Leading with Wonder: Brad Montague on Creative Compassion, Culture and the Power of Small Shifts

Entrepreneurs spend much of their time solving problems, making decisions, and pushing their organisations forward. What often goes unnoticed are the quieter forces shaping how teams think, connect and grow.

That was the focus of EO Melbourne’s recent session with Brad Montague, who travelled to Australia to deliver Wonder Work: How Creative Compassion Builds Better Leaders and Joyful Communities. Known for his thought-provoking storytelling and creative approach to leadership, Montague invited members to slow down and look beneath the surface of how they lead.

Rather than centring on tactics or frameworks, the workshop explored the human elements that influence every workplace. Curiosity, emotional safety, honesty and connection may seem intangible, yet they often determine whether ideas flourish or stall, and whether teams simply function or genuinely thrive.

Montague encouraged leaders to reconnect with a sense of curiosity and play, not as distractions from serious work but as catalysts for innovation. When leaders allow space for questions, experimentation and even a little joyful rebellion against unhelpful norms, new thinking can emerge in ways traditional processes rarely allow.

Storytelling also played a central role in the session. Leaders communicate culture through the stories they share and the moments they highlight. Montague outlined six stories every leader should be able to tell with clarity: the origin story that explains how the journey began; the adversity or “fiasco” story that reveals lessons learned; the values story that shows what truly matters; the us-at-our-best story that captures a team at its finest; the eureka story that celebrates breakthrough thinking; and the impact story that reminds everyone why the work exists in the first place.

When used thoughtfully, these narratives help teams understand not just what they are doing, but who they are becoming together.

The conversation also touched on the power of imagination in leadership. By vividly picturing the future a team hopes to build, leaders can recognise the gap between where they stand today and where they want to go. That awareness becomes a guide for the decisions they make and the culture they shape along the way.

Montague illustrated this idea through a simple but striking metaphor. When a massive rock travels through space towards Earth, avoiding collision does not require a dramatic explosion. A gentle nudge at the right moment can shift its path entirely. Leadership, he suggested, often works the same way. Small, intentional actions can alter the trajectory of a team or organisation more than sweeping, disruptive changes.

Those subtle shifts might take the form of encouragement, curiosity, or a moment of recognition. Over time, these small signals shape the emotional climate of a workplace and influence how people show up for each other.

The workshop also challenged traditional attitudes towards failure. Instead of quietly moving past mistakes, Montague proposed creating cultures that acknowledge them openly and learn from them collectively. Some organisations, he noted, even celebrate “fail-a-brations” that recognise the courage to try, reflect and grow.

At its heart, the session served as a reminder that leadership is not only measured by outcomes or growth metrics. People often remember how a leader made them feel long after they forget the specifics of a project or result.

By the end of the workshop, members left with a single concrete decision they would carry forward. It might have been a shift in how they encourage curiosity within their teams, a commitment to share more meaningful stories, or a deliberate effort to create spaces where people feel safe to experiment and grow.

Through humour, creative exercises and thoughtful reflection, Wonder Work offered a simple yet powerful message. Building strong organisations and joyful communities begins not with grand gestures, but with intentional human moments that invite people to think, connect and imagine together.