5 Pieces of Career Advice from Leading Ladies of Legaltech

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With constant, rapid change, complex rules, and high stakes, the world of legaltech can be difficult to navigate for those early in their careers. DISCO recently gathered five women who have risen to prominence in legaltech to share their candid advice about how to succeed in this high-pressure industry, from valuable skills to cultivate to building a personal brand.

Participating in the panel were:

Cat Casey: Chief Innovation Officer DISCO

Cristin Traylor: Discovery Counsel, McGuire Woods LLP

Debbie Reynolds: Founder, CEO, and Chief Data Privacy Officer of Debbie Reynolds Consulting

Sadie Khodorkovsky Koyfman: Executive Director, Legal Discovery Management, Legal Department, JPMorgan Chase & Co.

Stephanie Clerkin: Director of Litigation Support at Korein Tillery

A screenshot of the panelists

The full video of the hour-long panel is embedded at the end of this post.

1. Your unique background is an asset

Debbie entered the ediscovery world from a background in library science, helping university libraries create databases. Sadie was a programmer who liked tinkering with computers. Cat attended law school, then turned to selling BMWs before a customer convinced her to return to law in the ediscovery realm. 

The point is, although a background in law school or technology is helpful, it’s not absolutely necessary to be successful in the world of ediscovery. If you’re curious about the industry, always looking for new efficiencies, and eager to learn, there could be a place for you in the field. As Stephanie explained, “I can teach people basic technology, what I can’t teach is that intuition and problem solving piece. Regardless of your background, if you have that problem-solving piece, I can teach you anything else.”

2. Learn the essential soft skills 

So what makes someone successful in ediscovery? The panelists brought up several qualities that are beneficial for the field. 

The top soft skill discussed on the panel was empathy. Being able to put yourself in the shoes of whoever you are talking to — understanding not just what someone is saying, but why they are saying it — will help you both work towards a common goal. As Sadie put it: “If you don’t know what’s driving somebody to ask for something, you’ve gotta understand that. [...] That way, you’re not reacting all the time, and you’re coming from a balanced perspective.”

Some of the other skills brought up included: 

  • Remaining calm under pressure: The legal world is full of stress and deadlines. Bringing perspective, being willing to let things go, and helping others breathe can turn you into an essential asset for a legal team. As Stephanie said, “Unless someone is going to die, which they probably aren’t, it isn’t as bad as you think.”
  • Translating techspeak to simple language: Being able to explain technology in easy-to-understand terms is essential to bridging the gap with the legal world.
  • Thinking ahead: Cristin found that seeing several steps down the road and using that insight to provide recommendations as to what will or won’t work in ediscovery made her invaluable to the team.
  • Be willing to learn: “Some people think a mentor means they just give you a silver platter and say, here’s an opportunity,” said Cat. “The reality is, they say, here’s something I need to learn about, go learn about it.”

3. Get to know people

Building one-on-one relationships with your colleagues can ensure harmony when working together. Start conversations by asking about someone’s weekend, or how they’re doing that day, rather than jumping straight into the project. Cristin shares, “It’s not all about here’s what I can do for you, it’s also, who are you and how can we get to know each other?” Stephanie uses this understanding of someone’s personality to tailor her communication strategy to that person. Debbie recommends building this rapport when people are more relaxed at the very beginning of the case — as it will help later when everyone is stressed. 

4. Build your brand

“There’s never been a more important time to invest in your brand,” says Cat. “Roles change, industries change, but if you’ve created this authentic brand, people know to trust you generally, which leads to business opportunities and mentorship opportunities.”

Building your brand means building your credibility. This work can take many forms: writing a blog post, speaking at conferences, or even just a simple post or comment on LinkedIn. Debbie started with posting one article a week — which later led to one video a week, then a podcast, and business opportunities. She adds, “It’s not who you know, it’s not what you know, it’s who knows what you know.”

And, don’t be afraid to be yourself! Cat and Stephanie found they were able to create more authentic connections by putting their personality on display. 

5. Build your network

As Sadie pointed out, you’re never going to know it all, and you’re going to have to accept that. Your network can help you figure out what’s out there, and what trends you should look into. Stephanie also encouraged getting ideas from people in other industries, as she was recently inspired at a biotech meetup. “It’s amazing what’s out there and how much overlaps in so many ways,” she says.

Cat also recommends building a circle with not only your peers, but people who have the job you want to have, and people who are where you were five years ago. Talk with these connections to spitball ideas and identify emerging priorities. 

Not sure where to start? Sadie shared her strategy: “If there’s somebody I know I want to talk to, I set up a meeting with an intro email. People have been very generous with their time as long as they understand what your angle is.” And all of the women on the panel encouraged attendees and readers to connect with them on LinkedIn!

The women ended the panel with some parting words of advice, summarized here:

Cat — Stay curious, and don’t be afraid to reach out. There’s never been an email I’ve received where I’ve been like, “How dare they!” 

Cristin — Think long-term. Don’t get so caught up in the day-to-day. What do you want to do, what do you like doing, what is your plan? Then implement it. Set up conversations, attend webinars — don’t forget your own career development and plan. 

Debbie — I would like to see more people interact. If you’re daunted by what Cat does, comment on her posts. If that’s all you can do, do that. (Plus, comments help the algorithm boost her posts, so you’re doing her a favor!)

Sadie — Wherever you are in your career, think about what you wish had happened getting you to now. Seek out junior folks you want to build that relationship with. 

Stephanie — Don’t expect to get it right the first time. Own your mistakes — no one is perfect. If you have a random question, send it our way! It’s the best way to start building your network. 

Don’t forget to follow DISCO on LinkedIn to be the first to hear about future panels! 


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