Jack Covert Selects

Fail Better: Design Smart Mistakes and Succeed Sooner

Sally Haldorson

November 14, 2014


The authors of Fail Better take a popular subject a bit further by offering a methodology for constructing mistakes.

Fail Better: Design Smart Mistakes and Succeed Sooner by Anjali Sastry and Kara Penn, Harvard Business Review Press, 318 pages, $30.00, Hardcover, November 2014, ISBN 9781422193440

Anjali Sastry and Kara Penn admit that business failure is currently a very hot topic. (Simply google the words, “learning from failure,” and you’ll be overwhelmed with the results.) However, the authors of Fail Better: Design Smart Mistakes and Succeed Sooner want to take the subject a bit further by offering a methodology for constructing mistakes (yes, deliberately), actually taking lessons from those mistakes (“to ensure that every failure is maximally useful”) and then applying them to future iterations.


Our starting point is the idea that the right kind of failure—small-scale, reversible, informative, linked to broader goals, and designed to illuminate key issues—paves the way to success.


The right kind of failure? Sure. “In the most laudable cases, failures emerge from planned exploration of unknowns.” And more practically, every project you undertake—from development to launch to evolution—does exactly this.

Fail Better isn’t a flashy book; it’s not a tech industry book that lauds the failures of Silicon Valley giants, nor is it a social science book that encourages you to change your perfectionist mindset. It’s very specifically geared to a broad audience, everyone, because everyone who works is going to try something new, and, inevitably, fail at something.


The truth is, that to make something excellent happen, there’s work, more work, and then still more work. If you’re fortunate, only some of it is inefficient.


And when you are launching a new project, failure shouldn’t hold you back from acting on your good idea. Applying Sastry and Penn’s methodology actually releases you from the pressure of perfect performance.


You don’t have to hone every plan, consider every possible scenario or option, or calculate every detail in advance. … Rather than building your project around a one-shot effort, you can guide your team to an agile, responsive method of learning by doing. It all hinges on iteration—in which repetition of a series of activities or steps yields results successively closer to a desired outcome.


With ample “Guiding Thought Questions” to get you started, “Fail Better Process Products,” which aid your documentation before and during the process, and Checklists that will help you prioritize and progress your team’s work, Sastry and Penn truly evolve a common business idiom—fail better—into a practice.


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