Designing the future of healthcare with CVS Health

Heather Stern: Today’s guest is the incomparable Michelle Peluso. A pioneer wherever she goes, Michelle has created a career, building and transforming world-class brands in travel, banking, fashion, big tech, and now healthcare and retail. Michelle has been in the C-suite at six different organizations and has made a big impact in each of those roles, always with a focus on the intersection of technology and customer understanding. A few highlights: Launching Site59, a travel website that was acquired by Travelocity during the first dot-com boom. Guiding Citibank’s digital transformation and bringing CitiBike to NYC. Becoming CEO of Gilt, an early disruptor in online fashion retail. Redefining how the marketing team works at IBM by implementing the Agile method. And serving as a member of the Board of Directors at Nike, where she chairs the corporate responsibility, sustainability, and governance committee. 

Now as Executive Vice President and Chief Customer & Experience Officer at CVS, Michelle is revolutionizing the end-to-end patient experience across all of the company’s care delivery and customer service channels, as well as overseeing CVS’s brand and marketing efforts. A passionate advocate of diversity, equity, and inclusion, Michelle considers it her mission to create a culture of empathy and inspiration for her team and those around her. 

I am so excited, and yes, a bit intimidated to sit down with this groundbreaking leader to talk about her cross-industry career, what she sees on the horizon, and the core principles she lives by. Welcome, Michelle.  

 

Michelle Peluso: Well, I’m so excited to be here, Heather. Thank you for that warm introduction. 

 

Heather: Absolutely. 

 

Michelle: You could have just said, “I work and I’m a mom.” 

 

Heather: All right. Before we dive into your role, I know that you are on the board of Nike, and I hear that you’re quite a sneakerhead. How many sneakers do you own, and which is your most coveted pair? 

 

Michelle: Well, I am a sneakerhead and I’m passionate about the Nike brand. It’s a hard question though because now this is a really awkward time in our family. My son and my daughter both share the same shoe size as I do. So what is mine and what is theirs is blurring. So I’ll get some great pair of sneakers and then I’ll find I can’t find them. And then they’re sort of buried in a closet. So I’ve taken to taking my favorite pairs and hiding them in places the kids will never go, like the broom closet or the laundry room. 

 

Heather: Yeah. Exactly. They’re safe there. 

 

Michelle: Yeah, exactly. But it’s certainly them wearing sneakers. 

 

Heather: Well, that’s amazing. And amazing that you have the role that you do at Nike, and we can get back to that. But I want to start with your experience at CVS and your remit, which is continuing to broaden. Tell me more about being both Chief Customer Officer and Chief Experience Officer. What are you most excited about as you advance the customer brand and experience agenda? 

 

Michelle: Well, we had our investor day yesterday, so it’s a great time to talk about the future of CVS Health and our mission. And Karen has set, our CEO, really bold strategy that healthcare has to change, that it is an industry that is ripe for change. And that it’ll be led by putting the consumer at the center of everything we do. So, my job is a few things across the company, which is Aetna, Caremark, and CVS. First, it’s of course, about our brand. And yesterday, we launched a new brand with the help of you all, which is great. 

 

Secondly, it’s about driving demand. We have a $330 plus billion revenue company, so we have to drive demand for Medicare enrollments, and scripts, and front store sales, and Caremark PBM sales across our entire business. Third, it’s about that consumer centricity and patient centricity. And we are doing so much groundbreaking work to say, “How do we, in an increasingly omnichannel world, bring consumers together and connect our healthcare assets so it’s simpler for consumers to access the care they need?” That also includes things like innovative new formats. So how do we use our community footprint across almost every community in America to deliver care? Because care is, of course, local. And last but not least, you wouldn’t be surprised to know that I’m a passionate advocate of creating really learning agile teams, and also proud of co-sponsoring the Black Colleague Resource Group at CVS Health. 

 

Heather: It’s a big remit and it’s really challenging. I think it’s amazing how the brand has continued to make big bets and big moves. Talk to me about what is most challenging in trying to put the customer at the center. 

 

Michelle: Well, a few things. I think it’s a really important question. First, I think in healthcare it has to start with, do we really understand what the customer needs and wants? It has not been an industry designed around the consumer. And as a result, true consumer understanding is a little bit lacking. We tend to understand those moments of healthcare challenge like somebody just got a diagnosis, or somebody’s trying to get care, or somebody is sick, or somebody has a bill to pay. But one of the most important things we’ve been doing is really stepping back and really understanding, doing a lot more research about, how does she think about health and wellness overall? And what are those moments where we can intersect? 

 

Second thing that I think is really super, super important and can be challenging is, there are so many moments in someone’s healthcare journey. And as you can imagine across Aetna, Caremark, and CVS, we serve over a hundred million consumers in this country. As you can imagine, we have a lot of interactions. It’s really critical for us to instrument all those moments that matter with our consumers and patients with Net Promoter Score. We can talk about that more. Just so that we’re constantly getting feedback on what’s working, what’s not working, and what we have to do to improve. That’s important. 

 

But the third thing that is probably the most critical is that a lot of these systems have been developed over the years, and they’re antiquated. And if you think about so many other industries that have transformed with consumers at the center, that technology roadmap, that omnichannel experience has to be seen together. And it’s got to go between the apps our consumers use, the care delivery experiences they have in the home, in our clinics, and our call center. We, of course, have call centers all over our various businesses. Those have to be connected experiences. And so those three things are super important. But the one thing I would say is, technology is changing every single one of those areas. So keeping abreast of how basic technology improvements and changes even in the realm of digital marketing and now, of course, more advanced things like generative AI is really, really important as we design the future of healthcare. 

 

Heather: To make it work, at least most of the time, all of those pieces, you know, knowing the moments that matter, understanding the customer, ensuring all of your employees and those who are on the front lines, understand what great looks like, that all has to come to be. How do you do that, especially when it’s continually changing?  

 

Michelle: Right. 

 

Heather: Is it about a set of principles that everybody understands? I think that piece is something that really fascinates me. 

 

Michelle: I love that question. 

 

Heather: So what are you doing to engage those important stakeholders? 

 

Michelle: Yeah. I love that question, because I think what you’re saying is that you can’t be consumer-centric if you’re not colleague-centric. 

 

Heather: Right. 

 

Michelle: And I think that’s a really profound and important insight. And what I’ve learned over the course of my career, if we’re not doing everything we possibly can, that our 300,000 plus team feels like we’re making it easy for them to do their best work, they can’t possibly care for consumers in the way we want. And so, I would say as we think about the Net Promoter Score system or as we think about our culture, first, we have to instrument moments that matter. Secondly, we have to collect the feedback. And we get over 17 million pieces of Net Promoter Score feedback a year. Third, we have to have forums to address those pervasive issues for our consumers and for our colleagues. And invariably, when we’re letting a consumer down, there’s something we’re doing in the background, corporate, whether it’s technology challenges or whether it’s policy that make it hard for our colleagues to give great care. 

 

Fourth, I’m very passionate about the fact that we have to surprise and delight. You can do a great job from a Net Promoter Score perspective and people can say, “Zero through 10, I rate you an eight. It was good.” But if everybody rates you a seven and eight, your Net Promoter Score is zero. So you’ve got to really enhance those promoters, create surprise and delight moments. 

 

But you’re pointing to something that I think a lot of companies miss and one that we’re really passionate about at CVS Health, and perhaps it’s the hardest part. There has to be a culture of customer–centricity. When you think about the best companies in the world that are truly consumer-centered, they live by a core set of principles. So for us, we call that Helping with Heart. And our Helping with Heart service actions have been created and designed by colleagues all across the country. And we train and embed in onboarding and comm systems, et cetera, these service actions. 

 

So it’s simple things like I give a warm personalized greeting when I’m in touch. Now you could say, “Well, that only applies to people on the frontline,” but not really. Think about how many of us are sending, frankly, in our company, billions of texts and email messages. And is it warm? Is it friendly? Is it personalized? There’s a lot behind that. 

 

Heather: Yes. Is it clear? 

 

Michelle: Is it clear? 

 

Heather: Yes. It’s these simple things that matter. 

 

Michelle: That’s another thing, I remove obstacles, right? I take the time to remove obstacles. And then one that I really love is just that notion, a heartfelt moment. I take the time to have heartfelt moments with our consumers. So we have these set of service actions called Helping with Heart; we’re constantly embedding them. We work with the Disney Institute on them actually, and we’re constantly embedding them in training, and onboarding, and the like. That is a set of things that it’s not just for our colleague-facing employees, but it’s for all of us. And I’m constantly emphasizing in our company that it’s just as much for our corporate employees, because if we do a good job designing things that remove obstacles that put the consumer at the center, it’s so much easier for those in the frontline to deliver great care. 

 

Heather: Two follow-up questions to what you just said. The first, the partnership with the Disney Institute. That’s fantastic. What can you tell me about what that was and how that came to be? 

 

Michelle: Well, they are so incredibly well-known for their consumer-centricity and their cast, as they would call it, centricity. And we were really inspired. A group of us went down and spent some time with them in Orlando, and we were really inspired with the process and how they develop the things that matter for Disney. What I think I really liked most about it was that, one, this complete understanding that colleague-centricity and consumer-centricity are flip sides of the same coin. And to really change culture, you need to embed it in all the places that matter. So that process helped. 

 

The third thing I really liked is, we very much built this system as they did from our colleagues up. What did our colleagues think? So we had 100 colleagues all across the company, some of them in corporate, some of them in call center, some of them in stores, some of them pharmacists, some of them care nurses, et cetera, helping us design what they thought the service actions that would matter most. And that process that Disney helped us with has been really exceptional. 

 

Heather: Well, I think the fact that it is, as you said, bottoms-up, I mean, the people that are closest should know the things that are going to matter most. 

 

Michelle: Right. 

 

Heather: So, the second question was around surprise and delight, which is something I think we’ve talked about for a while across different experiences. As a CVS loyal customer, since I was little, there was the CVS in the corner. And we’ve all worked there and it’s… I’m very loyal to the brand. What can I expect that might surprise and delight me? 

 

Michelle: Sure. Yeah. We’re doing a bunch of different things. So for instance, we’re giving out stickers to kids getting their first shots. Or kids who are nervous about getting shots, we allow the pharmacist, or the pharmacy technicians, or the nurses who are giving the shots to take a moment to talk to the child, to let them pick a sticker out that they’re excited about, or a Pop-It, a little game that they can play with. It’s such a small thing. We put during Mother’s Day about hundreds of thousands of cards out that our colleagues could sign and give to mothers they knew in the community that were coming into our shop, in our stores. 

 

We also give a lot of flexibility to our store teams. I was in a store yesterday in Millis, Massachusetts. It was so adorable, they hide the elf on the shelf every day. 

 

Heather: Oh, wow. 

 

Michelle: So they have these kids, who are coming, and these parents who are taking their kids in each day to find the elf on the shelf. And then they have these little rewards for kids who find the elf on the shelf. In our call centers, women who are pregnant for the first time and maybe calling Aetna to let us know that they’re pregnant, we’ll send them a heartfelt, personalized card to congratulate them, to let them know that we’re here for their journey and we’re excited for them. So those are just a few simple examples of how we can scale those moments of delight and humanity across our call centers, across our stores, et cetera. We do welcome boxes for Medicaid members, that’s another one I love. If you’re new to Aetna Medicaid, in certain places, we’ll send you a welcome box. Or maybe it’s flu season, and we’ll send you some things for your family and also remind you to get your immunizations. 

 

Heather: The comment that you made about knowing from Aetna information that allows the care team to respond in different ways, to know more about that, wow, this customer is actually pregnant, and I wouldn’t know that, brings me to what you mentioned earlier, which is CVS Healthspire, which is very exciting. 

 

Michelle: Right. Yes. 

 

Heather: And you’ve announced that this week a platform that will bring your suite of care delivery, pharmacy, and health service solutions together with the goal of, again, delivering on this promise. Tell me about that and about how to think about what it’s going to do to further the goal that you have. 

 

Michelle: Yeah. Well, first of all, Lippincott was a terrific partner. So I’m so grateful for that. And here’s the thing that was fascinating, we acquired Oak Street Health, which is a leading care provider for seniors for Medicare, particularly those with chronic conditions in poorer communities. And we acquired Signify, which is in the home of hundreds of thousands of Americans, millions of Americans actually. We, of course, have our MinuteClinic HealthHUB assets and Caremark. And what we realized is, if we really want this to be truly consumer-centered, bringing together a brand that all these assets can share, so consumers can understand, and trust, and know that it’s a connected experience makes a lot of sense. 

 

Then the question became, well, what is the brand? What is the brand name? And what the research led to time and time again is that the trust and familiarity of CVS is really extraordinary. I mean, you cannot underestimate the value and the impact of that brand, and how expensive it would be to try to build a totally separate brand. At the same time, we wanted to show that we were standing for quality care and more sophisticated care. We wanted to have a little bit of a break as well. That’s where we came up with CVS Healthspire, and then the incredible treatment of the heart over the eye, and making it more approachable. The combination of CVS—that trusted community brand—with Healthspire, the new brand that stands for sophisticated care delivery is exciting.  

 

Heather: It’s a testament to the importance of when it makes sense, a bold move that will make customers stand up and notice like, “Hey, this is something different.” And so, I recognize the challenge of, do we create something new or not? But I think as things continue to change and evolve, and as you said, you’re looking to build on the equity, but expand how people are thinking about you, that’s the power of that brand. 

 

Michelle: That’s right. Well said. 

 

Heather: Okay. Let’s talk about HERe for Her. 

 

Michelle: Oh, I’m so passionate about this one. 

 

Heather: Fast Company named CVS one of the brands that matter for that. I think we often talk about all the things that you’re mentioning you need to do as a brand, but also having a point of view and a perspective that’s part of a broader cultural conversation. I know you spearheaded this initiative. I know you’re passionate about it. Tell me about it. 

 

Michelle: Yeah. Well, I think that brands have to do not just say. And I think that the world’s best marketers have an ability to influence the actions, not just the words. And that’s really important, I think, from an authenticity perspective. And I think consumers are demanding that more and more. And what we recognize as a company that believes in women’s health and health equity, drown out all the noise that was happening about women’s health and women’s reproductive rights, and we’re not here to make political statements. But we do fundamentally believe in being active in the health of women everywhere. So a group of CVS Health colleagues across marketing, but even ultimately across merchandising, the product teams, operation teams, Aetna teams, care delivery teams, started to really need to say, “What would a series of actions be that we could take that would signify in meaningful demonstrable ways our commitment to women?” 

 

And with that, we came up with a bunch of things. Of course, our Beauty Mark, which has always been important, but now more than ever that we’re not going to retouch images without letting you know. And we’ve done some amazing social videos of what’s really happening behind the scene, what somebody really looks like, and then what they look like when it’s filtered, and put on Instagram, and how damaging that can be for girls everywhere. It’s things like the Pink Tax, the average woman pays $1,700 more a year than her male peer for the same products because they’re pink, not blue. We think that’s unacceptable. So we’re the first national retailers to say, “We’re going to eliminate the pink tax in every store.” 

 

Third, we’re really passionate about menstrual health and really that there’s so much period poverty happening across the country. One of four girls don’t have the period products they need each and every day, which means they miss school. They’re self-conscious. I mean, all sorts of things. So another one for us along those lines is, believe it or not, wait for it, period products are taxed as the only thing in our store that’s considered luxury taxed in a bunch of states across this country. 

 

Heather: When I think of luxury, I really do think of period products. 

 

Michelle: Exactly. Right? 

 

Heather: I mean, that is the pinnacle of luxurious. 

 

Michelle: Exactly. When you’ve really made it. Is it the Gucci bag or is it the tampons?

 

Heather: Yeah, it’s the tampons. 

 

Michelle: Yeah. So we decided we were going to absorb that tax across all the states that issued it. We introduced new health services for women in our MinuteClinics, and HealthHUBs, and across Aetna to deal with the increasing rise in depression amongst women and girls to deal with things like perimenopausal, menopausal care. So we put all this together and said, “Okay, we’re going to take some really bold actions that cost a lot of money that are going to have significant kind of … We’re putting our money where our mouth is.” And we wanted to figure out how to talk about it. So how do you talk about those things? And that’s where we evolved the HERe for Her campaign. And what was so powerful about that campaign is that it became really iconic inside our company, but outside as well and garnered a lot of attention. And it unified all these different activities and investments we were making under the umbrella of allyship for women. 

 

Heather: Yeah. I mean, I think that’s so important. Often marketers, brands, businesses are doing so much, but the visibility into what they’re doing and how it’s connected to the higher order purpose or mission gets lost. 

 

Michelle: Right. 

 

Heather: And so the fact that this became an umbrella for all of those things, and just even hearing you list them all off, I mean, it’s pretty amazing. And it’s like the testament, as you said, of, “Do, don’t just say.” 

 

Michelle: And it has legs. I mean, this is something that it’s not temporal, right? I mean, there’s more stuff coming. Pharmacists are going to be able to prescribe birth control in certain states. Birth control is going over–the–counter in the first quarter. So there’s so many more things happening in women’s health, and this gives us a platform to continue to talk about those things that matter to women and that help us ensure. Heart health is another big one coming up in February. Women have disproportionate heart health challenges that go undetected, especially women of color. So we can continue to make progress and advance our passion for women’s health under the umbrella of HERe for Her.  

 

Heather: Yeah. That’s incredible. 

 

So I think one of the things you said when we first talked about this interview was about being passionate about technology and about moments of transformation. And that has been, I think, a red thread throughout your career. What excites you about the technology that we have at our fingertips today? And what, if anything, scares you? 

 

Michelle: Yeah. Those questions go hand-in-hand, to your point, right now. And I was early in the digital revolution, and cloud revolution, mobile revolution, social revolution. I’ve had the fortune of being at and choosing industries that were really transforming with technology and consumerization. So here’s what I have learned. One, you have to be a constant learner. You have to be somebody who is … Satya Nadella said this and it’s one of my most important leadership philosophies, “Be a learn-it-all, not a know-it-all.” That is so critical, because the environment is changing so rapidly and technologies changing so rapidly, and you’ve got to be an active, active learner. One of the things I cherish about my IBM years is just that constant drill we all had about training and development. And I loved that my kids would see me at a table studying cloud computing or quantum computing and really trying to understand and puzzle through while they were sitting there doing their math homework. And so … 

 

Heather: They’re checking on you, “Mom, did you do your homework?” 

 

Michelle: Exactly. Which is great. A great, hopefully, role modeling for them how important lifelong learning is. So that’s really critical. 

 

The second thing I would say is that there are lots of places where technology is transforming the process. So you have to start thinking about, “Well, what are those things that can change, that can be remade by technology?” And for us, we have a bunch of examples, of course, but I’ll pick on two. From a marketing perspective, we’ve been doing a lot of work with generative AI on content creation and development. And we’re finding some terrific, terrific examples of how we can use gen AI to create content that we still edit, we still run through our legal and regulatory review process. But it vastly simplifies, streamlines, and speeds up the process of content creation, and takes cost out. 

 

Another great example is, of course, our call centers. And I do a lot of work across all of our call centers in the country, and so have a lot of passion for how we’re using technology. One we’re rolling out now across the board is after call summary using gen AI, so that while somebody is talking on the phone, the agent doesn’t have to be taking notes or doesn’t have to spend 60 seconds after the call summarizing everything in the CRM system. That enables the agent to really be present for the consumer, and to listen or to identify things. 

 

Heather: An active listener. Yeah. 

 

Michelle: And it means they don’t have to spend an extra minute every single time after a call trying to summarize everything. So those are examples where technology can improve both consumer-centricity and colleague-centricity. But the last thing I would say is, none of this is without significant risk. I know there’s been a series of really fascinating articles in New York Times of late on all this. One, how fast it’s all going. Secondly, how quickly it can go in the wrong direction. So embedding the right reviews, the right framework, the right constant questioning is really critical. You can’t just start using this and keep going. You’ve got to have a process that allows you to keep reinvigorating like, “Are we doing this in a way that is responsible? Are we doing this in a way that’s not creating bias? Are we doing this in a way that allows for the trust and transparency we want to continue to maintain with our consumers and colleagues?” 

 

Heather: Yeah. 

 

You mentioned IBM and you did some incredible things there. Tell me about what you’ve brought to this role from that experience. 

 

Michelle: Well, I think a few things. One, IBM did, and always has done, I think, an incredible job of reigning in new eras. And when you think about reigning in the era of AI, IBM was at the forefront with Watson in many, many ways. So that was an incredible place to learn and to see the boldness and audacity of having a point of view. I think it’s so easy for brands to just take the safe road or take the … It’s like, “Well, we could do this. We could have a strong point of view. We could do a bunch of actions, but it’s going to cost a lot. And maybe it won’t be well … maybe it’ll alienate some people.” So they take safe pathways. I think IBM is a brand that has never been interested in the safe pathway, and I think that was a wonderful experience to have and to learn in that environment and to grow in that environment.   

 

The second thing I would just say is, embedding myself or learning so much about these emerging technologies was a gift and a gift in terms of just cultivating that curiosity to keep learning, keep growing, keep seeing what’s around the corner. 

 

Heather: Yeah. I think it’s just amazing, I think, both for CVS and others to see how there’s a lot of allure around startups and there’s some incredible things happening on the fringes. But to see a brand and a business that has gone through many lives and continues to evolve. So like do you think that there is an advantage as the incumbent, or do you feel starting from scratch in some cases is the way to go? 

 

Michelle: I’ve done both, so I love both. So I don’t have a strong preference. I think it’s super important to never get complacent. That’s what I really believe. So whether you have momentum and things are going well, or whether you’re going through a really tough time or transformation, whether you’re small, whether you’re large, I think it’s so important to never get complacent. 

 

One of the things I love about when I see how Karen is setting such a bold agenda for CVS Health is that, whether you’re doing well or not, you feel like you’ve got to move, you’ve got to change. I think that’s a very, very healthy environment for people to work in. And I’m not saying paranoia, or anything, or defensiveness. But I think as soon as you start to feel like, “Oh, we got this. We know it all. We are doing great, everyone’s following us,” I think that is a very, very dangerous time for a company and for a team because you start to become risk-averse, because you start to become lazy, because you start to be unwilling to learn. So I’m constantly trying to cultivate cultures where no matter how we’re doing, we’re actively avoiding complacency.  

 

Heather: I love that. Someone once said something like, “You just always need to be questioning, and even the things that are the sacred cows.” Right? 

 

Michelle: Yeah. 

 

Heather: There are things that are like, “Well, we are not going to …” Those are things you have to look at. 

 

Michelle: Right, right. 

 

Heather: So I love that notion. 

 

You’ve had so many incredible successes and accolades. You were named Woman of Power and Influence, which is an amazing title, by the National Organization for Women. Tell me about your leadership style. I mean, I think you’ve spoken about the culture of learning and not being complacent. And the keys to influencing change at such large and complex organizations. 

 

Michelle: Well, thank you. I’m going to go home and tell my kids that. I don’t know that they … 

 

Heather: I am a woman of power and influence.  

 

Michelle: Of power and influence. So when I tell you to eat your vegetables and clean up, make your bed, you should really obey. 

 

Heather: Exactly. You just have that on just everywhere. 

 

Michelle: Just take it. Yeah. Exactly. 

 

Heather: Hi, I’m Michelle. I’m a woman of power and influence. 

 

Michelle: How are you today? Yeah. 

 

Heather: Yes. Good to see you. 

 

Michelle: Exactly. Please eat your vegetables, kids. 

 

So Karen actually had us do an exercise I had never done before, and it was incredibly valuable, which was to write down your leadership philosophy. And of course, being I was sort of never satisfied person that I am, I wrote it, I rewrote it, I edited, I rewrote it, I edited. I ripped it up, I rewrote it, I edit it. And so I finally emerged on some core themes for me, and I’ll maybe share a few. So one is to live by your North Star. For me, that’s always been consumer– and people team–centricity. So that’s my guiding force. That’s how I start meetings. I want to understand what’s the implication for the consumer. I will get to all the operational issues and financial issues since this make sense, but I will start with our team and our consumers. That’s been true in every job I’ve ever been at. I think it’s a consistent North Star that works for me, and I think others know I live by that. 

 

The second one, and I mentioned this one, is to be a learn-it-all. It’s just an amazing time to learn and to spend your life constantly … I just want my life to keep opening. I want my life to keep opening. I never want to feel like I’m narrowing what I’m learning, or what I’m doing, or how I’m engaging with the world. 

 

Third thing for me is something I learned from Mark Parker at Nike, and it’s edit to amplify. And I love that because the idea, of course, is you’re surrounded by good ideas all the time, but the real power of a leader is being willing to edit to amplify, to edit those things down, to make sure that things that matter really have an impact. And HERe for Her was a great example of that for us. 

 

A fourth one for me is, lead for the betterment of others. I grew up with a dad who was an entrepreneur, and I watched his passion for his people every single day. I saw what that created in terms of culture and what that culture ignited in terms of performance. So my passion has always, always been, how do you help others be great? Now, am I good at all this stuff all the time? Absolutely not. But when I’m at my best, that’s important. 

 

And last but not least, and this is one that I think I’ve increasingly valued over time, is to play with joy. This idea that things are never as bad as they seem, and they’re also never as good as they seem, and to just play with joy to ride in the saddle a little bit easily. I think that spirit of feeling like, “This is my court. I own it, but I’m going to play with joy,” that, I try to bring that to work and to my home. 

 

Heather: Yeah, I love that. I mean, I think being joyful, and seeing silver linings, and staying open, and positive is hard. It’s a choice. And I think it is very easy, especially with what seems like [the] ever increasingly complex and fraught world that we live in, yet so much opportunity. And as you said, you’ve got to balance it. I think that’s really important. And of course, we spend a lot of time at work and it’s a means to an end, but for many people, it’s also a passion. And to be able to have joy in that I think is so important. 

 

What intimidates you? 

 

Michelle: Oh, lots of things. I mean, I think, for me, cultivating this idea of not complacency always means you always have to be thinking a little bit paranoid about next technology that’s coming, what other their industries are innovating, what might competitors do? How is consumer behavior shifting? I think those are the kind of things that I think about. Am I learning enough about new ways technology is reshaping, our crafts and our businesses, and our industries? Am I spending enough time on that agenda, so that I can really harness it in a way that’s responsible for our own company and our own teams? So I don’t know if it’s intimidation. I think I try to be fairly fearless about a lot of things, because I am a woman of power and influence as we … 

 

Heather: I mean, just to say. 

 

Michelle: Just to remind you. 

 

Heather: Yeah. 

 

Michelle: But I think that the thing for me is that I just always have a sense of wonder over all that’s still possible. 

 

Heather: Yeah. I love that. That’s really beautiful. And I think just broader than business. 

 

I think, am I focusing on the right thing? That’s something that I think about a lot. I mean, there’s so many competing priorities in every day, so many things you could or should be doing. And even you talking about all the things that you’re accomplishing, I’m rattling off in my head all the things I should be pushing on. So I think being fearless, but as you said, that notion that Mark Parker mentioned about editing, right? I mean, that’s a big part of it. 

 

Michelle: Here’s a thought, which helped me break through that a lot, because I think especially early in my career, I’m a CEO of Travelocity. I was pregnant. I didn’t know how I was going to do all this. And then when I moved to Citi, and I was global chief marketing and digital officer, and I was pregnant with a second child, so one thing I started doing and that really has had a big impact on me is, every quarter, I find a little bit of quiet space. And often it’s on a long flight when there’s really less distractions. And I will write down on those flights, in the next 90 days, what’s really important at work, what’s really important to my home, what’s really important to my community, what’s really important to my extended family and friends? How do I want to show up? 

 

Sometimes it might be like, well, my daughter’s starting a new school. I want to make sure I’m getting to know the moms—and she’s a freshman in her high school—moms and dads in the community. Or it might be that my son [has] is picked up a new sport and I want to make sure that I’m showing up to support him. Or it might be that one of our child[ren] is struggling with something and I want to be present for that. Or something about my husband or extended family. I do the same for Nike, for community, and most importantly, in some ways for work. 

 

Then I actually spend 45 minutes, an hour, going through my calendar, and I’m like, at both the past 90s and the coming 90s, I think, “Does this match? This is what I’m saying is really important and this is how I’m going to be spending my time. Does that actually match?” And invariably it does not match. So because things go on your calendar for … like you have these standing steering committee meetings that are on the calendar for the next year or whatever … 

 

Heather: Two years. Yes. 

 

Michelle: Right, exactly. 

 

So I then will craft a long extensive note to my team, my EA, and chief of staff, and others. And we’ll sit the next day and we’ll say, “Okay, how do we take these things off? How do we prioritize these things? How do we shift the calendar?“ And we’ll color code actually on the calendar. So it gives us a good visual response … 

 

Heather: Of how things are balanced and … Yeah. 

 

Michelle: Yeah. Maybe at work that maybe one of my teammates, one of my colleagues is struggling a lot, or someone who works for me is struggling, I want to spend more time. Might be that we have a really important priority, like HERe for Her, that I really want to double down on a launch of Healthspire, I need to spend a lot of time on. But those things are fungible. They can shift, they do change. So I try to be as agile with my time and my calendar as I insist our teams are with our work. And that was very liberating for me when I realized that I could control my time. Because I think before that, I was so used to letting everybody else control my time and I would pick these ridiculous things, like I have to be the class mom. 

 

Heather: Yeah. Yeah. Of course. 

 

Michelle: Because I felt so guilty, I had to be the class mom, and I would end up being the worst class mom because I would not … I remember once when it was this art project, our kids were in preschool, and my daughter’s class mom, I kid you not, had gathered feathers and twigs from the forest. And they handcrafted bird’s nests and … Yeah. 

 

Heather: Oh, gosh. 

 

Michelle: And I, the night before, I realized this, I have to go to school and do this art project. So I think it was probably a CVS, it was open. I’m buying, I don’t know, construction paper and straws to make these flowers. It was the saddest project you have ever seen in the world. And my daughter’s nest is probably, still to this day, on our shelves … 

 

Heather: As a reminder. 

 

Michelle: And my son was scarred for life. But then it’s like when you think about that, I don’t need to be the class mom. I need to show up in these ways. This is what’s important. So I think it encourages me to be the architect of my own time. 

 

Heather: I mean, that’s the most precious thing really that we have. I remember one time I also was like, “I need to be one of the moms that comes in the middle of the day to do something.” And it was up against all of the other things. And I ran from one meeting, and then I had to get home, and then I got in the car, and then I had to pick up something at CVS. And then I got pulled over by a policeman, because I made a turn where I wasn’t supposed to make a turn. And I was so late and came into it, and I was like, “Boys and girls, you’re not going to believe what happened to me.” And luckily nobody was hurt, and I didn’t get a ticket, but I was like, “I’m trying to get to my son’s class.”  

 

Michelle: Yeah. But then you ask yourself, “What is really the point? What are you really trying to do?” 

 

Heather: Exactly. Exactly. 

 

Michelle: I think that’s where there’s so much more flexibility than you think. 

 

Heather: Yeah. And I think taking control of that and taking the time to think about that and not just going-going. 

 

You’ve mentioned in your career you’ve been both CEO and CMO, and I’m just curious, what do you think with regards to the skillset of a CMO that is particularly valuable for being a CEO, and maybe vice versa? 

 

Michelle: Sure. I think you have to be incredibly outcomes-oriented. And I think too many times we, marketers, we’ll talk about metrics that don’t resonate for CEOs. And we’ll say like, “Oh, impressions or clicks,” or whatever. Or, “We’ve done this multi-variate attribution modeling,” and that doesn’t resonate for CEOs. It doesn’t resonate for me when I’m running companies. So I think challenging yourself to really align to the outcomes the business is committed to. And one great way to do that is understand board metrics. What metrics is the CEO presenting to the board on a regular basis? Earnings’ calls, investor days? What are the metrics that we say the company matter most? And how do you align the work that you’re doing to make sure you’re really advancing those metrics and those outcomes? And that’s a very liberating, important thing for anybody I think to go through, but especially marketers who, historically, have had a different set of metrics that we all understand, we all believe in, but don’t necessarily tie to the things that are being presented to investors. We’re not talking to investors about impressions or click–throughs. And I think that has become really important. 

 

At the same time, I think that, in being a CEO, I’ve had this amazing ability to harness creativity, and consumer-centricity, and culture building in a way that I think can be really powerful for having that job. So I guess, for me, the exciting thing is, how are you clear about the mission? How are you clear about the outcomes? How do you recruit and develop the best possible diverse, inclusive team to advance that? And how do you create a culture of learning and agility, and on a mission to succeed? 

 

Heather: Yeah. 

 

I wanted to go back briefly to 1999, you launched Site59. Just tell me about that. And then did you proactively look to be acquired? And then once you were by Travelocity, you ascended to be the CEO. I just would love to go back to that time and seeing how that’s led you to this time. Just reflections. 

 

Michelle: Yeah. Well, thank you. I mean, I grew up with entrepreneurs, so I had wanted to start something, and I had the incredible opportunity to start Site59. Boston Consulting Group, which had been my prior employer put money in and helped me there, which was amazing. And it was such an incredible experience to build a company at the beginning of the digital era in travel, which was digitizing as quickly as it was. Then we went through 9/11, which is a whole another story and actually an amazing story for me as a leader and learning how to lead. We were acquired by Travelocity and then had the extraordinary opportunity of becoming COO, and then CEO of Travelocity. And that, to take something that was … To write an idea on paper, to write a business plan, and then five, six years later to be CEO of Travelocity was a terrific journey, not just for me, but for the whole team. 

 

Heather: Yeah. Incredible. 

 

Do you have a pet peeve? 

 

Michelle: I think defensiveness, when people are really defensive about things. And I do it myself sometimes, too, and then I’m like, “Oh, I’m going to smack myself,” because I can hear it in my own voice. It’s human nature, of course, but I think that’s important. I do not tolerate well when people on my team are not leaning in to support each other. When I see politics or bad behavior amongst my team, that is not something I tolerate well. And I really, really work hard to recruit people who aren’t just the best at the what, but share a common set of values on the how. So that’s something that massive, massive pet peeve. 

 

Heather: Yeah. That’s a good one. 

 

The word grace, I know you’ve spoken about that being something that you think about as a leader. Tell me why that’s the word that has resonated with you. 

 

Michelle: Yeah. Well, I’ll start by saying my daughter’s middle name is Grace. 

 

And when she was born, I wrote her a whole … I write letters to my kids, and they go in a box that they’re each going to get when they go to college. So once or twice a year, I’ll write a letter, and the very first letter I wrote was about grace for my daughter’s box. So they’ll either appreciate these or not, but they get them when they go to college. And that word, I think, for me signifies a lot of things. But perhaps most importantly, it’s my desire, as I said earlier, to keep opening up pathways, to keep living a bold life, to take risk, to have an adventurous, bold life. But I also know that in choosing that, and choosing that path, and choosing that path of tak[ing] greater risk, put[ting] yourself out there, there will be more setbacks, more challenges, more times you let yourself down, you let others down. And it’s just risk and reward go hand-in-hand. 

 

So grace for me is keeping on that journey, the ability to learn, to be humble, to pick yourself back up, to find the ability to see the best in others. And I think if you’re going to lead … You could choose an easier life. But if you’re going to choose a life that is going to take risk, and is going to be bold, and it’s going to be adventurous, and it’s going to try things you haven’t tried before, and put yourself in places that are uncomfortable, I think you have to recognize you’re going to fail more. You’re going to stumble more. You’re going to have more setbacks. And it’s those times that grace is really powerful.  

 

Heather: Yeah, I love that. And grace for yourself, right? 

 

Michelle: Grace for yourself as well, yeah. 

 

Heather: In an effort to keep climbing, and growing, and evolving, I think there’s some time … 

 

Michelle: Yeah. It’s okay, take it lightly. Take it lightly when you stumble. Right? 

 

Heather: Yeah. There’s actually the idea of joy, too, right? I mean, it’s hard though. 

 

Michelle: Yeah. I mean, all these things, I think, are a journey from nature, like, “Oh, I nailed it today.” And then it’s like, “I was a disaster today on every single one of my leadership principles.” 

 

Heather: Yeah. Or, within the day, it’s like disaster. Totally living my truth. It goes back and forth. 

 

Michelle: Yeah. That’s okay. 

 

Heather: Oh my gosh, there were so many incredible things that you shared both as a business leader and your experiences and just your philosophies on living life. And I just thank you so much for being here with us today, being an advocate for Lippincott, and for women, and for inclusion, and for joy, and all of these things. 

 

I always close these sessions with a question that ties back to the name of the podcast. Who is your icon? 

 

Michelle: Oh, that’s a great question. So many. I’ve worked for extraordinary bosses. That’s been incredible to me. But I would actually have to say growing up, watching my dad, watching my dad build a company in a new industry, use technology in new ways. But most importantly, cultivate such a powerful, powerful culture around client-centricity for him and people-centricity, team-centricity. I mean, that was iconic. To grow up and watch my dad do that, that was truly, truly a gift. 

 

Heather: That’s incredible. Well, thank you so much, Michelle. You’re amazing. 

 

Michelle: Thank you, Heather. 

 

Heather: Keep those sneakers hidden away. Put that sign up, woman of power and influence, everywhere you go. 

 

Michelle: I’m going to try tonight at dinner. 

 

Heather: I just can’t wait to see all the things that you do next. So, thank you. 

 

Michelle: Thank you, Heather. Take care.