Microsoft gives him a useful point of comparison between traditional and distributed cultures.
What to Expect
A narrative-driven book at 258 pages that reads more like a memoir than a management guide. Berkun structures it around his year at Automattic, weaving practical insights into the story of his team’s work. The writing is engaging and often funny. Expect concrete details about tools, workflows, and daily routines rather than abstract frameworks.