The Art of the Challenge: How I Learned to Stop Worrying and Love Being Wrong

TL;DR: Growth happens when we're challenged, but only if we've built enough trust and psychological safety first. Creating an environment where people can challenge each other's ideas without triggering defensiveness is the biggest favor you can do for your team. This requires modeling vulnerability, separating identity from ideas, and consistently showing that you have your people's best interests at heart.

Embracing challenge has been a journey for me. I saw constructive feedback as a personal attack. I would visibly tense up whenever someone started a sentence with "I have some thoughts about your approach..." I would sit there thinking of my response and completley miss the feedback and the opportunity to grow. Because let's be honest, challenges and feedback provide the opportunity to grow and develop.

My Journey from Defensive Engineer to Challenge Champion

When i look back at my early career, I was the kind of engineer who would sweat profusely at the mere thought of sharing unfinished work. I'd polish and perfect in isolation, convinced that anything less than a near-final solution would make me look incompetent.

What I didn't realize then—but understand deeply now—is that I was robbing myself of the most valuable resource in engineering: diverse perspectives. Every time I finally (reluctantly) shared my work, people would offer viewpoints I hadn't considered, angles I'd missed, and solutions that were often elegantly simple compared to my over-engineered approaches.

The real epiphany came when I noticed something unexpected: the more I involved others in challenging my early ideas, the more invested they became in the solution. By opening the door to critique, I wasn't diminishing my contribution—I was creating co-owners who genuinely cared about the outcome. My defensiveness wasn't protecting my value; it was actively reducing it.

The Paradox of Growth and Building a Challenge-Friendly Culture

Here's the paradox I've discovered: Real growth only happens at the edge of discomfort, but humans are wired to avoid discomfort at all costs. We're essentially running evolutionary software that treats a challenge to our ideas the same way it treats a saber-toothed tiger—as an existential threat.

The trick is creating an environment where people feel safe enough to override that programming—where being challenged feels less like being attacked and more like being offered a better map when you're lost.

If you're nodding along thinking, "Yes, I too was once defensive, but now I'm the zen master of feedback," congratulations! You're either lying to yourself or you're a better person than I am. I still struggle with this, but here's what's worked for me as a leader:

1. Model the behavior obsessively

Nothing builds psychological safety faster than watching the boss get things wrong and respond with "Good spot!" or "Nice challenge!" I make it a point to publicly thank and celebrate people who challenge me. I've developed a genuine appreciation for good challenges and get excited to collaborate and improve an idea.

2. Separate identity from ideas

Reminder: "You are not your code. You are not your system design. We are all just temporarily attached to solutions that can always be better." This isn't hippie leadership talk—it's practical engineering wisdom. The minute you start identifying with your technical decisions is the minute you stop being able to take feedback and improve them.

3. Talk about the Third Entity

In any challenge situation, there are three entities: You, Me, and The Problem. Too often we merge The Problem with either You or Me. Instead, position challenges as both of you facing The Problem together. "This design has a scalability issue" works better than "Your design won't scale."

4. Create challenge rituals

Schedule a regular "Change My Mind" meeting where anyone can present a solution they're unsure about and explicitly ask for challenges. Having a dedicated space and time for this helps separate "normal work mode" from "please poke holes in this" mode. This is excellent for identifying risks and mitigating them, making your design, code or document more robust.

Trust: The Ultimate Challenge Enabler and Its Return on Investment

I realised late in my career that trust is the rocket fuel of effective challenge. When people trust that:

1. You genuinely want them to succeed
2. You believe in their capability to grow
3. You won't hold honest mistakes against them
4. You'll have their backs when things get tough

...then suddenly, challenge stops feeling threatening and starts feeling like support.

I have a theory that you can measure psychological safety on a team by how quickly people admit mistakes. When someone can say "I think I made an error in my approach" without hesitation, you know you've built something special. That's not because we're all flawless engineers—it's because we've built enough trust that no one fears admitting they're wrong.

And I've seen the business impact of both challenge-friendly environments and challenge-averse environments. Teams that can challenge each other without drama ship better code, solve problems faster, and generally don't make the same mistakes twice. Sold yet?

Finding the Balance: Confidence, Humility, and a Challenge for You

The truth is, your best engineering happens at the intersection of confidence and humility—being secure enough to put forward big ideas, but humble enough to accept when they need improvement. It's taken me a decade to find that balance, and I'm still wobbling on the tightrope.

So here's my challenge to you: Find something you're working on right now, take it to someone you trust (bonus points if they're more junior than you), and explicitly ask them to find everything wrong with it. Then—and this is the hard part—just listen. Don't defend. Don't explain. Take notes and say thank you.

I guarantee it'll be uncomfortable. But that is the feeling of growth. Or maybe too much coffee... Either way, it's worth pushing through.

But hey, at least now when I fall, I know how to get back up—and more importantly, how to thank the person who pointed out the tightrope was installed upside down in the first place.