William Delgado: “Seek first to understand”

As a society, we need to engage in respectful, cross-squad conversations without fear of repercussions — even (and especially) the really hard ones. If one squad says “let’s defund the police,” let’s have that conversation, even if another squad believes doing so would lead to increased crime and disastrous consequences. If one squad says “there is no […]

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As a society, we need to engage in respectful, cross-squad conversations without fear of repercussions — even (and especially) the really hard ones. If one squad says “let’s defund the police,” let’s have that conversation, even if another squad believes doing so would lead to increased crime and disastrous consequences. If one squad says “there is no data to suggest that race plays any role in police officer shootings,” let’s have that conversation, even if the other squad believes that can’t possibly be true in light of what we’ve seen. Upon having these discussions, we may or may not reach an agreement, but I can guarantee you this: if we aren’t having these conversations, we certainly will NOT reach an agreement.

As part of our series about ‘5 Steps We Must Take To Truly Create An Inclusive, Representative, and Equitable Society’ I had the pleasure to interview William Delgado of DTO Law.

William Delgado is a seasoned litigator and founding partner of DTO Law, an elite boutique law firm that is 100% owned by women and people of color. DTO Law is certified as a Minority Business Enterprise (MBE) by the National Minority Supplier Development Council (NMSDC), and several members of his team are bilingual in English and Spanish. Will is a supporter and member of various organizations that promote diversity and inclusion in the legal field such as the Cuban American Bar Association (CABA), the Hispanic National Bar Association (HNBA), the Leadership Council on Legal Diversity (LCLD) and the National Association of Minority and Women Owned Law Firms (NAMWOLF), where he serves as Vice-Chair of the Board.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you. Can you tell us a bit about how you grew up?

I grew up as the son of Cuban immigrants in Hialeah, Florida, a suburb of Miami. Ironically, Hialeah is the least diverse city in the country but only because over 96% of its residents identify as Hispanic or Latino. My parents divorced when I was very young, so I was raised by my mother and my grandmother, though I did see my father regularly. I realized early in life I would need to fund my own college experience (if I was going to have one), so I placed heavy emphasis on performing well academically. I was fortunate in that those efforts ultimately paid off, and I was able to attend college on a full scholarship and law school on a near-full scholarship.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I’m a huge fan of Malcolm Gladwell, and I’ve read nearly all his books. They are very well-written and thought-provoking. If I had to pick one, I would probably pick What the Dog Saw, because it’s a collection of essays on various topics. I’m a very curious person by nature and, because this book covered more than one topic, I was able to learn a little bit about a lot of different things.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

I love quotes. Some of my colleagues tease me because I throw out quotes and sayings frequently, including some that are obscure. As a result, it’s really hard for me to pick just one, but I will. It’s been attributed to various people, but I think James Bryant Conant is the originator: “Behold the turtle. He makes progress only when he sticks his neck out.”

I think this quote or ones that connote a similar lesson (e.g., “Fortune favors the bold,” “Jump and the net will appear,” etc.) represent the mantra of every entrepreneur. Leaving the comfortable confines of a steady job for an unknown future hinging on the success of a truly-held-but-untested belief — in my case, that my partners and I could build the best law firm for the 21st century both in terms of quality of service and diversity of staff — is not for the faint of heart. But meaningful progress means accepting meaningful risk, acknowledging the possibility of catastrophic failure, and nevertheless persisting.

How do you define “Leadership”? Can you explain what you mean or give an example?

Leadership is an exercise in two things: (1) helping those around you reach the highest possible level of individual success and achievement while (2) simultaneously bringing all of these successful individuals together in such a way that the organization, as a team, is always greater than the sum of its individual parts.

One person who accomplishes this remarkably well is Bill Belichick, the coach of the New England Patriots. Candidly, as a Miami Dolphins fan, it pains me to no end to admit that. Obviously, Belichick was lucky to have a fantastic quarterback for several years in Tom Brady, but several of his Super Bowl squads were otherwise comprised of players who would not be considered all-stars. Some players were downright castoffs. Nevertheless, Belichick is masterful at maximizing the potential of every single player and, then, incorporating them into a team-first system capable of achieving amazing results year after year. Take those same players and put them on another team with a different coach who has a different approach — I doubt you would see the same results.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

As a litigator, my most stressful interactions tend to be those in court — a hearing in front of a judge or a trial in front of a jury. I don’t do anything to try to calm down in advance of these. On the contrary, I want to lean into the adrenaline rush that accompanies stress as it tends to bring mental clarity. On the other hand, what do I do on a regular basis to decompress? I’m afraid the answer is neither exciting nor unique: I exercise. I try to vary what I do — lift weights, ride a bike, swim, or work on a heavy bag, so that I don’t get bored.

Ok, thank you for all that. Now let’s move to the main focus of our interview. The United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This is of course a huge topic. But briefly, can you share your view on how this crisis inexorably evolved to the boiling point that it’s at now?

Before I was a lawyer, I was an engineer so I tend to view problems through the lens of an engineer, and when an engineer is troubled by a system’s output before we dive into the system itself, we first go back to look at the inputs.

As applied to our current conundrum, we have a confluence of various unique inputs both past and present. First, there is a historical component — the institution of slavery, the passage of Jim Crow laws, the civil rights struggle, etc. Second, more recently, we have seen a resurgence among hate groups which not only reopens old wounds but also has the potential for creating new ones. Third, in the time of coronavirus, you have a lot of pent up frustration — people have lost their jobs, been confined to their homes, are struggling to make ends meet while simultaneously homeschooling their children, etc. As the months have passed without any real progress, frustration leads to anger. Lastly, we had a series of highly charged events in quick succession. Breonna Taylor, the incident in Central Park, George Floyd to name a few.

And, here’s the thing: with the exception of Taylor, we got to see these things happen firsthand. Consider the Christian Cooper-Amy Cooper incident in Central Park. I’m not sure the greater public would have even learned of that incident without a video taken from a smartphone. Perhaps Mr. Cooper would have shared the story with his circle of friends — but Ms. Cooper might have too. As a lawyer who often deals with conflicting eyewitness accounts, I can virtually guarantee those stories would have been very different. And if their respective stories are recounted to a friend of a friend or even a few others down the chain, the incident would have been even more fragmented.

Now, though, you have technology that allows two things. First, it allows us to see the incident, and there’s a reason why we say “a picture is worth a thousand words.” Witnessing the encounter as it happened in “real-time” allows us to develop an understanding and provides an appreciation we otherwise would not have. Second, it allows us to share the incident. Now the audience is not just their respective friends; a viral video literally has a nationwide, or even worldwide, audience.

When you take all these inputs and feed them into your system — and I don’t care what system you have — you’re going to get a disruptive result. Take away one of those inputs — say we weren’t stuck at home because of coronavirus or say the George Floyd incident is not caught on video — do we still have the same result? I don’t know.

Can you tell our readers a bit about your experience working with initiatives to promote Diversity and Inclusion? Can you share a story with us?

DTO Law is a certified minority-owned law firm that is 100% owned by women or persons of color. Seven out of 12 attorneys are women. Seven out of 12 attorneys are a racial or ethnic minority or LGBTQ.

I mention these statistics because they reflect my belief that D&I “initiatives” are fine, but if you really want to have a diverse and inclusive organization, you must bake it into the DNA itself. That is to say “diversity and inclusion” is not just the name of the latest training video or the new company buzzwords. It IS the company.

This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

Having a diverse executive team primarily accomplishes two things:

First, it ensures representation of a greater breadth of knowledge and multiple viewpoints at the company’s upper levels. In my experience, that always leads to better decision-making. Say your company wants to implement facial recognition software. A group of white, male leaders may not know or realize that facial recognition regularly fails to recognize Black faces. On the other hand, a Black executive who has experienced that firsthand would have particularly useful insight. When he shares that experience, it has the potential to alter the company’s direction — maybe they move away from facial recognition software or are more sensitive to how it needs to be developed in light of this concern.

Second, it serves as a powerful statement to the next generation. When a racial or ethnic minority can look up and see someone who looks and sounds like them in a position of power, a couple of things happen. They recognize they are working at a place where their diversity won’t be held against them — something that engenders trust and loyalty. In addition, they are encouraged and begin to believe “if that person can do it, I can do it too,” resulting in optimum performance.

Ok. Here is the main question of our discussion. Can you please share your “5 Steps We Must Take To Truly Create An Inclusive, Representative, and Equitable Society”. Kindly share a story or example for each.

For purposes of my answers, I’m going to borrow a term from Taylor Swift (“squad”) to mean a group of people with similar socio-political views.

  1. Engage in discussions — even (and especially) the really hard ones.

At the turn of the 20th century, Evelyn Beatrice Hall summarized Voltaire’s beliefs as: “I may disagree with what you say, but I will defend to the death your right to say it.” In 2020, our approach is starkly different: “If I disagree with any part of what you say, not only will I not listen to you but also my squad and I will do our best to silence you.”

This is a huge problem. Let’s assume you want two squads to work together on a solution to a problem. The first step is to find common ground. But squads cannot find common ground if they aren’t talking to each other. And people won’t talk to other squads if they feel they are going to be embarrassed, shunned, rebuked, or otherwise suffer some sort of negative repercussion for what they say. Rather, they turn inward to their own squad for support. Every time that happens, we’ve lost the opportunity to build a bridge and, instead, have built an echo chamber.

As a society, we need to engage in respectful, cross-squad conversations without fear of repercussions — even (and especially) the really hard ones. If one squad says “let’s defund the police,” let’s have that conversation, even if another squad believes doing so would lead to increased crime and disastrous consequences. If one squad says “there is no data to suggest that race plays any role in police officer shootings,” let’s have that conversation, even if the other squad believes that can’t possibly be true in light of what we’ve seen. Upon having these discussions, we may or may not reach an agreement, but I can guarantee you this: if we aren’t having these conversations, we certainly will NOT reach an agreement.

2. Seek first to understand.

If we bother to have hard conversations, then we should make sure they aren’t going to waste. And they most certainly will go to waste if we view them simply as an opportunity to get our point across. No one has ever successfully argued their position by saying “I haven’t listened to a word you just said because you’re wrong anyway. Now let me tell you why I am right. And, despite the fact I have not listened to you, I’m certain that my communication skills are so far superior to yours that, not only will you listen intently to what I have to say but also, you will instantly agree with me.” If that approach immediately comes across as nonsensical, it’s because it is nonsense.

The point of having these conversations is to see why the other squad thinks the way they do so that we can determine where there may be common ground upon which we can build. If we have not listened in the first instance, we will never be able to do that. In addition, we must go beyond listening. The advice here is not “listen when you have a conversation.” It is “seek to understand.” Was there ever a time in school that a teacher taught a lesson but, despite listening, we didn’t understand? What did we do then? We asked questions. We sought further explanation. That is what we need to do if we want to have any hope of moving the needle on our societal relationships.

3. Be careful when engaging in discussions on social media.

Social media can be a useful tool. As I noted earlier, a powerful viral video can help us all “see” elements of life to which we were previously blind. But social media has a terrible dark side — it too easily dehumanizes.

In the legal profession, we use the term “paper tiger” to refer to a lawyer who regularly sends nasty, vitriolic letters and emails but doesn’t carry that same demeanor into the courtroom. Why? Because while it’s easy to be a jerk to someone in an e-mail, most people find it’s hard to be a jerk to someone’s face.

Unfortunately, it’s rather easy to become a social media paper tiger. John posts something. His friend, Fred, makes a positive comment. John has another friend, Bob, who disagrees with the post, doesn’t know Fred, and doesn’t care for what Fred has said. Before you know it, Fred and Bob are in the middle of ad hominem attacks precisely because they don’t know each other and, perhaps, may never meet each other at all. Neither Fred nor Bob stops to think “hey, this is another human being with a family, a job, friends, etc.” Each is too busy figuring out what to say next to please his respective part of the audience. When you have that type of interaction happening over and over and over again, it frays the fabric of society.

Unfortunately, it’s very easy to fall in this trap, particularly when, to quote a young child, “(s)he started it!” Nevertheless, it’s imperative to reject our baser instincts and refuse to engage at such levels. We need to collectively change the tenor of these conversations.

4. Admit and address implicit bias.

This is one is relatively straightforward. We all have biases. Some of us are, unfortunately, explicitly biased, but all of us are implicitly biased in some way or another. The first step is admitting that. The second step is figuring out what those biases are. The highly self-aware person may already know, but for those of us who need help, Harvard’s Implicit Association Test can help us figure it out. Once we know our blind spots, we can be mindful in the future in addressing them. How to do so — well, that’s a whole other interview.

5. Embrace blind selection.

In another one of Malcolm Gladwell’s books, Blink, he discusses the issue of gender bias in orchestras. To solve that problem, orchestras started putting up screens during auditions so that decision-makers could not tell if the person auditioning was a man or a woman. Their decision as to whether the person moved on to the next round of the audition was based solely on how they played. That approach helped orchestras diversify, and all of a sudden, more women were in orchestras across the country.

We don’t need to work for an orchestra to implement blind selection. We can do this in all manner of contexts — hiring, promotion, RFPs, etc. Because we all have some sort of bias, blind selection ensures that someone’s race, ethnicity, or gender will not be what holds them back in getting ahead.

We are going through a rough period now. Are you optimistic that this issue can eventually be resolved? Can you explain?

I don’t know if I am cynical because I’m a lawyer or if I’m a lawyer because I’m cynical. Either way, my answer is going to be peppered with that cynicism.

Will we move on from this rough period? Yes. Will it be because we made progress in solving some of the problems we’ve been discussing? I don’t know. Across the world, attention span has decreased — that’s why I’m convinced we will move on from this eventually. In addition, it feels as though each day we are being assaulted with a new problem that demands our attention. In a world where everything needs your attention, nothing does.

On a more positive note, I’m cautiously optimistic we will finally start to see some real progress in the legal field, where we have struggled for decades to achieve meaningful diversity. For a long time, we have looked to law firms and asked, “why are you not more diverse?” while failing to acknowledge the unfortunate truth: there was no demand in the market. Thankfully, Corporate America has recognized that fact and altered their purchasing behavior.

Is there a person in the world, or in the US, with whom you would like to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them. 🙂

I’d love to have breakfast or lunch with Chief Justice John Roberts of the US Supreme Court. I’d love to pick his brain about all sorts of things but, especially, the diversification of the US judiciary.

How can our readers follow you online?

You can follow us on Linkedin @

This was very meaningful, thank you so much. We wish you only continued success on your great work!

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