Embracing Failure: How Leaders Can Transform Setbacks into Stepping Stones

In a world where the fear of failure often hinders progress, embracing and learning from our mistakes has become crucial for both personal and professional growth. In this episode of Bring Out the Talent, we chat with Jordan George, an award-winning HR leader, to explore how embracing failure can drive personal and professional growth. Jordan shares his "Learning Fail-osophy"—a practical approach rooted in acceptance, non-judgment, and present moment awareness—that helps leaders turn setbacks into steppingstones. 

Join us as we discuss actionable strategies to foster a workplace culture that encourages risk-taking, accountability, and innovation!

Transcript

David:
Bring out the talent. Welcome to Bring Out the Talent, a podcast featuring learning and development experts discussing innovative approaches and industry insights. Tune in to hear our talent help develop yours. Now here are your hosts, TTA's CEO and President Maria Melfa and Talent Manager Jocelyn Allen.

Maria:
I think we lost Jocelyn. She's having a little laughing fit here.

Jocelyn:
We don't know why. We got a recording of you being like the old cop in every action movie that says like...

Maria:
They're too old for this, because I did my normal dancing and I just stretched my back so bad.

Maria:
Oh gosh. That's David's fault. Yeah. Look at this.

Jocelyn:
Yeah, David needs to have less sensory-pleasing songs as our intro, because then I would sit here like a bump on a log and not be in any pain.

Maria:
I know. One of these days we should do something very serious, play like very somber music and just not laugh or smile.

Jocelyn:
Correct. All right, let's practice right now.

Maria:
You fail.

Maria:
Exactly.

Maria:
Oh yes. I like to laugh because I like to laugh. And sometimes I like to laugh because it's my coping mechanism. When I feel stressed, I like to laugh. When I feel happy, I like to laugh. When I feel tired, I like to laugh. When I feel busy, I like to laugh.

Jocelyn:
All of the above. I said it today. I cannot find a situation where I don't make a joke to make the atmosphere more appropriate for me. Like, we'll be talking about something serious and I'm like, "Yeah, that's what she said." And it's like, no Jocelyn, not the time.

Maria:
It is good that we have a guest today who we've had previously. And we know that he is all about working hard and having fun as well. So welcome, Jordan. Excited to have you back.

Jordan:
Thank you. Excited to be here. I was dying laughing watching Jocelyn pull a muscle from sitting in a chair, dancing to the intro music. And I've never...

Jocelyn:
I've...

Jordan:
I've never been more aligned. Thank you so much for providing the context, Jocelyn.

Jordan:
I feel a kinship now that was already there, but now it's like the next level. I get out of bed in the morning and I just make all kinds of groans that I never did. Like 10 years ago, I was like, my knee cracks in 10 different places just putting on a pair of pants. What's going on? Put the somber music back on, David. The pains and creaks of my broken body remind me of the trials and tribulations that I've been through.

Maria:
And how we cannot let failure let us stop. We have to overcome failure.

Jordan:
What a transition.

Jocelyn:
Yes. I mean, that's what we're good at. All right.

Maria:
Okay. So let's be serious. We apologize audience here for being extra silly...

David:
Slappy. Five people still listening.

Maria:
No, I think it's at least six.

Maria:
Okay. So in a world where the fear of failure often hinders progress, embracing and learning from our mistakes has become crucial for both personal and professional growth. In fact, according to a Harvard Business Review study, companies that encourage a culture of learning from failure are 30% more likely to be market leaders in their industry, highlighting the importance of transforming setbacks into stepping stones for our success. In our episode today... We welcome Jordan George, an award-winning HR leader, facilitator, and international speaker dedicated to empowering people and businesses to achieve their full potential.

With nearly 75 years of experience. See, that's how incredible you are. You are able to make the 20 years seem like 75 years, Jordan. So with nearly 20—exactly—20 years of experience, Jordan knows how to get people excited about learning. His transformative journey through personal and professional setbacks has equipped him with unique insights into developing a learning philosophy. Get it? His approach emphasizes acceptance, non-judgment, and present moment awareness to overcome the paralyzing fear of failure. Together, we will discuss how leaders can create environments where failure is seen not as a setback, but as a stepping stone to success. He will share practical strategies for fostering a culture that encourages risk-taking and innovation while maintaining accountability. If you're looking to build a resilient, innovative, and growth-oriented organization, today's conversation with Jordan is packed with actionable insights and inspiring stories that will help you and your team embrace the invaluable lessons failure has to offer.

Maria:
Welcome, Jordan, again.

Jordan:
Thank you. Thank you. Very excited to be back. Great to see you all again. And great to be getting to talk about this exciting subject of messing things up. We're setting a low bar with this subject, right? Because we can really do anything wrong and just say it was part of the podcast.

Maria:
A hundred percent. I think with every question and answer, we should try to fail hard and then...

Jocelyn:
Learn from it. I feel like that's been our philosophy since we started this podcast.

Jordan:
Yes. Not always intentional, but it...

Jocelyn:
Was there. There's always an edit button.

Maria:
Well, we are excited to dive into this topic because it is a topic that we're hearing a lot more about over the last several years. And a topic certainly that we all can relate to and we all can get better at because we certainly all fail or make mistakes. And sometimes it really throws us off our game and it leaves us with moments of doubt and wondering, what am I doing here? Should I be doing this? What's going on? But why don't you tell us where your learning to fail, the learning fail-osophy, originated from?

Jordan:
As it turns out, I'm bad at a lot of things. And that may be a sentiment shared by some of your listeners, right? And I decided I can be upset about that or I can try to find some value in it. And I've been really fortunate to have some great mentors over the course of my career. I was having lunch with one one day and I was sharing this difficult challenge that I was facing personally. And he surprised me with a question that I wasn't anticipating. He said, “Jordan, do you believe that everything happens for a reason?”

This was probably like 15 years ago. I was a little, this was a little younger before all the back pain of getting out of bed and the 75 years of experience under my belt or whatever else, right? And I said, “Yeah, I do.” And he responded back really quickly. He said, “Well, I don't.” I was like, okay, all right. And he said, “But I do believe we can find a reason in everything that happens if we're persistent enough to look for it.”

It was through that conversation and through that lunch that he taught me his own learning philosophy and this idea that every setback, every stumbling block, every failure that we have, we can respond with the question, “What can I learn from this?” That's been my approach personally and professionally ever since then, particularly as a training person, someone who's been in the learning development space for a long time. It just makes sense. What can I learn from this?

Jocelyn:
The forever learner, right? I think that's kind of a misconception about failure too. There's this fear around it and that like failure means you're bad, right? As opposed to this is a lesson and I'm going to put this into practice and see what I can do better next time. So what else do you think is preventing people from kind of thinking about failure in this manner—of how do I push forward and do better versus I'm going to let this keep me where I am so that I never fail again? What are some things that are, again, misconceptions about it that you think are preventing people from practicing that “what am I going to learn from this” approach?

Jordan:
Well, it's like you said, there's definitely this perception that failing is equivalent to incompetence or a lack of skill. And as a result, I think people are thinking of failure as something that needs to be avoided at all costs because nobody wants to be perceived as incompetent or having incompetent people on their team.

What I really challenge leaders to do and people in general is to just accept that failure is a natural part of the learning process. Particularly when we're talking about complex or innovative tasks—anything that requires some cognitive function—it's an inevitable part of the work that we do. We're going to make mistakes. We're going to mess up. None of it's permanent. All of it can be recovered from, unless we're talking about life and death situations, which the majority of people are not in those situations every day.

The worst thing that's going to happen is we make a mistake and we just try it again. And so reminding everybody that it's not permanent, that we can use this as a learning opportunity and an opportunity for us to come back and do it better the next time and to iterate and to build on it—it's so critical, particularly for any organization that is trying to grow, that is trying to be innovative, to shed that sort of outdated view of failure. Because it just stifles creativity, it stifles risk-taking.

That mindset—that only weak people or weak teams are the ones failing—is insane. It's so easy to debunk. It's really the high-performing teams that are tackling some of the most ambitious goals and tasks that are failing the most. But they're also the ones that are excelling the most. They're also the ones that are moving the needle forward the most. It's like that risk-reward... except the risk isn't really all that bad. And the reward is everything.

Maria:
Right on. I could relate to everything that you're saying. So how can leaders create an environment where employees do feel safe and able to take risks and not worry about if they made a mistake or fail?

Jordan:
I think sometimes there's an overemphasis on the outcomes—reaching the goal, achieving the thing, hitting the KPI, hitting the metric. What we can do instead is help people shift their focus to celebrating the effort, the learning, the perseverance that failure can bring. Everything along the way to the finish line matters as much as hitting the finish line. That helps reframe failure as a developmental opportunity.

I think one thing leaders can do specifically is just get more comfortable admitting their own failures—raising their hand and saying, “Yeah, I mess up too. I'm also a human being.” The act of making our own failures public and talking about what we learned from them, using them as learning opportunities we can share with our team, sends a message of humility and vulnerability. It lets people know it’s okay to make mistakes—but that you as a leader see them as learning opportunities and you want others on your team to learn from their mistakes too.

Jocelyn:
I believe Miley Cyrus said it: “It ain't about what's waiting on the other side, it's the climb.” Right?

Maria:
I don't listen to Miley Cyrus, so I don't know that song.

Jocelyn:
I'll play it for you later. You're going to love it. It's her Hannah Montana era—you’ll love it. I'll show you.

Maria:
I don't even know who Hannah Montana is.

Jocelyn:
I’m going to set a meeting for your education on Disney stars and what they're doing now after this. But the moment you said everyone focuses on the outcome, but the journey to get there is just as important—I was like, yeah, that Miley song. She said it. She said it. No, I would sing for you if I didn’t have a cough right now.

Anyway, so many of the things you said resonated, Jordan, because before we got on the call, we were having these same conversations. We're recognizing a shift in the industry, and we’re seeing momentum and growth and all this amazing energy. But the first conversations we’re focusing on are exactly this: learning from your mistakes, making sure you're communicative, not worrying about being perfect, and preparing better for next time.

It’s about fostering psychological safety to do that. Removing the fear of consequences. Leaders need to enable their teams by making it safe to say, “Maria, I didn’t get this done the way I wanted, but here’s what I’m thinking for next time.” Because Maria’s the type of leader who says, “Come to me with solutions.” That mindset opens doors for collaboration and growth.

How do we create a balance for all these things, though? Because accountability still matters. You have to recognize that a failure happened, and that there’s a lesson. But how do we encourage a culture that embraces failure and removes the stigma?

Jordan:
For every team I’ve led in the last decade, I’ve always said two things. First: It’s okay to fail, as long as the failure doesn’t sink the ship. It can’t be catastrophic, mission-ending, or put anyone at risk.

Second: We can’t make the same mistake over and over again. You can make any mistake once or twice—if it doesn’t sink the ship. That’s normal. That’s expected when you’re challenging the status quo or trying to innovate.

But we need to learn from our failures and do better next time. That’s where accountability comes in. It’s about supporting each other through learning—not letting repeated errors go unchecked. If someone confides a mistake to you privately, encourage them to share it with the team. Others may benefit from hearing that experience.

As a leader, don’t miss the chance to share your own mistakes. That helps build an environment where mistakes aren’t just okay—they’re expected. As long as we don’t sink the ship and we learn from them, that’s the culture we’re aiming for.

Jocelyn:
Agreed. That’s what makes a strong leader—someone who holds themselves to the same expectations they set for others. There’s a difference between delegating and dictating. When a leader says, “I could do this, but I trust you to run with it,” it builds camaraderie.

Maria gave me grace the other day by saying, “You are one person.” That might sound simple, but it made a huge difference. It wasn’t about me being incapable. It was about being realistic. Not every leader does that—and they should.

So how do we handle when personal failures affect professional development? How do we integrate the personal with the professional in a way that enhances day-to-day work?

Jordan:
You said it: permission to be human. Most of the time, mistakes are recoverable. Think about a time when you bombed a test or said something wrong to someone you care about. That feeling sticks. And if you're self-aware, that discomfort becomes a catalyst to improve. You study harder. You communicate better.

Those personal moments shape who we are and how we lead. When we talk about them, we normalize being human. That’s not “touchy-feely”—it’s practical. It creates a culture where people feel safe being real.

And for those of us in L&D, we know learners retain more from mistakes than perfect scores. The “aha” moment doesn’t come from getting 100%. It comes from realizing, “I need to do this differently next time.”

Maria:
So true. The people I respect most are those who make themselves vulnerable. It makes them relatable. We all make mistakes—and hearing others share theirs builds confidence.

Some people, though, grow up in environments where mistakes weren’t allowed. I remember one employee—excellent at her job—but when she went on vacation, we discovered she’d been covering up tons of things. She was just terrified of being wrong.

Even when leadership gave her grace, she couldn’t internalize it. So I’ve learned that leaders can say, “It’s okay to make mistakes,” but we have to keep repeating it, modeling it, and making it part of our culture.

Jordan:
Exactly. Sometimes it’s not your leader or environment—it’s self-imposed pressure. Life is hard enough without expecting yourself to be perfect.

So yes, leaders need to say it’s okay to fail—but also get to know their people on an individual level. Some may still need reassurance. “Just go fail” isn’t helpful. We have to learn to be okay with failure emotionally.

It’s uncomfortable. But if we can sit with it, process it, and learn from it—we get better. And so does the team. That’s the point.

Maria:
Yes, and I think for many of us, we’re our own worst critic. I can forgive others’ mistakes easier than my own. But I’ve grown the most from those moments—and I’m better for it.

Jordan:
Earlier in my career, I used to be proud that I got every job I applied for. I thought, “I must be great.” But someone pointed out, “You’re only applying for roles you know you’ll get. You’re not challenging yourself.”

That hit hard. And it changed how I approached my career. I started applying for jobs that made me uncomfortable—even if I didn’t get them. Because each interview taught me something I could use to grow.

Maria:
You won’t fail if you stay in the same lane.

Jocelyn:
Right. And think about it—how many breakthroughs happen at rock bottom? That’s when real change happens. You realize what you’re doing isn’t working, and you finally pivot.

The opposite of failure doesn’t have to be success. It can be growth. The win is the learning.

So how do we help leaders embrace this mindset? To be transparent about failure and show that it doesn’t disqualify them—it makes them stronger?

Jordan:
You used the word “struggle,” and that’s important. Because this isn’t easy. Like any muscle, it takes time to build.

You don’t go to the gym once and walk out ripped. You don’t swap fries for salad once and call it healthy. You have to commit.

Same with failing. We have to keep at it, internally and culturally. If you’re lucky enough to be in a culture that supports failure—amazing. If not, you have to lead the charge and create it yourself.

Two things I always say:

1. Failing isn’t permanent. You can recover.
2. Failing doesn’t make you a failure.

The mistake is not trying, not pushing yourself, and not taking intelligent risks. That’s the bigger loss.

There’s a quote I love by John Shedd: “A ship is safe in the harbor, but that’s not what ships are built for.” You’re not meant to stay safe. You’re meant to explore, challenge yourself, and grow.

Maria:
I love that quote. So what do you do when other leaders don’t buy into that philosophy and start doubting capable people because of a few mistakes?

Jordan:
You have to know your environment. We're not aiming for rock bottom, but we have to allow calculated risk. Start small. Encourage safe experimentation. And make it visible—market your approach internally so people understand the value.

You may not convert everyone, but you’ll start a movement. I remember a training director early in my career saying, “You’re never allowed to say ‘I don’t know’ in the classroom.”

I get the intent, but I completely disagree now. “I don’t know, but I’ll find out” builds credibility. There’s power in being real. That vulnerability is where trust begins.

Maria:
Love it. So true. And being open about your mistakes—telling the story behind them—helps people move forward.

Jordan:
You never know who’s listening or watching. Whether you’re in a leadership role or not, visibility matters. Sharing your mistake might save someone else from repeating it.

This isn’t just feel-good stuff—it’s practical. It saves time, resources, and energy. It helps people grow. Deconstruct the mistake in a non-blaming way and improve from there.

Jocelyn:
Outstanding stuff, Jordan. We could talk about this forever because we’ve all felt it—even if we won’t admit it. In L&D, it’s central: people are people, wherever they are.

It’s time to get human.

David:
Ditto.

Jocelyn:
Ditto.

Jocelyn:
But we’ve got one more thing. It’s time for the TTA 10!

David:
It’s the TTA 10—10 final questions for our guest.

Jocelyn:
All right, Jordan. You know what this is. The listeners know. I’m asking 10 questions. They’re fun. And you’ve already proven you don’t fear failure, so let’s go!

Jordan:
I’m ready.

[... 🎤 TTA 10 questions and answers ...]

Maria:
That was amazing.

Jocelyn:
Jordan, once again, super fun episode—really informative. Thank you so much for being here and sharing your insights.

Maria:
Absolutely. Thank you so much.

Jocelyn:
For more information on transforming failures into lessons, visit us at thetrainingassociates.com.