Are you a founder navigating the choppy waters of startup growth or a senior executive at the helm of a well-established company?
In today's rapidly evolving business landscape, the ability to lead with courage and clarity is more critical than ever. WeGotThis.org’s Founder (show friend and supporter) Elissa Kalver and I recently sat down with Ryan Berman (part of my ‘Worthy for Thirty is in LA’ series), founder of Courageous, a consultancy that helps Fortune 500 companies unlock their "courageous quotient," to extract vital lessons for leaders like you.
Check out and pre-order Ryan’s upcoming book, Headamentals.
This episode is a must-listen primer for anyone looking to build resilient teams, foster genuine connections, and drive meaningful impact.
Found below, I’m breaking out what I believe are salient takeaways from our conversation, complete with contemporary examples and concrete action steps to help you lead more courageously:
1. Cultivate a Shared Purpose Beyond Profit
In an era where employees, especially the younger generation, seek more than just a paycheck, a clear, shared organizational purpose is your North Star. As Ryan emphasizes, this purpose unites your team and fuels their passion.
Contemporary Example: Patagonia's unwavering commitment to environmental activism isn't just a marketing ploy; it pervades its business model and resonates profoundly with its customer base and employees, making it a purpose-driven powerhouse.
Action Step: Beyond your mission statement, clearly articulate the "why" behind your organization's existence. In your next all-hands meeting or ELT meeting, dedicate time to discuss how each team's work contributes to this larger purpose, making it tangible and personal for everyone.
2. Build Transparent Teams that Embrace "Tough Love"
Courageous leadership demands clear and honest communication, even when it's uncomfortable. Creating an environment where constructive feedback is not only accepted but encouraged is vital for growth and problem-solving.
Contemporary Example: Netflix's culture of "radical candor" is a well-known example. While sometimes intense, this direct feedback loop is designed to accelerate individual and organizational learning, ensuring issues are addressed swiftly and effectively.
Action Step: Implement a "feedback Friday" or a dedicated "courageous conversations" slot in your weekly leadership meetings. Encourage leaders to share one piece of constructive feedback they've received and one they've given, modeling the behavior for their teams. And make sure the feedback is shared throughout the company.
3. Strategically Invest Your "Courage Currency"
You can't be courageous all the time, nor should you try. Ryan advises identifying a few critical moments where leaning into discomfort and making a bold decision will yield the most significant impact.
Contemporary Example: When Satya Nadella took the helm at Microsoft, he made the courageous decision to pivot away from a "Windows-first" mentality to a "cloud-first, mobile-first" strategy, alienating some traditionalists but ultimately revitalizing the company's growth. This was a strategic investment of courage in a key moment.
Action Step: Identify one major strategic decision or challenge your organization faces this quarter. As a leadership team, pinpoint where a courageous, unconventional approach might break through stagnation, then allocate your focus and resources to that specific "courageous moment."
4. Lead with Authenticity to Avoid Transactional Relationships
In a world increasingly fatigued by corporate speak, genuine leadership stands out. If employees don't trust their leaders, the relationship quickly reduces to a purely transactional exchange, stifling innovation and loyalty.
Contemporary Example: Many admired tech leaders, like HubSpot's co-founders, are known for their transparent communication, often sharing personal struggles and learnings, which fosters a deep sense of trust and loyalty among their employees.
Action Step: Share a personal learning or challenge you've recently overcome in a team communication or leadership meeting. Demonstrate vulnerability and authenticity, inviting others to connect with you on a human level rather than just a professional one. EQ > IQ!
5. Embrace Continuous Adaptability and Evolution
The only constant in business is change. Leaders must act as "detectives," constantly examining and re-examining strategies, remaining flexible, and adapting swiftly to new information and market shifts.
Contemporary Example: Companies like Amazon exemplify continuous adaptation, constantly experimenting with new services and technologies (from e-commerce to cloud computing, and now AI) and quickly pivoting away from what doesn't work, maintaining their market leadership.
Action Step: Dedicate 15 minutes weekly to scan industry trends or disruptors outside your immediate niche. Challenge your team to identify one potential future shift that could impact your business and brainstorm proactive steps, fostering a mindset of continuous vigilance and adaptation. Set up Google Alerts, or use Perplexity.Ai for deep research
This is just a glimpse into the profound insights Ryan Berman shares in the full episode. To truly grasp the nuances of courageous leadership and equip yourself with the tools to inspire and innovate, I highly recommend listening to the complete conversation wherever you enjoy podcasts.
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