Why Failing Fast Wastes Time and Learning Quickly Gets Results

This week I am putting the finishing touches to a six-month leadership programme with an Asia-based market leader in manufacturing. A small Kiwi business, based entirely remotely, working with a global market leader. The amount of learning I have done over the last three years to reach this point is enormous.
Whilst my team and I were discussing the kick-off workshop, I was emailed a summary of the book in my newsletter this week: Fail Fast. Fail Often by Ryan Babineaux and John Krumboltz. They are psychologists, career counsellors, and creators of the popular Stanford University course "Fail Fast, Fail Often."
The Problem with the Language of Failure
I had a scan read and found myself fundamentally disagreeing with the title, because the core principles inside are far more positive than it suggests. That's not to say it's a bad book. It isn't. The Stanford course has been well known for a while. But the language of failure tends to conjure a sense of dread in anyone who thinks about it.
Another conversation I had this week was about trauma-informed learning, whereby we tend to remember trauma vividly and it shapes the way we act in the future. In the military, we call them battle scars. Battle scars are hard-earned, and the British military has done an increasingly good job at debriefing people who have experienced trauma and helping them reframe that experience into something more positive. In business, we call it a mess-up, a product failure, a massive loss, a write-down on the balance sheet. We need to acknowledge the impact failure has on people, knowing that trauma can disrupt future performance.
There are still many organisations that, whilst they talk about being supportive and developmental, cannot tolerate failure. A failure is still a failure to them, and therefore a risk most employees cannot afford to take. I've also noticed that most organisations have a Learning and Development function, not a Failing and Development function. I wonder why that is.
In my experience, positive language and framing nearly always has an advantage over negative framing.
So instead of failing fast, I prefer the term learning quickly. Some of you might think that's linguistic semantics. But from a small project I ran about a year ago, I found that groups we spoke to about failing fast were less likely to take risks because they still held that trepidation of failure. Those we spoke to about learning quickly were more ambitious, took more courageous steps, and stretched further than the "Failers," for neuroscientific reasons I won't go into here. A better outcome from a simple shift in language.
Why the Ability to Learn Quickly Matters
A recent IBM report outlines that the most important skills for future employees and their leaders are a willingness to be flexible, agile, and adaptable to change. People need the ability to learn.
CEOs rank investment in people as the number one way to accelerate performance for organisations of the future. Organisations need to help people learn, faster and more efficiently.
Organisations have a significant opportunity to learn quickly. Their clients, customers, and colleagues are also reassessing their business models, products, and services. There is an opportunity to learn quickly through collaboration and informed hypotheses about what to do next, and scope to run multiple experiments against controls to A/B test those hypotheses.
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The Experiment Approach to Learning
When I coach clients, each session we set up an Experiment for something they are going to try as a leader between sessions. It's deliberately called an Experiment because it's designed with an informed hypothesis and an expected outcome in mind.
That expected outcome may or may not be reached. If it is, we want to understand why. If it isn't, we also want to understand why, so we can work out what to do differently next time. At no point do we frame it as failure. We look at why the experiment didn't go as expected and reflect on the learning hidden within, to build experience.
This coaching approach was informed by my learning about Lean methodology and the Toyota Production System. The Japanese engineers were equally interested in whether they produced Y percent more or less in a set time when they intended to complete X. The hypothesis was that the result would be X. If the result was plus or minus Y, the experiment hadn't gone as planned, and they wanted to understand why. Many innovative breakthroughs came from exactly that process.
Three Ways to Help Your People Learn Quickly
The same applies to leading teams. Here are three approaches to support your people to learn quickly.
1. Encourage Experimental Curiosity
Try using phrases like: "Let's try. I wonder what would happen if. How might you?" This encourages an experimental curiosity. Then, if things don't go as planned, ask employees what they did rather than focusing on what went wrong, and encourage them to uncover what they learned and apply it. Some employees will fall short. They are already their own harshest critics, so you don't need to wade in and help with that part.
2. Create Low-Stakes Learning Opportunities
Try to create low-stakes learning opportunities before the stakes become higher. I often use the phrase with leaders: "How can you let them graze their knees and not break their legs?" Learning happens when things don't go as expected. If you can help employees experience that learning earlier in their careers, or when it won't bring the business down in flames, you should try to do so. Make sure you are there to pick them up, dust them off, and set them back on track.
3. Share Your Own Learning
Try to share some of your own learning. Admitting our own mistakes is hard. We want to preserve our credibility with our teams. But when we can address those moments and the learning we took from them, we demonstrate humility and humanity as leaders. That matters to younger or less experienced team members who are watching to see whether it's safe to try things.
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Why Lessons Learned So Often Go Nowhere
There is a related problem that undermines all of this. Even when teams do surface good learning, they rarely embed it. Lessons learned tend to get a bad wrap. They are the thing done at the end of a project, designed in most cases to pick up all the things that "we don't want to do again." Sadly, too many times these lessons get put into a weighty report, added to someone's reading list for "when there's time," and subsequently life moves on without the lessons ever being read, internalised or embedded.
In just the Fortune 500 companies, $35Bn is left on the table from lessons not being learned or communicated effectively.
Add to that all of the other businesses in the world and you can detect there may be some upside from doing this more effectively. The experiment mindset described above only delivers value if the learning is actually captured and carried forward. Here are three practical improvements that make the most difference.
1. Build a Better Process for Uncovering Lessons
Have a clear, short process for uncovering lessons, both positive and negative. Ask what went well as well as what didn't. This will surface the things you want to do more of, not just the things to avoid. Then plan what you will do next with this information and what might get in the way of acting on it.
2. Get Team Members to Internalise the Lessons Personally
Ask each person how they are going to personally change their behaviours and processes to capitalise on what was learned. Emailing a report of lessons tends to bounce off people's attention. The learning has to be owned individually, not just filed collectively.
3. Create a Follow-Up Process to Check That Change Has Stuck
Most teams who complete a lessons review have great intentions to change, and they may adopt new ways of working for a few weeks. But when pressure builds and stress rises, old habits have a way of creeping back in. Build a follow-up step into the process. That follow-up can also surface further refinements and additional learning, compounding the benefit over time.
None of this means encouraging flippant, rash, or ill-considered action, or suggesting that actions shouldn't have consequences. Times are pressured enough. But your approach to this small change in language, combined with a disciplined process for capturing and embedding what is learned, can make a meaningful difference to how your people perform.
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Get the Quick-Win PackQuestions managers ask about this
How can leaders encourage quick learning in their teams?
Leaders can encourage quick learning by using experimental language such as 'Let's try' or 'What if' to build curiosity. When outcomes differ from expectations, focus on what was done and what was learned rather than on mistakes. Creating low-risk opportunities to learn and sharing personal learning experiences also helps build a culture where people feel safe to experiment and improve.
Why is the phrase 'fail fast' less effective in business leadership?
The phrase 'fail fast' often triggers fear of failure, which can discourage risk-taking. It carries negative connotations that can affect team morale and performance. Using positive language like 'learning quickly' reduces anxiety, encourages ambition, and supports a more constructive approach to experimentation and growth within teams.
What role does language play in managing risk and learning at work?
Language shapes how employees perceive risk and failure. Negative framing, like focusing on failure, can inhibit risk-taking and learning. Positive, curiosity-driven language encourages experimentation and reflection on outcomes. This shift helps teams learn from experiences without fear, fostering a more adaptable and resilient workforce.
How can leaders create safe learning opportunities without risking business failure?
Leaders should create low-stakes situations where employees can experiment and learn without severe consequences. This might involve small projects or simulations where mistakes are less costly. The key is to support employees through setbacks, help them reflect on lessons learned, and gradually prepare them for higher-stakes challenges with confidence.
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Jimmy Burroughes
FounderFormer British Army officer and corporate GM who has transformed nearly 3,500 managers into leaders across 30+ organisations. Creator of the Simplify to Amplify methodology, author of Beat Burnout, Ignite Performance, and two-time Global Recognition Award winner.
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