How to turn mistakes into team growth as a product leader

July 10, 2025 at 07:00 AM
How to turn mistakes into team growth as a product leader

Ten years ago, in my first role as a testing engineer at a travel platform in India, I made what felt like a career-ending mistake. While testing a new "custom discount promotion" feature for hotel partners, I accidentally deployed a test scenario to production instead of our staging environment. Within minutes, every hotel room across India was bookable for just $1.

The result? Over 200 bookings processed before we could take the system down, thousands of dollars in losses, and a flood of angry calls from partner hotels. As a junior team member, I was mentally preparing for the inevitable blame and potential termination.

What happened next taught me more about product leadership than any framework or methodology ever could.

The moment that defined product leadership for me

My manager called an emergency team meeting. Instead of the finger-pointing session I expected, he said something that has shaped my understanding of leadership ever since: "This isn't Rishab's fault, or any one person's fault. We should have had better processes and safeguards in place to prevent this situation."

Rather than playing the blame game, his entire focus shifted to building better systems. After the meeting, he took me for coffee and helped me reframe the incident as a learning opportunity that would make me a stronger product professional.

That moment crystallized what effective product leadership looks like in practice.

Why product leaders must reframe failure

In product management, we're constantly making decisions with incomplete information, testing hypotheses, and iterating based on user feedback. Mistakes are guaranteed. The difference between high-performing product teams and those that struggle often comes down to how leadership handles these inevitable failures.

Product leaders who create psychological safety around failure enable their teams to take calculated risks that drive innovation, share problems early before they become critical issues, learn faster from both successes and failures, focus on solutions rather than blame assignment, and build resilience that strengthens the entire product organization.

Six leadership behaviors that transform product teams

Based on my decade-plus experience in product roles and observing exceptional leaders, here are the key behaviors that separate effective product leaders from managers who simply assign tasks:

  1. Invest genuinely in team growth. Great product leaders actively develop their people. They create individual development plans, provide stretch opportunities, and connect team members with mentors across the organization. They understand that product success is fundamentally about people success.
  2. Provide air cover when needed. When stakeholders push unrealistic timelines or question product decisions, effective leaders shield their teams from organizational politics while ensuring the team understands business context. They take responsibility upward and give credit downward.
  3. Encourage ambitious thinking. Instead of simply accepting "what's always been done," strong product leaders push their teams to think bigger. They ask questions like "What would need to be true for us to 10x this metric?" and create space for exploring breakthrough solutions.
  4. Demonstrate the behaviors they expect. Product leaders who talk about user-centricity but never talk to customers themselves send mixed messages. The best leaders model the curiosity, data-driven thinking, and collaborative approach they want to see throughout the organization.
  5. Recognize both outcomes and efforts. While product management is ultimately about results, effective leaders also recognize the process improvements, learning discoveries, and collaborative efforts that don't always show up in metrics but build long-term team capability.
  6. Show genuine empathy. Product work is inherently stressful—balancing competing priorities, dealing with ambiguity, and managing stakeholder expectations. Leaders who acknowledge this reality and provide emotional support create more resilient, engaged teams.

How to evaluate your current product leadership

Just as product leaders regularly assess their team's performance, product professionals should evaluate whether they're working under effective leadership. Ask yourself: When you make a mistake, does your leader focus on blame or on improving systems? Are you learning new skills and taking on new challenges regularly? Does your leader provide context for decisions rather than just directives? Do you feel comfortable raising concerns or suggesting alternative approaches? Does your leader advocate for the team in organizational discussions?

If you answered "no" to most of these questions, it might be time to either have a conversation with your leader about expectations or consider whether this environment will support your growth as a product professional.

Building this leadership approach yourself

Whether you're a senior PM mentoring junior team members or a CPO leading an entire product organization, you can implement these leadership behaviors immediately.

  • Create psychological safety in daily interactions. Start your next retrospective by explicitly asking "What mistakes did we make this sprint that we can learn from?" and celebrate the insights that emerge. When team members report problems, respond with "Thank you for bringing this up early" instead of "Why didn't we catch this sooner?" This simple reframing encourages transparency.
  • Structure meaningful development conversations. Replace status-focused one-on-ones with growth-centered discussions. Ask questions like "What part of your role energizes you most?" and "What skills do you want to develop in the next six months?" Create individual development plans with specific, measurable goals and check progress monthly.
  • Master transparent decision-making. When presenting product decisions, always include three elements: the context that drove the decision, the alternatives you considered, and the trade-offs involved. For example: "Given our Q4 revenue targets and user feedback about checkout friction, we considered three approaches. We're prioritizing the payment flow redesign over the rewards program because it addresses our highest-impact user pain point, though it means delaying the loyalty features until Q1."
  • Implement the "failure resume" practice. During team meetings, occasionally share your own professional mistakes and what you learned from them. This normalizes failure as part of growth and encourages others to be open about their challenges.
  • Build advocacy habits. In stakeholder meetings where your team isn't present, actively highlight their contributions and defend realistic timelines. Follow up with team members afterward, sharing how you represented their work and any feedback from leadership.
  • Practice active listening during conflict. When team members disagree on product direction, resist the urge to immediately provide solutions. Instead, ask clarifying questions that help each person fully articulate their perspective. Often, the act of being truly heard resolves tension and leads to better collaborative solutions.

Daily practices that build exceptional product leadership

Beyond the foundational behaviors, exceptional product leaders develop specific habits that compound over time:

  • The "context sandwich" technique. When assigning tasks or sharing feedback, always provide context before and after your main message. Start with why this work matters to users or business goals, deliver your specific request or feedback, then close by connecting it back to the bigger picture. This helps team members understand not just what to do, but why it matters.
  • Weekly "assumption audits." Dedicate 15 minutes each week to questioning one major assumption underlying your current product strategy. Ask your team: "What would need to be true for this assumption to be wrong?" This practice builds critical thinking skills and prevents tunnel vision.
  • The "reverse mentor" approach. Regularly ask junior team members to teach you something—whether it's a new design tool, user research method, or technology trend. This demonstrates intellectual humility and creates opportunities for bidirectional learning.
  • Implement "decision documentation." For significant product decisions, create brief documents explaining your reasoning, including what data influenced you and what outcomes you expect. Six months later, share these with your team to collectively analyze what you got right and wrong. This builds organizational learning and shows commitment to continuous improvement.
  • Practice "productive dissent." When your team reaches consensus too quickly, play devil's advocate or assign someone else to challenge the prevailing view. Ask: "What are we not considering?" or "Who might disagree with this approach and why?" This prevents groupthink and leads to more robust solutions.

Ten years after that production incident, I realize my manager's response fundamentally shaped how I approach product leadership today. When team members on my products make mistakes, I remember that coffee conversation and ask: "What can we learn from this, and how can we build better systems?"

The travel platform incident led to implementing staging environment protocols, automated deployment checks, and a more robust QA process. More importantly, it created a team culture where people felt safe to report issues quickly rather than trying to hide problems.

Great product leadership is about creating an environment where teams can do their best work, learn rapidly from both successes and failures, and continuously improve both the product and themselves. The best product leaders understand that their primary job is more than just managing features or roadmaps—it's also about developing people who can build products that matter. Everything else follows from that foundation.

Read more great product leadership advice on Mind the Product

Cait O’Riordan on how to hire, structure, and develop product teams (VP Product, Google)

Leading with fear, vision, and taste: Our lessons from the Mind the Product Leadership Forum

Lessons learned from leading products by Natalia Williams

About the author

Rishab Jolly

Rishab Jolly

With a deep background in cloud computing, observability, and product management, Rishab Jolly drives innovation as a Senior Product Manager at Microsoft. He leads strategy and execution for Azure Application Insights, helping businesses around the world monitor and optimize their digital experiences. A product thinker at heart, Rishab is passionate about building solutions that balance customer needs with business growth. Beyond the world of tech, he’s a podcaster, dog dad, and travel enthusiast. Whether he’s designing better monitoring tools or sharing leadership insights with his 20K+ LinkedIn community, Rishab blends curiosity, creativity, and customer obsession into everything he does.

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