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How Leaders Handle Failure: Are You Making Your Employees' Roles Toxic?

Oct 29
9 min read

How leaders handle failure can turn one bad result into a Toxic Myth that follows an employee for years — and changes the way that employee shows up at work today.


Last Updated: October 29, 2026


TL;DR (Quick Summary)


  • A recent Vox piece on pop-music “flops” makes a useful point: failure is partly a judgment created by expectations.

  • Leaders create an unjustified perception of a team member as a "flop" when one missed expectation hardens into a story about who an employee is, now and forever.

  • My Five Toxic Roles show how that story can cast someone as a Monster, Villain, Victim, Bystander, or Fool.

  • The coaching step is Name Your Toxic Myth: identify the story you may be writing for someone else and examine how your behavior may be helping it come true.


Futuristic Myth Slayer Café filled with patrons watching a screen announcing “Orpheus’ New Single Flops,” with a dejected Orpheus holding his lyre.
A “flop” is never just an outcome. It becomes a story about what that outcome means.

Sometimes, a promotion can be the worst thing to ever happen to you.


I once saw the devastating consequences with my own eyes. A fellow attorney and dear friend at an organization I worked for -- bright, charismatic, funny, and dedicated -- was given the unexpected opportunity to make a major professional leap. This position leveraged her energy and personal magnetism, while forcing her to learn an entirely new area of business and putting her squarely in the public eye as major initiatives rolled out.


The intellectual growth was not a challenge for her. But the emotional growth was. In this position, she was expected to drive her own professional development; a mentor was not provided. Soon, fights with her superiors began. Her insecurity blossomed into endless gossiping about others and acting like a queen bee. Her credibility and that of her department began to sink.


Later, my own boss -- a personal advocate of mine who sat in the C-suite of this organization, and was thus privy to discussions at its highest levels -- quietly let me know of a perception that she had been "over-promoted," a nice way of saying "unqualified" ... and that a stain could tar anyone who continued to associate with her.


In the months that followed, she became increasingly emotionally volatile, "difficult," and isolated. Not long after, she got another job, with a lower title that everybody noticed.


Her time in the position was widely considered a flop. Everyone believed that the soft-skill challenges she faced were simply a part of her character. Perhaps there was some truth in that. But was she really a failure -- or was the reality something more complex?


That question is what made a recent Vox piece called “What Makes a Song a Flop?” so interesting to me. I remember watching an interview years ago with one of the biggest stars in pop history discussing an album often blasted as a "bomb" -- which had sold over five million copies. How on earth, this singer wondered, could something that sold millions be considered an under-performer? One of the Vox article's clearest ideas is that a “flop” reflects expectations as much as raw performance. The meaning comes from the gap between what actually happened and what people believed should have happened.


Leaders in organizations large and small do this with people all the time. As an attorney who has served as an executive, and now as a coach and speaker, I have seen repeatedly how quickly a result blows up into a reputation -- and then an entire historical narrative.


My friend's promotion ended up not working out. That chapter ended. But the story -- and her role in it -- kept going for years.


Medusa-like executive in a red suit watches a dejected employee walk toward Hades at a fork in the road, while the other path leads to a gleaming Mount Olympus.
A leader’s judgment can become a fork in someone else’s road. Which direction are you sending them?

How Leaders Handle Failure Can Create a Toxic Myth


In the Myth Slayer framework, empowered leadership comes by claiming authorship over the stories that shape your choices and actions. Toxic Myths interfere with that authorship. Toxic Myths are categories of internal stories marked by self-sabotaging patterns of thinking, keeping you stuck where you once were, rather than where you need to go.


We usually experience the Toxic Myths from the inside, as the authors of our own limiting scripts. But being in a leadership position creates another possibility:


You may be the person writing the script for someone else.


It can look like this: after someone under your authority -- whose entire livelihood may be dependent upon your whims -- disappoints you, a sentence begins to form in your mind (and maybe even in your conversations with others):


⚡️ “She can’t handle pressure.”

⚡️ “He doesn’t have good judgment.”

⚡️ “I can never trust her with something that important again.”


Such a sentence might sound like an observation or a statement of fact. But it is not. Once it's planted in your mind, if it repeats -- even once -- it can start influencing your behavior. The standard default of trust in that person or their work begins to erode. To minimize risk, you become less willing to put that person into consequential work, or even pull them away from challenging projects they've already started.


A boss I had once told me that, with many of her employees, a fork appears in her mind regarding their capabilities. "If the fork points in the wrong direction," she said, "they can never, ever walk back."


In other words, any member of her staff -- and possibly of yours -- could wake up one day finding themselves in a radically different story than they had ever imagined telling themselves.


Rugged gray-haired storyteller in a leather vest addresses a diverse business audience and Spartan warriors in an ancient-futuristic amphitheater overlooking a neon city.
Once you lead other people, you become Homer.

You Are Homer


Homer’s epics helped give ancient audiences stories through which wins, failures, choices, and consequences defined our perceptions of the characters within them -- permanently.


Some of the events in his written tales had alternate versions; those alternates often shed a different light on the characters involved. Someone's actions may have been heroic in one version, but foolish or even monstrous in another. But as the versions that become dominant, Homer's stories and the roles he assigned within them ended up shaping what thousands upon thousands of people, over centuries, accepted as "definitive."


Leaders, as the Homer-like dominant storytellers within their teams or organizations, have a version of that power today. Whether the mythos they create around a staff member who has failed at something is toxic or not depends on the role their story assigns to the staff member.


My five Toxic Roles, based on recurring character motifs in Greek myths, are the Monster, Villain, Victim, Bystander, and Fool. They are identities people can occupy when a Toxic Myth starts shaping how they understand themselves and their choices.


⚡️The Victim becomes the employee you protect from difficult assignments because you assume the situation will overwhelm them.


⚡️The Bystander becomes the person you stop bringing into top-tier work because their abilities are as inconsequential as a movie-set's extras.


⚡️The Fool becomes the person whose judgment you keep checking until they become reluctant to exercise it.


⚡️The Villain becomes the person blamed for the failure, with new behavior interpreted through suspicion.


⚡️The Monster is the most dangerous story: the problem has moved from an action or skill into a judgment that something about the person is fundamentally wrong.


A quip my spouse loves to throw at me is "the monster I am is the monster you make me." The role you assign a staff member who has underperformed might be what they become, and that drives -- by dint of your own actions -- the story the end up playing out. A leader can create the employee they believe they are observing, every bit as much as Homer did with those inhabiting the Odyssey and the Iliad.


(As a related aside, a 2000 meta-analysis of 17 studies examining the influence of expectations and performance within management contexts found that the correlation can, indeed, be fairly strong -- with stronger effects involving persons for whom low expectations were initially held. Go HERE for an abstract.)


Black Athena works at a giant loom weaving a tapestry of diverse corporate leaders alongside Greek heroes while employees watch in a futuristic Greco-Roman training hall.
Leadership gives you enormous influence over the tapestry your people believe they belong in. Make room for Heroes.

How to Manage Your Mythmaking


Let's be real here: a failed project might reveal a serious skill gap or poor judgment. Repeated refusal to learn can tell you something important about readiness for a role. All of those things could have been said about my allegedly "over-promoted" friend.


Leadership requires judgment. It also requires knowing what the evidence actually proves. Statements like “she was unqualified” or "he is difficult" are inherently identity claims, which a single failure may or may not prove. A leader's judgment is compromised when an event becomes a character description -- a Toxic Role -- and that description starts determining every opportunity that follows.


By the way, KPI-only leadership makes this mistake frighteningly easy. A KPI records an outcome. Human potential stretches across a longer arc than one reporting period.


When coaching leaders, I normally ask them to Name Your Toxic Myth. We identify the story shaping how they see themselves so they can begin authoring something more powerful.


In this case, though, that process turns around: Name Their Toxic Myth.


Choose one person on your team who has disappointed you or failed at something that mattered. Then ask:


⚡️ What happened? Write only the facts; leave any identity statements or judgements about personality, motivations, or future potential aside.


⚡️ What story above and beyond the facts have I written about that person because of what happened? Write the sentence exactly as it sounds in your head -- and name it as the Toxic Myth it is.


⚡️ Which Toxic Role have I cast them in? Monster, Villain, Victim, Bystander, or Fool?


⚡️ What action step can I take in the next 24 hours so they have a fair chance to change roles?


Futuristic Myth Slayer Café filled with cheering patrons as a giant screen announces “Orpheus Is Back!” and shows a triumphant Orpheus holding his lyre.
Great leaders leave room for people to come back, rewrite the story, and become more than anyone expected.

The Mythic Mindset: How You Use Power


What I call the Mythic Mindset means living from your Inner Olympian. The Inner Olympian uses power unapologetically, impactfully, and creatively in service of a singular life mission, bound to something greater than ego, money, or related superficialities like becoming a "personality brand."


For a leader, that mission includes responsibility for the human consequences of the stories you tell.


Imagine workplaces where leaders routinely refuse to lock people inside the meaning of their worst professional day. How would you respond inside such an organization? My bet is that if that organization would keep you motivated, loyal, and always striving to do more, the high performers on your own team would, too.


That world begins with individual acts of authorship ... including yours.


The next time someone who works for you fails, remember: You have become Homer. Create the conditions in which they can write what happens next. Make sure that the people rowing your ship could all, in their own way, be like Odysseus.


Scott Mason speaks into a microphone to an audience during a leadership presentation, with a large screen behind him displaying a “Risk Dynamics” slide.
Mythic leadership ultimately shows up in how we lead real people, every day.

The Story's Epilogue


If someone on your team came to mind while you were reading this, send me a message with the word HOMER. We can look at the story you may be writing about that person, the Toxic Myth shaping your response, and what the Mythic Mindset could make possible from here. Just press the button below.


Because ...


I want your future to be EPIC!


Quick answers (FAQ)


Q1: What is the core leadership lesson here?


A leader’s interpretation of failure can become part of an employee’s working environment. Once that judgment changes trust, access, responsibility, or opportunity, it can shape what the employee does next.


Q2: What can you do in the next 24 hours?


Think of one person whose past failure still colors your judgment. Write down what happened and the sentence you now carry about them. Identify the Toxic Role embedded in that sentence. Then make one choice that gives them a fair chance to create new evidence.


Q3: How does this connect to mythic leadership?


Leaders have narrative power. Like Homer, they help determine which stories become attached to the people around them. The Mythic Mindset requires conscious use of that power so people retain authorship over what comes next.


Scott Mason, the Myth Slayer, smiling against a magenta background, wearing a dark shirt, leather vest, and bolo tie with a sun design. Energetic and cheerful mood.

I'm Scott Mason, The Myth Slayer. I am an attorney and former C-Suite executive, coach, speaker, podcaster, and Master of the Mythic. I graduated from Columbia Law School and have spent years drawing on the full depth of a background spanning the private, public, and nonprofit sectors to provide lawyers feeling stuck or stagnant in their careers or as leaders with a unique (and fun!) system to help them live a life that's epic.



Click here to discover more about me, my mission, and how it can help you.


If you've ever said, "I'm capable of more -- and I want it?" ... then download my five-minute self-assessment, and I'll show you how to experience professional rebirth, increase your inspiration, and create a bold impact NOW!



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