UniCourt Influencer Q&A with Cheryl Wilson Griffin of Legal Tech Consultants

Cheryl Wilson Griffin is a pioneer of bringing technology into the courtroom and into focus for law firms. 

From her experience of working nearly a decade as “the first, the most senior, and the only woman on a team” bringing technology into litigation to expedite and improve trial at Kirkland & Ellis LLP, which just reported over $6.5 billion in gross revenue last year, to her work at other global law firms ushering in the future of legal tech, and even more recently when she brought us Back to the Future with a DeLorean at Legalweek 2023, Cheryl Wilson Griffin has continued to expand her knowledge of and impact on the greater legal ecosystem.

We enjoyed getting to speak with Cheryl about her career path into legal and her advice for law firms, legal ops, and legal tech, and hope you enjoy learning from her insights as well!

UniCourt: Tell us your story. What is your background, and what led you to what you are doing now?

Cheryl Wilson Griffin: I feel like every story in legal tech starts with, “This wasn’t the path I started out on…” My journey is much the same.

My undergrad was focused on communications and graphic design and my early roles were in marketing. I thought I would one day be running some sort of modern, female-driven “Mad Men” agency. And I was well on my way, working with some big accounts at an agency selling a new concept – synchronized relationship marketing – what we call integrated marketing today. I was an ambitious, young professional and a woman who’d just bought her own townhome solo. I was on my way.

But then the September 11^th attacks happened. Though I was lucky to be safely in Chicago, everything changed overnight. Profits and revenue and selling weren’t the only things that mattered anymore, and much of the marketing and agency worked dried up overnight. As one of the youngest team members, I found myself unceremoniously laid off a few months later and the company largely closed shop.

Unfortunately for me, all that ambition had left me with a mortgage payment and a very minimal unemployment check. No one was hiring in marketing at my level, so it was time to pivot. I had to figure out how to apply my skills and talents to a new profession, one that was hiring right now and would survive the years post-9/11. Enter litigation consulting.

I joined a boutique litigation consulting firm focused on expert testimony, graphics for trial, and courtroom presentation as a project manager and graphic designer. About a month into being hired, I was sent on my first trial in Charleston, West Virginia, where I got to see big, multi-party defense litigation up close and personal. And it was just as creative, and exciting, and intellectual as working at any agency. I was hooked.

For many years, I thought I’d go back to marketing once things stabilized. But, a few years later I had the opportunity to join one of the first-of-its-kind groups focused solely on bringing technology into the courtroom on behalf of a single firm – Kirkland & Ellis. I spent nearly 8 years as the first, the most senior, and the only woman on a team which helped establish for the rest of the industry that technology could expedite and improve trial.

From there, I’ve always tried to keep expanding my knowledge, skills, and network so I could be ready to take advantage of the opportunities presented by new technology. And, hopefully, my career over the past two decades shows I’ve done that successfully.

UC: What is Legal Tech Consultants? Can you explain how it bridges the gap between business, law, and technology for law firms and legal operations teams?

CWG: Legal Tech Consultants was founded with the goal of improving legal service through the effective use of technology. In the simplest words, we help smart people get cool stuff done.

One of the things I’ve found limiting in all my roles, whether on the buyer or service provider side, was the singular focus on one firm or solution. I want to bring my whole self – all my knowledge,  experience, and talents – to the people I work with. If I’m focused on selling or buying a single product, I don’t have the freedom to explore the problem and potential solutions in the broad way the industry needs.

That’s why we’re committed to supporting all three groups involved in legal tech. We help law firms and legal ops teams make good buying choices and implement custom adoption strategies. On the flip side, we work with tech startups to help bring them closer to their customers and ensure that people know about some of the new and emerging solutions that are out there. I truly believe that collaboration is the key to the industry’s evolution.

UC: As someone who has worked as the Director of Legal Technology Solutions for King & Spalding, a Senior Trial Technology Specialist at Kirkland & Ellis LLP, and a Trial Technology Services Manager at Mayer Brown, how have you seen the use of legal technology in law firms evolve over the last decade?

CWG: I’d argue that the use of legal technology hasn’t evolved much over since I joined Kirkland in 2005. Why? Because our approach to legal tech hasn’t evolved much.

While more firms and legal ops teams are hiring innovation and legal tech strategy roles, most still don’t have the autonomy needed to operate effectively. In many cases, IT still drives tech decision-making because the Chief Information Officer controls tech spending. But how does someone who spent their lives perfecting phone lines and infrastructure make great buying decisions for lawyers? I encourage the industry to move budget control as close as possible to the users they’re buying for. This ensures the people closest to the problem to solve (i.e., the work to be done) are engaged in picking the tools that best serve their needs. It’s not that we’re not investing enough into legal technology, it’s that we’re spending unwisely today. It is my hope that better management and choices in legal tech spending along with advances in our understanding about how adults learn helps us take our use of technology to the next level.

UC: What are some of your top pieces of advice for legal tech companies selling to law firms? On the flip side, what also are some of your key pieces of advice for law firms looking to buy new legal technology software?

CWG: For law firms buying tech, my advice is always the same – make sure you fully understand and identify a valuable ‘problem to solve’ before you consider spending a dollar. If you’re not able to invest this time up front, it’s unlikely you have the time to successfully roll out the new technology. It’s that simple.

For legal tech companies, I’d suggest two things that I don’t see enough of today. First, intimately understand your buyers’ typical budget cycle, their typical fiscal year, and which department ultimately holds the money you want access to. The lack of awareness in this arena always surprises me – how do you expect to sell to someone without understanding the financial concerns they’re balancing? Second, make sure you hire former legal tech buyers… and listen to them. 

I’ll be hosting a webinar on May 23^rd targeting anyone who wants to understand the different budget cycles impacting legal tech buyers. Attendance will be limited to allow for good Q&A, so register now with this link.

UC: What do you see as some of the biggest challenges legal operations teams face when seeking to leverage legal technology to modernize their legal departments?

CWG: Bless your hearts, legal ops friends. Every year, your companies ask you to do more with less, and somehow you continue to succeed. I’m not sure how you do it.

There are three major challenges I hear regularly from these pros. First, there is no budget for anything. In most corporate legal departments, there’s a limited group of people who require legal-specific software and that makes it hard to legitimize versus other places the company needs to spend. Second, it can be hard to integrate legal department tools with the rest of the company’s tech stack, creating friction as other business leaders try to engage legal. And finally, differential power. Even where they know that the use of a particular technology could save costs or improve outcomes, law firms continue to push back, often hiding behind false security and liability tradeoffs to avoid change.

UC: What are some of your favorite sayings? What are some real-world examples of how you’ve seen those sayings come to life?

CWG: If you hang around me long enough, you’ll soon hear me ask, “What could possibly go wrong?” While this is a cheap joke for most people, it’s my first step in decision-making. If the worst thing that can happen is not that bad, I don’t put much energy into that decision. It allows me to preserve the limited mental resources I have for the most high-risk issues.  Try it – you’d be surprised how freeing it is!

UC: What are your goals for the rest of 2023? What projects are you working on? Are there any events in the legal tech, law firm, or legal operations space we should know about?

CWG: This is turning out to be an exciting year. I’m working closely with a handful of disruptive startups in the legal space, where I’m leveraging my years of experience as a legal tech buyer and seller. Whether it’s help with product-market fit, pricing strategy, sales and marketing, or raising capital, I’m helping startups scale their technologies, talent, and tactics and realize their most ambitious goals.

Most recently, I had the opportunity to help showcase the latest use of AI in legal, helping the folks at Altumatim launch in the LegalWeek exhibit hall with a DeLorean. In May, we’ll be launching a new talent network to make it easy to build diverse teams by allowing legal professionals to share more detailed information about how they identify in the world. And we’ll host the first in our Legal Vanguards series, a webinar series that aims to bring together technology and startup leaders in the legal industry to better understand each other’s needs, foster collaboration, and drive innovation.

In the Fall, I’ll be speaking in October in Palo Alto at the 2023 LegalTech Summit hosted by the World Litigation Forum. Hope to see you there.

Our last scheduled event of the year will be The Legal Tech Fund Summit, where the latest tech and investment professionals will meet in December. 

UC: Where can we learn more about you and your work?

CWG: I’d love to connect with your readers on LinkedIn, where I try to share content on everything from implementation strategies for law firm professionals, leadership  and general silliness. You can also connect with our Legal Tech Consultants social media channels here on Linktree.

Legal Industry Evolution through Better Collaboration

As Cheryl and her firm, Legal Tech Consultants, have highlighted, collaboration is the key ingredient for legal industry evolution. Law firms, legal ops, and legal tech all need to be taking advantage of the opportunities for collaboration present in the legal ecosystem of solutions and their corresponding challenges to evolve and grow. 

We always love hearing Cheryl’s perspective, and we’re excited for what she’ll do next in the legal tech space!

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