How communicators learn from structured failure

The idea of learning by failing isn’t new. Silicon Valley championing the “fail fast” mentality has been a beacon of inspiration to tech bros for decades, while folksy, inspirational messages about growing from our mistakes are stitched into pillows at home decor stores across the land. 

But as the communications function continues to grow increasingly obsessed with fast results and definitive solutions, Kerry O’Grady, Ed.D, a senior lecturer of communications at University of Massachusetts Amherst’s Isenberg School of Management and a Ragan Training Instructor, makes a compelling case for failing with intention, reflection, and iteration.  

Ragan caught up with O’Grady to learn how this principle shapes not only her classroom, but also her philosophy for organizational learning and leadership. 

The brain science of failure 

While many treat failure as a motivational cliché, Kerry takes a scientific view.  

“Failure is an integral part of success—not because of all of those writing-on-a-pillow situations, but because it actually changes your brain,” she said, explaining that true learning only happens when something goes wrong and forces the brain to adapt. “If you do not fail while you’re doing something, you are actually not really learning it.” 

Referencing “Productive Failure” by Manu Kapur, a formative influence on her thinking, O’Grady stressed that failing must be baked into the learning process, both strategically and proactively. “If it’s easy or seems too easy, that means you aren’t learning or growing,” she explained. 

The difference between fast failure and iterative failure 

O’Grady is clear to draw a line between chaotic startup culture’s “fail fast” ethos and what she sees as meaningful, strategic iteration. “Most of those sayings, even in startup culture, suggest we don’t need to think first—we just need to do and then fail,” she said. “That is not what I’m talking about.” 

Instead, she advocates a model grounded in thoughtful anticipation. “You sit down with stakeholders and ask: What could go wrong?” O’Grady explained. “You actually plan failure into the process.”  

This is the central logic behind the Plan-Do-Study-Act (PDSA) model, which O’Grady regularly uses. It involves planning ,executing, studying the results and optimizing before trying again based on any failures.

“It’s a cycle that you continue to iterate until you get it right,” said O’Grady. “Build the plane while trying to fly it, but make sure you have a flight manual.” 

Despite the value of this iterative approach, communicators often resist it. “It takes time, patience, and resources,” O’Grady said. “And while it’s tempting to immediately throw a solution at the problem, using this model, you can’t, because you don’t know what the solution is until you witness the failure.”

The real culprit, in her view, is a culture addicted to being right. “Everybody wants the golden ticket—to say, ‘I came up with that.’ That leads to a very dangerous disease called solution-itis—we’re basically throwing solutions at things when we don’t understand what the problem is.” 

O’Grady applied this concept to pedagogy, and her teaching experiences. “This is analogous to telling students to do all this homework, not giving feedback, and then being surprised when they fail the test,” she explained. “Then I say, well, the solution is they need more homework. No! That’s not the solution.” 

Instead, effective learning focuses on continual feedback and iterative assessment. “It’s about monitoring and measuring as you go,” she explained. “If something doesn’t work, you find the variable that didn’t work, tweak that, and then move forward.” 

Debunking the myth of knowing everything 

Amid periods of sustained layoffs, a scarcity mindset means that many workplace cultures discourage intellectual vulnerability. “The idea of not having all the answers is positioned as a weakness,” O’Grady said. “We need to reframe that.” 

She observed that this fear-based environment is mirrored in higher ed, where students are conditioned to follow templates and checklists rather than grapple with ambiguity. That tendency flies in the face of a core comms competency. 

For managers looking to operationalize this philosophy, O’Grady recommends integrating “genius hours” into the workday, or short, focused blocks of time set aside for learning, curiosity and problem-solving. “You build in 30-minute windows to just play,” she said. “Say to your employees: something’s going wrong and we don’t know why. Explore it. Don’t solve it. Just figure out why it’s happening.” 

 “It breaks the monotony. It gives them creative leeway. And it puts their brain in a different place to think about the problem—not the checklist.” 

Ultimately, O’Grady rejects the idea that pedagogy, or the science of learning, should only be considered in the realm of higher education.

“People in the workplace also have to learn how to learn in your space,” she said. 

Join Ragan Training to take O’Grady’s course on media training during times of change.