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Why Walgreens’ CHRO is championing an ‘unapologetically human’ approach to leadership

August 12, 2022, 1:12 PM UTC
Holly May
Holly May, Executive Vice President and Global Chief Human Resources Officer, Walgreens Boots Alliance, Inc.
Courtesy of Walgreens Boots Alliance

Good morning!

August is National Wellness Month, so for today’s Friday  spotlight, we’re speaking with Holly May, executive vice president and global CHRO at Walgreens Boots Alliance, about her “unapologetically human” approach to HR leadership and why she’s prioritizing mental health for all employees.

May joined the drug store holding company in 2021, following stints as the CHRO at Abercrombie & Fitch and Starbucks, where she served as SVP of global total rewards and service delivery. 

This interview has been edited for clarity and brevity.

You say you have an “unapologetically human” approach to leadership. What does that mean and why this approach? 

For the majority of my career, I intentionally kept my personal and professional lives separate. I had been taught that this was how to model professionalism in the workplace. Four years ago, my son was diagnosed with Autism Spectrum Disorder. My husband and I had just moved to a new city for my new job in a new company, and we were without any semblance of a support network. I did not know where to turn. This was my child, and I had no idea where to find him the therapies and medical care he needed. I had a mountain of research and countless appointments ahead of me. Suddenly, I knew that I could no longer keep my personal life separate. I needed to focus on my son. I opened up to my boss and my team about what was happening in my life with tears streaming down my face, crying in the office for the first time in my career. My colleagues, whom I had only known for a few months, reacted with warmth and sprang into action to support my family and me. 

It was through this experience that I realized that opening up and expressing real vulnerability builds trust and immediately strengthens new relationships. It also gave my team implicit permission to show up as raw and as vulnerable as I had been with them. What this created was an inclusive atmosphere where everyone felt comfortable being their authentic selves in the workplace. It enabled transparent conversations and allowed me to better understand how to support them to be the most productive and successful, whether that be providing flexibility between home and the office, development opportunities or forging cross-functional connections. Vulnerability can be as simple as admitting when you are not at your best or being open about arriving late, so you can be there on your child’s first day of school.

What does it mean to care for team members as “whole people” and how has the look of that changed in recent years? 

Caring for our team members as whole people means we commit to initiatives and investments that go beyond our team members’ time in the workplace, delivering both the personal and the professional support they need. We know that when we meet the needs of our people, our team is best equipped to meet the needs of our customers and patients. Over the course of the pandemic, the importance of this approach has only heightened.

What mental health programs and initiatives has Walgreens put in place to support employees and their families? 

I’m very proud of Be Well Connected, WBA’s new mental health and wellbeing program that we launched in May. It’s available at no cost to our U.S. team members and their immediate family members. Through it, team members will continue to have access to our existing Life365 offering, which provides online tools in combination with five free mental health counseling sessions—both in-person and virtual. In addition, two new platforms have been added: Journey Live, a web-based platform and mobile app that provides live and on-demand classes led by expert instructors, during which our team members can interact and ask questions. Class topics include managing stress, improving sleep and finding work-life balance. The second is IndieFlix, a documentary film series featuring mental health topics such as anxiety, social media addiction, cyberbullying and harassment. Each film includes strategies and practical tips and is “premiered” with an internal panel discussion led by WBA leaders and special guests.

For National Wellness Month this August, we’ve also launched a mini-campaign called “Commit to Wellness,” where we’re showcasing our resources and highlighting team members who champion various forms of wellbeing, whether it’s mental, physical or financial.

What advice do you have for CHROs looking to promote wellbeing programs that are well adopted?

Listen to your employees. Just because a program or offering is successful in one company doesn’t necessarily mean it will fit the needs of your workforce. Understand what your employees need and deliver it in an effective way.

I want to hear from you! What are the biggest HR challenges and priorities today? Reach out to me at I’m hosting 15-minute desksides with HR and DEI executives. You could see your response in a future newsletter.

Amber Burton

Reporter's Notebook

The most compelling data, quotes and insights from the field.

On Thursday, Salesforce announced a new representation goal for women and nonbinary employees at the company: 40% by the end of 2026. Women and nonbinary employees currently account for 35.7% and 0.2%, respectively, of Salesforce’s global workforce. 

The company published its first representation goal in 2019, when leadership announced its intent to hit 50% underrepresented U.S. employees by 2023. The company met the goal earlier this year. Like many tech companies, Salesforce's progress has been a slow creep forward, and its updated gender target is still far from parity. The company’s share of women employees globally, however, has surpassed its tech rivals. 

By comparison, women accounted for 30.9% of Microsoft’s global workforce and 30.2% of Oracle’s global employees in 2021. Lori Castillo Martinez, Salesforce’s chief equality officer, spoke with Fortune about the importance of public accountability and its role in pushing the company toward its stated goal:

“This goal is really connected to the ESG representation goals that we announced earlier this year, which we tied to compensation. I think that was an important part of this, not only for public accountability, but also making sure we had executive accountability as well…We've hired more than 20,000 people over the past year alone. It is really important, especially right now given the macroeconomic [events] and what's going on from the potential looming recession. We wanted to make sure that we really doubled down on our commitment to equality. We wanted to make sure that no matter what's happening in the world, equality really doesn't waver.”

Around the Table

- As demand for talent in the travel industry skyrockets, more seasoned workers are stepping in to fill the gaps. Seniors interested in travel perks are nabbing jobs in the airline and hospitality industries. New York Times

- Middle managers play a key role in aligning entry-level employees with senior leadership’s goals, and they’ll likely take on a larger role as companies try to navigate an uncertain future. The only problem? No one wants to be a middle manager anymore. Fast Company

- Starbucks employees have gone on strike 55 times across 17 states in the last several months alone. To dissuade union activity, Starbucks has raised pay at non-union stores and, in some instances, fired workers leading the efforts—one of whom had been at the company for 13 years. Guardian  

- Dropbox’s virtual-first policy requires employees to work remotely 90% of the time and get approval for larger in-person gatherings at the office. While a direct link has not been drawn, the number of job applicants has doubled and the company observed a 126% increase in job acceptances, according to Melanie Collins, Dropbox’s chief people officer. Time

- Walgreens is offering signing bonuses as high as $75,000 to pharmacists in some markets, as it struggles to fill jobs amid a worker shortage. The bonuses are said to be a part of a larger investment focused on recruitment and retention. Wall Street Journal

Roll Call

The latest in HR executive moves. 

Eli Lilly and Company announced the upcoming retirement of Stephen Fry, SVP of human resources and diversity. Eric Dozier, Lilly’s current vice president and chief commercial officer for Loxo@Lilly, will succeed Fry. USAA appointed Tamla Oates-Forney as its CHRO. Data analytics and advisory firm Escalent named Laura Lopez as its new CHRO. 

Have a move? Let me know:



Everything you need to know from Fortune. 

That doggone commute. Job postings for dog-friendly offices increased 23% from July to June, according to a study by Flexa Careers, a website that specializes in flexible job openings. It’s a new perk some employers are offering to entice new and existing workers back to the office. (About 23 million homes got new pets during the pandemic, so some separation anxiety is inevitable). —Jane Thier 

Job creators vs. job-doers. The term job creator can be misleading because it assumes jobs are disbursed by powerful people, which is false, writes John Benjamin, a lecturer at Columbia Business School, in a commentary for Fortune. “By using the phrase we give capital undue credit for creating opportunity, and falsely conflate the interests of owners and workers.” —John Benjamin

COVID-19 guidelines updated. The Center for Disease Control updated its COVID-19 guidelines Thursday. Individuals who have been in contact with someone who has tested positive no longer need to quarantine. However, those who have tested positive still need to self-isolate and wear masks. —Mike Stobbey and Collin Binkley

The crying CEO. The CEO of an Ohio-based B2B marketing company went viral this week when he posted a picture of himself crying after laying off two employees. He said it was the “toughest thing” he had to do. The internet thought it might have been tougher on his former employees. Fortune’s Paige McGlauflin has a guide on how to lay off employees empathetically in the unfortunate event it's necessary. —Paige McGlauflin

This is the web version of CHRO Daily, a newsletter focusing on helping HR executives navigate the needs of the workplace. Today’s edition was curated by Paolo Confino. Sign up to get it delivered free to your inbox.