Cultivating a Culture of Courage: Empowering Teams to Take Risks

January 27, 2025

Company Culture

Picture the last time someone on your team had a brilliant, unconventional idea. Did they share it immediately, or did they hesitate? That moment of hesitation – that’s where extraordinary organisations separate themselves from the ordinary ones, not through their market share or their resource pool, but through something far more vital: their capacity to nurture and embrace courage.

We live in fascinating times. Every industry is being reshaped by technological leaps, shifting consumer expectations, and global challenges. In this landscape, playing it safe has become the riskiest strategy. Yet most organisations are stuck in a bizarre dance. Their leaders stand at all-hands meetings championing innovation and bold thinking while their systems and processes quietly whisper, “Stick to what’s safe.”

It’s like installing a high-diving board but never draining the pool of shark-infested waters. No wonder teams hesitate to take the plunge.

The Hidden Architecture of Organizational Courage

Take Pixar. Everyone knows they make incredible animated films, but the real magic isn’t in their rendering software or artistic talent. It’s in something they call the “Braintrust” – a remarkable space where creators can hear the unvarnished truth about their work without feeling personally attacked. Imagine that: a place where criticism flows freely, but egos remain intact. Where a junior animator can tell a decorated director, “I don’t think this story works,” and instead of defensiveness, they get curiosity in return.

This isn’t just another corporate meeting format. It’s a masterclass in transforming courage from a personal virtue into something bigger – a shared capability that flows through the entire organisation. What makes it work isn’t just the freedom to speak up; it’s the careful attention to creating an environment where taking smart risks feels less like walking a tightrope and more like exploring with a safety net.

Building the Infrastructure of Bravery

How do we create an environment where courage thrives? It starts with understanding that courage isn’t just about individual bravery – it’s about building systems that make bold thinking feel natural rather than nerve-wracking.

Here’s how the most innovative organisations do it:

Psychological Safety: More Than Just a Buzzword

When Google studied their highest-performing teams, they discovered something fascinating: the key differentiator wasn’t experience, intelligence, or resources. Psychological safety is the shared belief that team members won’t be punished or humiliated for speaking up with ideas, questions, or concerns.

Take Netflix’s radical approach to vacation policy. Instead of tweaking existing rules, they abolished vacation tracking entirely. Risky? Absolutely. But they built the psychological safety net first, creating an environment where trust wasn’t just talked about but woven into their systems. The result wasn’t chaos – it was increased responsibility and engagement.

Anti-Fragility: Getting Stronger Through Storms

Remember Nassim Taleb’s concept of anti-fragility? It’s not just about surviving challenges—it’s about becoming more potent because of them. The best organisations don’t just tolerate failure; they understand that setbacks contain the seeds of future breakthroughs.

Columbia Business School professor Rita McGrath takes this further with her “courage capital” concept, a way to measure an organisation’s capacity for bold action. Like financial capital, courage capital can be invested in, grown, and even depleted. Teams build courage capital through trust, resilience after setbacks and a track record of experimentation.

From Permission to Practice

But here’s where many organisations stumble: they give permission for courage without creating opportunities to practice it. Fundamental transformation requires both:

• Innovation Sandboxes: Dedicated spaces where experimentation isn’t just allowed but expected
• Failure Fridays: Regular sessions where teams openly discuss what didn’t work and why
• Red Teams: Designated “rebels” who challenge assumptions and test ideas under pressure
• New Promotion Criteria: Recognizing and rewarding those who take thoughtful risks, not just those who play it safe

The key is to make these practices systematic rather than sporadic. When courage becomes part of one’s regular rhythms rather than a special occasion, culture really starts to shift.

The Systematic Cultivation of Courage

Creating a culture of courage requires a structured approach across multiple dimensions:

Risk Portfolio Management

Successful organisations manage courage through carefully balanced risk portfolios:

• Strategic Risks: Major market moves and business model changes requiring high-level oversight but also greater tolerance for uncertainty
• Operational Risks: Process improvements and workflow changes that serve as training grounds for building risk-taking capabilities
• Innovation Risks: New technologies and product features requiring dedicated resources and protected spaces for experimentation
• Cultural Risks: Changes to working norms and team dynamics requiring careful balance between preservation and transformation

Experimentation Zones

Organisations need designated spaces where failure is not just accepted but expected as part of the learning process. This includes:

• Innovation Time Blocks: Dedicated periods for experimentation, similar to Google’s famous “20% time.”
• Project Sandboxes: Isolated environments for testing new ideas without impacting core operations
• Innovation Budgets: Specific resources allocated for experimental initiatives
• Cross-functional Innovation Teams: Dedicated groups focused on higher-risk projects

Decision Review Frameworks

Effective review systems transform risk-taking from a fearful process into a learning opportunity through:

• Pre-Decision Analysis: Structured evaluation of potential risks and opportunities
• In-Progress Checkpoints: Regular assessment of decision quality and emerging lessons
• Post-Implementation Reviews: Comprehensive examination of both process and outcomes
• Learning Distribution: Systems for sharing insights across the organisation

The Implementation Journey

Creating a culture of courage requires a phased approach:

Foundation Phase (Months 1-3)

• Establish basic risk assessment frameworks
• Create initial experimentation zones
• Set up foundational decision review processes
• Train leaders on new approaches

Expansion Phase (Months 4-6)

• Roll out comprehensive risk portfolio management
• Expand experimentation zones
• Refine decision review processes
• Begin measuring cultural impacts

Integration Phase (Months 7-12)

• Fully integrate risk management systems
• Scale successful experiments
• Establish comprehensive review processes
• Measure and adjust based on results

Measuring the Unmeasurable

How do we know if we’re succeeding in building a culture of courage? Both quantitative and qualitative indicators play crucial roles:

Quantitative Metrics

• Number and diversity of experimental initiatives
• Speed of decision-making and implementation
• Rate of successful innovations
• Return on innovation investment

Qualitative Indicators

• Employee willingness to voice new ideas
• Quality of decision-making processes
• Depth of learning from failures
• Stakeholder feedback and engagement

Building Tomorrow’s Courage, Today

There’s no magic switch for courage in organisations. No company-wide email or sleek initiative with a fancy name can transform culture overnight. Leaders who try often find themselves months later wondering why nothing has changed.

The real work is messier and more organic. One day, a quiet team member speaks up in a meeting. A junior employee challenges a senior director’s assumption. A team takes a calculated risk that opens up new possibilities. Then, there are the days when old habits creep back in, where safety feels more compelling than innovation. Like tending a garden in unpredictable weather, the growth isn’t linear.

Consider the organisations that break new ground year after year. The ones that consistently surprise and delight. Behind their success lies something deeper than luck or perfect execution. They’ve built environments where sharing ideas doesn’t require extraordinary courage, where suggesting a different approach isn’t met with raised eyebrows or subtle dismissal.

The real opportunity isn’t about creating fearless superheroes. It’s about making it easier for people to do what they already know is right—to speak up, try new approaches, and challenge assumptions, not through another program or initiative but by reshaping the small, everyday moments that define organisational life.

Fear doesn’t vanish, even in the most innovative companies. The difference lies in building environments where people can acknowledge their uncertainties and move forward anyway. Where stumbling isn’t career-ending, and success is measured by learning as much as outcomes.

The path to organisational courage isn’t about eliminating fear. It’s about creating spaces where fear no longer has the final word, where the ground feels solid enough to take that next step, even without knowing exactly where it leads.