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Michelle Gass has spent more than three decades evolving and growing some of the world’s most recognizable brands, all while demonstrating what it means to lead with authenticity.
As the President and CEO of Levi Strauss & Co., Michelle oversees one of the most iconic brands in fashion. And while the brand has been around for over 170 years, she is steering its evolution from a heritage denim brand into a global lifestyle brand while upholding its tradition and core values.
This is no easy feat.
But as she discusses with Medley Co-Founder Edith Cooper in a recent Medley Moments conversation, Michelle’s path to the C-Suite, as she describes, was more like a jungle gym than a ladder with several twists and turns along the way.
After growing up in Maine and earning a degree in chemical engineering, Michelle began her career at Procter & Gamble. She then joined Starbucks, where she worked for 17 years, and among her many accomplishments, she helped bring the Frappuccino and Pumpkin Spice Latte to life. As CEO of Kohl’s, she forged bold and innovative partnerships with companies like Sephora and Amazon, and successfully modernized a legacy retailer while navigating the uncharted waters of leading the business through the pandemic.
What’s remarkable about Michelle’s legacy is how as she assumed more and more responsibility across increasingly complex businesses, the values underpinning her leadership remain consistent: stay curious, stay grounded, and lead with courage.
In conversation with Edith, she shared many of these values that resonate in contexts beyond business. Here are four of her leadership principles that leaders at all stages of their career can employ:
1. Asking Questions Leads to Discoveries
“It really does start with curiosity and problem solving. I love a good problem. Back in the day, that might’ve been lots of math equations. Now in business, it’s problem solving around the consumer … really asking the questions. That curiosity has led to discoveries… like the Frappuccino, or even the pumpkin spice latte, which early testing said sounded disgusting, and it became a legend.”
Michelle credits her engineering roots for her relentless curiosity. Her willingness to question assumptions, even when the data pointed elsewhere, has helped her be successful. For leaders, her lesson is to stay close to the problem, keep asking questions, and never lose your appetite for learning. Curiosity is about cultivating openness and resilience in the face of change.
2. Lead with Humility by Remembering Where You Started
“I never forget where I came from. I grew up in Maine, in a hardworking, gritty culture. I still see that person who was bagging groceries or working on the front line. When I connect with people, I want to hear from them. We’re there to serve them, not the other way around.”
Even while leading global brands, Michelle grounds her leadership in humility and service, paying homage, in her own way, to her own humble upbringing. She spends significant time visiting Levi’s stores to connect directly with employees, and ensures that leadership decisions reflect real experiences on the ground. Her philosophy echoes one of Medley’s core beliefs that leadership is relational, not hierarchical. When leaders stay connected to their roots, and to their people, they build cultures of trust and belonging.
3. Consider Careers as Jungle Gyms, Not Just Ladders
“Some careers are more like a jungle gym, not a ladder… I did take detours along the way, not knowing if it was going to be the right detour. … I stepped back from being CEO of a public company to take the role of president at Levi’s for a year. It was absolutely the right thing for me, for the company, and for the brand. I saw it as a rare opportunity, but it was a leap, a risk. You have to take bold moves in business and in your career, because those are the moments where possibilities you never imagined will unfold.”
Leading with courage is both strategic and personal. She has repeatedly chosen the harder, less predictable path. Whether experimenting with new products at Starbucks or moving into a president role from a CEO role, she embraced a mindset of confident experimentation. Her lesson for leaders is that the biggest opportunities may come disguised as risks.
4. Servant Leadership Doesn’t Mean You’re Soft
“You are who you are. I want to show up as who I am, and I want others to feel that same way. My number one priority is to make sure my leadership team feels like they have a safe space to be themselves — that their voice can be heard no matter what. Servant leadership doesn’t mean you’re soft. It means you get all the data, have the debates, and then have the courage to make the call.”
Authenticity is a cornerstone of Michelle’s leadership. She believes in creating environments where honesty and difference are valued, and where clarity replaces hierarchy. Her approach balances empathy with decisiveness, modeling that great leaders can be both open and firm. At Medley, we believe the essence of connection is in building spaces where people feel seen, valued, and empowered to contribute.
5. Be Urgent and Calm at the Same Time
“There’s no good in running around with your hair on fire and being panicked and frenetic. You can be urgent and calm at the same time. That’s really important for me, and for setting that standard for my team.”
From navigating the pandemic to navigating tariffs and leading through immense economic uncertainty, Michelle believes that being calm is contagious and most effective for leading her teams. By controlling what you can, staying focused on your “true north,” and “removing the drama”, leaders can reinforce stability in moments of chaos.
The best leaders, she says, help others find clarity even when the path ahead is unclear.
Michelle and Edith’s full Q and A is here: Levi’s CEO Michelle Gass on Authentic Leadership, Bold Moves & Growth
Explore more perspectives on leadership from recent Medley Moments conversations.
About Medley:
Medley is a leadership development company that brings people together in small, facilitated groups to grow through shared reflection, learning, and accountability. We believe that leadership is not a title but a practice, and that people learn best in community with others who offer diverse perspectives and experiences. Through our programs, members build greater self-awareness, develop key leadership skills, and cultivate meaningful connections that support both professional and personal growth.
Please connect with us here to learn more.
