Handling Failure: The Career Masterclass
By Joe Way, PhD, CTS
This month’s HETMA Community professional growth theme is about handling failure. Finally, a topic I’m a master of. And man, can I fail with the best of them. But it’s the failures I’ve had that became the steppingstones for my success. Every wrong decision, every conversation I wish I’d handled differently, every plan that looked brilliant in my head but crumbled in reality, those were the lessons that built me into the leader I am today.
People love to talk about success. We frame it on our office walls, post about it on LinkedIn, and celebrate it around the office. And rightfully so. But failure? We whisper about it. We hide it behind buzzwords like “learning experience” or “pivot.” Or, more commonly, we just avoid it and hope that enough time will pass that people won’t notice or will forget completely. Yet the truth is, failure is the greatest leadership masterclass ever designed. It’s raw, it’s humbling, and it forces you to face the parts of yourself that success never challenges.
Early in my leadership journey, I believed good leaders always had the answers. I thought confidence meant certainty, that decisiveness meant control. So I charged ahead, leading with boldness but not always with wisdom. It took a few painful lessons, projects that didn’t land, people I unintentionally alienated, opportunities I rushed, and being escorted out a few doors, to realize that leadership isn’t about being right all the time. It’s about being responsible all the time. It’s about accountability. When things fall apart, true leadership shows up in how they take ownership.
Failure has a way of stripping away ego. It reminds us that titles don’t guarantee wisdom, and experience doesn’t exempt us from mistakes. The higher you climb, the lonelier it can feel when you fall, but that’s where authenticity begins. A leader who can look their team in the eye and say, “I got this wrong, but here’s what I’ve learned,” earns more trust than one who pretends nothing ever goes wrong. Vulnerability, when paired with accountability, builds credibility.
There’s a particular sting that comes from letting your people down. I’ve felt it more than once. You see their effort, their faith in your direction, and when it doesn’t work, the weight can sit heavy. Personally, it’s one of the few things that will send me into a spiraling depression. But that’s also when leadership becomes real. Leadership isn’t about preventing failure, it’s about navigating through it for the benefit of yourself worth and the value you truly hold for your team. It’ seeing that a setback isn’t a verdict, it’s a lesson. It’s a reminder that our worth isn’t tied to outcomes, but to our character in the moment. And truthfully, many times, I’ve failed there too.
The best leaders don’t shield their teams from failure; they teach them how to grow from it. They debrief, reflect, and reframe. They ask, “What went wrong?” but also, “What went right that we can build on?” Because every failure contains both loss and potential. The art of leadership is helping others find that potential in the ashes. I’ve come to believe that failure is leadership’s mirror. It reveals what’s inside us when things don’t go according to plan; it magnifies our patience, our empathy, our courage, our true care for one another. When the plan falls apart, people don’t follow your strategy anymore, they follow your steadfastness. They don’t need a flawless leader, they need a faithful one. They need someone who stays calm when the storm hits, who listens more than lectures, and who chooses growth over guilt.
One of the hardest parts of leadership is forgiving yourself for the failures that ripple beyond you. (Mental note to self.) Maybe you made a call that cost someone an opportunity. Maybe your vision outpaced your communication. Maybe you burned yourself out trying to hold everything together. Maybe you just did something plain stupid and mistreated people who didn’t deserve it. It’s easy to carry that guilt like a stone, while really it should be used as a cornerstone for recovery. Every failure you own gives you the empathy to lead others more compassionately moving forward.
And here’s the irony: The leaders who embrace failure are the ones people trust the most. Why? Because they’re real. Transparency and vulnerability are strong towers. Leaders who exemplify these don’t lead from a pedestal, they lead from the trenches. They know what it’s like to doubt, to fall, to start again. They’ve wrestled with their pride and come out humbler, stronger, and more human. The scars of failure don’t make a leader weaker; they make them relatable. They give others permission to grow.
Leadership also means teaching people how to fail well. In high-performing environments, perfectionism can masquerade as excellence. But excellence isn’t about never missing the mark, it’s about what you do after you miss. “Fail fast” is the overused buzzword, but it has merit. Recognize, rationalize, realign. When failure happens, do you freeze? Do you hide? Or do you analyze, adjust, and return stronger? The healthiest teams I’ve ever led weren’t afraid to fail, they were afraid not to learn. In fact, strong teams view failure as the line to reach in order to bust through to create true change. When learning becomes the culture, failure becomes the fuel for innovation.
Every time I mentor emerging leaders, I tell them: your greatest growth won’t come from the wins that pad a résumé (while yes, career-defining wins are important), it comes from the moments that test your resilience and make you stare reality straight in the eyes. You’ll grow most when your confidence is shaken, when your plan implodes, when your voice cracks as you apologize to your team…. When you feel you’ve let down the people you care about the most. That’s where leadership gets forged. You can read every management book in the world, but nothing will teach you more than standing in the aftermath of your own mistakes and choosing to rise anyway.
One of my favorite metaphors for leadership comes from the golf course: You can’t play 18 holes without hitting a few bad shots. The key isn’t avoiding the rough, it’s learning how to recover. You take a breath, adjust your stance, and swing again. Leadership works the same way. You’ll slice it into the trees sometimes. You’ll misread the green. But the goal isn’t perfection, it’s progress. You learn to keep your composure, to play your next shot wisely, and to finish the round with integrity, even if the scorecard isn’t perfect.
The truth is, every great leader is a collection of recovered mistakes. The speeches, the decisions, the vision, all of it is built on a foundation of lessons learned the hard way. The difference between a leader who grows and one who stalls is simple: the willingness to reflect. Failure without reflection is just pain. But failure with reflection becomes wisdom. So, if you’re leading right now and something’s not going as planned: Pause. Don’t hide it. Don’t spin it. Sit with it. Ask what the situation is trying to teaching you in this moment. Maybe it’s telling you to listen more. Maybe it’s exposing a blind spot. Maybe it’s simply reminding you that leadership isn’t about controlling outcomes, it’s about shaping people, including yourself (most importantly).
I’ve failed enough times to know this: Failure is not the opposite of leadership, it’s the evidence of it. Because leadership isn’t about standing above the storm, it’s about learning to walk through it with grace. Every stumble, every misstep, every humbling moment becomes part of your credibility. As the saying goes, “the only real failure is the one you refuse to learn from.” So yes, both me personally and my career are a master of failure. But I’m also a student of it, and that’s the secret. The best leaders never stop learning. They fail forward, fail honestly, and fail with purpose. While it sounds cliché, in the end, success isn’t built by those who never fall, it’s built by those who got back up.
Connect with Joe Way:
LinkedIn: https://linkedin.com/in/josiahway
X (Formerly Twitter): https://www.x.com/josiahway
Instagram: https://www.instagram.com/josiahway
