How to Become One of the Most Powerful Lawyers in New York State Government


As chief counsel and principal legal adviser to New York Governor Andrew Cuomo, Alphonso David oversees all significant legal and policy deliberations affecting New York State. It’s an ambitious and surprising role for a civil rights lawyer. But how Alphonso came to become one of the most powerful attorneys in New York State government is even more ambitious and surprising.

How I Got My Legal Dream Job™ is a series of interviews with lawyers about their careers.

Shauna C. Bryce’s interview with Alphonso David, Esq., Counsel to the Governor, Office of New York Governor Andrew M. Cuomo. With supplemental interviews and career advice from Gloria L. Sandrino, Esq. of Lateral Link; Jared Redick of The Redick Group; Nancy W. Newkirk, Esq. of Major, Lindsey & Africa; and Deborah Ben-Canaan, Esq. of Major, Lindsey & Africa.

Check out the whole series >

Table of Contents

The Making of a Civil Rights Lawyer

The New York Governor’s office may seem like a long way from house arrest in Liberia, but for Alphonso, it’s a kind of homecoming. “I was introduced to politics early,” he says.

Alphonso was born in Silver Spring, Maryland to Liberian diplomats who were in the U.S. for school. His father studied at Georgetown University and then Howard University, and his mother was enrolled in school. Education completed, they returned to Monrovia, the capital of Liberia, in 1971, when Alphonso was a year old.

In Liberia, Alphonso’s family was well known. The same year his family returned to the country, his great uncle, William R. Tolbert, Jr., was elected president. In 1975, his father, Edward A. David, Sr., became the first democratically elected mayor of Monrovia in 54 years and the family moved into a large home, which encompassed an entire city block. His mother was also a public servant, working at the Liberian Department of Finance.

It was a privileged life, Alphonso laughs. “I had access to everything and anything I wanted, assuming of course that my parents approved.” He and his siblings had three dogs (a Dalmatian, Golden Retriever, and a black Lab, for you dog lovers out there) and “toys galore” like roller skates, but they also traveled internationally. “I got to see snow in Germany as a kid,” Alphonso reminisces. Just how privileged was it? In 1978, Alphonso’s father presented the keys to the city to visiting U.S. President Jimmy Carter.

One day I was playing with my dogs, and the next evening there were gunshots at the door.

But on April 12, 1980, when Alphonso was ten years old, everything changed. He had—against his mother’s rules—sneaked one of his beloved dogs into his bedroom. When the dog started barking, Alphonso worried his mother would find out. As a child surrounded almost entirely by family, he had no inkling anything larger was amiss. Then the shooting started. “One day I was playing with my dogs, and the next evening there were gunshots at the door,” he says.

It was a military coup.

Alphonso’s father threw him and others from a window before leading them running to the home of another aunt, who was the principal of a school. A short time later, armed men appeared at the house, demanded Alphonso’s father, and led him outside in handcuffs.

Alphonso and members of the family were placed under house arrest. His great uncle was killed during the coup. Several high-ranking ministers were executed. Alphonso and his family awaited their fate, not knowing when—or if—they would be next.

What was it like to live through a violent coup and house arrest as a child? “You lose everything that you think has value. You are forced to reexamine what you value. You’re also forced to think about—in a very real way—what democracy means and what freedom means. I had to grapple with those ideas—those complicated, interesting issues of safety, security, liberty, democracy—as a ten-year-old child,” Alphonso says.

He didn’t discuss these big issues with his family. Instead, Alphonso took a different path. He was fortunate, he says, to be locked in a teacher’s house. The home was full of books, which he devoured. Science, history, literature, philosophy…. “I read a lot of Shakespeare, Edgar Allen Poe, Tennessee Williams, and James Baldwin,” he laughs. The experience of arrest and the books “shaped my viewpoint on a lot of things,” he says.

Including gender. Other than Alphonso and his brother, everyone in the house was female: “The men were all arrested or killed.” So for nearly two years, he did not engage with any adult men. “I understood, in a visceral way, the strength that women have and that women often demonstrate strength in a different way than men do. There’s a level of fearlessness that many women have; it’s a fearlessness that many men project, but that women actually have.” During this time, women weren’t just his nurturers, they were also his “selfless protectors and guides.” As an adult, Alphonso recognizes that these traits aren’t unique to one gender or the other, but as a child, he says, “it seemed like a dramatic contrast.” (He remains a staunch advocate of women’s rights and works hard to ensure advancement in economic opportunities and equal pay for women.)

After a privileged childhood in Monrovia, surviving the trauma of the coup and arrest, and studying Shakespeare and Baldwin, moving to the U.S. as political refugees was jarring.

Nearly two years passed before Alphonso saw his father, when he was released from prison. The family sought and was granted political asylum in the U.S. because Alphonso and his brother are natural born citizens.

In 1983, they arrived in New York City.

It was strange, alienating, and disorienting to be back in the U.S. The family stayed in New York with his great aunt, the former First Lady of Liberia, and her family for about a year and a half. They then moved to Baltimore to live with his godparents until the family obtained their own apartment. After a privileged childhood in Monrovia, surviving the trauma of the coup and arrest, and studying Shakespeare and Baldwin, Alphonso says moving to the U.S. as political refugees was jarring.

American kids he met were provincial, to put it mildly. In Baltimore, for example, Alphonso was taunted and bullied for being African. “They kept looking for my tail,” he recalls, “because if you were African, then you must be an animal, and if you’re an animal, then you must have a tail.” Their ignorance was “astounding,” he says, “but the experience built character. I had to decide early on whether I was willing to acknowledge and celebrate who I am.” He could have tried to pretend to be just another American kid, but he refused. “You have to decide—as human beings we arrive at crossroads in our lives. And we have to decide at that point who we are. Principles only mean something if you stick by them at inconvenient times.” Alphonso embraced his identity as an African and a Liberian “because if I didn’t, I would lose myself. It was more important to me to hold onto my essence than to assimilate in a way that would compromise my soul.”

Principles only mean something if you stick by them at inconvenient times.

A Military Coup Creates a Civil Rights Lawyer

As a child, Alphonso assumed he would pursue medical school, but the coup changed that. “I realized that the law governs how we live our lives. It defines our concept of democracy. As I grew older, I realized how lawyers can use their skills to advance certain interests by, for example, helping defining how laws and existing jurisprudence are interpreted.” But he wanted to do more that just study the law. “I also wanted to understand the real world application of the law. Over time, it became crystal clear that I wanted to use the law to advance the rights of the disenfranchised and to challenge our perceptions of justice and equality. These are lofty ideas ingrained in the U.S. Constitution and we evoke them all the time, but they have to be more than abstract principles. They have to mean something to real people.”

Determined to pursue a career in law—but not yet certain what type of law—Alphonso majored in criminal justice at the University of Maryland, College Park. He was fascinated by criminology and philosophy. After graduation, “I thought maybe I would work for the FBI or the CIA,” he laughs. “Why? I have no idea. I interviewed with the FBI—and it was fascinating, but the experience did not click for me so instead I worked at the District Attorney’s Office and then managed a government contracting firm.”

Alphonso was sure he’d go to law school, but he wasn’t sure when or why. “It was more important to answer the ‘why’ question than the ‘when’ question,” he says. “I took four years to answer the ‘why’ question. Plus I needed to pay off my student loans and experience life. College was the first time I had lived outside my parents’ house. When I graduated from college, the last thing I wanted to do was enter into another academic phase. I needed to really take a break—to think about what I wanted to do and why.”

He eventually decided to attend Temple Law School, “to the dismay of my family,” he laughs. His father wanted Alphonso to pursue Harvard or his own alma mater, Georgetown. Alphonso’s temperament and background—remember, as a child he studied literature and philosophy as a solitary pursuit—might have led him to down the path of academia. “There are these overarching principles of justice and equality that people use when talking about the law. And I wanted to understand what those meant,” he says. But Alphonso was interested in Temple’s nationally renowned Trial Advocacy Program. “Going to Temple may not have made sense to my father,” he jokes, “but it made sense to me in so many different ways. I wanted to be a trial lawyer. I wanted to master oral advocacy and the courtroom—which are core components to effective lawyering—and Temple has the most prestigious trial advocacy program in the country. Oral advocacy is just as important as your written work product. If you’re not able to effectively communicate your point through speech, then you’ve lost—even if your legal brief is the best brief ever written. And I wanted to go to an institution that valued practical lawyering skills.”

Nancy W. Newkirk, Esq., Managing Director, Major, Lindsey & Africa

Nancy W. Newkirk, Esq., Managing Director, Major, Lindsey & Africa

Alphonso’s strategic planning—his consciously weighing risk and reward—would prove to be a key factor in his success, just as it did for Rana Dershowitz, another lawyer I profiled in the How I Got My Legal Dream Job series. “This ability to think about goals and act on them is an important component of a successful career,” says legal recruiter Nancy W. Newkirk, a managing director in Major, Lindsey & Africa’s Washington, DC office.

And so Alphonso attended Temple against his father’s wishes. “As a child, I was driven by my instinct and intuition. And I did not want to lose that as an adult. Logic, statistics, and science are, of course, important but so are intuition and instinct. I saw things during the war….” He pauses for a moment here. “My experiences during the coup helped confirm for me that instinct is critical for survival, and can help be the difference between success and failure, so instinct drove my decision to go to law school and to choose Temple.”

I was interested in changing the landscape for as many people as possible.

But the goal of law school isn’t just to master the principles of law and democracy. “How you master those concepts also matter,” Alphonso says. “If you’re not able to persuasively communicate your point and apply them to real life, then you’ve lost. When you see what I saw as a child, you quickly realize that you have to engage actively if you are looking to effect change. I was interested in changing the landscape for as many people as possible. Academia is a different type of engagement, one that we do not value culturally as much as we used to. Decades ago, philosophers and professors had a much greater impact on the public discourse than they do now. Today, one of the best ways to change the legal paradigm or advance an interest is as a litigator in a courtroom. That is where you touch people’s lives. That is where we decide how to adapt to changing circumstances. I did not want to only write books and articles that very few people would read.” (He did later publish “Bragdon v. Abbott: The United States Supreme Court Refined Disability under the Americans with Disabilities Act” in Temple Political and Civil Rights Law Review.)

And so at Temple Law School, Alphonso was a member of National Mock Trial Team and trained to be a litigator “who can take a text and interpret it in such a way that is so persuasive that everyone else will agree that that’s the only way to interpret the text.”

His team won the 1998 National Institute for Trial Advocacy Tournament of Champions.

Intensive Practical Skills Training Build a Foundation for a Legal Career

After law school, Alphonso stayed in Philadelphia—first as a law clerk for the late Hon. Clifford Scott Green (U.S.D.J.) and then as a general commercial litigator for the law firm Blank Rome. While civil rights work still interested him, a career in civil rights seemed “unattainable and unsustainable,” he says, “considering law school debt and the understandable focus of most law schools on the private sector. I thought civil rights work would remain a passion, but not the core practice, because I did not think then that it was possible to make a decent living as a civil rights lawyer.”

At the law firm, he quickly developed practical legal skills that were highly transferrable. “I was lucky to work at a law firm that pushed me quickly. I was not relegated to reviewing documents. I had—and won—my first trial within a few months of starting at the firm. It was a very small case but a meaningful landmark for me. After that experience, the firm engaged me with complex white collar investigations and commercial litigation, and more trial work.”

I was interested in creating a company from scratch—something I’d never done before.

Then while on vacation, Alphonso met a shareholder of a new addiction treatment center. They pursued him as corporate counsel to help create Canyon at Peace Park in Malibu, California. He never thought he’d have the opportunity to serve as in-house counsel, and jumped at the chance to be involved in an organization’s creation. “I was interested the concept, but really I was interested in creating a company from scratch—something I’d never done before.”

“Again, Alphonso demonstrated ability to take a chance and to build something,” says Nancy Newkirk of Major, Lindsey & Africa. Both are critical for successful legal careers at the top levels.

But within a year, things changed for Alphonso yet again.

Landmark SCOTUS Ruling Changes American History

Within the United States, there has a long history of regulating personal relationships, including sexual behavior—criminalizing not only LGBT relationships, but any relationship the government (at all levels) considered undesirable.

While Alphonso and I were in high school, for example, the U.S. Supreme Court, in Bowers v. Hardwick, 478 U.S. 186 (1986), upheld Georgia’s criminalization of sexual activity between consenting adults—even within the privacy of their own home. Homosexuality, the Court declared, was a crime against nature and morality that should be condemned.

Lawrence v. Texas forced me to look into a mirror,” Alphonso tells me, “and decide whether I was going to take ownership of my future.

In June 2003, however, SCOTUS changed its mind. In Lawrence v. Texas, 539 U.S. 558 (2003), the Court determined that private, intimate conduct—regardless of the sex or sexuality of the participants—was protected by substantive due process under the 14th Amendment. SCOTUS struck down sodomy laws in Texas and, by extension, similar laws in 13 other states. (The majority opinion in Lawrence was authored by Justice Anthony Kennedy, who would later write the majority opinion in Obergefell v. Hodges, 576 U.S. __ (2015), finding that same-sex couples have a fundamental right to civil marriage.)

Alphonso had been out personally since college to friends like me and to his family following graduation from college, but—with the legacy of Bowers weighing heavily—he had not come out professionally. Lawrence changed the law, but not necessarily attitudes toward LGBT individuals, including gay lawyers. After Lawrence, Alphonso contemplated joining Lambda Legal Defense and Education Fund in New York as a staff attorney. A protective friend from law school tearfully pleaded with him to reconsider—she feared he would ruin his career. Everyone, she believed, would assume (correctly, in his case) that any lawyer working for an organization devoted to the protection of LGBT civil rights was gay. Joining Lambda Legal was effectively coming out as a gay attorney. And there was little place for gay attorneys. “She worried that I would be stripped of opportunities at law firms, or the opportunity to serve on the bench. She was worried about a parade of horribles,” he says.

Joining Lambda Legal was effectively coming out as a gay attorney. And there was little place for gay attorneys.

His friend wasn’t wrong to be worried for him. In that time and place, being gay “wasn’t exactly celebrated,” Alphonso notes drily. “At that time, simply saying that you were a gay man automatically limited your opportunities.” Law firm life wasn’t easy for gay attorneys; being known to be gay usually resulted in less work and advancement within law firms. As a law firm associate in Philadelphia, for example, he was careful about sharing information about his personal life to ensure no one at the firm learned he was gay.

Like many LGBT professionals at the time, Alphonso self-censored. “My professional life and my personal life were completely separate and had nothing to do with each other. It creates an interesting schism that you justify because you’re uncomfortable aligning the two,” he tells me. But it’s a schism that’s hard to keep up and that forces sacrifices. For example, he didn’t talk at all about his personal life. He didn’t have personal photos in his office and he didn’t date at all during the years he was at the firm. “Dating someone would have meant that I had to reconcile my personal life and my professional one. Rather than do that, I just decided that I wasn’t going to have a personal life.”

But after Lawrence Alphonso says, “I decided that it was more important for me to live my life honestly than to live someone else’s. I was no longer concerned about anyone’s perception of me.” He left his in-house position in California to join Lambda Legal in New York, and it was the first time most people in his professional life knew he was gay.

After those years of self-censorship, how did Alphonso feel about coming out professionally? Was it scary? Overwhelming? A relief? Exhilarating? “All of the above! There was a press release when I joined Lambda Legal,” he says. “Everyone knew I was going to fight for the rights of gays, lesbians, bisexuals, and transgender people. I believe in that mission to my core, but I also recognized there was no turning back.”

I decided the authenticity of my reflection in the mirror was more important than anyone’s perception of who I was.

The negative repercussions would come, but Alphonso was ready: “I decided the authenticity of my reflection in the mirror was more important than anyone’s perception of who I was.” How did his family feel about him going public as a gay man, with one of his first official duties representing Lambda Legal at events like the Gay Men of African Descent’s forum on same-sex marriage at NYC’s Lesbian, Gay, Bisexual and Transgender Community Center? “The great thing about being from a family that’s not entrenched in U.S. culture is that they don’t necessarily connect all the dots,” Alphonso laughs. “They knew Lambda Legal was a nonprofit organization fighting for civil rights, but they didn’t initially focus on whose civil rights. Ultimately, my family became comfortable with it, but it took them a while.”

For the next three years, he litigated precedent-setting civil rights cases impacting LGBT individuals in federal and state courts around the country. He worked on New York’s first marriage equality case (Hernandez v. Robles, 7 N.Y.3d 338 (2005), with co-counsel Jeffrey S. Trachtman and Norman C. Simon from Kramer Levin, who Alphonso—on behalf of Governor Cuomo—would in 2011 present with awards for their work), discrimination related to education, HIV, employment, insurance, healthcare, and more.

Moving to State Government to Effect Change on a Greater Scale

Alphonso wasn’t initially interested in being a government lawyer. When he started receiving phone calls from the New York State Government, he turned them down—that is until the opportunity arose to work in the New York State Division of Human Rights.

His interest was piqued.

Deborah Ben-Canaan, Esq., Partner, Major, Lindsey & Africa

Deborah Ben-Canaan, Esq., Partner, Major, Lindsey & Africa

On the government side, there was the possibility of doing work on a larger scale. This was an opportunity to work on civil rights issues at large—helping every protected class. Additionally, after years traveling around the country suing government entities, private employers, and others, he had begun to see some limitations of working as a civil rights litigator in a nonprofit. He had, for example, dedicated “three years of my life” to the Hernandez case—suing the state of the New York, New York City, and several municipalities on behalf of same-sex couples seeking civil marriages. They’d won the case at the trial level, but suffered a devastating 4-2 loss on appeal in 2005. At the time, 53% of New Yorkers believed same-sex couples should have the right to marry. Chief Judge Judith S. Kaye dissented, including this forward-thinking comment in her opinion: “I am confident that future generations will look back on today’s decision as an unfortunate misstep.” Judge Kaye, a graduate of Barnard College and NYU Law School, was no stranger to historical moments: she was the first woman to be New York’s chief judge and its longest-serving chief judge ever.

[Watch Alphonso’s interview after the loss, “New York, Georgia Courts Reject Gay Marriage” with Democracy Now! Independent Global News, or read the transcript. Not many lawyers are passionate about what they do, says Deborah Ben-Canaan, a partner based in the Washington, DC office of Major, Lindsey & Africa and the leader of its DC In-House Practice Group. “So when you talk to someone who is, you can see it in their eyes, you can hear it in their tone and they radiate an energy that is impossible to miss.” Here, Alphonso’s exhaustion and disappointment are palpable.]

“It was three years of my life,” he repeats. “I thought about the impact of litigation and whether or not it made sense for me to continue to litigate cases, compared to the value of exploring the same issues from a different perspective. I wondered, could I effect more change in a more effective way from the perspective of government rather than the perspective of a nonprofit?”

I wondered, could I effect more change in a more effective way from the perspective of government rather than the perspective of a nonprofit?

Being on the government side meant that he might change regulations and clarify pending issues. As a litigator, he’d been fighting the government—but always from the outside. Inside the government, Alphonso hoped he could be more effective in creating change. As it turns out, it's this “sense of vision and service that motivates many lawyers in public service,” says legal search consultant Nancy Newkirk.

Even so, he anticipated being in government for only two or three years. But within a year of his joining the State government in the Division of Civil Rights as the Deputy Commissioner for Operations and Special Counselor to the Commissioner, the governor of New York—Eliot Spitzer, a graduate of Princeton University and my alma mater, Harvard Law School—abruptly resigned after little more than a year in office. Spitzer, as Attorney General, had been on the other side of Alphonso in Hernandez defending the state’s prohibitions against same-sex marriage, but had pledged to legalize same-sex marriage as governor. In 2008, Lieutenant Governor David Paterson, who also supported a marriage equality bill, succeeded him as Governor of New York. Paterson became the first African-American governor of New York and the second legally blind governor in the U.S.

In the government change up, Alphonso had a decision to make: stay, leave for academia or the private sector, or move somewhere else within state government. In the end, he left the Division of Human Rights. In his new role as Special Deputy Attorney General for Civil Rights, he ran the Civil Rights Bureau of the New York State Attorney General’s Office under then-Attorney General Andrew M. Cuomo, a graduate of Fordham University and Albany Law School.

“I loved everything about it,” Alphonso tells me. “I loved being a prosecutor. I loved the diversity of the work. I loved the impact.” The AG’s Office could make fast civil rights changes on a statewide scale. Unlike at Lambda Legal, Alphonso was no longer working on individual LGBT claims. Instead, at the AG’s Office, he was lead counsel on all high-profile, high-impact litigation—identifying whether there was a pattern or practice of discrimination, and then conducting investigations, filing complaints, or taking other action in cases relating to immigration fraud, credit, employment, housing, education, and more.

Then in 2010, Alphonso’s boss was elected Governor. Incoming Governor Cuomo asked Alphonso to join the Governor’s Office, even creating a position especially for him—the Deputy Secretary and Counsel for Civil Rights. It was (and, I believe, still is) the only cabinet-level position of its kind in the country.

There had long been key policy advisers for education, health, transportation, the environment, and other areas. Governor Cuomo had long advocated for advancing certain civil rights issues related to immigration fraud, housing discrimination, and marriage equality. Creating a key adviser role that would focus exclusively on designing New York’s civil rights policy.

For Alphonso, it was a natural fit.

[Watch Alphonso address Marriage Equality Day attendees at a 2011 press conference, where he discusses the right and need for citizens to communicate with elected representatives, as well as the advancement of LGBT rights, with comparisons to the threat of death—and actual murder—LGBT individuals and activists face in countries like Uganda. He also talks about Governor Cuomo’s commitment to making marriage equality a reality in the New York State.]

Within six months of Alphonso joining his team, Governor Cuomo made good on his promise to change New York law to give same-sex couples equal right to civil marriage. This was a particularly profound time for Alphonso—after failing to achieve marriage equality through the New York courts on Hernandez case, he found himself negotiating key portions and drafting the Marriage Equality Act of 2011, which finally achieved marriage equality for millions of people in New York State. The Act was passed in June 2011 and took effect a month later.

[Read Alphonso’s October 2011 interview with The Advocate, which also details reaction in the LGBT community and its allies to the Marriage Equality Act’s passage, as well as the logistics of the rollout. Or watch Alphonso discuss implementation of the Act, as well as its practical and financial impact on same-sex couples, in the symposium “After ‘I Do’: What’s Next for LGBT New Yorkers?” hosted by New York State Senator Daniel L. Squadron (New York’s 26th Senate District). Alphonso appears from 20:06 to 28:00.]

“It was surreal,” Alphonso remembers. And when the U.S. Supreme Court’s decision in Obergefell made marriage equality the law of the land, he felt “vindication that in all those years when we were litigating those cases—arguing that denying same-sex couples the right to marry amounted to a constitutional violation—we were right. There is a fundamental right to marry, and it is not limited by an individual’s sexual orientation. To see that we were able to successfully advance that principle is amazing.”

After many other civil rights and social justice advancements ranging from unemployment insurance reforms and sustainability to changes in contracting with minority and women-owned businesses, in 2015, Governor Cuomo asked Alphonso to make another change—to serve as Counsel to the Governor. It’s a position that you wouldn’t expect a civil rights litigator to fill, but in April 2015, Alphonso made the transition. He’s now chief counsel and principal legal adviser to the Governor and oversees all significant legal and policy deliberations affecting New York State. He’s also both the first openly gay person and the first African-American in that role.

[Watch Alphonso in action testifying at a March 2015 New York State Senate Public Hearing on police safety and public protection, as well as engendering public trust in the criminal justice system, after the death of Eric Garner at the hands of police. Additional videos of the hearing are available.]

Landmark Cultural Shifts Change the Experiences of LGBT Lawyers

‘It’s staggering,’ Alphonso says about the changes he’s seen over his career.

"It’s staggering," Alphonso says about the changes he’s seen over his career.

As an adjunct professor of law at Fordham Law School (from 2005 to 2009) and then Cardozo School of Law (since 2008), for example, Alphonso has taught a constitutional law course that focuses on sexual orientation and the law. In his early days of teaching—back in 2005—several students told him they wanted to take his course, but they worried about having the course name appear on their law school transcripts. They feared “the impact of identity politics, the assumption that only LGBT people care about LGBT rights.” Taking his course would lead to the perception that they themselves were LGBT and that perception, in turn, would limit their opportunities in the private sector. Alphonso, of course, had lived through the same.

Since then, marriage equality and LGBT rights have seen a huge growth in support, as well as a backlash. Has it surprised Alphonso how quickly attitudes toward marriage equality have changed? “Yes and no,” he says. “It surprises me how quickly attitudes have changed related to marriage equality as compared to other social justice issues. On the other hand, we live in a 24-hour news cycle, in a global economy, and information travels quickly and we do not live in myopic spaces anymore—even people who want to live myopically and be shielded from reality have a hard time doing so. It’s getting better, but we still align ourselves in very narrow ways.”

[Watch Alphonso present a leadership award to Christine Quinn, the first woman and openly gay speaker in the New York City Council, at the 2014 Empire State Pride Agenda Fall Dinner, and talk about the millions of people impacted by social justice advances. Alphonso is introduced at 2:52. Other videos from the dinner are available.]

The Impact of Student Debt on Career Choices

Finances can end up making career decisions. “They did for me,” Alphonso tells me. “It doesn’t take a lot of math to compare your student debt against the salaries of lawyers at nonprofits and lawyers at BigLaw. Even if we encourage people to enter into the nonprofit sector, in many cases, the numbers simply don’t add up. You end up having to leave civil rights work as something you do pro bono.”

We do not value public service and public interest work in the same way we value private sector work.

This is a societal problem. “We do not value public service and public interest work in the same way we value private sector work,” Alphonso says. “Many people are passionate about civil rights work. I had to make sacrifices and life choices. I did not go out to eat for a year and a half. But it just doesn’t seem possible to pursue social justice or nonprofit work if you have $100,000 in debt and two kids.”

The tight budget allocated for attorney compensation is not a problem limited to Lambda Legal. It’s the norm for nonprofits, which means that it’s not uncommon for attorneys to take 70 to 75% pay cuts when transitioning from BigLaw to nonprofits.

Making Choices and Finding Your Place in the Legal Profession

Gloria L. Sandrino, Esq., Principal, Partner and Group Recruiting, Lateral Link

Gloria L. Sandrino, Esq., Principal, Partner and Group Recruiting, Lateral Link

“Exploring is so important. If you don’t explore, then you’re not going to find your core,” Alphonso says and Gloria L. Sandrino of Lateral Link agrees. Yet, lawyers are often unwilling to take initial exploratory steps. “I find that many lawyers that I speak with are often hesitant to explore,” Gloria says, “even just to have a conversation about the opportunities that are available. Exploration opens many paths and may lead to the next career path.” At the same time, “lawyers are creatures of habit and it is very difficult to come to a decision that it is time to move on. There is a link between exploration and deciding to move on, but moving on requires actually taking action. Alphonso seems to have mastered the ability to both explore and deciding to move on if the current job is not his dream job.”

Alphosono says, “I was willing to explore my interests, my passion, and my drive. Over the years, it became clear that my passion was in civil rights, social justice, and equality.” He was willing to make sacrifices to pursue that passion, and his sacrifices continue. His schedule is just nuts. We traded voicemails and emails for well over a month trying to schedule our talk, and finally managed to have it after 10:00 p.m. when he was coming home from work. (From conception to publication, this article will have been in the works for nearly a year!)

A quick funny: Alphonso called me from a car, “I’m sorry, I’ve got to cancel,” he said. “I’m on my way to a press conference.” Later that evening, I had NPR’s “All Things Considered” on in the background and suddenly heard his voice, announcing reforms to solitary confinement procedures in New York State prisons.

It’s a schedule that doesn’t leave much room for a personal life. But, for now, he’s okay with that. The work he’s privileged to be a part of is bigger than he is as an individual.

It’s a schedule that doesn’t leave much room for a personal life. But, for now, he’s okay with that. The work he’s privileged to be a part of is bigger than he is as an individual. “I’m focused on doing the best job that I can, and I’m focused on ensuring that when I wake up every day, I’m excited about what I do. That’s really what drives me. Life is too short and, from my perspective, if you’re not doing something that you’re excited about—and if you’re not engaged in making meaningful change—then, for me, I’m no longer interested,” he said in the 2014 interview with Raj Mehta (see below).

“I think we’d all be happier if we were more comfortable acknowledging when we’ve made a bad decision. It’s okay to change our minds when we realize something is not right for us.”

When I pick up on that theme and ask him whether he has any regrets, he quickly and firmly says no. “I don’t because all of my choices and decisions have brought great value to my life and have defined who I am as a person. Every day presents a series of choices—whether to take that case, whether to return that phone call from a headhunter, whether to be civil to your colleagues. And I try to be guided on those choices by my instinct and intuition. When I have made decisions that turned out to be wrong, I have changed them quickly.” He laughs, “I think we’d all be happier if we were more comfortable acknowledging when we’ve made a bad decision. It’s okay to change our minds when we realize something is not right for us.”

[Watch Alphonso discuss the impact of his personal history—including the coup and his time under house arrest—on his career decisions, civil rights advancements in New York that widen economic opportunities, and ongoing civil rights challenges, in a 2014 interview with Raj Mehta as part of the “Interviews That Matter” series.]

Top Three Legal Career Development Takeaways

Jared Redick, Principal, The Redick Group

Jared Redick, Principal, The Redick Group

One of the main reasons I’ve been working on this series is to give attorneys real illustrations of the career development and transition principles I talk about as a speaker, trainer, and career coach for lawyers. While there are many, many lessons to be learned in Alphonso’s journey, here are three of the most critical ones, with thoughts from top legal recruiters Gloria L. Sandrino, Esq. of Lateral Link; Nancy W. Newkirk, Esq. of Major, Lindsey & Africa; and Deborah Ben-Canaan, Esq. of Major, Lindsey & Africa. I also spoke with long-time collaborator, Jared Redick of The Redick Group, a former executive recruiter who now serves as an expert career consultant for c-level executives and rising stars in Fortune 100 companies, including some of the world’s most desirable brands.

1. Be willing to explore non-linear career paths.

“It used to be working in one organization for 20 years was the norm,” says Deb, a partner based in the Washington, DC office of Major, Lindsey & Africa and the leader of its DC In-House Practice Group. “Not so much anymore. More and more, I see lawyers who deviate from the traditional career path in order to take a risk or to pursue a personal passion (inside or outside the law).”

Nancy, also in MLA’s DC office, agrees. “What I’ve learned in my career is that life can offer unanticipated opportunities which lead in unanticipated directions. Being open to transitions is important, learning to land on your feet in new terrain is a skill, and using your past experience to inform your current career is important. Lawyers who have these skills, like Alphonso, are effective advocates and impress those around them with their commitment, integrity and sense of purpose.” Moreover, Nancy says, “Lawyers who have taken a risk and done something interesting and meaningful have a lot to offer, although it is sometimes difficult to translate these skills into marketable skills in the law firm market.”

Again, willingness to explore is key. “In working with law firms,” Gloria says, “I often suggest that instead of an interview, the first meeting should be a meal—just to discuss the opportunity. Likewise, I tell my lawyer-candidates that the meal is just an exploration, no strings attached. Other times, I have told candidates to attend a conference where I know that a particular lawyer is on the panel discussing the firm’s practice area. If the lawyer likes what he or she hears, I then will suggest a meeting in person with that particular lawyer. Again, the idea is to facilitate exploration.”

2. To thine own self be true.

One of the themes that struck me most about Alphonso’s story is his determination to stay true to himself. That determination doesn’t come easily, and while it potentially brings great rewards, it also potentially comes with great costs. Again and again, Alphonso took huge career risks and made major sacrifices in order to stay true to who he is and what he values.

“It’s easy to forget that becoming ‘true to you’ frequently doesn’t happen overnight,” says Jared. “Even with a strong internal locus of control, a person who falls outside a narrow cultural norm is frequently forced to undertake intensive reflection and inner work in order to reconcile ‘self’ with potentially hostile external influences.”

Gloria was reminded of works by Kimberle Williams Crenshaw, her Harvard Law School classmate and now highly regarded law professor at both Columbia Law School and UCLA Law School (yes, simultaneously). “Kim has written many articles on intersectionality in the legal space,” Gloria says, “but I think it’s important for us to look at our multiple identities as a guide to developing our legal careers. I am struck with the manner in which Alphonso has been guided in his legal career path by his African ancestry, his sexual orientation, and his passion to serve and make a difference. I am impressed that while his decisions have required sacrifices, he has remained true to who he is and what is important to him. Alphonso’s legal career path demonstrates that indeed being true to all of our identities is not an easy task—but at the end it will lead us to where we are meant to be.”

3. Leadership and executive presence can take different forms.

Too often, lawyers think of leaders as the stereotype of the blowhard law firm partner. But that isn’t the type of leadership that’s successful in many types of environments. Much of Alphonso’s success, for example, comes from combining his high IQ with a high EQ (emotional intelligence) and CQ (cultural intelligence). CQ is a new term for many, but Jared says, “cultural intelligence has become increasingly sought as a part of candidate selection in today’s executive search world.”

In addition, Alphonso’s personal honor, integrity, and loyalty breeds loyalty in those he works with. All those traits together create an effective executive presence. “Executive presence is the holy grail of what we look for in a General Counsel,” says Deb. “Someone with high emotional intelligence, confidence without an ego. Someone who inspires others to listen, to think, to engage, to follow, and to grow. Leadership comes in many forms, but for us, we almost always know it when we see it.”

Government and non-profits can be great places for lawyers to build leadership and executive skills—even if those lawyers want to work in the private sector. Nancy has helped many public interest attorneys shift to the private sector. “Government service can be an exciting opportunity for those interested in using their legal skills to effect and influence public policy and public governance. It is a career option that can provide opportunities to grow, learn and have impact on matters of current import.” On the other hand, for those interested in transitioning from government to the private sector, she adds, “It’s important not to stay in government too long as this can make the transition difficult.”


Every job was legal dream job when I was in it. And when it wasn’t, I moved on.

Alphonso not only genuinely loves his work, but he’s also seen the astonishing impact of his work—and he’s still only 45. “I’m lucky,” he says. “At some point we all have to think about our purpose and ask ourselves why we wake up every day. I wake up every day doing something that I love—as taxing, exhausting, and complicated as it is. I’ve always been fortunate to find myself doing work I love. Every job was legal dream job when I was in it. And when it wasn’t, I moved on.”

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