Great leaders are often shaped by failure, discomfort, curiosity, and the courage to seek something more. If you’ve ever felt trapped in a role that no longer fits, or called to lead in a way that’s more authentic to who you are, the story of Howard Schultz, and others like him, may well strike a chord.
In this article, we’ll explore how Schultz’s bold journey from a modest upbringing to transforming Starbucks into a global brand offers deep insights for leadership development. We’ll also highlight five other inspiring leaders who’ve modelled growth through personal discovery and failure, and the key lessons any leader can take from their stories.
Whether you’re investing in leadership coaching, guiding a team through change, or taking responsibility for your own personal leadership development, this is for you.
The Starbucks Vision: How Howard Schultz Role Modelled Authentic Leadership
Before Starbucks became the global symbol of coffee culture, it was a single store in Seattle selling beans and coffee equipment. Howard Schultz joined the company in 1982 as Director of Retail Operations and Marketing. It was, however, a business trip to Italy that changed everything.
While in Milan, Schultz was captivated by the Italian espresso bars: not just the quality of the coffee, but the experience, the sense of community, conversation, and connection. In his own words:
“What I saw was a third place between home and work, and the barista knew the customer’s name, what they drank… it was an extension of the front porch.”
As a result Schultz returned to Seattle with a vision. He wanted to bring that Italian espresso bar culture to America, offering not just coffee, but a place where people could feel seen, connected, and uplifted.
This vision was, however, rejected by the original Starbucks owners.
So, in true explorer spirit, Schultz took a risk. He left the company to start his own coffee shop, named “Il Giornale”, which embraced his vision based on the Italian experience. An incredibly bold move, built on self-belief and a commitment to something he knew mattered. Just a year later, in 1987, Schultz acquired Starbucks and began building the global coffeehouse chain we know today.
How can we use this story to reflect, learn and grow as leaders?
Leadership Lessons from Schultz:
-
Growth Comes from Going Against the Grain: Schultz didn’t follow the script, he rewrote it. Leaders grow when they challenge assumptions and step into the unknown.
-
Innovation is Rooted in Observation: His vision was sparked by curiosity and openness, not a business case, but a lived experience. A powerful lived experience, he saw would create a unique vision.
-
Authenticity Inspires Loyalty: Starbucks didn’t just sell coffee. It created meaning. Schultz understood that real leadership development begins with self-awareness and personal values.
Growth, Failure, and Discovery: 5 Other Leaders Who Modelled the Way
Schultz isn’t the only leader who’s walked the path of risk, failure, and reinvention. Here are five others whose leadership journeys reveal the power of resilience, reinvention, and reflection:
1. Arianna Huffington – From Burnout to Redefining Success
Arianna Huffington was running The Huffington Post when she collapsed from exhaustion in 2007. This experience led her to radically reassess the definition of success. She went on to launch Thrive Global, a platform focused on well-being, performance, and workplace culture.
Leadership Lesson: Burnout isn’t a badge of honour. Personal leadership development requires tuning into your limits, aligning your values, and redefining what fulfilment looks like.
2. Satya Nadella – Humility and Empathy at Microsoft
When Nadella took over as CEO of Microsoft in 2014, the company was struggling with internal silos and a lack of agility. He led with empathy, embracing vulnerability and encouraging a growth mindset throughout the organisation.
Leadership Lesson: Self-awareness and emotional intelligence are foundational to team leadership. Leaders grow when they lead with curiosity and humility, not ego.
3. Oprah Winfrey – Turning Trauma into Purpose
Oprah’s childhood was marked by poverty and abuse. Yet her relentless commitment to learning, authenticity, and service transformed her into one of the most influential media leaders in the world.
Leadership Lesson: Personal history doesn’t define you. How you process and grow from that history does. Leadership coaching often begins by helping individuals reframe their stories and reconnect with purpose.
4. Reed Hastings – Reinventing Netflix
Netflix began as a DVD rental service. Hastings didn’t just adapt to change, he anticipated it. Shifting the company to streaming was risky, particularly at that time, but visionary. He also learned from his early failures at Pure Software, where rigidity stifled innovation.
Leadership Lesson: Innovation often requires unlearning. Leadership development thrives in environments where experimentation is encouraged, and failure is seen as a step forward.
5. Sara Blakely – Founder of Spanx
Blakely turned $5,000 into a billion-dollar company, with no formal business background. She faced multiple rejections but kept learning, adapting, and innovating. Her resilience and self-belief carried her through.
Leadership Lesson: A clear vision, combined with adaptability and inner drive, beats experience every time. Great leaders don’t wait to be ready, they start, then figure it out.
What These Leaders Teach Us About Role Modelling and Leadership Development
Each of these stories highlights the essential traits of modern leadership: courage, curiosity, resilience, and the willingness to grow. But most importantly, they remind us that the best leaders role model what it means to be human.
They don’t pretend to have it all figured out. They show up, do the work, reflect deeply, and share what they learn.
So, what does this mean for your own leadership development?
Five Practical Takeaways for Growing Leaders
Whether you’re developing your leadership team, investing in leadership coaching, or simply feeling the itch to evolve, here are five ways to build growth into your leadership journey:
1. Turn Discomfort Into a Compass
If something isn’t sitting right, don’t push it away. Explore what’s missing or unaligned. Growth starts by noticing.
2. Create Space for Reflection
Great leaders don’t just take action, they pause and reflect. Journalling, coaching, or simply asking “What did I learn from this?” can deepen your leadership presence.
3. Role Model Vulnerability
Let your team see the learning process. Share your mistakes. Model the mindset you want others to embrace.
4. Seek Out New Environments
Just like Schultz in Milan, get outside your normal bubble. Visit different industries, attend new events, or talk to people with very different perspectives. It will spark creativity and challenge your assumptions. Or even the reverse. The Rugby World Cup winning manager, Clive Woodward brought in observers from different industries to comment on what they saw happening.
5. Invest in Development, Not Just Results
Leadership development isn’t just about hitting goals, it’s about becoming someone who can lead in more authentic, impactful ways. Consider leadership coaching or structured personal development as a powerful investment in long-term growth.
🧠 Learn More About Growth in Leadership
For further reading on evidence-based leadership development, check out:
-
Centre for Creative Leadership – “Failure Is Essential to Leadership Development”
-
Harvard Business Review – “The Best Leaders Are Constant Learners”
-
McKinsey & Company – “Leadership Development Reimagined”
🏔 Final Thoughts: Don’t Fence Yourself In
Howard Schultz’s journey, and those of Huffington, Nadella, Winfrey, Hastings, and Blakely, remind us that the most inspiring leaders are those who go beyond their comfort zones. They evolve through failure. They also model what it means to grow, and evolve. Success is much more complicated that an a straight line.
If you’re a leader who is interested in a path to growth and ready to evolve, then that is where true leadership really begins.
Want to explore your own leadership journey?
Whether you’re supporting team leadership, seeking leadership coaching, or guiding personal leadership development, now is the time to grow. Reach out for a conversation about how our programmes can support your next steps. Simply contact us or book in for a free Insight Call