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28 Min Read

HR Superstars Podcast: Unapologetically Human w/ Holly May, Global CHRO at Walgreens Boots Alliance

Adam Weber, SVP of Community

Holly May is a seasoned HR professional with a background in total rewards and business partnering in diversity, equity, and inclusion. She has held CHRO roles at Starbucks, Abercrombie and Fitch, and now at Walgreens Boots Alliance, where she has championed the importance of mental health strategies in the workplace. Below is a transcript of our interview on the HR Superstars Podcast:

Adam: Early in her career Holly considered herself to be pretty private. Her coworkers didn’t know much about her, she didn’t know much about them, and they kept it that way. But that mindset was quickly shifted when she found herself in a brand new city without a support system and she needed to ask a direct report for help. And that experience not only forced her to be more vulnerable, but it opened her up to the leader’s responsibility and role in accounting for their employee’s mental health. So if you’ve ever experienced the tension between that desire to connect more deeply at work, but feeling like it’s risky, then I’ve got a feeling this story will resonate. So with that, let’s get into Holly’s story.

Holly, welcome to HR Superstars. We’re so thrilled to have you and just to learn a little bit about your journey and some of the ways that you are on the leading edge of putting mental health strategies at place and work, and I want to just start by hearing a little bit about your own journey into HR and how did you get into HR?

Holly: Well, I’ll start by saying my journey into HR was not planned. When I got out of school, I really didn’t know what I wanted to do, but it’s something that found me, I would say. My resume when I was applying for a role at a financial services company, came across the desk of a total rewards leader who had a background similar to mine and asked me to at least try it out. I won’t lie to you, I was a bit resistant at first, but after about two months in role, I knew this was the career path for me. I spent the majority of my career in the total rewards space. I’ve also done stints as a business partner in diversity, equity, and inclusion, also leading strategy, and this is my second CHRO role, and made the path from Starbucks to Abercrombie and Fitch to Walgreens Boots Alliance, where I’ve been for over a year now and having a great time.

Adam: That’s great. What is it about HR that compels you today? What is it that you love about HR?

Holly: It’s funny, I’ve gotten that question before and usually it’s framed as what is your favorite part of HR? And to me, what I love most about it is how everything fits together. So spending most of my career in a center of excellence, in compensation and benefits, by itself, it is not a powerful tool. It’s how it connects into everything else. And essentially that the sum of the parts are stronger than the individual parts. And I love how you connect performance into pay, how you incentivize people, how you motivate people, how you engage people, and how you really drive managers to deliver the culture that you’re looking to build within an organization. That’s what gets me out of bed in the morning.

Adam: That’s awesome. I can’t wait to dive into some of those topics. I am curious, though, just because you talked about your path. I’m always interested, this is your second CHRO job, and you’ve been at some really amazing prominent brands, Abercrombie, Walgreens, and I was curious, at the macro level, what are some of the biggest differences between organizations like that? Those two types of organizations?

Holly: Oh, well I’ve been across a number of industries. I actually started in financial services and banking. I went to, really, FinTech to electronic payments with Visa, and then made the move into retail with Starbucks, then Abercrombie, and of course now with Walgreens Boots Alliance, that’s a healthcare company. It’s interesting. Of course you have industry differences and I think there’re some things that everybody realizes, cultural differences within organizations based on industry. But what I have found has been important to me and has attracted me to these different organizations is really the mission and the values driven culture that I’ve been able to experience in so many organizations. And to me that’s what motivates me. Connecting to the mission of an organization, being excited about the difference that an organization can make in the lives of others, whether that be your employees, whether that be your customers. And I’ve been very fortunate to work for some really amazing brands.

Adam: Yeah, that’s great. One of the things that I really resonated with that you talk about, and I have a book called Lead Like a Human, and you have this phrase that you use called being unapologetically human. So I was like, “Oh, we have to talk about this.” That phrase really resonated with me and I’m sure it will with our listeners too, but tell me a little bit about what it means to you to be unapologetically human.

Holly: Well, I would say first of all at its core it’s about having the ability to bring your whole self to work every day, flaws and all. You don’t park who you are as an individual at the door when you get to one of our stores, our distribution centers, or our offices. You get to be who you are. And I think what’s critical about that is your line manager, the person that you work for, I think they have to deliver that experience for you. In terms of senior leadership, we have upheld this value. It’s been really critical to how we show up to the organization. And I know our CEO, Ros Brewer, has really championed that and role modeled it herself, but it really has to go deep down into the organization.

And I think it’s a business value that has a real ROI to it. I think it really unlocks performance within the business. Because it starts with that manager employee relationship and the trust that’s built within the two. And to me, you build trust, and I truly believe this, you build trust through showing authenticity yourself as a manager. So what does that look like in practice? So if I show up every day as a leader and I pretend life is perfect, I show up with polish, I act like everything’s wonderful all the time, I’m doing my team a disservice because I’m telling them they need to show up like that every day by behaving in that fashion.

But if there are days when my son woke up sick and he might have thrown up before I left the door and I had to call and figure out childcare before I left, and I’m 15 minutes late, I’m honest with my team about that. I don’t make up an excuse. I tell them what’s happening in my life, and I think through that they feel that they can share with me what’s going on in theirs. And it unlocks a lot. It builds a relationship that looks very different than one that you talk only work all day long, you keep it purely professional. And I think we’ve seen a real difference in really championing this behavior and role modeling that for the organization. It’s a real unlock for leaders, and I think it has benefits on both sides.

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Adam: There’s a phrase I use a lot called the story behind the story, where it’s just a good reminder we’re all a little bit more human with each other when we realize that your child was up last night. It might be a metaphor, it might be the real story. And that when we create environments where we are able to share those things, it also creates a little bit of empathy, it makes conflict resolution a little easier, all of those things. So I like that. And you talked about this a little bit, but I want to bring it to life, this relationship between HR and the manager, and HR who has these great visions of how to live this kind of unapologetically human mindset, but then it actually only comes to life through those managers. It can’t be done through the brute force effort of HR. So what are some ways you’ve equipped managers to bring that to life for you?

Holly: What I would say is it starts with empowerment. It starts with supporting your manager and understanding what their role is within the organization. And it goes to every aspect of how they’re performing their jobs. So I was talking a bit about trust. So if you think about how a manager gets the best out of their team, a manager can’t really deliver effective feedback to an individual, really clear feedback that’s going to be constructive, that’s going to benefit that individual, unless they’ve built trust in advance. And I know we all talk about when you’re onboarding, how important relationship building is in an organization. I can’t emphasize that enough, but the trust building part of that is critically important, because if you really want to help your teams, if you really want to get the performance needed to drive the business, it starts from a place of trust and relationship building.

I’m a strong believer in clear is kind, and I’m a strong believer that people should be upfront and transparent when they communicate, and it all starts with that. So there’s a clear link between this authenticity, empathy, trust building, and then driving performance. And I think that’s what we’ve really tried to emphasize with our leaders, and it starts with empowering them to make decisions for their team. A great example of how we’ve done this is with our approach to hybrid work. Instead of dictating that our hybrid workforce needs to be in the office three days a week at minimum, or you have to be in Tuesday through Thursday, we’ve left the decisions to the leaders. So we’ve said, “You know your teams, you know what you have to deliver, you know how to create the moments that matter that are going to be important to your teams, so you make the decisions about when they’re going to be in the office. We’re leaving it to you and we’re leaving you to drive the performance of the team, and we’re empowering you and trusting you with that.” And I think that’s really where it begins.

Adam: Yeah, I like that balance that you’re finding of support and empowerment on one side and trust and autonomy on the other. It’s like we want to equip them with the resources to be successful. We also want them to be the ones who do this. That they have to have personal ownership of living this out. I want to ask about one phrase you said, because I resonate with it a lot, this clear is kind concept. Can you tell me a little bit about what you mean and how that lives out?

Holly: Absolutely. And I can’t take credit for the phrase, this is definitely a Brene Brownism.

Adam: But if we’re not talking about Brene Brown on this podcast, we’re not doing it right. If Brene Brown or Adam Grant doesn’t come up, we’re kind of in the wrong… We don’t know our market.

Holly: Well, I’ll maybe first talk from a personal level, and I will tell you the biggest moments where I can say I changed or developed as a leader are really my career pivoted at certain points. It was when I had what I sometimes talk about as tough love conversations that were the most painful probably to hear, but were delivered to me in such a way from a person that I trusted, that I knew had my best interest at heart, that I knew was telling me for the good of my career, for the good of me personally. That’s those real moments of pivot and trajectory shift that I can remember. And it’s not easy. It’s not easy on the side of the manager, it’s not easy on the side of the person receiving the information, but it’s critically important to someone’s development.

And everyone has development areas. It doesn’t matter what level you’ve reached in an organization, you’re constantly working on yourself. And it can be received from a variety of places. I mean, there are times when I’ve gotten the tough love from managers, there’s time when I’ve gotten the tough love from peers, and also from my team, which is wonderful. And I just think when it comes to being clear, your conversations need to be constructive. And if the person really understands and feels, and you’ve built that trusted relationship where they feel like you’re really trying to support and help them, I mean, sky’s the limit with what you could do to help a person perform at their best, not only at your company, but perhaps where they go after that. So I think by being authentic, by being someone who’s truly caring for the individual that you’re speaking to, it goes a long way.

Adam: And it’s reflective of the research too that shows that one of the top values of employees today is personal growth. Can I grow here? And I think managers sometimes misinterpret that to mean, “Can I get promoted here?” Which that is one component, compensation is one component, but the forgotten piece is, “Am I developing?” And the only way to develop is inside of that trusting relationship where you’re actually getting that feedback to go, “How could I get better? What is the thing that’s missing?” And boy, that does not work without trust. It comes across as very heavy handed and you put up walls and blinders, you know, that…

Holly: And it can be rejected if that doesn’t exist. The person could choose not to believe it. And that’s in no one’s best interest.

Adam: I think you really nailed it earlier when you said that foundation of trust. I think when the employee knows that the manager has that person’s best interest is really what unlocks the freedom to be kind, not nice, but kind and really share. Yeah, that’s beautiful. I want to talk about mental health. And in the HR Superstars Community, we actually did a whole month dedicated to mental health and resources we put together to try to help the HR leader account for mental health strategies that are practical, that are realistic, all of those things. And it’s just a topic that constantly comes up from HR leaders. So first I just want to hear about your own personal experience and how that’s informed you and the strategies that you’ve put together as it relates to mental health at your company.

Holly: So I would start by saying my journey, my personal journey to become really an authentic leader, I did not start out this way. It’s something that I was almost forced to develop as a skill. And if I go all the way back, I grew up in a family that was pretty formal. Do not speak unless you’re spoken to, as a child, speaking with a lot of deference to adults, always referring to adults as Mr or Ms, or Mrs, and I would say going into the world of financial services and banking, that was a culture that benefited me, and that was something where there was a lot of formality, there was a lot of hierarchy, and I did well in that environment and I very much kept my personal life to myself, and everything was work and it was how I led for many years.

And I didn’t fully understand when I’d get feedback from my team that, “Oh, we don’t really know who you are or we can’t get a read on what you’re thinking.” I never really understood what that meant. And several years ago, after I had my first child, actually just having done a relocation to Seattle, I had to bring my son to a pediatrician for the first time because I was noticing really significant differences with how he was behaving compared to children of the same age in daycare. And shortly thereafter I learned that he had received an autism diagnosis and he was on the autism spectrum.

And it was a very challenging moment for my family. I was new to the Seattle area, I didn’t know where to turn, I didn’t know what therapist to go to, I didn’t know what to do next, and I didn’t have a support network there, I didn’t have family there, I didn’t know where to go next, and I had to, and I will always remember this, go to one of my direct reports, who was the head of benefits, and say, “Help me.” Because it was a moment where I was putting my child and my family above everything else, and I realized I had to be honest about what was going on in my life and ask for help and support, and to do that from someone who had just started working for me. And I had to be honest with my boss about what was going on and the time I was going to need to take care of him and get everything set up.

It was something I had to do for the first time. But what I realized so quickly, as my team, as my boss, as my organization put their arms around me and did everything they could, even though they had practically just met me, to help me, that I realized how powerful opening up in this way was, what it did in terms of the relationships I had with my peers, with my direct reports. And it just unlocked something that I could never have imagined. And to be honest, I don’t know that I could have shifted this quickly if something that significant had not happened to me, but it completely shifted the way I managed going forward, and just the trust it built, the relationships that unlocked was something I couldn’t have imagined.

And I tell this story, and it was a very stressful time in my life, because I hope others learn from it without having to go through something that’s significant in their own lives, but just to try it out, because this is something that is a very, very powerful tool. And it’s not weakness to show vulnerability. It’s an incredible point of strength. People will get to know you and your teams will get to know you.

Adam: Yeah, that’s beautiful. Thank you for sharing that story too. I think about that moment of you talking to your new direct report and just sharing, and I’m struck also by just even… To get to the level where you have, you’ve had this great level of success in your career, and supporting these incredible brands. And I think one thing that’s easy to take for granted is that there’s a real life really happening at the same time, and that level of ambition and then it’s like, “Oh, but there’s a real life too.” Sometimes those two things, there can be tension, or there can be this conflict almost that can take place between the two where it’s just hard to go, “Oh, wait, hold on, pause, this is real life. Real life is happening right now and it takes priority,” and in this instance obviously it feels like it obviously jumped to the forefront and maybe it was that kind of turning point for you.

Holly: What I think has been the differentiating factor for me and the companies that I’ve worked for is the last two CEOs I’ve supported have been two phenomenal women who are mothers and who have prioritized balance for all their leaders. And with both of them I would say that I would see their children call them during the day, their adult children, and they will drop everything when they get that call. And they expect the same level of balance from their senior team, to know that when their employees come to them, when they’re at senior teams come to them and say, “I’ve got a doctor’s appointment,” or, “I have to go see my child’s play today at three o’clock,” that we’re going to offer that same level of balance.

Because really that’s how you get the best performance out of people. People have lives outside of this building, and it’s okay to bring it into your work every day. And it makes you a better leader, it makes you more empathetic to others, makes you relate to others better, and it makes you understand your customers better as well. So I think I have been very, very fortunate in my career to have leaders that have championed balance, almost even interviewed to make sure that their leaders prioritize their personal lives as well as their lives.

Adam: And it sounds like it’s a value, I mean, it’s a true value that’s actually vibrant and lived out. But when that starts at the top too, it continues to ripple throughout the entire organization because just like they’re doing it to you, you’re doing it to your team and they’re doing it to their team, and you end up in basically doing exactly what you were sharing, just actually being able to be human. So when you talk about this experience building your empathy and helping you become a better leader, are there any… One of the interesting things about HR is then you can put policies or things in place to actually live that out. So is there any way that has translated into the HR work that you do for employees?

Holly: I’m a firm believer, when you are… Let’s talk about the benefits area for a moment. So when you are looking at benefits to implement and it’s pretty standard process, you benchmark your benefits against peer companies or the general industry, you look to see what’s market leading, what are others doing, you determine, I guess, what you would consider to be table stakes and then you might choose to do investments above and beyond that. But that is different from the approach I’ve taken and the team has taken here at WBA and would’ve taken in past organizations, which is that you have to deliver benefits that are going to meet the needs of your employee population. And it could look very different depending on… It could be the part of the country where you operate. It could be the composition of your employee base. It could be the type of work they’re performing every day.

So it was very important to us not only to understand the general market and what others are doing, but to go far beyond that and ask people, “What is it that you need? What is important to you? What are we not delivering today that you would like to see?” And something we heard loud and clear from our people was that mental health was a real concern. I mean, you could only imagine at Walgreens, going through the pandemic, pharmacists on the front line, not only dealing with the day-to-day of what they might be dealing with at home and for the hours they’re working, but also they’re interfacing with our patients and our customers who were going through a lot during that timeframe, who were quarantined at home, who might be going through mental health issues themselves. So there was a huge need there. And we not only understood it was this broad category of mental health, but we thought really hard about, “Okay, what specific type of support would be most effective to them?”

So what we ended up doing was introducing a program that we call Be Well Connected. And we really rolled out three different tools intended to meet the different needs of our team members across the organization. One being our EAP solution, which offers five free counseling sessions, and the second being Journey Live, which is an app and mobile solution offering classes that our team members can attend live or on demand, taught by expert instructors on a variety of mental health topics, where within that class they can ask questions of the instructor, they can talk amongst themselves about these topics. And it’s gotten enormous accolades internally, and we’ve had enormous participation. And we’ve even started working with Journey Live to create custom content. So mental health resources for pharmacists, as an example. Mental health resources for parents of children with disabilities. So things that we’ve even been able to partner with them on the content to make sure we’re meeting the needs of our people.

And then third is IndieFlix. So we like to jokingly call it our own Walgreens Sundance channel. It’s a series of documentary films on different mental health related topics. I mean, I’ll give you an example. One of them is social media addiction. So think about a pharmacist in one of our stores and they go home at night and their child comes to them and is in tears because someone just posted something negative about them on Instagram. So how do you deal with that? These are films that provide tools, strategies about how to manage through a situation like that. So that’s another way that we can reach a people.

But these tools, all three of them, they’re available not only to our team members, but also to their families. And that was something that was really important to us, making sure we’re going beyond time in the office or stores or distribution centers, and also reaching their families at home because we know that that’s going to factor into their day-to-day. It’s something we’re proud of. But with our benefits, we never stop. We never say, “Okay, we met the need, we’re done.” We’re constantly out there, we’re listening. We’re out in our stores. We’re trying to better understand the evolving needs of our team members.

Adam: There’s a specificity to your benefits that I love where it really reflects you and the values of the organization and the needs, and a genuine understanding of your specific employee population. Like the mental health resources for pharmacists. What a unique way to take a benefit and make it align to your company values and really bring that to life. When you think about HR as a whole over the next five years, how do you see HR evolving in the next five-ish, five, ten years? Where do you think HR is going?

Holly: I’ve talked to a lot of my peers about this at length because I think if you look back over the past three years, our roles have completely changed. The expectations of what we’re going to deliver to the business and what we can bring to the business has shifted significantly. I mean you, you’re seeing more CHROs move into the CEO spot. Boards are acknowledging it. And I think that the seat at the table that CHROs have, I think there are organizations of course where this spot has always been seen as a very strategic partner, but I think on the whole now leadership teams, executives are seeing that these roles are shifting in importance and impact and they’re really acknowledged as a performance driver of the organization. I’ve been fortunate to work for organizations that have seen that, and I think you’re seeing others understand that more.

But I think the boundaries have blurred in so many ways between functions within the business. The organizations that know how to leverage people and talent, boards that understand this, they really understand the importance of linking everything together. So how are you unlocking performance of individuals? How are you engaging them? How are you attracting the best talent? And how are you making sure you have the capabilities and the skills to really deliver on your strategy? And I think you’re seeing more HR leaders come to the table who have backgrounds in analytics, who understand how to use data in different ways, who understand how to solve problems differently, and doing that through talent. I think we’re going to continue to see this space evolve, and I’ve been very excited to see the talent that’s been coming into these functions. And I think you’re seeing a lot of lateral moves too. There’s a new interest in HR. We’ve had people come in from finance, from legal who want to be part of this journey. So I’m excited about the road ahead and how HR is really going to continue to evolve in the future.

Adam: That elevation from administrative to strategic and being this critical asset has both… It is happening. You’re a great example of someone who’s been an early adopter with the leaders that you’ve been fortunate enough to work with, but what I hear you saying is in these next five years, it’s like other people are going to be right there as well in these roles. Even that the role of an HR leader could have the aspirations of being a CEO and really being a strategic asset to the business. My last question I want to ask, I’ve been struck by this stat that I saw this week. Forbes released a study that said 98% of all HR leaders right now are burnt out, which is a pretty painful stat when those are the people that you serve in your role. So I was curious for you. You’ve had this tremendous success, you’ve had an amazing career, and you’re doing incredible work right now, and you’re trying to find that balance between being a mom, being a professional, all those things. How do you recharge for you and how do you find rest for yourself?

Holly: Yeah, that’s a good question. I mean, as I said, I’m very fortunate for the balance I am provided with. This is a role… And I think this is an important thing if you get in into this world and you’re starting your career in HR, you’ve got to love it. You have to wake up excited to go to work, and you have to really be energized by the impact that you’re making every day, because you’re dealing all day with the emotions of others. You’re seeing a lot, you’re trying to support other people, and sometimes we fail to put our oxygen masks on first before we help others. So it could take a lot out of you if you’re not re-energizing yourself, if you’re not taking time for yourself. So I think that’s a really critical part.

You may laugh, but something that I do, I am a person who… My brain just keeps going. So I’ve had problems sometimes getting to sleep at night. I’m always making lists, I’m always thinking about things. And the only thing I have found, and you might see some examples behind me, that I have found to turn my brain off and to really allow me to clear my head is Lego.

Adam: I love that so much.

Holly: So actually I have a Lego room in my house and it’s one of those things where get some time for myself and I build, and I’m telling you, I come out with… My head is clear, I feel re-energized and it’s a strategy. It might not work for everyone, but it’s worked for me.

Adam: This just made it for me because I like something so practical and tangible and real. That’s what you really do. And we all have things like that that are just like, “When I do this, I can kind of let go.” Really let go, and Lego, I think I just-

Holly: Let go and Lego.

Adam: Let go and Lego. I might have come up with their new phrase. Well, Holly, thank you so much. I’m inspired by your story and how you’re taking work in your… You’re living out something that’s personal to you, but you’re doing it at scale and you’re impacting thousands of people’s lives in the process, and I’m hopeful through this podcast, maybe you’re creating some inspiration and sparks for other people too. So thank you so much for being willing and vulnerable to share your story with us.

Holly: Of course. And thank you for having me. This was fun.

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