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At Medley, we believe leadership isn’t defined by titles. It's practiced every day through curiosity, connection, and courage. In this Medley Moments conversation, Medley Co-Founder Edith Cooper sits down with Michelle Gass, President and CEO of Levi Strauss & Co., to explore what authentic leadership looks like in a rapidly changing world.
With more than 35 years of experience across Procter & Gamble, Starbucks, Kohl’s, and now Levi’s, Michelle shares how her journey, which started from humble beginnings in Maine and has culminated in leading one of the world’s most iconic brands, has been guided by three enduring principles: stay curious, stay humble, and stay bold.
Their conversation offers a window into how one of today’s most dynamic leaders builds trust, leads through uncertainty, and remains grounded in purpose while shaping the future of an enduring brand.
Edith: In May, you gave the commencement address to your alma mater Worcester Polytechnic Institute. As you prepared for that, what elements of your leadership style have remained consistent through your career?
Michelle: It starts with that curiosity and problem solving. I love a good problem, and maybe when I was studying engineering, it was more math equations and I always had to try to find the answer. But now in business, it's problem solving around the consumer and really asking the questions. That has led to discoveries.
I'm also a big believer in humility. I never forget where I came from and I still see that person who was bagging groceries or working on the front line. And it's so important for me when I connect with people and I spend a ton of my time out in stores. Starbucks really ingrained that in me.
The last piece I would say is the importance of being courageous. Of being bold. Throughout my career, it's one of those traits that I've honed and become more confident in over time.
When I worked at Starbucks, I worked with Howard Schultz and Howard Behar and others who really embraced the sense of entrepreneurial spirit. And so, you get to try things. Most decisions are not company-deciding decisions, right? They're mostly two-way doors. There's very few that are one-way doors. The reason we could do pumpkin spice is because … I could tell you a whole bunch of Starbucks drinks that ultimately didn't stay on the menu. And so those are some of the principles that still carry me to this day.
Edith: Whether it's fellow board members or ordering your coffee at Starbucks, you engage with people as they're humans. And now as you travel in circles that are very important, how do you show up in those rooms? Is it any different than how you show up leading your teams?
Michelle: Yeah, it's a good question. I go back to the philosophy of servant leadership, and one of the first principles is authenticity. You are who you are. And so I want to show up as who I am, and I want others to feel that same way. Let's start with my leadership team as an example.
The number one priority for me is to make sure that they feel like they have a safe space to be themselves. And to ensure that they know that their voice can be heard no matter what the situation is. It could be a crazy idea.
When we're dealing with tough decisions, and there's plenty of those, especially in today's world, you want to make sure that every perspective can be heard. If I haven't heard from someone around the table, I ask, what do you think? As a leader, it's part of the responsibility to draw that out.
Being a servant leader doesn't mean you're soft. It's actually quite the opposite. It's making sure that you get all the data you need. Back to that engineering mindset and problem solver. But then sometimes if there's not a clear decision, you're the leader and you're going to use the data and your instinct to say, “this is the way we have to go.” I think in leadership it's also really important to have clarity and decisiveness as you're leading a team, and a company.
Edith: You have a voice and you want to hold yourself personally accountable for delivering your best. Is it easier to do when you get to be authentic and real? How do you work yourself out of those awkward moments where you just don't feel like you're being heard?
Michelle: I always want to do a good job every day, and I think it's important for young professionals as well,to be listening to those around them, those who have seen more, who have experienced more. It was leaders who saw things in me before I saw it myself and who pushed me.
And somewhere along the way, in my journey at Starbucks, I had leaders saying, “someday you can be a CEO.” And I'm like, what me? I just couldn't even imagine it. But they're like, “yeah, we see things.” And then they gave me the experiences that started to build my confidence and build my experience base.
By the time you're in this role you do have to have the right experiences and skills. But I think just being aware and present, taking advice on business, and on yourself when people see things in you. Don't ignore it. Listen to it and say, okay, let’s try this out.
Edith: And have there been instances where you've stepped up and it didn't work out. How did you rally from those difficult moments?
Michelle: I've been very fortunate that I was surrounded by lots of great advisors and leaders and coaches. My journey, the way I like to describe it, and I borrowed this from Patty Sellers from Fortune: She talks about how some careers are more like a jungle gym and not a ladder.
My career path was very much a jungle gym. I did take detours along the way, not knowing at times if it was going to be the right detour. Luckily they have worked out.
My move here to Levi's is a perfect example of that. I was a sitting CEO for five years at Kohl's, a very big company, with revenue at that time like $18 billion. We had just come through the pandemic and had been going through some challenging times.
I got this call from a dear friend Chip Bergh, who was the CEO of Levi's at the time. And he is like, “Hey, I'm getting ready to retire. What do you think? Would you ever consider coming to Levi's? And I was like, “You know. I love that brand.” And I had utmost respect for Chip. Let's have a conversation. And what it led to was not a traditional “he retires, I come in as a CEO,” but we did a one-year transition and I came in as president.
So I stepped back from being the CEO of a public company to be president for a year to then get myself ready to then take over and, you know, I think it was absolutely the right thing for me, for the company, for the brand, because it's Levi's. It's 173 years old. It has such heritage. I've only come more to appreciate how special and unique this company, this brand, this culture is.
I saw it as such a rare opportunity, but it was a leap. It was a risk. But given all the experiences I'd had, I felt like it was a measured risk and the right one, knowing what I knew of the company, and of course, Chip and the board.
Edith: There's a lot out there, the geopolitical environment, tariffs, the impact that AI will have … How are you leading through this moment?
Michelle: The metabolic rate of how the world operates today is just at a completely different pace and energy than it was even, you know, five years ago.
This is just how we have to operate and I think making sure that, as a leader, the people you surround yourself with are resilient to whatever comes our way.
It starts with some of the principles we were talking about, which is creating that clarity for people, knowing where the true north is, what the priorities were, not being distracted by things that don't matter.
For any issue that comes our way, you have to make sure that you are providing that leadership. One of the metaphors also that we use here is the microscope telescope. And I don't know if you're familiar with that, but you know, the microscope of how you're managing the day-to-day and the telescope and not losing sight of your big strategy, your true north, so to speak.
For us at Levi's, our telescope is a we want to be a best-in-class retailer. Levi's has long been known as a brand that sells bottoms, jeans, and largely sells through other people. Whether that's a Kohl's or a Macy's or an Amazon, or you name it. And globally, because we're in over a hundred countries, we are making this big change to become a retailer.
So take tariffs. That's a good example. It wasn't like we put the pause button on all our product development and all our denim lifestyle work to say, okay, everybody, we don't have time for our strategy. That everybody needs to just be focused here on the tariffs. No, like we have to do both. Let's make sure we do both really well. So, again, kind of like any kind of initiative or surprise that you get, we quickly rallied and it's the decisiveness and the maintaining calm through those moments.
And that's the model I like to embrace and for leaders. There's no good in running around with your hair on fire and being panicked and frenetic, right? You can be urgent and calm at the same time. And that's really important for me to operate in that way and to set that standard for my team.
Edith: In an organization like Levi's, how do you balance between the legacy and the power that the brand brings, and the innovation and growth that is required fueled by the increased leverage that you can get from AI tools. Is there tension there or does one support the other?
Michelle: I think about it as one supports the other. You have to be really deliberate, right? It has to be all connected to Levi's. And you know, candidly, part of the rituals that we do inside this company and how we operate is honoring our past like heritage. Levi's is a brand that's never been frozen in time. We've grown over the years. Over 170 years, this company has seen a lot and has maneuvered through many industrial revolutions.
AI: It's something that the team and I talk about a lot. When brands try to do what we're doing, which is to become something more than we are today, you've got to be very disciplined and very thoughtful.
Because we never want to dilute the brand. There are many examples of brands and companies who have done that. So it’s our work to become a lifestyle brand. We call it the denim lifestyle in particular because there's a part of the market that we are mapping out. We're not going to be everything to all people.
The other piece I would say for us is we need to make sure that our brand remains at the center of culture. And over time, Levi's has had moments where the company didn't do well or the brand was less relevant, especially to the youthful generation. The fact that Beyoncé named a song after Levi's, that was no accident, right?
We've got a great campaign happening with Shaboozey right now. We have more next year, the year of sports. Levi Stadium is hosting the Super Bowl. You can't take this stuff for granted. You've got to deposit and you've got to do the things that are big and bold, but you've also got to be doing the humble things to make sure that you're relevant, because if we lose that, it is very hard to get it back.
Edith: I really do like this concept that you've highlighted of making deposits over time. Because these relationships are built over many years and are a reflection of the commitment that your former future colleagues have made, and will make in the future. What’s one piece of advice that you would share with someone trying to define their leadership?
Michelle: You have to stay open and curious and learn. I didn't grow up in a tech background, but I am spending so much time learning and listening so that I can help lead in this era. And we're doing all kinds of exciting things in the company. Well also by the way, respecting our 170 year heritage.
And then I guess final words of advice: I go back to servant leadership because it is my touchstone. It's to be authentic to who you are. Don't try to be someone you're not. Go after something you're passionate about, that you care about, because you're going to be doing this for a long time.
Be courageous. Take the bold moves in business and in your career because those are going to be the moments where possibilities you never imagined will unfold. The last thing I'd say is be grateful. I'm grateful every single day for what I get to do.
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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.
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