In the Cut Leadership Conversation with Delida Costin

Committed to equipping individuals and teams to get to where they want to be, Delida has spent more than 3 decades serving as a chief legal officer, chief people officer, corporate secretary, board member and investor. You can learn more about Delida on her website and view her Defying Imposter Syndrome TedX talk.

How do you identify?

Personally, I am a Blackwoman, still a Blackwoman, have always been a Blackwoman—one word, no space in between which has a lot of meaning to me—born in the United States. Professionally, I am a principal advisor working with the top seats in legal departments, helping them move from being great lawyers to powerful executives.

One of the things that I’m really committed to is figuring out how do we get wealth to move through the generations. How do we take what we have today and push it through 7 generations? And I have a soapbox about being a defiant imposter.

Before we move forward, what is the meaning of having no space between Black and woman?

We're kids first and our identity is our own, but then the world labels us to inform us about the actual or perceived obstacles about our place in society. For me, those labels have been black and woman.  I've been told they matter, and I've come to see that because they matter to other people, they need to matter to me.  I'm one person, but those labels can mean very different things. I don’t divorce myself from one label to fit in with another label. I try to be the Venn diagram, to keep rooms where the subject might be women’s issues from perpetuating the obstacles that face black folk and to keep rooms where the subject might be black and brown folk from perpetuating the obstacles against women. 

Why 7 generations?

I love history and I am drawn to future stories, but I want those stories to be stories where all people thrive. The realities that we live today are grounded in decisions people made seven generations, or approximately 175-200 years, ago.  Wouldn’t it be cool if we tried to make decisions today that will push things like knowledge, wealth, and health through to 175 years from today?  One of the ways I can be a part of the story is to find ways to help people who thrive less today find the means to push that knowledge, wealth, and health forward into tomorrow and tomorrow’s tomorrow.

“I was set up to run this race as a child of the 60s.”

As the exceptionally talented Blackwoman you are, what was the runway to the work you do today with other exceptionally talented people? And why was this the thoughtful consideration of your ‘next’?

I have spent a long time as a lawyer, practicing since 1995. I’ve been lucky and I worked hard for opportunities so I could take advantage of them when they showed up. I’ve often been the first lawyer into companies and I take them through going public or being sold with revenues up to $1.5B. That was not something that was easy.

When I first started in corporate law, I didn’t know the difference between a stock and a share! So, for me to have come from that moment in time to taking companies public, helping companies get capitalized and issue equity, I’ve had a really successful run. But in looking at what I wanted to do in the next chapter, I’d done that, I’d been in the top seat as a lawyer, and I found myself wanting to do something different. I’m a little bit of a dabbler. And while 30 years as a lawyer isn’t dabbling, the dabble bug came out.

When I looked back and thought about what I liked doing, it was really about developing people and teams so they could be more efficient. And even more importantly for me, was a focus on lawyers who have a unique kind of training and perspective on the world. I wanted to help them broaden their horizons and become more well-rounded so they could fit better into the executive suite and boardroom and contribute all of their wonderful unique perspective. That’s why I started my business.

Sheila: You have always been able to extract the thing that others don’t necessarily see as important. It’s a critical trait for an attorney. Here, you have extracted something from your career and are seeding it in other people. You could have taken that seed and replicated it for yourself, but you wanted to plant a seed for the better good creating a cascade of successful attorneys with broader vision and greater impact. It speaks to who I’ve always known you to be.

What was your first “known to you” leadership moment and what sticks out about it?

One of the things I am very proud of is that I started the Women of Color Caucus as an undergrad at Northwestern University. This was the late 80s/early 90s and I was heavily involved in the women’s movement. The women’s movement was about taking back the night but men were not always allowed in those spaces, and I understood that. But at the time, I was so attached to my 2 younger brothers and what I couldn’t understand was how there could be a space where I was allowed and they weren’t when we had the same kind of dangers coming at us. The night wasn’t safe for my brothers, either. And I wanted to march and work with people who understood the totality of what I was trying to take back.

So, I started the Women of Color Caucus to allow women of color to start to have conversations. There were mini-caucuses for Black women, Latin women, Asian women, white women and men. Then we came together for a large talk session.

When I think back on that, I’m proud of it because it lasted for a while after I graduated. I’m proud of it because it spoke to a need that I had to really look deeper than surface assumptions and try to connect dots and people. And I’m proud of it because it really spoke to something inside of me which is that we all need to get better and we all need to win.

That was one of the first moments of leadership for me and then I went to law school.

Was there resistance to caucusing?

There were some people on campus who were activists and saw caucusing as more social service as opposed to doing something to make change. And, we were young, and some just wanted to go to the party! I joined the others when I could but the caucuses were important for me becaise that was what I was called to do.

Sheila: Thinking of those who chose activism, what you knew is that there were a lot of ways to get where you all wanted to go. We can get better by doing a lot of different things. You do you, I’ll do me. And together we’ll all move the needle on the things that are important to us. That’s another trait that makes you a really good human and attorney.

“I look for people beyond the check boxes of ‘acceptability’.”

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How does your identity inform your leadership style?

When I started working, we didn’t talk about race, money and politics at work. At the time, there was a sense in my mind of making a choice – on this half of myself was this rich whole world that I’m not going to share with my professional world. But that didn’t mean that half should disappear or be subjugated to the other.

I was never comfortable with that dichotomy. So, the question that I’ve always wrestled with is how to bring these 2 pieces together and allow myself to be able to exist in the professional world representing all I am. Because of this, I’ve always been willing to look beyond the check boxes of “acceptability” to find community, friends or people to work with. It’s this dichotomy that I suspect other people have, too.

So, when I hire people, I don’t do so based on where they went to school or their law firm. I hire on how we are clicking and how you think. Are you aware of your blind spots or even know that you have them? Are you listening to feedback from other people? How are you teaching yourself? How do you learn? How do you take initiative, or why don’t you?

If you take those traits into consideration, you end up with really amazing teams of people.

You just described what is a strengths-based model of evaluating humans. It’s not a deficiency model. You’re looking for all the reasons why this person could potentially work. So, speak to that as a Blackwoman because it seems like this is a necessary thing as we are most often looked at for our deficiencies. How is it that you have the wherewithal to push against the thing that pushes against you?

This may be getting into my defiant imposter conversation. If imposter syndrome is a jerk in your head telling you that you don’t belong and you’re going to be called out; imposter status is having jerks outside your head actually putting up obstacles and telling you that you don’t belong.

What I try to live by and have come to articulate is that there are real moments when obstacles get thrown in front of us. Our job is to get around, over or through them. That doesn’t always mean trying to explain why they should not be there, why they’re unfair, or how they make us feel. Sometimes getting around, over, or through them means being an undercover agent, an infiltrator to get beyond the obstacle.

The wherewithal to push back comes from a solid understanding and confidence in my education, work history and capability as a lawyer… and in myself as a Blackwoman. I was set up to run this race as a child of the 60s and have been training to be a defiant imposter since then.

“It’s a big feat to exercise courage.”

What surprises you most about leadership?

Courage. At the end of the day when there is a decision to be made, one person, a leader, has to make it to put something into motion. Sometimes the amount of courage that it requires is immense and often underestimated. It’s a big feat to exercise courage. You have to live with what it’s like to tighten up and go.

What’s one of your most favorite quotes or songs that fuels you during leadership challenges? Why?

I started a playlist a few years ago that has its seeds in the music that my grandparents listened to, especially on Sundays. The first songs I put on that list were from people like Mahalia Jackson, Paul Robeson and Leontyne Price. My playlist has now evolved, not surprisingly, to all kinds of religious and spiritual music and now includes traditional and modern gospel, chants, and global music. It also includes instrumentals like Duke Ellington and his volume of sacred music. All of it has some connection to faith or belief.

Sheila: Interesting that you bring up faith after mentioning courage because there can be no fear (lack of courage) in faith. Make sure that you put that playlist somewhere that the next gen in your family can find it.

What do you know your life’s purpose to be?

Despite all the systemic barriers that face all of us, I want all of us to be okay. You know, you blow out a candle, you wish on a star, you throw a penny into a wishing well and since a child I’ve had the same wish… for everyone to be all right in the world because I had a sense that we were all interconnected. This also goes back to ways to push wealth in terms of health, knowledge and access out 7 generations from now.

Sheila: That’s a tall order for leaders to want everyone to be okay. But in fact, that’s one of the key requirements if you want to do it well. It doesn’t mean that everyone is going to agree with you or get their own way, but it means they will be okay. And you’re describing leadership in a way that takes on a whole lot of responsibility. Some people would say that leadership is about getting from here to there and you’re describing it as putting your arms around a whole lot of people and that’s admirable.

What talent do you have that you’re not using?

I need to tap back into the things I did as a kid like riding a bike, snowboarding and climbing a big mountain. I need to remember what it felt like to have that sense of accomplishment.

If this 5 years is a chapter in your life, what’s the chapter about?

It’s really about a huge pivot and courageously leaning into it. It takes a lot to say that I no longer practice law in the way that I have for many years. These next five years is about walking toward whatever this next thing will be. It’s advising. It’s about figuring out how to make things better for the next 7 generations. It’s about teaching lawyers to go beyond legal analysis and deliver results that move businesses forward. It’s about helping people, especially at this time, know that you can be successful being a defiant imposter.

It’s a year from now, what are you celebrating?

My book will be published, and I’ll be on my way to the TED Main Stage to talk about being a defiant imposter.

Anything else you’d like to add?

What has been fun for me is taking the rigor of the law and combining it with the humanity of who I am and figuring out a way forward. That’s where I say “heartbeats matter just as much as the dollars” because that’s true. We don’t pay enough attention to the heartbeats, and we should.

Check out Delida’s website and view her Defying Imposter Syndrome TedX talk. And leave her a message below if you’d like!