Women of Color Blazing Trails: A Conversation with Issa Rae & Laysha Ward

Show Notes:

This episode is a special way to kick off Black History Month by bringing you an extraordinary keynote conversation between producer, actress and writer Issa Rae and Target’s EVP and chief external engagement officer Laysha Ward. This conversation happened at the October 2020 Texas Conference for Women.

Featuring two pioneers who are blazing trails for women of color and all women and girls around the globe, Issa Rae and Laysha Ward talk about many timely issues—including leadership, breaking barriers, race, justice and women supporting women.

“Unfortunately, part of the frustration is we’re going to have to do a lot of the work.

I think Black people have been doing the work to be recognized and to achieve equality and fairness for centuries now. But, while we continue to do that work, we have to have allies, white people specifically looking around and deciding to take action, deciding to hold one another accountable.

Progress is only going to come when white people can recognize that we’re not equal. We don’t have the same opportunities. We’re operating at a deficit.

It’s up to the people who understand existing systems to understand that and do something about it, and want to do something about it.”—Issa Rae

This Month’s Guest:

ISSA RAE is a producer, actress, and writer. With her own unique flare and infectious sense of humor, Rae first garnered attention for her award-winning web series and the accompanying New York Times best-seller, The Misadventures of Awkward Black Girl. She created and stars in the hit HBO show, Insecure, for which she received an Emmy® nomination and two Golden Globe® nominations. Rae made her film debut in the acclaimed drama, The Hate U Give, and most recently starred in the romantic comedy, The LOVEBIRDS. @IssaRae

This Month’s Special Guest Host:

LAYSHA WARD is an accomplished C-suite executive with thirty years of leadership experience at Target. In 2017, Ward was named executive vice president, chief external engagement officer, overseeing Target’s enterprise-wide approach to engage and deepen relationships with cross-sector stakeholders to drive positive business and community impact. In 1991, Ward began her career with Target as a member of the store sales and management team of Marshall Fields in Chicago. In 2000, she was named director of community relations and promoted to vice president of community relations and Target Foundation in 2003. In 2008, President Bush nominated, and the U.S. Senate confirmed Ward would serve on the board of directors of the Corporation for National and Community Service, the nation’s largest grantmaker for volunteering and service, which she continued to serve as board chair under the Obama Administration. Later that year, she was promoted to president of community relations and the Target Foundation. She serves on the Aspen Institute Latinos and Society Advisory Board and the Stanford Center for Longevity Advisory Council, is a member of the Executive Leadership Council, the Economic Clubs of New York and Chicago, Alpha Kappa Alpha Sorority, The Links, and serves on the boards of Greater MSP, the Minnesota Orchestra, and the Northside Achievement Zone, and Denny’s Corporation for-profit board of directors. She received a bachelor’s degree from Indiana University, master’s degree from the University of Chicago, and an honorary Doctorate of Laws from the University of Minnesota’s Humphrey School of Public Affairs. She and her husband, Bill, reside in Minneapolis, MN.

Additional Resources:

Visit IssaRae.com
Buy The Misadventures of Awkward Black Girl from Austin-based independent bookseller BookPeople
Register for the all-new March 4 California Conference for Women – featuring Stacey Abrams, Jane Goodall, Angie Thomas, Ursula Burns, Glennon Doyle, Adam Grant, and more!

Issa Rae & Laysha Ward Conversation Transcript:

Laysha Ward:
All right. You’ve gone from TV to film to music. You’re not only an actress and a writer, but a director and an executive producer with your own production company. And on top of it all, you’re a music mogul with an audio content company that includes a label that’s a joint venture with Atlantic Records. That’s just dope. It is. It’s dope, totally dope. Tell us about being your own boss and the boss of others and what that’s like.

Issa Rae:
Ooh, that’s a whole different muscle. I came into this wanting to be a creative and I think by way of starting out on YouTube actually and being online, you’re kind of being your own marketer, you’re starting a business, you’re collaborating with others, which means you’re managing others in some way, if it’s your vision. And as all of that is grown and I started to attempt to cement my place in this industry, it means hiring with people, hiring people who are absolutely smarter or more capable and who are experts in certain areas and trusting them.

Issa Rae:
But that’s a different muscle. Managing people is one thing and then trying to create is another thing and then building a business is another thing. And so that’s not exactly what I signed up to do and I find myself stumbling a lot and learning along the way, but luckily I ha I work with patient people who are also learning as well and they may have experience in areas that I don’t. And for me sometimes I just want to be like, “Y’all, figure it out. I have to do this,” and the drama, like, “Get over it because I have to get over it too,” but that’s not what bosses or good leaders are supposed to do, so I find myself really struggling to navigate that part. But it’s part of the territory.

Laysha Ward:
But clearly, you bring something quite magical, right? You have a growth mindset. You’re curious. You’re a lifelong learner. But what’s also interesting to me, Issa, is that you didn’t study business.

Issa Rae:
Outside of trying to take the GMAT, no, I did not at all.

Laysha Ward:
I’m not going to ask you your score, girl. It’s okay.

Issa Rae:
Don’t.

Laysha Ward:
How did you learn to be a successful entrepreneur and leader? You have a lot of hustles going on. How did you make all of that happen?

Issa Rae:
I think once people see that you’re serious about you and you’re serious about your product, you’re serious about your journey, they’re more inclined to come along for the ride with you. I think I’ve been fortunate enough, again, to work with people who are passionate, who are driven, who are entrepreneurial themselves. And so as I mentioned, they have different fields of expertise and they’ve been instrumental in informing me. And I am, like you said, a lifelong learner. I know what I don’t know and then I find out what else I don’t know and I’m confident in what I do know and what I do bring to the table.

Issa Rae:
Being very collaborative and not getting hung up on, “I have to have all the credit and people need to know that I did this by myself,” is not who I am at all. And I think that that’s been beneficial just in terms of growing and building. I’m learning on the job, and I’m candid about learning on the job. You kind of have to be because nobody wants … Yeah, I’m not trying to be the emperor with no clothes, so I’m showing you that I’m naked.

Laysha Ward:
But I think that is inspiring probably for your team and other collaborators who are working with you, right? That you’re on a learning journey, that you’re building a high-performing, creative, diverse team, and that you’re all getting better together I would imagine makes you someone people really want to work with.

Issa Rae:
If you’re patient, which you kind of have to be, because again, I will say that for all my missteps, I will always learn from my mistakes and I’m a fixer. If you come into me with a problem, I hope you weren’t just trying to vent because I’m going to fix it. And so I think in that way, sure, I’d be great to work with. But yeah, I think we foster a community of being forgiving of mistakes and yes, we’re on a journey together, and I think that’s what makes it exciting is that you can take risks and fail or fuck up and it’s okay because we’re resilient and we’re going to keep going.

Laysha Ward:
But that is a bold thing for you to say that it is okay to take risks and it is okay to fail because we will learn from that and get better. People don’t always hear that. And I think it’s sometimes even harder for people of color, black folks, women who often aren’t given the additional airbag and the opportunity to fail in the same way. And so I think you’re creating a safe space for people to do that.

Issa Rae:
Yes. I think you have to, but make no mistake, the risk has to be a good risk. You can’t just be out here risking and fucking up every day. But I think especially for us, we always have to be twice as good and all of that. But I think in our environment in particular, there’s a recognition that you’re good enough to be here and as long as you want to be here, that’s part of it. And then how are you going to stay here? And it makes it competitive, but in a very fun way.

Laysha Ward:
Yeah, which is awesome. We all have to believe that we’re worthy, that we deserve the opportunities that are given to us, for sure.

Issa Rae:
Definitely.

Laysha Ward:
Okay Issa, you’re making badass boss moves and it’s so inspiring to see your success. And the theme of this conference is leading the way forward. And many women in this community are leaders in corporations or their businesses. Would you share some of the most important things that you’ve learned about growing into a role as a leader, especially in what remains a male-dominated industry?

Issa Rae:
I always have to say, relying on my female peers. I have to foster a community of women who support one another. I think that that’s so essential because we’re constantly pitted against one another and underestimated and I think there’s nothing more valuable than a support group of women who understand and whose power, whose intelligence, whose drive that you also respect and appreciate. Fr me, I’m always about fostering that kind of community for myself and surrounding myself with women who are capable and who I admire.

Laysha Ward:
I love that. We often hear that, as you said, women are pitted against one another and that there’s only room for one woman at the table or in a leadership role. And we know that’s just not true.

Issa Rae:
No.

Laysha Ward:
There is room for multiple lights to shine. And in fact, when you have more than one woman in a leadership role in an organization, the organization is usually infinitely more successful.

Issa Rae:
Oh yeah.

Laysha Ward:
We need to create that space for one another. And if there is no seat at the table, we need to pull up another seat. We need to build the table ourselves, whatever it takes to get more women in leadership positions.

Issa Rae:
Yeah, absolutely.

Laysha Ward:
Now, you have been so successful at bringing other women along. What has been your secret to success? Do you seek out women in particular roles in the companies that you’re leading or do you then provide opportunities through women networks that you’re a part of? Where is it that you’re creating this community of women so that there are more of us in positions of power?

Issa Rae:
That’s a great question. I think know I’m naturally drawn to other women I think just because I appreciate the leadership style of many women. A lot of the women that I’ve worked with in the past have been extremely ambitious but also very lax and absolutely intelligent and knowledgeable. They’ve always had to do more. They’ve always had to compete and they have a lot to prove. And so I think I found them like I find a lot of my people that I’ve worked with, just through natural environments, like did I go to school with them or by recommendation, friends of friends?

Issa Rae:
But I really just seek out people who want this, who want to be a part of this, who are innovative, who are excited. And I’m really just naturally drawn to passionate people because I feed off of that. When someone else is excited about a particular vision, it can get you excited too. And there’s just nothing more valuable than that. I feel like women just have a special skill in terms of motivating people around them.

Laysha Ward:
So true, right? You’re creating the shared community and you’ve been very intentional about building a network of supportive women, which is so encouraging. There’s a group of women I meet with every week now on Zoom. We call ourselves the Mocha Moguls. It’s 10 black women-

Issa Rae:
Love it.

Laysha Ward:
… and we’re there to support one another, learn from one another, lift each other up and cheer on our accomplishments, but also to catch each other when we fall. And there’s something about that sisterhood that is so sustaining.

Issa Rae:
It really is, and there’s nothing … I have a similar group weekly and there’s nothing like being around people who understand you in a way. It’s so underestimated. There’s a certain empathy that we share with one another that is unmatched and it’s so comforting.

Laysha Ward:
What do you see as the problem with the portrayal of black people and women in particular in the film and television industry and why does that matter in our quest for justice and equity?

Issa Rae:
It matters … The problem is that the portrayal has been extremely limited. I grew up in the ’90s where I had a plethora of options for representation, whether that was Laura Winslow or that was Will Smith or Myra Monkhouse, whatever. I felt like I had options growing up as a young black girl. Moesha, of course. And as I grew into a black woman, I noticed those images going away and I saw that the representation of black women, black people in particular, it wasn’t great. And I witnessed myself and my peers shape who they thought they were, who they thought black people should be by the images that were represented onscreen.

Issa Rae:
The more … The less options we had rather, the more narrow the definition of blackness became and the more harmful in many cases, whether that was the stereotypical criminals or the hypersexual black women and all of these harmful stereotypes that shape America’s perception of black people. And even thinking about the cop shows and Law and order and things like that, that is shaping an entire society’s perception of who black people are. And so I think I find it extremely important to showcase alternatives of the negative representation that we’re constantly seeing, and it’s realistic.

Laysha Ward:
So powerful that you’re talking about making sure that you’re bringing attention to the need to help us reshape the narrative and that you’re doing the work and challenging others to do the same. Thank you for that. Two of your best known projects, Awkward Black Girl and Insecure, focus not on portraying black people in the most positive or ideal light, but in the most human and relatable one. Why is that?

Issa Rae:
Because while I think that positive representation is healthy, I think that it’s unrealistic and it’s unachievable. I think it can be sometimes harmful and perpetuating black people as flawless and fierce and superhuman when we are just human and we are flawed. And I’m more interested in telling those stories because those are the stories that are relatable and those are the stories that are universal. And I think that there’s something unifying in telling stories where people don’t have to have the same experience as you, but understand you by way of being human, that you’re able to bring them into your world and you’re able to make them empathetic and there’s something powerful in that, as opposed to constant positivity in an effort to negate a history of negative images, and those stories are just fun to tell.

Laysha Ward:
Let’s stay on this point of being true to yourself, your authentic self. Now, one of the things that so many people love about you is your authenticity. As one writer put it, you’re a great reminder that stereotypes stink and that being your authentic self is the key to happiness and success. What helps you break through stereotypes and to be your true self?

Issa Rae:
I think just by understanding who I was. I think that as a creator and as a writer, you’re always trying to find your voice and your voice is useless if it’s like everybody else’s or if it’s diluted in any way. What’s the point of having a voice if you’re not going to make it your own? And that’s something that I had to develop and hone over time.

Laysha Ward:
Powerful. The world needs an original version of you, not an imitation of somebody else, right? You got to do you.

Issa Rae:
Absolutely.

Laysha Ward:
And I think being your authentic self also gives you the energy to do the hard work toward racial equity and social justice that’s needed, right? Because change isn’t going to happen overnight. But some people do worry that as time goes on and that we focus on recovering from COVID and a disrupted economy, the energy to confront racial injustice is just going to take a back seat. What do you think we need to do to keep it alive amid all of these important priorities?

Issa Rae:
Unfortunately, which is part of the frustration, is we’re going to have to do a lot of the work. I think black people in particular have been doing the work for centuries now to be recognized and to get equality and fairness. But while we continue to do that work, we have to have allies. We have to have white people specifically looking around and deciding to take action and deciding to hold one another accountable and progress is only going to come when white people can recognize that we’re not equal, that we don’t have the same opportunities, that we’re operating at a deficit.

Issa Rae:
And so it’s up to these existing systems and the people that work these systems to understand that and to actively do something about it and to want to do something about it because there’s comfort in the status quo and the way that things are. And the sooner that you realize that you’re contributing, whether or not you have your own personal views of racism, you’re contributing to racism by not doing anything, by essentially being complicit in allowing things to continue the way they are. I can only do so much. We can only do so much. It’s up to you to ensure that things change.

Laysha Ward:
Right. We need allies. We need partners in the fight. We need people to have the will to stay with the work over a multi-year time horizon. We didn’t get here overnight. We’re certainly not going to get out of it overnight. But you raise this important point that black folks have been doing this work for centuries. And there is a level of exhaustion and yet we don’t have an option. We have to keep doing the work, but we just need other folks to come along on that journey with us.

Issa Rae:
Yeah. I thought I had the luxury of being tired, but I don’t. Unfortunately, that’s our battle to fight until it’s right.

Laysha Ward:
Yeah. It’s interesting that there are some folks who are saying that they just wish things would go back to normal, post-COVID, racial uprisings, but at the end of the day, don’t want things to go back to normal because normal in this country has not been good for black and brown people. I want a new normal, one is more just and more equitable and that requires all of us, as you just said, Issa, to do no work.

Issa Rae:
Yeah. Normal is almost like … It’s like we’ve been living under this rock and someone lifted the rock and you’re seeing just all the gross shit that was underneath it. And you’ve seen it now. You can’t just put rock back. It’s still going to be there. So yeah. There’s no such thing as going back to the normal. It’s always been fucked up.

Laysha Ward:
Yep, and it’s time to flip the switch. It’s powerful to hear you talk about how you’re using your agency and power to be the change that we seek. And I’m curious if as you’re doing this work with your peers throughout the entertainment industry, are they looking to you as a role model to speak the truth, to use your voice, to drive action in a way that sets you up in a different position of power as a leader in this moment?

Issa Rae:
Maybe within the industry. I think we’re all looking to each other to use our voices most effectively. But I think if anything, this pandemic has taught us that we’re not the most important voices. There’s certain things where we need to take a step back. I think if we need to financially support things, if we need to encourage from behind the scenes, but nobody wants to hear from voices in our industry. It doesn’t matter. In some ways people consider us above the fray of it. We’re not on the ground in many cases suffering in the same way the everyday person is. I think it’s up to us to empower the everyday voices, those who are most affected.

Issa Rae:
But I know for me, the last thing I want to do is hear from a celebrity about what to do and what to care about. And again, this pandemic and some of the messaging behind it has been obnoxious coming from us. I navigate where to speak up and what to do and find that there are certain issues that … like voting and encouraging people to become poll workers and getting involved and things like that, I feel absolutely comfortable speaking out about it if that’s how my platform can be helpful. But beyond that, I’m not really who you need to hear from.

Laysha Ward:
I love your candid conversation about you being clear about what you think your role should be, what lane you want to swim in and where you also want to ensure that leaders who are on the ground, place-based workers, right, black-led organizations who have a different perspective and are representing a different voice, should be taking the lead. Thank you for that. I’ve heard you talk about the influence of so many successful women and how they have provided inspiration for you and you said that you’re modeling yourself after Oprah, and yet you’ll do it in your own way. What’s next for you?

Issa Rae:
So much. I mean, as you mentioned, I have a music label right now. I’m opening an office in South LA, which is where I was born and raised. I want to use up all the opportunities that I can while trying to bring as many other people that I love, that I respect, that I admire, that I want to see through the door as well. I think that for me is just the most part is building businesses around other people and seeing what they do and who they bring through the door and creating … a pyramid scheme is the wrong word. I’m sure there’s a way better way to put that … a pyramid scheme without the scheme. But I think that there’s so much value in … We’re the only ones that are going to support one another. We’re the only ones that are going to pull each other up and to be able to in the spirit of fostering communities, do that in the entertainment industry and maybe outside of it, hopefully one day is my mission. And that’s kind of what’s next for me.

Laysha Ward:
You’re paying it forward and you are-

Issa Rae:
That’s a way better way to put it. Thank you.

Laysha Ward:
Instead of a pyramid scheme, we’re talking about opening up doors of opportunity.

Issa Rae:
Yes. Way better.

Laysha Ward:
Right, because at the end of the day, there is an opportunity gap for so many people, including women and people of color and certainly for black folks. And so it really is about breaking glass ceilings and opening up doors of opportunity so that more people can flow through and sending the elevator back down and bringing other folks back up. And so it is super inspiring to hear you talk about that as a part of your personal mission.

Laysha Ward:
Whatever you choose to do next is going to be phenomenal because you are a bad sister, and I know you have so much creativity and so much that you’ll be doing over the next several years, and I don’t know how you keep it all going. And so I am curious to hear you talk about prioritization. You have so many things on your plate. You’re so busy. How do you manage all of these different opportunities that are coming your way?

Issa Rae:
Well, first, thank you for the well wishes. I receive that. I have found that it can be overwhelming, but like it has for so many people, this pandemic and the quarantine has really allowed me to recognize that my time is important and to focus on the best way to manage my time. And I’ve always been very routine-based and where productivity is concerned, I realize that I’m only good during specific hours and to maximize those hours, and the more freedom I have to do me and to tap into what makes me me and to generate free time for myself, the better I am. And so I’ve been really fortunate enough to get back to the roots of my creativity and focus, because that’s what fuels me as well.

Laysha Ward:
It’s really interesting to hear you talk about prioritization of time, right? Time is a precious resource and you’re treating it like that so that you can make the time and space in your day and in your life to do the things that give you energy and bring you joy, which is just a great lesson to be sharing with people.

Issa Rae:
And I will say that I definitely, again, rely and trust the people that I put in place to also work with me. And that’s something that I had to learn because I used to be a micromanager. I used to be a control freak. And in some ways I feel I’m definitely still a control freak, but it’s really comforting to be able to trust the people that I work with to do their jobs and to sit back and let them come to me when they need me.

Laysha Ward:
That is a sign of a great leader, right? Trust your team, don’t micromanage them, give them the space to do what they do well, and that gives you the space to do what you do well and to fuel all the other things, quite frankly, that you want to do.

Issa Rae:
100%.

Laysha Ward:
Yeah. And thinking of new things you want to do, you recently starred in the HBO series, Coastal Elites, which explored the pursuit of connection during a pandemic. Timely, right?

Issa Rae:
Yeah, quite.

Laysha Ward:
Yeah. Quite. Connection is central to the conference for women communities. What have you learned about connection through the experiences of 2020?

Issa Rae:
How much I need them, how central they are to our entire existence, our dynamics. I think I would have never imagined, even something as simple as the writer’s room that we’re in. I’ve been in for five seasons now and seeing how different everything feels just on a computer screen and not being able to have the in-person energy, not being able to feed off of the connection of people in the room. And on my personal side, in my personal life, realizing how focused on work that I’ve been that I’ve neglected a lot of my personal connections and those connections have also fed who I am and my point of view and I’m not nurturing those connections or wasn’t nurturing those connections as much as I should have been. And so 2020 has taught me to put more value on those connections than ever before and I think specifically, I want to … I guess I realized even being outside in and living life and seeking more connections is also valuable to my work. It’s inspiring.

Laysha Ward:
This has been an extraordinary conversation. Thank you for keeping it real, speaking your truth and challenging us to claim our agency as women and girls who will lead the way. Thank you to the entire Texas Conference for Women community, and please enjoy the conference.

Issa Rae:
Thank you so much, Laysha. This has been an extreme pleasure, the highlight of my day. And thank you, Texas Conference for Women, for having me.