‘Do not be afraid to pick up the phone’

Keeping Tabs is a Q&A series that follows alumni on their careers after graduation, the lasting impacts of their clinical and pro bono experiences at Harvard Law School, and their experiences in a variety of sectors of law.

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Patricia Alejandro ’17 joined the Transactional Law Clinics (TLC) as a Clinical Instructor in 2022, bringing with her a robust portfolio of legal experience and a commitment to community lawyering. Prior to her current role, Alejandro served as a staff attorney at TakeRoot Justice in New York City, supporting community-based organizations, worker cooperatives, and small businesses with legal services, policy development, and community education. Her career also includes a tenure as a transactional associate at White & Case LLP, where she worked on international project finance, asset management, and corporate transactions, as well as teaching negotiation and leadership at Bay Path University. Alejandro, who received her B.A. from Yale University and her J.D. from Harvard Law School, has returned to her alma mater to instill in students the importance of community-based lawyering as she directs TLC’s Community Enterprise Project.

In this interview, Alejandro delves into her role at the Transactional Law Clinics, the mission and impact of the Community Enterprise Project, and how transactional law can be a catalyst for community empowerment.

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Office of Clinical and Pro Bono Programs (OCP): Please tell us about your role as a Clinical Instructor at the Transactional Law Clinics (TLC). What is the mission of the clinic? What does your day-to-day work consist of?  

Patricia Alejandro (PA): The mission of the Transactional Law Clinics (TLC) is two-sided. We aim to provide comprehensive training to Harvard Law students in substantive law, practical skills and legal judgment while educating them on the impact of law and social policy on the lives of our clients. For the community and our clients, we aim to provide high quality transactional legal services in the areas most needed by our client communities and to assist our clients in creating engines of economic opportunity. We work with small businesses, entrepreneurs, not-for-profit organizations and community groups, providing legal services that include business and not-for profit formation, contract drafting and negotiation, commercial financing and leasing, permitting and licensing, and trademark applications and other intellectual property matters.

Every day is different – the great thing about this work is that there is never a dull moment! During the semester, students usually work with at least three different clients on various matters. I meet with students at least once a week to go over their case work, prepare for client meetings, or discuss any other questions they may have. We are usually in daily communication either in-person or over Teams. We may have client meetings, which I also attend, or meetings with community partners when working on a project or educational workshop for community members. Part of my day is also spent reviewing students’ drafts of contracts, organizational documents, or research memoranda for clients and providing feedback. Given the demand for our low-cost or pro bono services, I also have my own cases that I work on during the year. Some of my time is also spent doing outreach in the greater Boston area, connecting with community organizations and finding ways of supporting their work within the clinic.

OCP: You also direct the Community Enterprise Project at TLC. What is the Community Enterprise Project, and what are its goals? What type of work do students do, and what issues are facing the clients they work with?  

PA: The Community Enterprise Project (CEP) began at Harvard Law’s Legal Services Center in Jamaica Plain in 1995 with a focus on the urban districts in Boston, to directly help individuals and groups foster economic vitality in their own neighborhoods. CEP later combined with the Recording Artists Project in 2009 to form what is now TLC.

The focus of CEP is on combining the transactional legal aspects of TLC with community economic development in the greater Boston area, using a community lawyering approach to stimulate business development, increase access to capital, promote job growth and sustainable affordable home ownership. Students work closely with community organizations to identify and respond to community legal needs, including leading community workshops on legal issues relevant to small businesses and not-for-profit organizations in the community and developing guides to support the different kinds of community economic development work that is needed (such as developing a guide on commercial leases and on business entity options for immigrant entrepreneurs). For example, in 2017, CEP partnered with Spare Change News to help vendors, many who are either currently or formerly unhoused, understand their legal obligations as business owners (you can watch a video clip of it here!).

In addition to offering direct legal services to clients, CEP partners with community organizations to identify organizational and community needs and develop comprehensive strategies to address those needs. To this end, CEP often develops educational materials and facilitates community workshops on legal issues relevant to entrepreneurs, homeowners, non-profit organizations, and other individuals and organizations in the community.

OCP: How can transactional lawyering be a tool to empower local communities?  

PA: Transactional lawyers doing community economic development work provide much needed, and scarce, legal services to small businesses, startups, and beginning entrepreneurs. These legal services can help prevent conflict (and costs) down the road – helping negotiate a commercial lease that the small business owner understands and can adhere to, and that is properly negotiated with the landlord; drafting organizational documents that tackle the difficult questions about governance and profit allocation from the onset and that model what discussing challenging topics can look like; and protecting the intellectual property of creative entrepreneurs early on. A transactional attorney working within a community benefits from learning and being able to practice in different areas, from affordable housing development and financing to nonprofit law and intellectual property. These are just some examples of the many ways in which direct transactional lawyering can help protect and support the small entrepreneur or not-for-profit organization as it begins to operate.  

Given the scarcity of low-cost or pro bono transactional legal services, we must grapple also with the tension that exists in our practice: how do we contribute to the empowerment of local communities more broadly? At CEP, we have done so through providing legal workshops, developing guides for different groups of entrepreneurs, and partnering with organizations on projects that they have identified that they need for their communities.

So much has been said about this by others that have come before me! There was a great panel at HLS in 2018 where TLC staff shared how transactional lawyering empowers entrepreneurs and communities and what some of the work looks like.

OCP: As an alumna of HLS, what was it like to return to TLC, which you participated in as a student? What memories or lessons stand out when you reflect on your time as a student in the clinic?  

PA: Honestly, at first, I was conflicted about returning to HLS. Being a student here had been challenging in many ways, and while I had made life-long friends, I had never envisioned then that I would be returning to HLS or Boston. I had also been here for the “Snowmaggedon” winter of 2015 and had some traumatic memories of walking thirty minutes to campus in a snowstorm because 1L classes were not cancelled. But teaching at TLC, being able to support students in envisioning fulfilling paths, and supporting clients and community development directly, was enough to overcome my hesitation.  

My time as a student at TLC in the Community Enterprise Project was transformative. I had just returned from doing my 1L summer internship as a Chayes Fellow in South Africa and was grappling with the intractability of some of the challenges I had witnessed there, including poverty and inadequate access to education for children. I felt the same about so many of the challenges we continue to struggle with in the U.S. and was at a loss on how to contribute as a lawyer (who did not necessarily want to litigate). I called this my “quarter-life crisis” – I had come to law school wanting to do human rights work and could not picture that for myself in the traditional international human rights paths.

Luckily, I had registered for CEP in my 2L year and was able to see what economic justice work as a lawyer looks like in practice. Under the support and guidance of my clinical instructor, Amanda Kool, I learned about community economic development and working in partnership with our clients and community. I remember presenting on the basics of commercial leases and intellectual property to creative entrepreneurs, my first client meeting, and being challenged to learn and figure things out on my own. CEP also helped me feel more connected to greater Boston, less transient as a student and more aware of the community I was briefly living with.

In law school, certain areas of law, like venture capital financing and startup law, receive more attention and glitz. At CEP, I learned that many of those skills are transferable and needed to support small businesses in our communities and help them achieve financial stability and durability.  Assisting small entrepreneurs in achieving their dreams and demystifying the law was incredibly rewarding, giving me a new path to follow for the remainder of my time at HLS.

OCP: Prior to your return to HLS, you spent time as an attorney at TakeRoot Justice, an organization that partners with grassroots and community-based groups in New York City to dismantle racial, economic and social oppression. What were your takeaways from that experience, and how do you apply lessons learned there to your work today?  

While at TakeRoot, I mainly provided legal services to worker-owned cooperatives (many made up of immigrant owners) and other legal and advocacy support to community groups organizing for the development of worker cooperatives in NYC. I will always be grateful to the team at TakeRoot Justice for supporting me in transitioning from a law firm setting to a bootstrapped, hands-on, community lawyering context. I worked closely with my teammate, Cheryl Walker, to learn the substantive law that I needed and to get to know our partner organizations. We had a horizontal, collaborative team structure, and, with our supervisor Ted Wan, were able to always be there for each other, discussing challenges that came up and planning for the future of our team. I had to learn quickly, with no law firm hierarchy to tell me what to do or how to do it. Working at TakeRoot gave me the confidence to quickly learn new areas of law, ask questions within my team, and build better support communities.

Even more importantly, working at TakeRoot enabled me to put into practice real community lawyering, prioritizing the agency and needs of our clients while supporting the needs of our organizational partners. We tried to communicate to all our clients that we were there not to tell them what to do, but to answer their questions and accompany them on their journey to forming a new worker cooperative, for example. We worked hand in hand with our clients, often balancing tensions that exist within the worker cooperative community so that we could better serve our clients directly and support our partner organizations.

OCP: Throughout your career, what qualities have you recognized in successful attorneys? What qualities do you think are important for law students to foster as they enter their careers? 

PA: What comes to mind first is: pick up the phone. Law school tends to train us in skills that we use as crutches often, getting in the way of real problem solving. While we need to conduct research, follow proper administrative procedures, and adhere to ethical rules, we need to do so while prioritizing our clients’ needs. I will forever remember a pro bono case I worked on while at the law firm. It was a clemency petition that I had started working on as a summer associate. When I returned to the firm as a first-year associate, all the other associates who had been on that team had left. Thankfully, the clemency petition had been granted during my 3L year and our client was going to be released soon. He had some driving violations on his record from a couple of decades earlier, and some were violations for which he could be imprisoned again.

I was not sure what I should do or how to move forward, and I remember that as soon as I showed up to the partner’s office for our first meeting, he asked me directly what I had done so far. He was not happy to hear my response, to say the least, and right away picked up the phone and called a contact he had in our client’s home state to see if they would be willing to represent on client pro bono in removing the violations from his record so that he would be able to drive again when he was released.

The partner was thinking about our client’s needs holistically – yes, we had succeeded on the clemency petition, but that was not the end of our representation in supporting our client with his reintegration. He modeled what a problem-solving lawyer looks like: he had built a network that he did not hesitate to tap into to support our client, and prioritized getting our client the resources he needed so that he could drive himself to work without fearing returning to prison. It was a lesson I will never forget and try to pass on to my students now.

Law schools and law firms can sometimes be demoralizing, with young attorneys losing confidence in their skills and ability to lawyer well. Big law firm structures are not always supportive of problem-solving lawyering when you are starting out as a young associate. I have found that much is up to chance, with some young attorneys being fortunate to work with a team that mentors and supports their growth and learning. I was lucky to work with several associates and partners who showed me how to be a better attorney, but that is not always the case.

This is why I bring up this example often. Do not be afraid to pick up the phone and problem solve. Ask questions (and know when you need to do your research beforehand, of course!). Build your legal and greater community, among your HLS friends and beyond. The challenges we face in our world today will not be solved by any one person or any single field, but by us working together and not being afraid to take on a new challenge. To be effective community lawyers we must hold onto two truths: you have what it takes to learn, problem-solve and help others, and your clients and community have much to teach you so listen and serve with humility.

OCP: What advice do you have for students hoping to dedicate their future legal careers to community-based public interest work?  

PA: There are so many career paths that fall within community-based public interest work. Some will have you lawyer, some will have you organize, some will have you do a little bit of something else. Find what works for you and what you enjoy most. Your career is long, and the legal skills you are learning at HLS can be used in many ways. Many of my classmates are doing great work in communities while no longer practicing as attorneys. Some contemplate returning to legal practice, some have found other ways to contribute.

Be interdisciplinary in your approach to community-based work, keep learning and working with others to tackle the problems you want to solve. We can easily get siloed in our legal practice and forget that we must work across disciplines and practices to really have a chance at resolving the structural problems we care most about.

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