Checking our privilege as white DEI professionals with Megan Dalessio

Welcome to Crescendo Chats: Scaling Diversity & Inclusion. In this series, Crescendo co-founder Stefan Kollenberg hosts conversations with HR and diversity & inclusion practitioners, sharing valuable insights from their work. 

This week’s conversation with Megan Dalessio, Senior Manager of Equality and Belonging at Gap Inc.

Listen to the podcast or read below for the edited transcript. 

Stefan: For people who might not know you, can you share a little bit about yourself and the work you do?

Megan: I work on the Gap Inc. Equality and Belonging team. Gap Inc. is the parent company of six different brands, including Gap, old Navy banana Republic and a few more. We have a pretty small, but a growing team that supports the entire enterprise. So that includes our headquarters, all of our brands. 

I manage our portfolio of external partnerships, most notably with this really amazing organization called Harlem’s fashion row. I also support our seven equality and belonging groups, some places call them affinity groups or ERGs.

Before I joined Gap Inc., I started my career as a first grade teacher, and after doing that for a couple of years, I transitioned into the high tech sector. That was where I got into recruiting, and from recruiting, is where I got into diversity work full time. Once I made that switch, I ended up building two separate DEI programs, one at Cruise most recently, a self-driving car company, and the other at Box, a cloud software company.

Gap Inc. is an entirely new and different scale for me. It's an entirely different industry. It's been really fun to figure out how to work within all these new parameters and also get to work for a legacy organization that has a tangible product that we can impact.

Stefan: Something I love to talk about with guests is identity. It’s something I personally do a lot of reflection on, and so I‘d love to hear from you - what do you think of as your identity and how does that shape the way you view the world?

Megan: Yeah, absolutely. As white people working in the D&I space, it is incredibly important for us to constantly be interrogating our own biases, our relationship to whiteness, and other vertices of oppression. For me, I definitely own my identity as a white woman and all of the complexities that come along with that, particularly in the line of work.

Other aspects of my identity that impact how I move through the world are that I am able bodied and I have struggled with mental health issues for many years in the form of clinical anxiety and depression. Outside of that, I am cisgender. I'm recently starting to really own and come into my identity as queer. The last thing relevant to the work I do for Gap Inc. is that I sit at the top of what we call the straight size range, so I have been into learning more about the fat liberation movement, and really trying to understand weight as a dimension of oppression, particularly because it impacts my life on the daily. I'll say identity is definitely super complex and there are lots of other factors, but those are probably the aspects that are most top of mind for me recently.

The thing that has been most interesting is the body positivity movement, which is all about the self. The idea of fat liberation is about not putting all the pressure on yourself, but contending with the burden of how all of us, regardless of size, think about and process our own bodies and our weight as something that is systemically oppressive. That has been super transformative for me.

Stefan: What privileges has whiteness afforded you throughout your career?

Megan: It's indisputable, right? Specifically, really in a way that it has enabled me to assert myself in spaces that don't often feel safe or even accessible for people of color. Particularly when it comes to issues of inclusion. It's afforded me a lot of privileges. Whiteness predates my career, so I'll share a story from my college days that I think helps kind of illustrate that.

It's my sophomore year at Berkeley and I joined this white anti-racist group and we were discussing the concept of taking up space in predominantly people of color or POC spaces. At the time, it was something that I really struggled with because I felt like my unique personality just wasn't fully taken into account. I'm just the kind of person who grapples with new ideas by thinking out loud. I'm very conversational. It's not that I'm taking up space.

Our facilitator said, “Megan, that may be the case. And it's important to recognize that in POC spaces, that is likely not how you are being perceived.” I return to that moment a lot for the way that my own relationship with whiteness meant that I felt entitled to be treated as an individual without considering my impact or even the disparity of experience for people who don't look like me. A really important part of my practice as a DEI professional is to actively be cultivating curiosity and self awareness so that I can be a better accomplice in the struggle for justice and a more critical, double agent in my work.

Stefan: How have you gone about unpacking your own privilege along the way?

Megan: It's lifelong work, it doesn't stop. It's not like I graduated from Cal and was done with my learning. I'm still learning all the time. The most part of unpacking my privilege has been having a community. A community that is also committed to reckoning with white supremacy and other systems of oppression that I benefit from, and to have friends and colleagues who are committed to that same kind of ongoing process of interrogation.

It is really helpful to have folks that I can talk through those big ideas with, and the other thing I'll share that has been probably the single most important thing that I do as a pretty avid consumer of social media, is diversifying my social feeds.

I used to have a pretty long commute to work and I'm a huge podcast head because of that. I remember going through my podcast one day and realizing that every single podcast I listened to was hosted and produced by white men. From there, I made a really concerted effort, in the same way I had already done with my Instagram, to mix it up and get some new voices and perspectives. It's super important to actively seek out perspectives different from your own and I do that across every platform. 

Having the point of view of queer people, Black people, indigenous folks, people who are disabled, people who are experts in immigration, and fat liberation activists has contributed to and continues to contribute to my own personal growth.

Stefan: What are a couple of podcasts you'd recommend listening to?

Megan: First and foremost, I am a die-hard Code Switch fan - it's a really fantastic podcast, all about race and culture, hosted by Gene Demby and Shereen Marisol Meraji. She's half Persian and half Puerto Rican and Gene himself a Black man. They regularly have guest hosts that are entirely people of color. 

I've been pretty obsessed with Throughline, which is all about connecting current events to parallel moments throughout history, so that we can understand the current moment better. 

Stefan: a lot of white people have been woken up to the reality of racism and discrimination - and so I think it’s crucial that we talk about white supremacy & privilege to start our conversation today. As a white D&I practitioner, what are some of the things that you are mindful of when doing this work?

Megan: Absolutely. There's often this real cult of personality in this space, and I feel pretty strongly that it's important for me as a white woman in this space to primarily use my platform to amplify the voices of people of color. This looks like crediting the POC leaders that I learned from. It means that I defer to the leadership of people of color. I'm always in that process of suspend your disbelief. Let's honor the fact that for this person, that experience is true. If there's a disconnect here, what am I missing? Constantly arriving with curiosity and humility to those conversations.

Stefan: What mistakes have you made along the way? 

Megan: I think that it’s really important to be open and honest about our own learning. At Cruise, I was pretty new in my role. I had been there for a little over a month and we were coming up on Juneteenth, the celebration of the end of slavery.

The prior year, Box had this really beautiful, amazing, Juneteenth celebration. It really was an inspiring and uplifting moment for the Black community at that organization. So I came in, fired up, and I went to the Black employee group meeting. “We got Juneteenth coming up. Let's pull our committee together. We got to get to planning.” And I was pretty much met with blank stares, which I was surprised about. The first thing going through my head, in all transparency, was what is wrong with these folks? Why don't they want to celebrate Juneteenth?

I had to take a step back and say, help me understand what the disconnect is here and what it came down to was the fact that that community just wasn't ready to have a visible celebration centering around the end of slavery within the organization. My assumption put everyone in an awkward position. I hadn't asked the right questions. I did my best to receive that feedback and gratitude, and to apologize sincerely for my mistake and rectify the way that I had been so hasty, to listen. It's important to be a continual student in this space.

Stefan: Did someone call you out or call you in for that mistake? How did you respond?

Megan: In the previous example, the blank stares were a bit of a call out, right? I would say the most important thing is to receive feedback. However, it comes with a spirit of gratitude because you think about the amount of discomfort and energy it takes for a lot of folks to call out a racist moment or an inappropriate moment.

I often think about all the times that I have made hurtful comments that I wasn't aware of that impacted people. They just swallowed it and wrote me off. I think feedback in general and call outs can be such precious gifts to us in our own growth. It's a sign of mutual respect and what I mean by mutual is that whoever is calling me out is showing respect for themselves, either their identity or their values, by naming a behavior that's problematic. They're respecting me enough to trust that I can and will do better, and I'm able to receive it. 

Stefan: When someone is being called in or called out for a comment that they didn’t perceive as racist, but is racist, how should they react and respond in order to reduce any further harm being caused to the individual who took the time to share that feedback?

Megan: In terms of responding to feedback. The approach that I take first is pause, breathe, sit with it. Try not to react because when it comes to issues of identity, belonging, fundamentally, those are questions about our values, and our values are at the core of who we are as people. When people are generous enough to really share that feedback and to say something important, receive it. 

First is pause, the second is to be curious. “I didn't realize that I was doing that. Can you help me understand?” Ask questions and know that no one owes you answers to those questions. It's important to be interrogating yourself in that moment. 

The third thing is you have to own it. Own a mistake, own the impact it had, and most importantly, commit to doing better. The thing about all of this is no one owes you any follow up. White people must reckon with the fact that people of color may not ever fully trust you, which is fair and deserved given the history.

Stefan: How can you effectively create space for Black employees to be open and vulnerable with the challenges they face at work without putting the burden to solve those problems on them?

Megan: It's not Black people's job to educate folks on the Black Lives Matter movement or why their personal Black life matters. It is our job. We have chairs of our Black employee group, called AANG, an African American networking group.

I had side conversations with the two leaders of that group and I said, “I want to fully empower and give you space to lean into this conversation. However much you want. You're a valued extended member of this team, and this is a huge moment for the community. At the same time, it's an exhausting moment to be a Black person, so whenever you need support, throw it my way, because it's my full time job. I literally get paid to field these questions.”

I think there's a little bit of a balance where you give people the space to lean in and make sure they know that they have your support. Give them the permission to act out what I had noticed in a lot of conversations.

We've been doing these listening tours, with our Black and Latinx employees. A lot of the Black people on the call expressed a feeling of guilt around not having been more actively engaged in conversations before, and actually the lead of our Black employee group, Carrie, made a really beautiful return question when this one employee mentioned that and said, “but did you feel safe to do that at the time?” 

I want to help make this as safe as possible for you at this time and feel free to lean out. They've been stepping up and doing amazing work and they're very high in demand. Every now and then, I'll get an email saying, “Hey, I'm looping in Megan from the equality and belonging team, she's actually a better resource for you on this than I am.” So it's a little bit of a give and take, but that's how I've been navigating that specific conversation.

Stefan: What are some of the things you’ve done at Gap Inc. to help employees start their anti-racism journey?

Megan: The one thing that I’m most excited to share is this virtual series that we're hosting called Real Talk. It's essentially a moment for all of our employees across the company to tune in or to watch a recording of a conversation about race. This past week, the discussion topic was microaggressions, and we've talked about Black lives matter versus all lives matter.

Not only are we hosting these real talk sessions, we are also providing tools and resources for teams to have follow up and debrief discussions. For a lot of folks, this is the first time they're being exposed to this information. We've seen a lot of really amazing vulnerability come out of those sessions. It's been a good reminder to me that everyone's in a different place. It's super important to create space for newcomers to learn, mess up, and recover and acquire new knowledge. 

It's also really important to protect people who are living through those experiences. The other thing is supporting and coaching leaders, people leaders, for how that conversation is going to look different when you have Black people on your team.

Stefan: Who are three amazing Black Practitioners that you look up to in the DEI field? Can you share a memory that really sticks out for each of them?

Megan: On the Real Talk series that we're hosting, one of the main featured guests who has been creating and planning a lot of that content is Amber Cabral, who owns and operates Cabral Co., a full cycle DEI consulting firm. The memory I'll share about her is when she was delivering her first quote, “Real Talk” to the organization. There was a moment going through the content where she was talking about how being Black is a never-ending experience. You could kind of hear it in her voice and see the emotion in her face. That generosity of spirit to share herself in that way to be engaged in this work, in this way, when it is so deeply personal, that is part of what makes her so effective.

I want to highlight Stacy Parson and Angela Taylor, two folks who operate the Dignitas Agency together. I worked for them for a time, and the memory that I'll share from my time partnering with them was when we got together at this cafe in Palo Alto for a brainstorming session. Just getting to watch them bounce off each other - they are both such big thinkers who are truly taking off on systemic change. What is brilliant and beautiful about their practice is the way that they managed to break it down into bite sized pieces that are digestible for individuals. Both of them have backgrounds in executive coaching and have been mentors and coaches to me.

I would also give a shoutout to Abby Maldonado, now an HRBP at Pinterest, who was the person that really built up their D&I program in the early days. When I was starting to dip my foot in at Box, Abby was super generous with her time and resources. We were trying to figure out how to redefine our university recruiting practices and our employee referral program. We talked through her journey and her experience and that advice was fundamental to my own development and establishing myself.

I want to give a shout out to Kisha Modica, Head of Equality and Belonging at Gap Inc., and then an educator, an activist, a writer who does not work in the D&I space specifically, but has been an incredible teacher to me, Sonya Renee Taylor. If you're not following Sonya Renee Taylor on Instagram, I strongly and highly recommend checking out some of her videos.

Stefan: Do you follow any Black Yoga Teachers? Any recommendations?

Megan: Anasa Yoga is co-founded and managed by two Black women, Jean Marie and Zola, and they are currently offering virtual classes online right now during the shelter in place, which is exciting because it means everyone has access to them.

They use a variety of different instructors as well, so there is a little something for everyone. The other Black Yogi that I really admire is Jessamyn Stanley, and if you're not following her already, definitely missing out. She's someone who really understands the mental and physical connections between well-being and brings that lens of body positivity to the yoga space.

Stefan: Lightning round: Favorite quote? 

Megan: Everyone thinks of changing the world, but no one thinks of changing themselves, which is a Leo Tolstoy quote.

Stefan: What motivates you in life?

Megan: Justice, the goodness of people, ice cream and my dog Peperoncini.

Stefan: Top recommendation for social media accounts to follow?

Megan: Sonya Renee Taylor, but I would also give a plug for the Fat Liberation Movement, Your Fat Friend @yrfatfriend.

Stefan: Favorite podcast? 

Megan: Code switch.

Stefan: What is the coolest tech product you've ever come across?

Megan: I got to tell ya that I am not much of a gadget gal, but what I will say is I did buy a battery operated handheld fan that saved my life when I was in Italy last summer.

Stefan: How can people connect with you?

Megan: Absolutely LinkedIn.

Stefan: Thank you so much for joining us today!