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Pearls On, Gloves Off: The Best Advice for Growing Your Legal Ops Career

February 8, 2023 4 min read
Hand holding a phone displaying an episode of Pearls On Gloves Off

It’s no secret that legal ops has become a hot topic of discussion for law firms, GCs, and in-house legal departments. Want to scale your legal department the smart way? Hire a legal operations professional. Want to optimize your GC’s time? Legal ops. Need to modernize your legal tools and processes? Yep – legal ops.  

A good legal ops department functions as a strategic partner to the rest of the legal organization, and to the overall business. From risk management and compliance monitoring to strategic investment and technology planning, a proactive legal os team can anticipate and plan for challenges before they arrive, and their expertise often spans finance, marketing, data analytics, learning and development, and more.

Our own Head of Community, Mary O’Carroll, has been speaking with some of the sharpest, most creative legal minds she knows — people who’ve made the move to legal ops — for her podcast, Pearls On, Gloves Off, which launched last year. Here are some pearls of wisdom from the first five episodes, focused on growing your legal ops career. 

Recognize the Value of Uncharted Careers 

First up is our own Alex Su. Alex is the Head of Community Development here at Ironclad. He’s also a former lawyer and current social media star — seriously, his @legaltechbro TikTok account has more than 100K followers!

Alex’s journey off the beaten, “partner track” path to legal ops and TikTok fame isn’t for everyone. As Alex told Mary, when he first told his friends back in 2016 that he wanted to get into legal tech, they weren’t exactly enthusiastic about the idea. “My lawyer friends were like, ‘What are you doing? This is not a charted career path. Are you crazy?’,” he said. But as Alex explains in the episode, there’s value in the experimentation itself. “Doing something weird, before it’s cool, is a part of it,” he said. “It becomes sort of a muscle…where you see some patterns and things start getting traction. And the ones that [get] a reaction from the world, I [stick] with.”

Let Passion Take the Lead

Next, some wisdom from Mike Haven. Mike is Sr Director, Associate General Counsel, and Head of Legal Operations at Intel, and he’s now also the President of CLOC. Mike’s own move into the field was born out of a passion for creating change. During his time as a law firm lawyer, he saw an inherent conflict of interest between his obligations to his clients and his obligations to his firm. Namely, that he was being compensated based on how many hours he billed. “To provide the best service to my clients, I should be really efficient and not bill a lot of hours,” he said. “I should be compensated for being efficient, not for being inefficient.”

As Mike explains in more depth during his Pearls On, Gloves Off episode, he found passion and meaning in legal ops, embracing his new role as a changemaker. But he cautioned that the field isn’t necessarily a great fit for everyone. “Looking at a job in legal operations because you’re not happy in your current job isn’t likely to yield much happiness in and of itself,” he told Mary. “It’s no cakewalk — it’s actually really hard because we are changemakers in a profession where people really hate change.”

Bring Your Creativity in Full Force

Finding a way to bring your whole self to work can be a challenge for anyone. Artists and performers, in particular, often find themselves living a dual life split between a day job that pays the bills and after-hours pursuits that fulfill their creative spirits. But what happens when we find our way to a job that lets us bring our full creativity to our careers? Magic, that’s what!  

Jenn McCarron, Director of Legal Operations and Technology at Netflix, told Mary about the moment it all came together for her. “I was going out at night, playing in bands and promoting, and then doing my day job,” she explained. “When I flipped it all to one thing and brought it all into work every day, it really went up sharply from there.” In legal ops, Jenn found a work space big enough to put all of the force of her creativity into. “The more I put creativity in, the more that people liked it,” she said. “Legal liked it, businesses liked it… people liked it!” Lesson learned: When people can bring their full selves to work, the results tend to be pretty good. 

Build Buy-in for a Legal Ops Department

Last but certainly not least on our highlight reel is Mark Ross, Principal and Co-Leader at Deloitte Legal Business Services. Mark joined Pearls On, Gloves Off to share advice on convincing reluctant leadership to invest in legal ops. “Contracts are strategic business assets. They serve multiple interests, they serve multiple purposes,” he explained. As contracts typically affect multiple stakeholders within an organization, identifying what each stakeholder group stands to gain from legal ops is key to winning executive buy-in. 

In this information-packed episode, Mark details the type of research needed, the information you need to gather, and how to present everything to get support in building out a legal ops department. He also talks about the benefits of garnering executive support that go beyond getting sign-off to stand up a team. “You need a really discriminatory lens through which you look at all those requirements being gathered,” he said. Listen to the episode to get the full scope of how the right in-house backers can help you build a more successful legal ops department. 

Subscribe for more pearls of legal ops wisdom!

Keep up with the best conversations with the brightest minds in legal ops and beyond. Subscribe to Pearls On, Gloves Off on Spotify, Apple Music, or wherever you get your podcasts. Questions? Please connect with Mary on Twitter and LinkedIn

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