Washington Lawyer September/October 2026
By Jeremy Conrad
Imagine you have been denied public benefits. You call a phone number you found online, looking for legal assistance.
You hear: "Thank you for calling the D.C. Bar Pro Bono Center. This help line can connect you with legal aid programs in D.C. if you qualify, help you find a lawyer, or assist with attorney complaint questions. How can we help you today?"
"Can I get some help contesting the denial of public benefits?" you ask. The voice on the other end of the line informs you that you can get free legal help contesting the denial from several organizations in D.C. and proceeds to ask if you would like to be connected to them.
"Mhmm," you reply, hardly noticing that your response was somewhat inarticulate. You have a lot on your mind.
You may or may not later realize that you have just interacted with L.E.S.L.Y., the D.C. Bar Pro Bono Center's new artificial intelligence agent.
Leveraging AI for Good
The D.C. Bar Pro Bono Center has long contemplated leveraging emerging technology to better serve District residents in need of legal assistance. Staff and leadership debated how AI tools could be deployed ethically and effectively to improve the organization's ability to deliver information and connect members of the community to legal services. The increasing demand for civil legal assistance heightened the urgency of these discussions, along with uncertainty over funding for pro bono legal services.
Then in 2025 the D.C. Bar presented an opportunity to move these discussions to actualization. That year the Bar launched an internal technology challenge for staff to develop moonshot proposals for the innovative use of AI to better serve Bar members and the larger community.
Pro Bono Center staff members Gurdeep Singh, Kyndall Jones, Jenadee Nanini, and Lesly Amaya Arias sprang into action and proposed the creation of L.E.S.L.Y. — Legal Education and Information Support Line for You — which ultimately won the Bar's AI Olympics.
The Pro Bono Center's information and referral service has historically received approximately 1,300 calls a month, averaging more than 15,000 calls annually. The majority of calls went to voicemail, and one staff member, along with the occasional intern, spent 10 to 15 hours a week responding to them.
With L.E.S.L.Y., the Pro Bono Center envisioned a help line that went beyond the phone tree prompts most are familiar with when calling customer service hotlines. They wanted a service with natural language inquiries and responses, resulting in a more accessible and less frustrating experience for users.
"The [overarching] concern that we had, given the nature of our organization and the nature of our work, is that we still wanted [the help line] to feel very human and very personable," says Singh, training and volunteer specialist at the Pro Bono Center.
"There is a lot of emotion involved in the issues that individuals are facing when they contact the help line. You can imagine that someone who is being evicted, or having a custody or domestic violence issue, may still need to speak with a person. In other cases, AI could answer a simple question, direct you to a service, or give you an opportunity to leave a voicemail," he explains.
L.E.S.L.Y. does not provide legal advice, evaluate the merits of a person's case, or recommend a legal strategy. Instead, it delivers consistent legal information, explains available services, helps callers understand the next steps, and directs them to the appropriate Pro Bono Center programs or external resources.
Highly Customizable Tool
The Pro Bono Center outsourced the design to Assembled, a company specializing in the development and maintenance of AI products for companies. Samantha Webster, who managed the Assembled team that developed L.E.S.L.Y., says the AI-powered help line is designed to recognize when a caller would benefit from human interaction.
"Our underlying base prompt accounts for a lot of different kinds of needs," Webster says. "High frustration, cursing, raising your voice, asking for a human — all of those sorts of things are calculated on the back end to a threshold that can lead to a handoff. There is also the ability for the Pro Bono Center to specify that when certain topics are raised, there is an immediate handoff. So, the system is highly customizable, allowing [staff] to decide what goes through a person and what doesn't."
Jones, program technology specialist at the Pro Bono Center, helped coordinate the buildout of databases; conducted tests to ensure that L.E.S.L.Y.'s responses are accurate, concise, and helpful; and set criteria for the escalation of cases for human assistance. "We looked at how L.E.S.L.Y. responds to the urgency of something someone says," Jones says. "Can L.E.S.L.Y. recognize an emergency by a person's tone of voice? We also want to be certain that the voice agent isn't frustrating to deal with. We want L.E.S.L.Y. to be as natural as possible, and to answer questions as concisely as possible, so that it isn't a troublesome experience."
D.C. Bar Pro Bono Center staff were not the only ones involved in the testing. "We make these types of decisions in partnership with our client community," says Executive Director Kelli Neptune. "We have a Client Advisory Board whose members consist of former clients of the Pro Bono Center. They advise us on how to improve services to best meet the community's needs. The board serves as a valued consultant by participating in testing and informing us about the impact of this new platform. It was important to us that their voices were heard in the development and implementation of technologies intended to serve them."
A Force Multiplier
Neptune has high hopes for L.E.S.L.Y.'s potential to improve the Pro Bono Center's delivery of legal information and services to clients and increase access to justice dramatically. "This system is really a force multiplier," she says. "A significant portion of our clients do not have access to the internet, and the volume of calls we receive is high. D.C. residents are in need of legal information and resources at all hours of the day."
"L.E.S.L.Y. is interactive, ethically creative, and sympathetic to the needs of our clients; it answers their questions in real time and refers people to additional services," Neptune adds.
Neptune also stresses that the new system is intended to enhance rather than substitute for the critical services provided by humans at the Pro Bono Center. "L.E.S.L.Y. gives callers better access to staff because it allows program specialists more bandwidth to deal with crisis situations and callers facing exigent circumstances," Neptune explains. "The system provides information about our clinics, connects callers to services, and answers basic questions as the first tier of interaction."
"Nonprofits like ours have limited staff [and] limited resources. Providing services in an ever-changing legal landscape requires that we think outside the box, like turning to technology, to expand capacity. This platform is one way for us to do that," she says.
L.E.S.L.Y. will also continue the Pro Bono Center's ongoing efforts to connect individuals in need with the broader network of legal services providers operating in the District. Resources like the Landlord Tenant Legal Assistance Network and Family Law Assistance Network offer single points of entry for residents in search of legal help by connecting them with the organizations providing such service. L.E.S.L.Y. offers another clearinghouse point of access, making the Pro Bono Center a hub through which residents can locate help for a variety of legal problems.
The Pro Bono Center will continue to facilitate these connections and intercede when human interaction is needed. Someone facing a filing deadline will reach the right resource in minutes rather than waiting for a callback. Anyone who prefers to leave a voicemail can still do that, and staff will return those calls.
With L.E.S.L.Y. providing basic information and routing simpler questions, Pro Bono Center staff can spend their time on the cases that are legally complicated or emotionally hard. The technology simply supplements staff rather than replacing them. The system is launching in phases, with all features expected to go live this fall.
D.C. Bar staff writer Jeremy Conrad is an attorney who has spent much of the past decade writing about the legal profession. Previously he practiced in immigration law and criminal defense.
