June 27, 2024

Attorney Spotlight: Leah Druckerman on Developing a Distinct Data Privacy Practice and How Her Mid-Career Gender Transition Led to More Authentic Client Connections

10 min

For more than a decade, counsel Leah Druckerman has challenged traditional thinking in her legal career, building a thriving practice focused on the privacy and data protection issues inherent in transactions and helping clients navigate hacks, data breaches, and other cybersecurity crises. More recently, Leah also began to challenge traditional gender roles after discovering she was transgender. In the last few years, she has begun the life-changing and life-saving process of transition, including medical treatment that has dramatically improved her personal and professional life.

In this Q&A, Leah discussed how she built her uniquely focused data protection practice, her inclusion in Crain's New York Business's Notable LGBTQIA+ Leaders, and how no one ever stops transitioning.

You were recently selected for inclusion in Crain's New York Business's Notable LGBTQIA+ Leaders. What does this honor mean to you?

The big thing that it means to me, and I hope that it means to others, is that I kept my career and my professional life together, despite the chaos that transitioning can inflict upon your life. I figured out who I was mid-pandemic, working in a small NYC one-bedroom while my then-wife was four months pregnant. It was an extremely difficult set of circumstances. There was a lot of personal change, but I maintained my work focus and continued to develop and build my practice and grow personally and professionally despite that.

We as a society have come a long way regarding LGBTQ+ rights and acceptance, but the recent uptick in anti-trans hatred, misinformation, and legislation sometimes makes it difficult to simply exist as what I know myself to be. Carrying that weight and maintaining a level of professional success is therefore an enormous accomplishment for me that I have worked very hard to reach, and I am thankful that this award has given me an opportunity to celebrate and reflect on that.

What were some of the challenges of a mid-career gender transition?

It takes an enormous amount of time and energy, which are traditionally in short supply for lawyers. There are a lot of medical appointments, and transition also takes up a lot of mental space. Once you have that realization that you are trans, it is just chaos. We call that the "egg-crack" moment. The closest analogy I have is that my mind felt like the end of Die Hard, when the bomb goes off at Nakatomi Plaza, and there are papers fluttering everywhere. Important information and memories are swirling around in my head, and my internal foundations, walls, and mental organization that used to hold them are gone. So, I just catch these things as they fly by in my head, process them, and sort of recontextualize them with the new information that I have.

Another challenge is that the privilege loss is real. I have been talked over and questioned and had my ideas taken or misattributed to other people in a way that I did not experience pre-transition. Also, hormone replacement therapy (HRT) often makes you look younger. So, I look younger and less experienced than I actually am, which is nice personally but can make it harder to establish credibility as an experienced lawyer.

How have colleagues and clients responded to your transition?

Folks have been excellent at the firm. In fact, the first place that I wore a dress outside my own house was the DC office.

Generally, clients have reacted positively. Clients come to me because they're dealing with complicated issues, and they want someone to help cut through them, regardless of that someone's gender, sexuality, or presentation. I'm very good at that, and I'm very up-front and articulate about who I am, and clients respond well to both of those things.

In fact, something that I think is very interesting about existing as a trans person is that clients and people in general are very willing to open up to me and tell me things because I'm similarly open and laying it all out there. Clients really appreciate that authenticity. I get more information from and about them, I develop a more personal relationship, and I get more buy-in because I'm very clear and honest about who I am, on both a personal and a professional level. People respond to that authenticity and want to extend their own.

I listen closely and carefully, I read people, I figure out what matters to them, and then I try to connect on a deeper level. It was harder to do this pre-transition because I was sort of connecting as a mask, but now it's me connecting. I don't have to put on a show.

What makes your privacy and data protection practice unique within Venable?

There are two main components of my practice: privacy in deals and transactions, and data breach response. These two pieces feed into each other because what I learn on the data breach response side impacts the approach I take with contracts, and vice versa.

On the transactional side of privacy and data protection, every company has information that is valuable, sensitive, or regulated in some way. My work deals with what happens with that information, especially when it is shared or used in new and interesting ways.

For example, anytime two companies want to do anything together, data is going to be shared, whether it is personal or confidential information or trade secrets or intellectual property, and that information needs to be protected. I deal with scoping and figuring out the risks involved and dealing with regulatory requirements and risk allocations. This applies in both day-to-day technology transactions and in larger corporate transactions. After all, the goal is to avoid buying a lawsuit, or at least avoid buying a lawsuit that outweighs the benefits that you're trying to get in the deal.

The second piece of my practice is data breach response and related crisis management. Each incident presents unique and interesting challenges, and it is so rewarding to help a client navigate from the initial fear and worry into a confident "Okay, we can do this, and here's how." It also provides a lot of room for business development, as often we are called in to help with the crisis, and then stay on afterward to help the client improve their processes and protections post-incident.

What drew you to focus on privacy and data protection?

I was always fascinated by technology and grew up in a family of engineers, journalists, and technical writers. In 1999, Napster came out, and everyone was using it to download music. My friend's dad was a patent lawyer, and I remember him saying, "Do you realize that this is illegal?" My friend was not allowed to use Napster at home. It was fascinating to me because it showed this tension between what technology enabled and what the law required. Similar tensions continue to exist between what technology allows us to do and what the law permits, and finding creative ways to solve the problems presented by those challenges is very rewarding.

How has your career evolved since starting your practice more than a decade ago?

I started in employment law at a small boutique firm because it was difficult to find employment as a recent law school grad at that time and because I enjoyed the entrepreneurial nature of small firm practice. Because employment law is essentially the law of relationships in the workplace, there were a lot of technology, privacy, and intellectual property angles that I could work while staying within my firm's practice area. Soon people remembered me more for the technology work than for the employment work, and when I had an opportunity to make a switch to full-time technology transactions and privacy work at another firm, I took it.

In 2019, I came to Venable to join a more established privacy team. In both of my prior legal employments, I was the first and/or only associate who did what I did. So, there was a lot of back-end work building out practices, developing forms, and learning and educating. Venable's privacy group is much larger and more established, which meant that I could spend more time focusing on what I love most about my job: solving thorny technology-related problems for clients.

What are some trends and changes you are seeing in privacy and data security law?

Privacy laws mostly function as notice-based arrangements, based on the idea that consumers should know how data about them is used to make informed decisions. These laws require clients to explain how they're going to use information about individuals. Because we are still very much in that paradigm, every time we get a new law, all the privacy policies and contractual data protection terms get longer, more complex, and more operationally challenging for organizations to develop, implement, and comply with. These privacy requirements are often ambiguous or poorly defined, create technical and operational challenges, or don't easily map onto cutting-edge data-focused products and business initiatives.

One of the newer trends is the provision of EU-style individual rights, or data subject rights, that give individuals some control over information a company holds about them. These may include the right to opt out of processing of data about you in certain ways, such as for targeted advertising, the right to access or correct the information that a company holds about you, or the right to have information about you deleted or provided to you in a such a way that you can take it and go somewhere else.

Recently, the biggest trend has been an increase in complexity and cross-jurisdictional challenges caused by a proliferation of new privacy laws, particularly in the United States. After all, the Internet crosses borders, bringing data and associated legal requirements with it. The more jurisdictions that impose obligations on information, the more things we must consider. There's a lot of complexity there, which is great for privacy lawyers, but it's a real challenge for most other folks.

How do you handle these increasingly challenging laws?

My approach is to try to be as practical as possible, learning about the client's business needs and technological considerations, and try to find ways to address these privacy and security requirements while still helping our clients say yes to new opportunities, customers, and product offerings. Venable's broad and experienced privacy practice is very helpful for this, as we can provide a market perspective to our clients; for example, we might say to a client, "If you take this compliance approach, you're pretty much in the middle of the market. A lot of your competitors' market participants are taking a similar approach." It gives clients a little bit more clarity on what's going on in the market and helps them figure out where they want to be in terms of risk: whether they want to be in the middle of the pack, pushing the envelope, or more conservative than their competitors.

Do you have any advice for other attorneys or business professionals who are transitioning or considering transition?

Everybody's experience is different, so I can only speak from my own. But the most important thing is to give yourself time and a lot of rest and care. Hormones work slowly. The medical system is challenging to navigate. Anti-trans misinformation and discrimination are rampant. Grief and the accumulated trauma that you've built up over the years of not being able to be yourself take a long time to process and heal from. It is critical to give yourself room to experiment and figure out what makes you happy, and to allow that to evolve as you get to know yourself better and what you need.

It is the hardest thing I have ever done. But it is absolutely, positively, 100 percent worth it. Even with all the challenges, I am happier and more myself now than I have ever been in my life, and I would not go back.

The way that I looked and felt on six months of HRT is very different in a lot of ways from the way that I look and feel now at just over two years of medical transition. And that continues. You never stop transitioning. People sometimes ask, "Oh, when will your transition be done?" And I'm like, "Well, when do you stop changing in your life?" The answer, of course, is "never."