Women of Legal Tech: Charity Anastasio

Charity Anastasio is a Practice Management Advisor for the American Immigration Lawyers Association’s Practice & Professionalism Center. Find her on Twitter @charityanas.

How did you become involved in legal tech?

I graduated in 2007—one of the all-around worst times to enter the legal field, so I gave myself a job by opening my own practice. I worked in estate planning and family for five years and moonlighted at a bar exam preparation company. I wasn’t happy, wasn’t in love with the law like some of my colleagues were. After some self-reflection, it became clear to me that teaching and training were what I wanted to do more than anything, so I wrapped up the practice in 2013 and joined the Washington State Bar Association’s Law Office Management Assistance Program. Over the last seven years, I’ve learned all the things I did right with my firm, the many things I did wrong, and how legal tech can be the answer to so many of the aching questions and pain points in a law firm. It’s been an eye-opening journey and I’m still learning every day.

What projects have you been focused on recently?

Our team in the Practice and Professionalism Center of the American Immigration Lawyers Association is on a mission to prepare practices for the challenges immigration firms will face in the next decade. While the world is angling into the subject of immigration law from a political and humanitarian view, we angle into the life of the lawyer—their ethical obligations in a time of upheaval, the firm’s stability and financial security in spite of market and political pressures, and the immigration lawyer’s wellbeing. A major part of that is technology adoption and automation. In 2019, I helped plan the first AILA Immigration Technology Summit. In 2020, I will help plan the second, bigger Technology Summit, develop trainings and resources on automating and streamlining law firm processes, and start an exciting new top-secret project involving collaboration and innovation in the legal tech immigration space.

Is there a legal tech resource of any kind that really helped you when you were starting out in the field?

There’s a group of other practice management advisors (PMA) who were generous with their time and knowledge, who shared their experience and strength as I grew in this field. Someone would tell me, “You have to read the 2013 Solo and Small Firm Technology Guide written by Sharon Nelson,” and I’d do it. Someone else would say, “Follow Bob Ambrogi’s blog or LTRC,” and I’d do that. Another would tip me off that the TECHSHOW written materials were gold. If I asked, I received, and it’s been the making of me.

What technology do you think lawyers could look at in a different way that would benefit society?

I am convinced that we are over-valuing our participation in many processes, that we continue to reinvent the wheel with each client when we could create a logic-driven chat-style platform that would use peoples’ answers to questions to take them to the right conclusions and automate the creation of certain documents or deliverables most of the time. Then lawyers could focus on the deeper, more powerful aspects of practicing law: counseling clients and helping them prepare. There are some examples of this being done—Boundless and Docketwise are examples in the immigration space—but more would benefit society. I think programs that use technology like this will be built, with or without lawyers, in the next decade. It would be incumbent upon lawyers to get ahead of this wave, to be a part of it so that they could steer the technology to an ethical, sound solution earlier. But it’s going to take collaboration with technologists and an open mind about what we do and how we do it. Some are on that path, and some are holding firm that the old way is the only way. I have hope.

What advice would you give to other women who want to get involved in legal tech?

Adopt a healthy curiosity. Always ask if there is a better way. Whatever the program or project, get in there and monkey around. And don’t be intimidated by the guys or the tech. The guys need us to make better technology solutions and the technology is just another tool you can master.

Give a shout-out to another woman in legal tech who you admire or have learned something from!

There are so many. Natalie Kelly, the PMA for Georgia State Bar, and Catherine Sanders Reach, PMA for North Carolina, taught me that lawyers can understand technology if you explain it right and how to just jump in wherever you see the need. Jess Birken, the owner of Birken Law, scares me with her innovative, self-challenging projects, which makes me believe “it” is possible. Sherri Davidoff, CEO of LMG Security, made data breaches, encryption, and passwords accessible. Heidi Alexander, PMA for Massachusetts, said if you want to write a book, write a book. (I haven’t yet, but I still want to and I believe I can because she says I can. Oh, and she did write a book!) I’m leaving out so many great women I admire.