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Aparna Dasai Williams is the Chief Legal and Compliance Officer at Coalfire, a cybersecurity firm providing technology-enabled professional and managed services. Previously, Aparna was the Head of Legal and Compliance at Shippo, AGC at Imperva, and a Senior Director at Symantec. Aparna also serves as an advisor to Riscosity.
As a first-generation American, you make different choices than if you were a second or third-generation American. I loved theater, history, and art growing up, but I felt pressure to live up to my immigrant parents' sacrifices and pursue a professional career — a doctor or lawyer. Everyone told me, “Oh you like to talk, so you’d make a good lawyer.” That was in my head from when I was a kid, so I had it in my mind that when I grew up; I was going to law school.
In college, I was an English and History major, with a focus on Eastern Europe. I was fascinated by the whole region — Romania, Bosnia Herzegovina, the Slovakias — and its exciting history, literature, art, and culture. I thought, “This part of the world is breaking down. I want to go to law school, and then I want to use those skills to help rebuild their governments, their structure, and their society.” I didn't have any lawyers in my family and didn’t know many lawyers, so I didn’t really understand what law school would actually entail.
After law school at the University of North Carolina, Chapel Hill, I was trying to figure out what I wanted to do. I thought I'd probably end up near my family in the Washington, DC area. I was actually struggling with how I would fare in a traditional law firm setting — it didn’t seem appealing. Our career center put on an alternative legal careers panel with a diverse group of attorneys. One speaker was a young woman from IBM who started talking about being a contracts negotiator — reading, writing, talking to people, negotiating deals in the technology business. Contracts was one of my favorite classes in law school. My family is very entrepreneurial, so the idea of combining law with business really attracted me.
When I graduated, I didn't have a job lined up. Luckily, coming from an immigrant family, my parents were happy to take me in. I took the bar exam and told myself if I didn't pass, I'd get a master's degree in marketing and switch careers completely. I passed the bar, and a recruiter reached out about an opportunity at a software company in Virginia looking for a contracts administrator and negotiator. It didn't pay nearly the big law firm salaries, but it was what I was interested in. The lead attorney offered me a permanent role right away instead of starting as a temp. She thought I had the right attitude and wanted to train me. I was there for about three months when they got acquired. Another recruiter contacted me about an opening at a small cybersecurity firm much closer to my parents' house. I got the job and four months later they were acquired as well. One of the VPs at the company assured me I shouldn't jump ship again. He said “This new company, Symantec, is amazing and they’re going to want to keep you. You have this expertise in cybersecurity and they’re going to make an offer.” He was absolutely right, and I ended up staying there for nearly 19 years.
So, I sort of accidentally fell into an in-house corporate role right out of law school, instead of having the typical law firm experience first. I focused more on finding work I'd enjoy and wanted to do. I knew, from watching my family, that doing what you enjoy is really important. When I was in seventh or eighth grade, my dad was laid off from his accounting job at a big university, so he started his own CPA practice. He’s 82 years old and still doing that job.
I did not have aspirations to be a general counsel. I love operations, being a manager, running teams, and career development. When I was leaving Symantec when it had turned into Norton LifeLock, I told the general counsel there that I didn’t know what I was going to do next, but I needed to try something different since I’d been there for 19 years. He told me that I would actually make an excellent general counsel. I told him I didn’t think so — I didn’t want to deal with the politics and I’d never worked with a board of directors. He said, “You’re really operational. You know how to solve problems. You’re good at communicating with people. You take on challenges. Those are the skills you need to be a general counsel.” That was surprising to me because I was an average law school student; not top of my class. I thought being a GC was for the kids who did exceedingly well at law school.
When you don’t have mentors and coaches and people to bring you in, you have no idea. I learned as I went, but I was lucky to have amazing women who took me under their wing. I had a good attitude, great knowledge, and a good work ethic, so they were willing to help me along. No one succeeds alone — so you need to pay it forward and pull others along too. A great mentor allowed me to work remotely early on. Now it’s become my brand — I’m the remote general counsel. I’ve taken two jobs where I never met anyone in person before I got the job.
Keep an open mind, raise your hand for opportunities, and seek out people who are willing to mentor you. When young people ask about law school, I connect them with three practicing lawyers to share with them what exactly their day looks like. Have informational conversations to learn about roles.
When I was single without children, I was running 24/7 with work — you have the energy and nothing stops you when you're younger. I was the person they relied on for multi-million dollar contracts because it was something I was good with, and I actually did burn out. After five years I took a sabbatical to give myself a break. I wanted to see what else was out there. I tried my hand at writing some books because I love creative writing. I renovated a small house that I bought. I worked part-time doing policy work for a nonprofit. The company was open to me coming back after my time off, since I hadn’t left them for another job.
I was working in DC but moved to Roanoke, Virginia in 2006 and started working remotely. I didn’t have the car commute anymore and had to balance when I was working and when I had to shut off and transition to home. I lost that space to listen to the radio on the commute and started working all the time. I’m very Type A and it’s hard for me to leave something if it’s not done yet. I started doing calendar gymnastics to block time for work, exercise, and meals, which was helpful. But at the same time, being available all the time burns you out more quickly.
As an in-house lawyer, you get pulled in so many different directions. One thing that worked well was that I started making my calendar visible so people could see my meetings. Then, they were much less likely to double-book me. I made a conscious effort to block my time and let people know what I was doing. Yes, I have a reputation for being the one to call, but I make sure expectations are set correctly. When we did a major acquisition, I was literally sleeping from 9pm to 2am, working for 3 hours, then going back to sleep until 7am. I had a small child, so I had to prioritize my evening hours so I switched it to the early hours of the morning, which isn’t sustainable in the long run. I knew my sleep was going to be interrupted, but I made sure I got to sleep. It was crazy and I did it for a year. I just had to do what worked at the time.
It’s a constant struggle with different stages of life and having a young child who has practices and many activities. I went through postpartum depression and anxiety after having my child, and it just brought it all home that you cannot be all things to all people. You cannot give a hundred percent of yourself all the time. You really have to find a way to rejuvenate. The pandemic just just emphasized how important that was. Now, to recharge, I love reading and creative writing. I turn everything off by 8pm and go to bed with a book.
My biggest tip to anybody is to raise your hand for opportunities. Keep an open mind. If something different comes along, volunteer. Ask to shadow people and seek out people who are willing to mentor you. If there's something you're interested in, ask an attorney or teammate working on it for an informational interview: “How do you do that? Could you use some help? Can I try it to see how I do?” I was never afraid to ask out of curiosity. Don’t be afraid to request opportunities to expand your skills, even if it doesn’t lead to a promotion.
To become a general counsel, you must embrace being a generalist. I may not have deep knowledge of privacy, IP law, or 10-Ks. But at the end of the day, I know enough to be dangerous in everything. You have to become conversant across domains and learn what the specialists do. You have to ask questions and learn from them.
Honestly, I’ve learned more in the last 5 years than the first 15 of my career just in terms of the sheer volume and variety of work. I’ve learned how to manage so many different things. One key skill is knowing how to work with outside counsel. It’s a balance of “what can I do” and then “when do I rely on outside counsel and how do I make that work?” A lot of younger or less experienced attorneys don’t realize that you don't have to be able to do it all in-house. It's okay to rely on an expert who has niche knowledge. You shouldn't be spending your time on things that will make you an expert for only five minutes. You should be spending your time on things that will prepare you for the long term.
Practice law with a lot of humor and fun. When you see me stop smiling, that's when you should worry. You only live once, so make the best of it. I do enjoy what I do. The law has brought me a lot of cool things, particularly making me realize I can have an impact on the world that I'll be really proud of when I leave this world. That's kind of what it is for me — that's my driver.
The next generation comes in all shapes and sizes — not just fresh law school grads, but career switchers who've returned for law degrees and now join legal teams with experience in other fields. The next generation was raised with different tech, systems, and learnings. My brain was already full when privacy became a hot topic. Now you see waves of privacy experts realizing that they can build a career on it. When I mentor someone or I try to coach anyone, I try to tell them, “Look for what your strengths are. Look at what the hot topics are in the market and see if something speaks to you because that's a good way to go from a practical perspective.”
Keep in mind that you're never going to be successful if you keep aiming for something that doesn't play to your personal preferences and strengths. I’ve tried it. I was the sole counsel at an e-commerce shipping company. I could do the work, but I wasn’t passionate about it. That's difficult because there were a lot of people there who were passionate about what they were doing. So I went and looked for a job back in cybersecurity because that's what I’m passionate about and I love learning about the products and the industry. I’ve focused on litigation, employee relations, and other varied issues recently — not my passion, but it makes it all palatable.
I don't know how many times I can say this, because sometimes it comes off the wrong way, but don't always chase the money. Of course, you have to support your family and make enough money, but at some point when you're making enough, so you shouldn’t just chase getting the highest paycheck. You have to live with that every day. You do not want to be a highly paid miserable lawyer because that's not going to sustain you for very long, and will affect your health and create bad coping mechanisms.
It’s important to know your own measure of success. Success is defined differently for a first-generation American. I checked a lot of boxes by just graduating from law school. From that point forward, anyone in my family who was looking forward to me doing better than they did — that was already done. So what's next? Is it having a family? Is it making money? Is it living a particular lifestyle? You just have to realize that it's really personal to you what that success looks like. I have friends who have taken pay cuts to become the general counsels of nonprofits and they are the happiest I have ever seen them. They just love it. They knew it came at a particular type of sacrifice, but they also did it at a point in their career where they could make that sacrifice. I absolutely love that quote by Jackie Robinson: “A life is not important except in the impact it has on other lives.”
Know your legal stuff, but you have to know what your personal preferences are. You have to know where your interests lie, and then you have to figure out how to put all that stuff together and then take specific steps to grow your strengths. You're not always going to be able to make any of your natural weaknesses your best strength. I'm not good at math. I'm not going to become a calculus professor. So, I'm just going to learn as much as I need to and then rely on other people who do that better than I do. But then I need to strengthen my skills so that someone else who's not as strong in that relies on me. The way I built and even figured out what my strengths were was from raising my hand. I asked “Can I help you with that? Can I try that?” I had reached out to our corporate VP to talk about how to deal with SEC filings, and I had talked to our IP attorney about patents and trademarks and stuff. And I learned I didn’t enjoy it.”
Remember, it’s all symbiotic. Nobody makes it on their own. You cannot be in an in-house legal team by yourself, just like you can't be in a law firm by yourself. Everybody is organically codependent.
I was at one company for 19 years, and then I’ve switched jobs three times in the last four years. One of my mentors gave me great advice: “Never go to a company where you’re not in love with their product.” If it’s a technology company and the technology is not good, don’t go there. Look for places where you can wake up every day and say, “I’m proud of working here.”
In the interview process, don’t be afraid to ask all of the questions you’re curious about. I will talk to the general counsel or whoever the hiring manager is, but don’t be afraid to also talk to the business people. Talk to the recruiter and HR. Talk to the head of engineering or the head of manufacturing or production. Make sure you speak to someone in customer service and someone in finance. Ask for a more diverse interviewer portfolio because you want to know what you’re really going to be doing. These are the people you will spend every day with — not just your legal team. You’re going to be talking to and working with HR a lot.
Get to know the actual company, and don’t be afraid to ask those questions. A lot of times, we’re just so focused on what the job is. How much does it pay? Am I going to get more experience? Will I be able to grow my resume? All those things can be fine in a vacuum in the legal team, while the rest of the company could be falling apart, and you won’t know until you get there.
I've always loved to travel, so I love going anywhere new. I've been doing a little more of that in the last couple of years. The pandemic put a big kibosh on that, so I'm happy to get back into going to places. You know, we've got a fun spring break planned in Charleston. I just came back from Las Vegas, which I've been to a bunch of times.
I love that energy that I get when I travel to a new place and see everything and experience it. Because even if I have to work a little, doing it with a different vista is something I love. I read a lot — I love to read. Right now, it's mom life. I take my kid to all his practices and drum lessons, and we're pretty involved in our faith community. That's life outside of work right now. It's very family oriented and just enjoying the world.
When the pandemic put us all on lockdown and it felt very Groundhog Day, I really thought about how valuable experiences are. So we’re focusing on that — just doing things. We go to new restaurants, we go to see different places, we go to a different museum.
As part of focusing on experiences and things we enjoy versus material things, I’m in purge mode as well. I actually gain a lot of satisfaction from just regifting things to different homes — “Hey, I have this instant pot. I used it twice. Enjoy.” Simplifying my physical space is another part of taking care of my mental health. My physical space has to be clear before my mental space can be clear.
I am turning 50 this year and so excited for this next decade of new experiences and choosing joy and family over prestige and accolades. I am also focusing my contribution to the legal community on more mentoring and being a support network for folks who are still trying to figure out what to do when they grow up!
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