The Role of Failure in Resilient Leadership

Lessons from a Workshop with The Failure Toy

Michelle Da Silva, Community Recreation Supervisor with the City of Toronto, shares why she brought Twenty One Toys' Failure Toy Workshop to the Recreation Conference, an annual professional development event for leaders and managers working across the City's community recreation centres.

Each year, the Recreation Conference brings together staff with a wide range of experience levels, from employees who have spent decades serving their communities to those who are just beginning their leadership journeys. With the conference theme focused on change, the team was looking for an experience that would help participants explore resilience, innovation, and authentic leadership in a playful and memorable way.

Why Failure?

For organizations navigating ongoing change, failure is often viewed as something to avoid. But meaningful growth, innovation, and adaptation require people to try new approaches, take risks, and learn from what doesn't work. As Michelle explains:

“Our theme was really focused on change. We wanted to bring in a workshop that would really help us focus on change, but also on the successes and failures of change.”

The Failure Toy Workshop challenged participants to reconsider their relationship with failure and explore how leaders can create environments where experimentation feels safe.

“We wanted to bring in this workshop to challenge the mindset that failure is bad and provide a different lens in how failure can actually be a positive in the workplace. The more we fail, the faster we're getting to the right answer.”

Once the Games Began...

As participants worked through increasingly difficult challenges, many of the dynamics of workplace change began to emerge. Different communication styles, varying levels of confidence, and diverse approaches to problem-solving all became visible through play.

Michelle noticed how participants naturally stepped into different roles.

“I saw folks sitting at the table who immediately are going forward, grabbing all the pieces, doing all the things, coming up with ideas. And then there's the people who are like, 'Oh, I don't want to talk. Don't ask me.”

But as the challenges became more complex, the quieter voices became essential.

“Those people started stepping up, and they had a place because we needed new ways to think of how to make this work.”

What emerged was a powerful reminder that successful teams need a variety of perspectives, especially when navigating uncertainty and change.

“I saw this transformation where everyone, by the end, was really engaging. That was really cool to see people just become more comfortable and use their voice.”

Failure, Leadership, and Psychological Safety

One of the strongest themes to emerge from the workshop was the connection between leadership and psychological safety.

When leaders create environments where mistakes are treated as opportunities to learn, people become more willing to contribute ideas, experiment, and take initiative. As Michelle reflected:

“Leaders who are open to failure and make it safe to fail will have people become more confident to try."

That confidence creates a ripple effect throughout teams. People become more engaged, more innovative, and more willing to contribute their perspectives, even when outcomes are uncertain. For organizations experiencing rapid change, this mindset can be the difference between resisting change and embracing it.

Key Takeaways and Insights from the Participants

Throughout the workshop, participants reflected on the value of diverse perspectives, experimentation, and creating space for learning. Many observed that innovation often emerges when teams are willing to test ideas rather than waiting for certainty.

Others reflected on the importance of making room for every voice, especially during periods of change when fresh perspectives can reveal solutions that more experienced team members may overlook. For Michelle, the workshop reinforced an important truth about the work of community recreation:

“Everything we do in community recreation is absolutely about humans. It's the core of our job."

And when people are willing to approach challenges with curiosity, playfulness, and openness, failure becomes something more than a setback. It becomes a catalyst for growth, resilience, and innovation.

“It's okay to be playful, and it's okay to learn in this way. It really is reshaping how people view failure and how it can really inspire innovation."