Women in leadership roles: A Q&A with Maureen Calabrese & Erica Alioto
Erica Alioto, global head of people at Grammarly and Maureen Calabrese, chief people officer at Modern Health share their experiences being the only women in the room and advice on how they’ve worked their way up the ranks.
Women in leadership roles are leaving the workforce at alarming rates according to new research from McKinsey & Co — a huge step backwards in a decades-long effort to diversify corporate top ranks. Erica Alioto, global head of people at Grammarly and Maureen Calabrese, chief people officer at Modern Health share their experiences being the only women in the room and advice on how they’ve worked their way up the ranks.
How did your career evolve to where it is today, supporting workers and workplace culture?
Maureen Calabrese (MC): My career has definitely not been linear. I started on an analytical path but my move to the people space came when I was approached for a role created to support the learning and development of a distributed team of client service professionals. I almost missed it though when I said no, because I liked the work I was doing. I’m grateful that I had a leader in my corner who encouraged me to think more broadly about the impact I could have by taking on a role charged with elevating the performance of an entire team.
This was my first turn into the People world, and I soon learned that you can have the tightest analyses and the best strategies in the world, but unless you have the right people and they are inspired, aligned, and equipped to bring that to life, then those strategies never get off the page. It was here that I made the decision that I wanted to fully focus my career on building incredible teams and cultures designed to drive business success.
Erica Alioto (EA): I have a very nontraditional career path. I started out as an attorney, then I decided to join a startup. The startup I wanted to join (Yelp) was only about 15 people at the time, and they weren’t ready for an attorney, so I joined as the second salesperson. As the sales team grew, I started leading larger teams, which included leading the Learning and Development and recruiting teams that supported sales.
Yelp invested a lot of effort into building a great culture and developing its employees. So I learned firsthand how strong cultures are built, and at the same time I kept noticing opportunities to improve the employee experience, so I decided to shift to leading the People Team at my next role.
During your career did you ever face moments of adversity or inequality as a woman? How did you overcome those moments?
MC: I feel pretty fortunate that throughout key points in my career, I had both female and male allies that really supported me in my success. As I started to advance through higher levels of leadership, I have experienced moments where I’ve had to work harder than the men in the room to make my voice and ideas heard. Like many women, I’ve certainly spoken up to little acknowledgement only to see my idea/point shared by a man shortly thereafter to head nods and agreement.
I’ve had to get comfortable advocating for myself in those moments. I’m appreciative of the strong women leaders around me who work together to make sure our ideas are attributed and recognized.
EA: Of course, I think almost every woman has. I won’t go into details about my own experiences, but suffice to say that HR has changed a lot in the last 10 years – for the better. So we put up with a lot, with the hopes that we would be able to change things when we had a voice at the table. And sure enough, I think we’ve seen that happen. It’s also a huge generational shift with the conversations that are happening and what younger generations expect vs. what we expected 20 years ago.
I’m pretty resilient and focused on the long game, but there were definitely a lot of frustrating moments. Seeing a man promoted ahead of you when it’s both objectively and subjectively clear you’re more qualified is demoralizing. In these situations, I would address the issue with my manager or another leader, and make my point heard. But I’m not the type to walk away when I don’t get what I think I deserve; instead, I just kept going and worked even harder until it was impossible to deny I was the best candidate.
Being a new mom was also challenging in different ways than new parents face today because of less generous parental leave policies and because as women many of us felt like we couldn’t openly talk about the struggles; I often felt like I had to pretend like I had it all figured out. And there were times where I didn’t. So one day when my daughter was about 4 months old, my childcare provider was sick and I just put on a baby carrier and brought my daughter to the office. She was strapped onto my chest for all the meetings, and that was definitely a first for the office. But I realized I could do that and people thought it was pretty great to see me being a mom and not just the boss.
One of the best things to come out of the pandemic is this realization that everyone has lives and responsibilities and sometimes those responsibilities may need to be incorporated into the workday. It’s created an awareness that we need to acknowledge this whole other part of who we are and find ways to make it all work.
Have you ever suffered from imposter syndrome? How did you overcome those feelings?
MC: First off, I think the term “imposter syndrome” can be harmful to women and other underrepresented leaders. While it can be comforting to know that others – even those who are very successful – feel uncertainty about their position at times, I wish we could normalize it in a different way. Turning it into a syndrome and attaching the word “imposter” to it, reinforces the feeling that you don’t deserve to be where you are or you’re a fraud because you’re somehow not perfect at it all of the time. Or, maybe you don’t feel that way, but as so many other women talk about imposter syndrome, potentially you start to feel it a little bit.
Term aside, I have definitely felt over my skis at various points in my career. With the perspective I have looking back, I can now see that these were the moments that I was learning the most and usually taking leaps in my career. So, now when I feel that way, I try to reframe it in real time as a growth moment.
EA: Yes, many times. When I’ve felt this way, I remind myself that I worked hard to get where I am and I’ve earned it. And I ask myself what I would say to a friend in that situation. It’s usually a lot nicer than how I’m talking to myself. I also meditate often, which helps me push out the unhelpful thoughts that may pop into my mind.
How would you describe your leadership style? Was there a pivotal moment in your career that helped you become the leader you are today?
MC: When I think of my leadership style, the word that would come to mind is authentic. From what others have shared with me, I tend to lead with empathy. That’s a quality I always want to retain in my leadership style, but it’s also important to create some level of boundary in an effort to avoid burnout. This is something a lot of leaders in the people and benefits space are susceptible to because we’re often supporting people through challenging situations and it can be a lot if you take all of that on.
I consider myself an introvert, which makes being a CPO – a job with people in the title itself – interesting at times. Because of that, it’s not my first or natural instinct to speak up in a group conversation. I also tend to think through every possible way to frame my response in my head and by the time I get to what I want to say, someone has already said my point or the conversation has moved on.
A pivotal moment for me was when a mentor of mine told me that if I did not speak up and express my views, then I actually was not doing my job. Harsh words on one hand but also really powerful. It’s important to me to perform to the best of my abilities, so when she pointed out that I was hired to bring a perspective and expertise to the conversation, this advice gave me a sense of purpose and from there the strength and courage to speak up even when it is uncomfortable. Even now, so many years later, I think back on this moment. I remind myself that I am at the table, in this conversation for a reason and it allows me to own my expertise and contribute from a place of confidence.
EA: I would describe myself as a situational leader. The approach I take in any given situation depends on the context, the people involved, and the impact of the decision. When possible, I prefer to solicit input from stakeholders to make sure I understand all sides of the issue before making a decision. If there’s someone on my team who is more of an expert than I am, I will often defer to their judgment. I have heard myself described as “approachable” and like to make myself available to others, so I hold office hours every week that are open to anyone.
In terms of how I developed my leadership style, I chalk it up to a LOT of reading (I love autobiographies of great leaders and leadership books that contain a lot of case studies) and a LOT of mistakes. I don’t think you can become a great leader without making a lot of mistakes. It takes a lot of missteps and reflecting on what you might do differently the next time to improve.
What can leaders be doing to make sure we are empowering the next generation of female leaders?
MC: I’m a huge proponent of mentorship and coaching for emerging female leaders. There is no one way for a woman to lead. We each have to find our own path but we don’t have to do it alone. Having people in your corner who bring the experience to see the long game, but also support leaders in defining their own authentic form of leadership is incredibly valuable.
When I’m mentoring young leaders, we talk a lot about humble confidence. Humble enough to always be learning from those around you, which can include things you want to emulate and things you don’t, and the confidence to really believe that you deserve to be in the space and role that you’re in. I have an eight year old daughter who plays ice hockey. She’s frequently the only girl on her team and she’s learning early what it takes to own your right to be there and to back it up with what she brings to the game. This doesn’t mean she has to “be one of the boys” to try to fit in. It means finding her own way by being confident in her skills and what she brings to the team. I see parallels for young women in the professional world regardless of industry.
EA: There are a few things they can do.
(1) They can encourage open conversation. One of the biggest drawbacks of not being in the office regularly is that the conversations that used to happen aren’t happening as often. If I had a tough moment, there were five women I knew whom I could go into a conference room with and ask for their perspective on something that had just happened. It’s harder to do that now with remote work. And we don’t always get the same cues from the body language when we’re on Zoom, so it can be more difficult to see how things are landing. So checking in with other women and making ourselves open to others who may be experiencing the same challenges we’ve been through is critical.
(2) They can give each other unsolicited feedback, both positive and constructive. Whenever someone is presenting, I try to give some feedback immediately afterward (regardless of the presenter’s gender) that they can implement fairly easily. I also offer to do run-throughs with people who might have a big meeting or presentation coming up so I can help prepare them for it.
(3) It’s critical we advocate for each other. I don’t mean supporting someone just because they are a woman, but I do mean advocating for those who deserve it, especially when they don’t have an advocate in the room.
Finally, (4) focus on your own development. We all have things we need to work on; maybe we could improve our communication style, or learn how to influence better or whatever it might be. We need to not feed into a narrative that it’s always about gender because this prevents us from actually addressing other issues that may be holding us back, so we need to be honest with each other about our opportunities to improve.
What advice do you have for women who are early on in their careers?
MC: Be open! When I work with early career employees, it often feels that they’re on a hyper fast timeline to get promoted and climb the ladder, whatever that means. The problem with that is you may climb that ladder with a single minded pursuit of the next promotion only to find you don’t like the view. I would encourage people to use the first five years to explore what they really love to do – what problems they want to be thinking about, what impact they want to have – and be open to opportunities that come their way even if the immediate payoff isn’t evident.
My career would have never taken the pivot it did if I wasn’t open to an entirely new path than what I set out for myself when I declared my major or got my first job. I suspect FOMO is in the mix – the fear that you’ll fall behind if you’re not moving in a forward line at all times. That’s real and I get that, but careers are long and the early years are the best opportunity to redefine the idea of career growth in terms of learning and developing skills and experience that will have a greater payoff down the road versus climbing the first career ladder you step on.
EA: (1) Find managers and mentors who believe in you and are willing to advocate for you and who are willing to be honest with you about your strengths and your opportunities to improve.
(2) Ask for a lot of direct, specific feedback. I have found that asking questions like “If you had a magic wand and could change the way I do something, what would it be?” or “What are three things I could have done better in that meeting/presentation/etc.?”
And (3) don’t wait for the opportunities to come to you. Some of the best experiences I’ve had in my career came about because I sought out an opportunity before it existed. This could be a project you’d like to work on or a role that may not exist yet. If you want it, go after it rather than waiting for it to come to you.
Lastly, who is your role model? Why?
MC: There are a lot of women I admire. One who comes to mind as a role model is Amanda Lannert, CEO of Jellyvision. Amanda has been a successful female CEO for over a decade. In addition to building an incredible company with an enviable culture, she is deeply invested in supporting founders – especially women and underrepresented tech leaders – throughout Chicago and beyond. She is a mentor, a super connector, and relentlessly committed to lifting others up around her.
EA: I have many. There’s a print of RBG (Ruth Bader Ginsburg) on the wall in my office. I went to law school because I wanted to advocate for others. I admire her ability to influence in creative ways and to fight tirelessly for what she believed was right. She didn’t let anything stop her from pursuing justice, and I admire that.
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