Leadership Lessons from Failure
The Day I Thought I’d Failed — And the Leadership Lesson I’ll Never Forget
I want to share a story I don’t often tell – about a time I genuinely thought I’d failed. The kind of moment where your heart races, your mind spirals, and you think, “That’s it. I’m done. I’m not cut out for this.” However, it’s also a story about one of the most powerful leadership lessons from failure I’ve ever learned — a lesson that shaped who I am today and how I lead others.
So, let me take you back to that moment.
Out of My Depth (and Out of My Comfort Zone)
I had just been offered a Sales and Marketing Management role—and not just any role. It was a position based in the Middle East, working for a huge American oil and gas company.
Here’s the thing — up until then, I was an engineer. That was my world. Pipes, machines, construction, and engineering — things I understood inside out.
Sales? Marketing? Management? I hadn’t a clue.
So, when they offered me the job, my gut reaction was, “What do I know about that?!”
But for reasons I still can’t explain — maybe stubbornness, maybe curiosity — I said yes. I took the leap.
The Boss Who Saw Something in Me
On my very first day, I was called into my boss’s office — the Vice President of Sales and Marketing. He looked like someone who owned that space — confident, sharp, and fully in control.
He sat me down and said:
“James, you’ve just joined a Premier League outfit. We’re not here to make up the numbers. You need to be a top-calibre player to stay in this league.”
As you can imagine, I was sitting there thinking, “How do I do that? I’ve never done this before!”
However, what he said next has stuck with me ever since:
“I don’t know how you’ll do it, but I know that I did, and others did too. It’s a choice you have to make.”
Then, he handed me a massive sales script — like a phone book — and said:
“You’ll be presenting this next week.”
I walked out thinking, “SH*T… What have I just agreed to?!”
Panic Mode: Activated
For the next week, I was glued to that script. It went everywhere with me. I practised constantly.
Still, no matter how much I prepared, the nerves didn’t shift.
The night before, I barely slept. You know that feeling when your stomach is in knots, and your brain just won’t switch off? That was me.
The Presentation Disaster (Or So I Thought)
Walking into that boardroom, I felt sick. Six senior leaders sat waiting, watching.
As I stood up, palms sweating, heart pounding, and mouth dry, I launched into it.
Honestly? I flew through that script at breakneck speed — thick Glasgow accent and all — like I was on autopilot.
Before I knew it, it was over.
A 40-minute presentation, finished in under 30 minutes.
The room was silent. Everyone stared at me — a mix of shock and confusion.
The Silent Walk
Leaving the room, I thought: “That’s it. I’ve blown it. I’ll be on a flight home by the end of the week.”
Walking to the car with my boss, my mind was racing:
“Why did I think I could do this? I’m an engineer, not a sales leader!”
The 3 Questions That Changed Everything
Once we reached the car, I braced for the worst.
Instead, he looked at me and said:
“James, I’ve got three questions for you.”
I expected him to tell me I’d failed.
But this is what he asked:
What did you do right?
I was stunned. No one had ever asked me that — especially when I felt like I’d messed up.
I hesitated but said: “I think I got through the script, in the right order?”
He smiled.
“James, it was flawless. You didn’t miss a word. That’s impressive.”
What did you do wrong?
I grinned nervously.
“Maybe… rushed it a bit?”
He laughed:
“You didn’t stop for breath! But we can work on that.”
What would you do differently next time?
By now, I was really thinking:
“I’d slow down, pause, take a sip of water, and engage with the audience.”
He nodded:
“James, I know you’ll smash it next time. You’re willing to reflect, learn, and grow — and that’s what great leaders do.”
The Leadership Lesson I’ll Never Forget
That day taught me one of the most powerful leadership lessons of my career.
Those three questions are now a habit I share with every leader I coach:
- What went well?
- What didn’t go well?
- What would you do differently next time?
Because leadership isn’t about never getting it wrong — it’s about how you respond when you do.
Most of us, when things go badly, jump straight to self-criticism. I did it for years. But that conversation taught me to see failure as feedback, not as proof that I wasn’t good enough.
Final Thought: If You Feel Like You’ve Failed, Read This
If you’re reading this thinking, “I’ve messed up. I’m not good enough. I can’t do this,” — I’ve been there.
But here’s the truth: You can.
Ask yourself those three questions.
Learn from it. Grow from it. Get back out there.
Because great leaders aren’t the ones who never fail — they’re the ones who choose to learn and grow when they do.
And if you ever want to chat about this stuff — really chat, no jargon or corporate nonsense — that’s what we do at The Power Within Training.
Reach out. We’d love to help.
James Fleming
The Power Within Training,
The Motivational Intelligence Company
james@tpwtd.com
