The Leader’s Lens: Dr. Amy Edmondson, Harvard Professor & Best-Selling Author, Fail Often? Not So Fast

Jacob Morgan
5 min readApr 11, 2024

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Today’s Leader’s Lens comes from Dr. Amy Edmondson, the best-selling author of books including The Fearless Organization and Right Kind of Wrong. She’s also a a professor at the Harvard Business School AND a guest on the Great Leadership Podcast.

I had the chance to read an advance copy of her recent book and there was a lot of connection between the work she was doing and the book that I was writing, Leading With Vulnerability. In fact, if you go on Amazon our books get recommended together and she is one of the amazing researchers I interviewed for that book. I asked her if she would be willing to write something for my newsletter about failure and the concept of failing fast…is that really a good idea?

Here’s Amy

If you find yourself cynical about the pro-failure rhetoric in certain management books and articles, don’t worry. No one really likes to fail, and popular ideas like failure parties and failure resumes can be difficult to put into practice in companies. Even with my new book, Right kind of wrong: The science of failing well, I would not call myself an outright failure evangelist.

“Fail fast, fail often” — the oft-repeated slogan, popular in Silicon Valley and elsewhere — is useful for helping people become less risk averse and more willing to innovate. And it is indeed good advice — in certain situations. It’s very bad advice in many others, perhaps even most others.

A simple point about context comes to life in a thought experiment: Imagine yourself saying ‘fail fast, fail often’ to an entrepreneur, or perhaps to a scientist. No disconnect there. They will smile and say, “I get it.” But say ‘fail fast, fail often’ to the manager of an automotive assembly line — or to a surgeon in an operating room — and they will respond, rightly, ‘Are you kidding me?’ The advice is beyond unhelpful; it’s absurd.

Context Matters

In what kinds of situations does ‘fail fast, fail often’ make sense? First, and most important, they should be novel — situations where the only way to make progress is through trial and failure. When coming up with a plausible idea and testing it out to see what happens is your only option for making progress, then fail fast (and learn fast) is good advice. In other words, when there is no playbook to follow, you must accept the reality that the path toward success will entail failure along the way. Second, without a worthy goal — a motivating reason to endure the risk of failing — setting out on a path that will entail failure may not be such a smart idea. Relatedly, it’s important to take a thoughtful approach to experimenting. Even in a novel situation, taking the time to formulate a hypothesis about what might work is smart, and it lowers the risk of preventable failure.

It comes down to this: realistically accepting the risk of failure so as to make progress in new territory is not the same as deliberately setting out to fail.

Another point that may be lost in the cheerful failure rhetoric is size. My advice is to take pains to ensure that any failure that does happen is as small as possible — to conserve resources and maximize learning. In novel situations, and following these guidelines, I categorize the failures that do occur as “intelligent failures.”

Conversely, in familiar territory, where a playbook exists, the best advice is “please use it!” Of course, you can — and should — look for ways to improve the playbook, but using existing knowledge and practices is the best way to get results and accomplish goals in familiar territory.

In any situation where established practices exist and the stakes are high, it’s both possible and admirable to avoid failure as often as humanly and managerially possible. In these situations, most of us would be well served by doing everything in our power to ensure success. Sometimes this means relying on a combination of expertise and vigilance, as in passenger air travel. In others, it’s about fast problem solving to overcome an unexpected event — whether in an operating room or piloting a flight through unexpected turbulence. A learning culture helps make this possible.

Build A Learning Culture

When human safety is at stake, vigilance and problem solving are called for in equal measure. It helps to have a psychologically safe environment where people know without doubt that they are expected to speak up quickly with questions or concerns. Many failures, both small and large, can be prevented when mistakes and problems are caught early and corrected quickly. Doing this well is not just about individual self-awareness; in fact, I call it a team sport. The work and operational activities in most organizations are sufficiently complex that disrupting the path between a mistake and a failure usually involves more than one person and a collaborative spirit.

We all make mistakes. But research shows clearly that powerful psychological forces make it hard for people to admit them. And our natural desire to look good in the eyes of others is exacerbated in the hierarchical context of organizations. Anxiety about what bosses or peers will think has led many an employee to hold back an important concern, question, or idea at work. The desire to look good thus inhibits our ability to catch and correct mistakes and small problems before they turn into significant failures. In organizations where people hide their mistakes, don’t speak up when they need help, or stay silent about ideas for improvements, failing well is difficult.

Leaders, at every level, must do their part to make it psychologically safe for people to speak up quickly and to experiment appropriately. Psychological safety matters as much for innovation as for failure prevention in familiar territory. Failing well means equally taking smart risks as well as preventing failures in familiar territory.

There are a few things managers can do to build a healthy culture that respects vigilance, mitigates risk, and understands the importance of context.

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Jacob Morgan

4x Best-Selling Author, Speaker, & Futurist. Founder of FutureOfWorkUniversity.com. Exploring Leadership, Employee Experience, & The Future of Work