Want Your Audience to Learn? Encourage Them to Get Straight Fs

June 3, 2020
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"Failure should be our teacher, not our undertaker. Failure is delay, not defeat. It is a temporary detour, not a dead end. Failure is something we can avoid only by saying nothing, doing nothing, and being nothing."

– Denis Waitley, The Psychology of Motivation

We live in a society obsessed with success. So it may seem strange, but we’re going to encourage you to let your learners fail—again and again. According to a University of Texas study, a new skill "must be culled from a string of mistakes." So, the truth is—failure is the backbone of learning. 

Consider a child who’s learning to read. If her teachers make fun of her mistakes or her parents mock her stumbling, she’ll be afraid to try. If she confuses how good she is as a person with how good she is as a student, she might even face paralysis. But, if her teachers make it safe for her to get it wrong, if her parents are patient and encouraging as she tries again and again, eventually, she’ll be reading herself bedtime stories. 

Some benefits of making space for failure in learning: 
Here’s how to encourage your learners to fail better:


Bill Gates once said, "In the corporate world, when someone makes a mistake, everyone runs for cover. At Microsoft, I try to put an end to that kind of thinking. It’s fine to celebrate success, but it’s more important to heed the lessons of failure. How a company deals with mistakes suggests how well it will bring out the best ideas and talents of its people, and how effectively it will respond to change."

Creating space for productive failure doesn’t start in the training room. It’s part of the everyday work you do with your employees and association members, part of building a culture of learning. When your employees and members make mistakes, skip the dressing down. Instead, push them to look for the lessons within their failures. 


  1. Remind your audience that they can constantly improve. No one’s expected to get everything right from day 1. Instead of striving for instant perfection, your employees and members can work to continually improve. 
  2. Develop a mistake management plan with your team. Just as you have plans for responding to emergencies and for reaching strategic goals, a mistake management plan gives you a structure to triage an unfortunate situation and to foster team improvement. Peter Coffee, VP of Strategic Research at Salesforce, says of mistake management plans: "A culture of learning from failure arises when every team member shares ownership of the plan–or better still, when every team member is author as well as owner of a personal plan."
  3. Encourage transparent discussions about how things have gone south. If frank, honest self-reflection and self-criticism are a regular part of your team dynamic, you can all learn from mistakes together. 
  4. Keep track of mistakes and the lessons they taught your team. Though it may seem like a record of embarrassment, an error log can actually remove the stigma of messing up and encourage team learning around missteps. Sarah Nahm, CEO of Lever, says, "Our marketing team started an internal spreadsheet of ‘Marketing Mistakes’ that they periodically review in meetings, to show that it’s not the end of the world when things go wrong and that the main thing is to learn from the experience." 


Dave Finocchio, CEO of Bleacher Report, says, "I make mistakes all the time, and talk about them openly with people up and down our hierarchy. It fosters a culture where people should feel comfortable critiquing themselves honestly."

Take the lead in being open and proactive about your mistakes. 


  1. Analyze why you made the mistake. Was it a result of mismanaging your time? A failure of communication? A misunderstanding that snowballed? Share what you find with your team. 
  2. Discuss the process you used to come up with a solution or remedy. Let your team into your post-error thought process. This will be helpful for them when they’re searching for the lesson in their own failures. 
  3. Practice radical honesty. Invite your team to discuss what they perceive as your failures with you, too. You’ll all learn more quickly as a result. 
  4. Avoid self-deprecation or speaking harshly about your own errors. This still sends the message that errors are to be feared. 


Experimenting takes the stigma out of failure. The point of trying new tactics, looking at challenges from unique angles, or thinking a little differently is not to get anything "right." It’s simply to learn, explore, and investigate. 

Evgeny Morozov, author of To Save Everything, Click, said, "Creative experimentation propels our culture forward. That our stories of innovation tend to glorify the breakthroughs and edit out all the experimental mistakes doesn’t mean that mistakes play a trivial role. Without some protected, even sacred, space for mistakes, innovation would cease."

By giving your audience room to experiment when they’re learning, they can move away from a rigid and limiting definition of success towards a mode of thinking that allows for more innovation. 


  1. Invite your learners to explore new devices, software, and other resources in an unstructured way. Giving them hands-on time simply to get acquainted with tools will free them from pressure to perform correctly. 
  2. Don’t provide the answers. Get comfy with a bit of protracted silence in your training. By resisting the urge to jump in with a ready-made answer, you encourage your team to take more risks and think on their feet. 
  3. Extend your brainstorming sessions. The first responses are likely the most standard or conventional. They’re the solutions that are top of mind. Be patient and hold out for some more innovative ideas (sitting with the silence when necessary). 
  4. Create space for spitballing. Establish an accepted, low-risk way to try out any idea on the rest of the team. Building off an in-training discussion, start a “Wild Ideas” Slack channel or Facebook group. Or hold a monthly happy hour in which your team only talks about the weirdest, most creative ideas they’ve been kicking around. 


Just like nailing a sales pitch or mastering a new CRM, failing well is a skill to be practiced. Along with the topic-specific curricula, you can embed training with a little failure practice. Over time, your team will not only learn the latest regulations or ace Advanced Photoshop, but they’ll become skilled at understanding the lesson embedded in their professional mistakes. 

Tips on creating failure playgrounds: 

  1. Have your team role play the wrong way to do a task. Then, have them discuss the errors and methods of improvement. 
  2. Conduct free writing exercises around a pertinent topic and challenge your team to share what they’ve written on the fly. This will encourage your learners to be messy with each other sometimes and to think in front of each other, even if it isn’t perfect. 
  3. After hands-on exploration, ask your learners to discuss a challenge they had with a new tool. By walking through the place they stumbled, they can both draw attention to specific areas which need more learning and give insight into how they worked through a difficulty. 
  4. A few weeks after a training, check in with your learners and ask them to share both their successes and failures around their recent learning. This will give you an opportunity to reinforce the lessons of the training and provide targeted micro-learning lessons to address trouble spots, and for the team to practice discussing errors constructively. 

There you have it, how to get your audience to learn more by helping them fail better. 

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