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Thoughts On Two Decades in Legal

March 28, 2024 6 min read
AI generated image of a road winding through a colorful valley

It’s hard to believe. Twenty years ago, I walked into Orrick to start my new job, and along with it, my career in Legal. I had no idea that I was starting a journey of discovery, connection, and growth that would consume me for the next decades.

I’ve changed companies, titles, and zip codes plenty of those years, but one thing has never changed. I never lost my passion for the people,  problems, and opportunities of Legal. I never lost my belief that we could find a better way to make this industry work. It’s been a long and winding road, with plenty of frustrations along the way, but it has always felt important and worthwhile.

I couldn’t let this milestone pass without taking advantage of the opportunity to look back and think about the lessons I’ve learned.

Change is hard and slow

My first job at Orrick set the tone for my career in a lot of ways. I came in with a mandate to help the firm grow quickly and profitably, certain the skills I learned in investment banking and management consulting would allow me to make a rapid impact.

I was in for a surprise. Orrick was then, and continues to be, one of the most progressive and modern law firms. Still, it was a huge culture shock after the professional services and finance organizations where I had worked. I learned that new ideas in law firms could be met with skepticism or even rejected simply “because we’ve always done it that way.” Orrick certainly made some industry leading moves like opening their global operations center in West Virginia,  but there was no chance of making deeper changes that affected the business model.

I once brought in a vendor to pitch a new technology that would significantly speed up the amount of time our associates spent doing research. One of the partners’ reaction: “Why would we want to do that? That’s how we make our money.” As broken as things were, as misaligned as the business model was to client interests, the people that mattered liked things just as they were. As Richard Susskind famously says, “It’s hard to tell a room full of millionaires that they’ve got their business model wrong.”

This industry has a way of teaching you humility! When I started with Google, I thought that, because we were a tech leader, we would be able to perform as a modern, connected legal team right away. I assumed we had all the best systems and dashboards in the world, only to learn that our leaders were tracking their matters on post-its stuck to the back of their laptops. I also assumed that, because we were a marquee account to our firms, we would be able to demand real changes from our firm partners. I discovered otherwise when I sent our new billing guidelines to all of our firms, only to have one of the biggest ones respond with a message that simply said, “Acknowledging receipt, but no thank you.”

I was learning the biggest legal innovation lesson of all: Just because it is obvious does not make it easy. So much of what we were talking about felt like common sense, but it was so different from existing ways of thinking and working that getting people to buy into it was hard. Shifting long-entrenched behavior and beliefs in an industry resistant to change is a slow and steady game. You need creativity and ingenuity, for sure, but what you need most of all is patience and resilience.

I’ve been having the same conversations about the billable hour, law school curriculums, and why legal ops matters for the last 20 years… many of them are exactly the same conversations. It’s easy to think nothing has changed because for many departments and corners of our industry, it’s true. But there are moments of brightness when you talk to a GC that gets it, and it makes it all worth it!

There is power in community

There is only one way that I found to speed up that long, hard journey towards innovation: Tapping the power of the community. Time and again, I have seen how groups of people working together towards a common purpose can achieve far more than they would have on their own. They can share ideas and practices, uplift each other, and break through barriers together. They stop being a collection of isolated individuals or small teams and become a movement.

From the earliest days of CLOC, this was the vision. People came together from all parts of the ecosystem, turning their diverse skills and perspectives into common value. And from their collaboration emerged a new set of practices and ways of working that together helped change the way much of Legal operates.

I believe more than ever in the power of community, particularly when it comes to uncovering new solutions through the power of crowdsourcing.

Lead with compelling technology when you can

When I started working in legal innovation, the conventional wisdom was always: “Start with people and process, don’t touch technology until later.” And this was the right approach for a long time, because the technology was clunky and hard to use, and would not deliver compelling value on its own. You needed to do a ton of deep change management work to prepare the way and get people ready. We used to do entire marketing campaigns with swag and contests, posters, slogans, emails, happy hours, even signage in the bathroom stalls to get people’s attention. We used to joke that our team needed frying pans so that we could walk around and hit people over the head to get them to change their ways.

With the rise of Legal Ops, and the subsequent investments in Legal Tech, we began to see much more compelling solutions emerge. These were no longer awkward compromises but compelling, intuitive systems that aligned to the actual people and realities of Legal teams. At this point, it sometimes became easier to lead with the technology and let it “speak for itself.”

Think of a consumer solution like DoorDash. You don’t need to show someone a presentation about why they should use it. They can just try it for themselves! When tech gets simple and easy enough, you can just get out of the way and let the experience and value come through.

This type of user-friendly, simple technology is so helpful to driving adoption. That’s what drove me to join Ironclad in the first place; it is just so easy to work with. I remember right after I started we were working with a company that laid underground pipes and infrastructure for cities. They were concerned about launching a CLM solution because their stakeholders were general contractors and plumbers, a community that they believed would struggle with self-service software. But it just worked! Adoption was 100% right from the start. Their CEO was so happy he wrote our CEO a letter!

When you can lead with compelling technology, it is such a better model for deployment. Instead of begging people to try the new tools, you can simply sit back and watch while your pilot users encourage and persuade others to try something they love.

We still have a long way to go

If you spend a lot of time with “expert” people and organizations, it can be easy to think that our industry is much more advanced than it actually is. The reality is that, for all the remarkable innovation and progress that we see from some teams, and some of the amazing best practices out there, most teams and companies are still in an absolutely basic state. We still have so, so far to go.

Most companies still do not have a legal ops role. Most still have no real tech or tools and are essentially doing things the same way they were done 50 years ago. And yet if you ask many of them, they’ll tell you that everything is just totally fine and that they are meeting their clients needs.

This is why education still matters! Because as an industry, we still have so much growing up to do. It’s one of the reasons why AI is so exciting, because it offers the chance for some of these lagging organizations to leap forward. But even though there are enticing new possibilities for ramping up quickly, the answer can’t come from technology alone.

For all the progress we have made over the twenty years I’ve been working in the industry, we still need a knowledge transfer at scale across Legal. We need to do far more to spread the word about legal operations and its possibility for transforming and growing business. If we don’t, we risk leaving the great majority of people and companies behind.

“The hard is what makes it great”

I’ll close with a quote from one of my favorite movies, A League of Their Own: “It’s supposed to be hard… The hard is what makes it great.” Tom Hanks’ character was speaking about baseball there, of course, but he could have been describing the work of legal innovation.

There were so many moments where I wanted to scream with frustration… where I felt like I was hitting my head against a wall. But without those hard times, there would be nothing like the same sense of reward and validation when you finally break through! Doing this type of work is hard and at times discouraging, but ultimately so, so worthwhile.

I still go to work excited and challenged. I still feel the drive to make things better. And I feel like there are more exciting things happening in our space than ever. What else can you ask for? On to the next twenty years!

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Mary Shen O’Carroll is Ironclad’s Chief Community Officer. Previously, she was the Director of Legal Operations at Google, as well as the President of the Corporate Legal Operations Consortium (CLOC). In her early career, she served as the Profitability Manager for Orrick, Herrington & Sutcliffe LLP and was an investment banker and strategic management consultant. Mary is also a passionate leader pushing forward disruptive technology and processes designed to change the future of the legal industry.