Civil-Rights Attorney Maya Wiley on How to Keep Fighting the Good Fight

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When Maya Wiley was 5 or 6, she and her brother heard a commotion downstairs at their house. “We were never allowed to get out of bed, but on this particular night, we snuck downstairs, and no one stopped us. All these powerful women leaders — who were also welfare recipients — were sitting there, angry and upset.”

The women had been arrested for civil disobedience, and the judge in their case was ideologically opposed to what they were protesting. He decided to use the bench to keep them and humiliate them individually. This was the first time, at a very young age, that Wiley realized it mattered who has power and who does not. “We used to watch my father, who was a civil-rights activist, get arrested on TV sometimes, and we never knew if he was going to be home for dinner,” she told the Cut.

“My mother told me, ‘Don’t have children until you’re 30, and get a graduate degree. You’re going to have your own checking account. You’re going to have your own credit cards.’” Wiley got a psychology degree from Dartmouth, and then went on to study law at Columbia. She spent a large portion of her career as a civil-rights lawyer working for the NAACP, the ACLU, and the Open Society Institute, eventually becoming the first black woman to have been counsel to the mayor of New York City.

In June, she left the de Blasio administration to become head of the Social Justice Department at the New School, where she teaches, and the chairwoman of the Civilian Complaint Review Board, where she fields NYC residents’ complaints about police misconduct. In October, I met Wiley at her office at the New School to discuss what inspired her to get into public service in the first place, whether progress is actually possible in such a divisive time in history, and why it’s so essential we see more women in office. Here’s her advice.

Find your cause early — and stick with it.
At a certain point, there was this kind of epiphany moment where, as a young child, I realized that it actually matters who is sitting in that seat on the bench. Somebody has to sit there who recognizes that people like these women that I encountered at a young age, even though they’re poor and black, are still people with dignity, people who are committed to their families, people who aren’t given an opportunity to work or get an education sufficient to support their families and who are subsequently humiliated as a result. I learned early on that I wasn’t an organizer, that’s not who I was, but there really was some power and importance in getting people in those seats of government who were actually going to understand human dignity.

Set clear expectations for your future goals, and if you don’t meet them, move on to something else.
Law school is expensive, and I didn’t have money. A lot of folks feel like they have to go into corporate law to pay their bills. I don’t pass judgment for anyone making that decision. There were also not a lot of jobs getting paid doing what I want to do. It was highly competitive. I made two cold open-eyed decisions. The first was that I had to go to a top-ten law school. I told myself that if I wasn’t going to get into a top-ten law school, I wasn’t going to go because I thought it would be too difficult to do what I wanted to do. The second decision I made was to find schools that either had scholarships or loan-forgiveness programs for public-interest law.

I was fortunate because I did get into top-ten schools, and I had a choice, and that was a very pleasant privilege, but I also had the option of schools that had both the combination of financial-aid packages and loan forgiveness. It was a totally unwavering path for me.

Being a multi-disciplinarian and having a varied career can only help you in the future.
We’re no longer in a binary world. The innovations we need at our systems level require an understanding of business, psychology, and policy, but doing it with a deep, deep understanding of how our decisions create barriers for fairness and opportunity for some people. What can we do to change that? First, it requires open-mindedness — not becoming such a technocrat in your craft that you are not open to what you can learn from other fields. And secondly, it means exploring those other fields, whether it’s by what you read, who you talk to, or even when you think about what it means to innovate by engaging outside of your field. I used psychology as a lawyer, and if anything I use it more now than I did even back when I was in law school.

I think women are particularly open-minded, partly because we’re cultivated to be and also because we’re collaborative. It’s about having those conversations and figuring out — even where it’s not obvious — if there’s a way to connect. I wouldn’t be a civil-rights lawyer who started working on digital equity if I stayed narrowly to what people consider civil-rights issues.

Don’t always presume the most obvious answer is the correct one.
In our time, we’re in a paradigm shift around technology. It’s changing everything, so we can’t think in the same terms of “What is gender equity? or “What is racial justice?” We actually have to think about where the economy is going. That’s a very different set of entry points, which requires me to talk to people who are technologists. What does it mean to be an inclusive society when technology is changing everything and when not everyone has access to the technology?

Technology holds the promise of democratizing. Our telephone lines discriminated based on race. We’re building broadband lines now based on where telephone lines were as our starting point, but that means we have digitally red-lined communities. Phone companies would say, “We meet subscribers who can pay $100 a month.” Well, guess what: Race and poverty means in a lot of those communities of color (not exclusively, because there are some rural and white) that they can’t pay and can’t afford it. The business model doesn’t work, and that means there’s not the same access to technology.

Then some people say, “Well, now even low-income people have smartphones.” That’s true. Have you ever tried to do your homework on a smartphone?

So if you struggle even to do your homework based on what technology you have, how do you become a technology innovator in a changing economy? How do you engage in not just economic development, but problem-solving, if you only have a smartphone? It’s actually limiting. It’s right to say this is the opportunity to further democratize our society, but we have to be careful not to make the assumption that technology will necessarily do it for us.

As hard as it may be, you have to respect people with different perspectives (even if they’re wrong).
My mother had to walk into police departments full of men cat-calling her as she led training sessions on why they should let people of color and women in. I actually learned from people who were in the front lines and in much more polarizing and scary circumstances than I’ve been in. You have to start looking at people, even people who don’t share your views, as people with a set of experiences that you have to recognize and understand. You need to start from that place of lowering the temperature and anxiety so that you can have a real dialogue. If you tap people’s racial anxieties, you’re not going to get them to be able to hear any of your facts.

You really have to take out that personal aspect of “You’re a good person” or “You’re a bad person.” You’re really just trying to make visible to them things that are not always visible. I watched my parents navigate all this with incredible grace, humility, and humor. This presidential cycle has made it clearer than any I’ve ever seen that we’re so polarized that we’re losing the humanity we need to actually have these hard conversations.

Women, more than ever, need to show up to jobs in public office.
When I was in the de Blasio administration, he walked in the door saying women are going to be represented in this administration at the senior levels. And sure enough, he had 50 percent of women in the top positions of government, and that’s almost 1,200 positions. So some of it is about the level — not whether women are going in — but the level women are placed at. I think the de Blasio administration demonstrated if you want the best talent, you can elevate it.

I would say that one of the things that needs particular attention is investing in women of color’s leadership because women of color experience particularly unique ceilings as a demographic.

If you’re in management, saying that there are no qualified women to hire is a cop-out.
This is really important: There’s an assumption that if you’re looking for diversity, you’re sacrificing quality. The reality is that often people make selections based on biases that they’re not even aware they have. “Well, I know this candidate, so I know what this candidate can do. I don’t know this other candidate.” I’ve had people say this to me: Even though the résumés were equal in terms of qualification, we picked this man who is white because we know him. And I was like, “Well, that’s not picking the best person. That’s picking the person you know.”

In the de Blasio administration, my team insisted on pulling from a diverse pool of applicants, and if you didn’t have a diverse pool, the assumption was we didn’t do a good enough job in getting the opportunity out there. And so we took more time. My unit was one of the most diverse, and we had a very diverse administration. I did that because I went out and found the best talent. I found the best talent by making sure that the right networks were notified, that we were encouraging people to apply, and that we didn’t do something that in psychology we would call “pattern recognition.”