Interviews

AI, Mentorship and the Future of Law: Insights on Embracing Change in the Legal Profession – Bill McCormick, Legal Expert and Mentor, Greater Chicago Area, United States.

This interview has been published by Anshi Mudgal and The SuperLawyer Team

In your profile, you described AI as a “young associate” in the legal field. Could you elaborate on how AI is redefining traditional legal roles and the kinds of responsibilities we might pass on to AI? How can lawyers adapt to this shift?

I came to law from a manufacturing and engineering background, which gave me a unique perspective. The legal industry differed dramatically from manufacturing and engineering—specifically the accountability and lack of measurement. Much of law is learned through apprenticeship, which is vastly different from the formal training in engineering. In fact, I felt law school left me far less prepared for my career compared to the preparation engineering school provided for engineers.

When I entered the legal field, I realized law practices could be more efficient. I compared it to medicine, where patients now play an active role—researching symptoms, diagnosing themselves (sometimes overly so), and bringing their questions to healthcare professionals. Medicine became somewhat democratized, allowing patients to take ownership of their health, for better or worse. This shift hasn’t happened in law on the same scale.

Most of my career has been in corporate law, and I observed real changes in other corporate departments, like accounting and finance, which moved away from manual tasks toward insightful, risk-based processes supported by software. By contrast, legal departments stayed static for many years. While there were incremental innovations, such as moving from typewriters to word processors or shepherdizing cases online, none of these fundamentally transformed the legal industry. 

One significant development came with Alternative Legal Service Providers (ALSPs), which began specializing in areas like eDiscovery in litigation. They didn’t threaten traditional lawyers because these tasks were in untraditional fields. Similarly, in-house legal operations began to introduce the idea of running law as a business, but even that didn’t fundamentally change legal practice, which remained heavily relationship-driven.

We also saw the rise of skilled paralegals, legal process-outsourcers, and other support, but the core practice of law didn’t evolve significantly. In the U.S., access to justice remains a major issue. A large portion of the population can’t afford legal assistance unless they are at a very high-income level. While many dedicate themselves to justice-based work, the problem persists.

Where I see generative AI playing a significant role is in finally shifting some of the ways legal services operate. Generative AI has the potential to fundamentally change the role of outside counsel by improving productivity, reducing rote work, and allowing legal professionals to practice at the top of their expertise. It could bring greater satisfaction to legal roles by enabling lawyers to focus on higher-level thinking, problem-solving, and client strategy. I’d like to believe this will make the field more engaging—and even more fun.

Many lawyers fear AI might take over the legal profession. You’ve been teaching AI engineers to understand “how humans do law.” What surprising or challenging aspects of this collaboration have you encountered? How has your legal and engineering background shaped your perspective?

I wouldn’t go so far as to call myself a “professional” engineer, but my engineering mindset informs everything I do. Regarding AI, I understand the fear—that it might replace lawyers. But I see it differently. As AI reduces costs and improves productivity, legal services become more accessible. More people will be able to afford legal help, and demand will rise. In turn, lawyers will manage more clients while performing at a higher level.

AI isn’t going to take over the legal profession. It’s going to be a tool—a partner and an enabler. This means lawyers can focus on preventing problems, conducting root-cause analyses, and understanding systemic issues instead of repeating the same tasks or racing against time. That’s why I encourage younger associates not to fear AI but to embrace it, adapt to the inevitable pace of change, and maintain a mindset of continuous learning.

What have been the most important skills or mindsets you developed while working on more than 35 M&A deals across 13 countries? How did you navigate the cultural and demographic differences in those deals?

Every culture, country, and even corporation has its own personality. Two key lessons stand out from my experience: humility and collaboration. I don’t assume I know everything. For example, even if I’ve done M&A work globally, the local counsel advising me always knows far more about the nuances of their jurisdiction. They bring priceless insights that I wouldn’t have on my own. Similarly, I’ve learned to be transparent about my preferences, expectations, and objectives while fostering trust.

In any negotiation, it’s critical to show truth, trust, and vulnerability to create an environment where others feel safe to reciprocate. That allows for the best possible collaboration and outcomes.

You’ve negotiated with Fortune 100 companies and Big Four banks. What challenges and rewards have you faced in those negotiations, and how have those experiences influenced your role as a mentor?

The hardest part of negotiations is working with someone unprepared, especially when you’re doing most of the work for both sides of the deal. It doesn’t make for great results. On the other hand, negotiating with the Big Four banks was challenging but rewarding. They were experts—specialists who deeply understood nuanced regulations like credit reporting laws. Collaboration required me to respect their expertise and remain concise and factual while educating them on where our roles aligned. 

In negotiations, preparation and confidence are essential. But you must also align closely with your team and communicate openly to achieve success.

You heavily emphasize mentorship and learning. What’s the most impactful piece of advice you’ve received that you pass on to mentees?

Be true to yourself. Focus on developing your strengths rather than obsessing over weaknesses. I believe we’re all given unique gifts. While it’s important to address our shortcomings, trying to “fix” them at the expense of our strengths does more harm than good. The key is to leverage your natural abilities while minimizing distractions from your weaknesses.

You seem to live a life of continuous learning. How do you practice implementing new knowledge in both your personal and professional life?

The key is repetition. Whether it’s a new skill, concept, or even something as simple as someone’s name, using it consistently helps retain it. Skills, particularly technical ones, are perishable if not employed regularly. Teaching, in particular, has been a way for me to cement what I learn. When I share knowledge with others, I not only reinforce what I know but also open myself to learning from their insights.

Your profile mentions a love of backpacking. How has that hobby helped you manage stress or shaped your approach to life and law?

Backpacking forces me to unplug. It takes me back to the essentials of life: reaching the destination, managing supplies, and supporting those hiking alongside me. The simplicity is both grounding and rejuvenating. It reminds me to keep stress in perspective and appreciate the privilege of the work I do.

You’ve had a diverse career across industries like fintech, MedTech, and law. How has this versatility shaped your perspective?

My career has been a journey of curiosity and learning from diverse environments. Moving between fields allowed me to bring insights from one industry into another. For example, working across corporate governance allowed me to see how brilliant leaders approach complex issues. These experiences have helped me ask better questions, foster collaboration, and apply versatile approaches to newer challenges.

Ultimately, people matter more than tasks. Empathy, kindness, and respect guide my interactions, whether I’m working with a Fortune 500 CEO or a junior colleague. Maintaining humility and staying true to these principles is essential.

As technology and societal shifts disrupt the legal profession, how are you preparing for the next decade? How do you mentor others to adopt a similar mindset?

The legal profession is undergoing the most significant inflection of my lifetime, and I’m excited to be part of the generation ushering in this change. To prepare, I focus on continuous learning—keeping up with technology, gaining simulation-based experience, and staying abreast of fast-paced changes.

Personally, I see the democratization of justice as a key issue for the next decade. I hope to leverage my skills and technology to support pro bono efforts and improve access to justice. While the system is imperfect and broadcasts its flaws, history shows us that societies cannot exist without the rule of law. Ensuring we uphold and adapt that system responsibly is a challenge I’m ready to embrace.

Get in touch with Bill McCormick –

Click to comment

Leave a Reply

Your email address will not be published. Required fields are marked *

Most Popular

To Top