You’ve likely heard the saying, "Failure is the key to success." But accepting it can be easier said than done. When mistakes happen at work, the instinct is often to assign blame rather than view it as a chance to learn and grow.
Understanding how to fail well helps teams avoid unnecessary obstacles, encourages experimentation, and builds a culture where continuous learning is the norm. When failure is reframed as a tool for progress, leaders can move the organization forward.
To truly take advantage of failure, it’s critical to understand the different types, recognize how embracing it fuels success, and discover strategies for turning roadblocks into growth opportunities.
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DOWNLOAD NOW3 Key Types of Failure
In a world quick to stigmatize failure, Harvard Business School Professor Amy Edmondson, faculty chair of the Credential of Leadership, Impact, and Management in Business (CLIMB) program and author of Right Kind of Wrong: The Science of Failing Well, offers a refreshing perspective rooted in decades of acclaimed research. In her book and online course, Dynamic Teaming, she presents a framework for thinking, talking about, and practicing failure wisely—outlining three different types, explored below.
1. Basic Failure
Basic failures are often the easiest to prevent—but also the easiest to overlook. They tend to stem from human error, lapses in judgment, or simple oversights during everyday tasks.
“These are the types of failures caused by mistakes or carelessness in familiar territory,” Edmondson says in Dynamic Teaming.
While they might seem minor, these missteps can snowball into inefficiencies, costly setbacks, and missed opportunities.
HBS professor and former senior U.S. military officer Hise Gibson, featured in Dynamic Teaming, saw this up close while managing a war training zone, where lost weapons and damaged gear had serious consequences. Rather than assigning blame, Gibson focused on the value of failing fast and learning faster.
“It’s not the failure that’s the problem for organizations,” Gibson says in Dynamic Teaming. “I think it’s their tendency not to acknowledge when failure becomes a trend and respond inappropriately to those trends.”
Leaders don’t need one-size-fits-all solutions but practical, proactive strategies to spot and prevent basic failures early. When caught promptly, small errors can build resilience, improve operations, and make work smoother at all levels.
2. Complex Failure
Complex failures occur when multiple issues collide unexpectedly, often in familiar territory, leading to broader disruptions due to unknown variables.
“When we think about complex failures abstractly, it’s easier to acknowledge the unpredictable interconnectedness of daily work that leads to errors,” Edmondson says in Dynamic Teaming.
Even in routine environments, unforeseen factors can create unexpected challenges. However, when teams identify them, they can take steps to prevent them.
A notable example featured in Dynamic Teaming is the UK Vaccine Taskforce’s response to the COVID-19 pandemic. Led by venture capitalist Kate Bingham, the team aimed to fail well by anticipating that early hypotheses might not work. Rather than avoid the topic of failure, they prepared the UK government for potential risks in vaccine distribution by walking them through scenarios.
Instead of waiting for things to go wrong, her team embraced system awareness, a skill highlighted in Dynamic Teaming, which involves understanding how different parts of a system interact and influence outcomes.
Through rapid experimentation and problem-solving, the task force developed a diverse vaccine portfolio, addressing domestic and international distribution and reducing the chances of large-scale failure.
3. Intelligent Failure
Intelligent failure is the way to fail well. It involves taking calculated risks, testing new ideas, and exploring uncharted territories—knowing there are no guaranteed outcomes but plenty to learn.
Unlike basic or complex failures, intelligent failures are small-scale experiments designed to uncover valuable insights while minimizing resources.
A compelling example comes from Meghan Joyce, former regional general manager at Uber, featured in Dynamic Teaming. Joyce led her team through planned experiments, using outcomes to guide next steps and inform future strategies.
One experiment occurred in Boston during the summer, when the team expected a dip in demand as college students left town. They lowered prices to test a possible solution to see if it would help sustain customer interest. The move was a classic case of intelligent failure—deliberate, controlled, and reversible.
Joyce made sure the team was ready for any outcome. Depending on how the pricing change played out, they could extend the experiment or revert to the original model. By remaining responsive to real-time data, the team could assess whether the strategy had long-term value or posed a business risk.
As Edmondson notes in Dynamic Teaming, “Becoming comfortable with intelligent failure and codifying what you have learned from it is your best chance at ultimate success."
Related: Listen to Professor Edmondson discuss how organizations can foster teaming through clear communication, psychological safety, and intelligent failure on The Parlor Room podcast, or watch the episode on YouTube.
How to Fail Well
Failing well means learning and evolving. When experiments fail, teams can still progress by analyzing data-driven outcomes, reflecting on what went wrong, and applying those insights to the next move—turning failure into an essential tool for innovation. Here are steps to help you and your teams master the art of failing well.
1. Foster Self-Awareness
Failing well begins with self-awareness—an important trait for leaders and team members. It promotes reflection on mistakes and helps eliminate personal biases, allowing for a more rational analysis of failures.
“Self-awareness helps us challenge our immediate emotional response to a failure and turn a destructive feeling of defensiveness or shame into a productive feeling of curiosity about what happened and what you can learn from it,” Edmondson emphasizes in Dynamic Teaming.
To develop this mindset, Edmondson suggests practicing a simple cognitive habit:
- Stop: Take a moment to pause and disrupt your natural response.
- Challenge: Examine your initial reaction—was it rational or productive? If not, reframe the situation.
- Choose: Select the interpretation that best empowers you to move forward.
By practicing self-awareness and viewing failure as a chance to grow, teams build perseverance and make more informed decisions.
2. Promote Organizational Transparency
Organizational transparency enables everyone to learn from failure instead of burdening one individual with the blame. Open communication encourages a culture of shared learning and continuous improvement.
In fact, over 80 percent of workers want a better understanding of how decisions are made.
In Dynamic Teaming, the UK Vaccine Taskforce prioritized transparency while developing its distribution strategy. The team invited the entire organization to reflect on failures while evaluating potential projects and investments. By actively incorporating various perspectives, this collaborative approach helped them prepare for the highest level of risk and develop creative solutions.
3. Implement Prevention Systems
Addressing issues in the early days can minimize the impact of future failures. Although predicting every error is impossible, leaders can significantly reduce potential damage by focusing on prevention.
A key strategy mentioned in Dynamic Teaming is blameless reporting, which celebrates the identification of failures and creates an environment where team members feel safe discussing mistakes without fearing blame.
To build on this tactic, leaders can introduce proactive systems, such as clear protocols, safety checks, and routine reviews, to catch potential issues before they spiral. They can also build a culture where failure is accepted and encouraged through fostering psychological safety. When people feel safe speaking up, taking risks, and challenging assumptions, prevention becomes ingrained in the culture rather than just a checklist item.
4. Understand When to Slow Down
Sometimes, stepping back is more strategic than pushing forward. This is where pilots come into play. They provide an opportunity to experiment, gather insights, and learn from mistakes before a full launch.
The goal of failing well is learning, even if things don’t go as planned. As Edmondson notes in Dynamic Teaming, “A well-informed team will not waste time experimenting on what is already known or what has failed before.”
In Dynamic Teaming, Joyce saw an opportunity to address the seasonal population surge and limited transportation options in Cape Cod, Massachusetts.
Joyce and her team didn’t rush into a launch. Instead, they treated the rollout as a pilot. They had a plan to expand if demand was strong—and a fallback strategy to scale back service to weekends if it wasn’t.
This flexible, low-risk approach gave them room to adapt and minimized the chance of costly mistakes. By treating the launch as an experiment, the team gained valuable insights and moved closer to their broader goal of expanding Uber into suburban areas.
“Pilots, experiments, and tests are all ways to set your team up to fail well,” Edmondson says in Dynamic Teaming.
When leaders know when to pivot or pause, they can make more strategic decisions, save valuable resources, and guide their team toward growth most efficiently.
5. Exclusively Encourage Intelligent Failure
Helping your team scale requires distinguishing between productive and unproductive failure. True progress doesn’t come from avoiding failure but from understanding which failures to embrace and which to avoid.
An atmosphere that encourages intelligent failure focuses on purposeful learning, while minimizing avoidable mistakes and reducing the impact of more complex challenges. As a leader, nurturing this perspective is crucial for building momentum and achieving meaningful success.
In Dynamic Teaming, Gibson illustrates how this is demonstrated during military training, where teams simulate high-pressure situations, such as combat, in a controlled setting. “We practice and pressure test in a more benign, structured environment to create the muscle memory,” he explains.
By fostering a culture that welcomes learning from missteps and promotes failing well, leaders provide teams with a secure environment to succeed without the fear of costly errors, all while directing them away from failures that impede accomplishments.
Embrace the Power of Failing Well
Failure is often seen as a barrier, but it can be the catalyst for growth and lifelong learning. When leaders change their perception of failure, they unlock its true potential. Instead of an endpoint, failure becomes a powerful driver of innovation and progress.
Leaders play a vital role in guiding their teams through failure by creating an environment where it’s embraced, not feared. When failure is reframed as a necessary part of the journey, it fuels success.
If you're ready to cultivate a culture of intelligent failure within your organization, consider enrolling in an online course like Dynamic Teaming, which can be taken individually or as part of the yearlong Credential of Leadership, Impact, and Management in Business (CLIMB) program.
Ready to lead a team that embraces intelligent failure? Explore Dynamic Teaming—one of our leadership and management courses—or apply to CLIMB. If you want to learn more, download the CLIMB brochure to explore its curriculum, learning paths, and admissions requirements.
