How In-House Lawyers Can Reframe Mistakes as Strategic Learning Opportunities

What if mistakes weren’t failures—but fuel for strategic growth? In a profession obsessed with perfection, the idea might sound radical. But for in-house legal leaders navigating complexity, ambiguity, and scale, reframing mistakes as learning opportunities isn’t just helpful, it’s essential.

That’s exactly what Victoria Libin believes. She’s served as General Counsel and Corporate Secretary at Bright Machines, bringing legal leadership to high-growth tech companies following roles at Viacom and Accenture. Through each chapter of her career, Victoria has embraced a rare but powerful leadership mindset: mistakes aren’t setbacks—they’re strategy.

Her insights reveal a new way forward for in-house lawyers who want to lead with courage, not just caution.

Watch the full conversation with Victoria Libin here:

Victoria shared one of her most powerful mindset shifts: stop asking how to avoid mistakes, and start asking what you’re learning.

This simple reframe has helped her lead through complex decisions—like a delayed SPAC transaction that didn’t unfold as planned. Instead of treating it as failure, she walked away with lessons in IPO prep, board dynamics, and audit strategy that continue to serve her today. For strategic legal leaders, these lessons become part of your long-term value.

In-house lawyers are trained to minimize risk. But Victoria points out that overcorrecting for risk can lead to stagnation. “What’s the risk of doing nothing?” she asks.

She brings this question into her leadership style too. When someone on her team makes a mistake, the default response isn’t punishment—it’s curiosity. What happened? What can we take from it?

That approach builds psychological safety, lowers burnout, and fosters a resilient, high-performing legal culture.

Another recurring theme in Victoria’s leadership playbook is guiding teams through complex risk decisions—even when the right path isn’t obvious.

She shared a story where her company faced a copyright challenge on a viral campaign video. The safe response? Pull it. But after a careful analysis and consultation—including backing from the Electronic Frontier Foundation—Victoria stood behind a fair use defense. The video stayed up, and the company’s visibility and revenue soared, eventually contributing to a successful acquisition. This example showcases strategic legal leadership at work.

Her takeaway? Legal leadership means knowing when to say “yes,” not just when to say “no.” It means understanding the human side of risk, and helping others make brave, informed decisions.

Lawyers are high-achievers, but that drive can come at the cost of self-kindness. Victoria’s reminder is simple: “Fail better.”

Borrowed from tennis psychology, that mantra emphasizes learning and iteration over perfection. If you wouldn’t berate a client for a misstep, don’t do it to yourself. Ask: What am I learning? How can I show up better next time?

It’s not weakness. It’s leadership.

Mistakes aren’t threats—they’re training. If you’re building a career in strategic legal leadership, perfection is not your measure. Your real value lies in how you respond when things don’t go perfectly.

Lean into complexity. Guide your teams through ambiguity. Build trust through reflection, not blame. And the next time something doesn’t go according to plan, ask the most powerful question a lawyer can: “What am I learning?”

Because in this next era of legal leadership, failing better might be the most strategic move you make.

Watch the full conversation here:  Notes to My (Legal) Self: Season 4, Episode 5 (ft. Victoria Libin )

AtNotes to My (Legal) Self®, we’re dedicated to helping in-house legal professionals develop the skills, insights, and strategies needed to thrive in today’s evolving legal landscape. From leadership development to legal operations optimization and emerging technology, we provide the tools to help you stay ahead.

What’s been your biggest breakthrough moment in your legal career? Contract content transformation is one approach. Let’s talk about it—share your story.