Diary of a Leader: Embracing Failure as a Pathway to Growth

Lindsay Sheldrake
Nov 11, 2024
4 min read

Welcome to "Diary of a Leader" - Real Stories, Leadership Lessons, and Personal Growth

Lindsay Sheldrake - Embracing Failure as a Pathway to Growth — Diary of a Leader - Embracing Failure as a Pathway to Growth

Failure is usually treated as something to avoid at all costs, especially at work. But without it, growth is limited, creativity gets stifled, and the freedom to explore new ideas disappears.

Embracing failure as a pathway to growth means rethinking that instinct entirely.

This is the first of a two-part lesson on failure, specifically, how we help our teams get comfortable with it.

No one can be perfect all the time

I'm reminded of a senior industrial designer I once worked with. Exceptionally skilled, over 20 years of experience. I'd go as far as to say he was practically flawless: always prepared, always meticulous. Sure, he'd occasionally miss a minor detail, but he'd catch it and correct it instantly. After a while, I noticed something: he never really failed.

That might sound ideal. As a leader, it made me uneasy. It reminded me of the old idea of "fail fast." Small, manageable mistakes provide crucial learning moments. When those moments are missing, there's a chance that a much bigger error is building up somewhere out of sight.

The moment of failure: a six-inch miscalculation

Then it finally happened. He'd been working on a complex design: an installation mounting a heavy piece of art on both sides of a glass wall. With glass as the substrate, even the slightest misalignment would be visible.

While he was on vacation, the team received updated site dimensions and adjusted the model without his oversight. He hadn't briefed his colleagues on two critical measurement changes. When he returned and started preparing the pieces for shipping, he found a six-inch misalignment. The two parts of the art piece wouldn't line up correctly during install.

He walked into my office looking pale, and laid out the situation. It was a real mistake, and in that moment he had no solution. But as he explained it, I couldn't help but smile.

He looked at me, baffled, and asked why such a huge oversight would make me smile.

"Because," I said, "I've been waiting eight months for you to mess up, and I'm glad it finally happened."

I explained that the longer we go without a mistake, the bigger the eventual failure tends to be. By learning to handle mistakes in real time, he'd build the resilience and flexibility that strengthens his ability to solve complex problems. That's the essence of "fail fast." Small, timely failures are what let you course-correct before things get out of hand.

The turnaround

Within 24 hours, he came back with a solution that avoided any structural changes to the design, just a few minor adjustments to the art piece, and the project was back on track. The experience taught him something he couldn't have learned any other way: mistakes aren't the end of the world, and he could trust his skills to solve even the big problems.

A few months later, during his quarterly review, I asked my usual starter question: "How did you feel about this quarter?"

He said something I'll never forget:

"I've never felt more comfortable with failure, and more confident in my ability to solve problems."

In that moment I saw real growth in him. Failure had become a stepping stone, not a stumbling block, and his confidence as a designer had reached new heights.

The leadership lesson: why embracing failure as a pathway to growth matters

It's a leader's job to build an environment where failure isn't feared. When people feel safe making mistakes, they become more innovative, more resilient, and more engaged in their work. A few ways to encourage that "fail forward" mindset on your team:

Encourage small risks. Make room for small, calculated risks, and be explicit that taking them in pursuit of growth and learning is welcome, not penalized.

Celebrate problem-solving, not just success. Recognize people not only for avoiding mistakes but for how they solve problems when things don't go as planned. That shifts the focus from perfection to resilience.

Use failure as a teaching moment. Share insight, offer guidance, or simply listen, whatever the moment calls for, as long as it comes from a genuine desire to help someone get better.

Show you believe in their abilities. When mistakes happen, make it clear you still trust their skills and judgment to find a solution. Your confidence in them builds their own, and that's what lets them tackle the next hard problem without flinching.

Embracing failure as a pathway to growth: common questions

Why is embracing failure important for leadership? Without small, manageable failures along the way, mistakes don't disappear, they just get bigger and show up later, with higher stakes. Teams that are allowed to fail small learn to course-correct early. Teams that aren't tend to hide problems until they're much harder to fix.

How do you build a team culture that treats failure as a pathway to growth? Make space for calculated risk, recognize problem-solving as much as you recognize success, and respond to mistakes with trust rather than blame. The goal isn't to lower the bar, it's to make sure people feel safe enough to tell you the truth when something goes wrong.

What's the difference between "fail fast" and just being careless? Fail fast means surfacing small, low-stakes mistakes early enough to learn from them before they compound. It's not about lowering standards, it's about creating an environment where issues get caught and corrected while they're still small.

Wrapping up (because time is precious)

Here's the takeaway: failure is an essential part of growth. When you build a work environment that values learning from mistakes, you give your team room to innovate and stretch their capabilities without fear.

Catch you next time, fellow leaders-in-training, and remember, real growth often starts with failure.