Michael A. Jacobs has been translating foreign languages his entire career. Not literally, (though he did spend time in the Foreign Service before law school). Michael’s speciality is interpreting the nuances of technology for judges, juries, and boardrooms.
His cases span the history of the technology industry: Fujitsu v. IBM on mainframe software; SCO v. Novell on Linux; Oracle v. Google on APIs and Android; Apple v. Samsung on the smartphone; and The New York Times v. OpenAI on LLMs and copyright. Each case involved a brand new technology, and a novel set of legal questions with no clear precedent. And, perhaps most challenging, to translate the new technology and its potential implications to a room of people who have never written a line of code.
GC AI founder Cecilia Ziniti was a summer associate at Morrison Foerster when Michael was managing the San Francisco office, and credits him as an impactful early career mentor. Their conversation covers what it takes to lead billion-dollar litigation, how to deliver bad news in a useful way, and how AI is affecting a profession that’s about humans talking to other humans.
"Number one thing that remains the same is the challenge of interpreting this foreign language to a lay audience, to lay decision makers. It is the principal task, I think, of a great IP litigator: to be able to analogize things in a way that makes sense."
What Billion-Dollar Litigation Looks Like From the Inside
According to Michael, the first thing that changes when billions of dollars are on the line is the case’s information architecture. His immediate contact is generally the head of litigation, the general counsel, or sometimes an executive tasked specifically with running the case. Whomever the point of contact, they’re ultimately an intermediary who is processing what outside counsel tells her and translating it into something her own internal audience can act on.
It took Michael the better part of four decades to see things through this lens, and he says the most important thing you can do for your client contact is to arm her with the exact information the company needs to make wise decisions.
“Give that person the right words to say to their internal audience,” Michael advises. “You have to look behind what you're seeing right in front of you and understand the dynamics of a corporation. Even at the board level, there may be discussions that are pretty serious about big cases."
Michael aims to create a true operational partnership where the company and outside counsel have all of the information, where lead counsel stays involved from the beginning through the end, and where the chain of command is clear on both sides.
"I used to describe the launch of a big case as opening a new line of business,” he says. “There are certain risks, certain opportunities. You do a SWOT analysis. Who is the decider? The same kind of errors that occur in business can occur in litigation management."
The Two Voices Every Lawyer Needs to Master
One of the most common and costly errors Michael has seen across four decades of high-stakes litigation is a lawyer using the wrong “voice” at the wrong moment. He describes two distinct voices every trial lawyer needs:
The Advocacy Voice – In this mode, you are the client's warrior. Your job is to demonstrate, unambiguously, that you are going all in for your client's position, and avoid the tendency to argue. Sometimes clients need to feel you’re on their side before they can hear anything else.
The Advisory Voice – This is the mode where you give an honest, unvarnished appraisal of the situation, because the GC needs to take exactly what you tell her and convey it accurately to her internal audience. If you sugarcoat it for her, she sugarcoats it for the board, who will not be able to make well-informed decisions.
"You want your GC client to know exactly what she should be communicating internally,” Michael said. “This is going to be a long and difficult road. I don't want you to get caught up in sugarcoating it for your audience because they're going to remember that. So let's give it to them straight."
He’s seen errors happen in both directions. Some lawyers lead with the advisory voice before they have established the advocacy voice, the equivalent of pouring cold water on a client who needed to feel heard first. Other lawyers never become a true advisor because being the client’s warrior is more comfortable than being honest. Both produce the same outcome: a client who either doesn't trust you or doesn't have the critical information they need.
Note from CZ: I had a mediator tell me in a case that sometimes you pay money to get crazy people out of your life. At the time I was furious; I had been so convinced the case was meritless that I had softened the financial projections when I presented them to the board. I should have delivered voice two clearly, early, and in writing, so that nobody was surprised. It was a lesson I learned the hard way.
How Big Tech Litigation Has Changed Over 40 Years
Michael's career spans the full arc of technology litigation, and he’s had the opportunity to write the rules of some of tech’s biggest advances:
Fujitsu v. IBM – This case established that copyright applied to mainframe operating system software at a time when that question had barely been asked.
SCO v. Novell – A case fought entirely over who owned the Unix code embedded in Linux, a multi-front battle that ran through Salt Lake City, a Zurich arbitration, and bankruptcy court simultaneously.
Oracle v. Google – This case asked whether APIs were copyrightable.
Apple v. Samsung – This case defined smartphone design protection rules.
The New York Times v. OpenAI – This case is currently arguing the ethics of training an LLM on copyrighted material.
"What stayed the same is the challenge of interpreting this foreign language to a lay audience. Applying traditional legal principles to new technologies remains the same,” Michael said. “As each new case came out, the complexion of our case would change."
What is genuinely new about our current AI boom is the organizational context surrounding the litigation. The companies at the center of the biggest AI cases are young, and their employee bases may have tripled in the time between the alleged conduct and the first deposition. Most of the people who made the key decisions in the case have been at the company for less than a year, and their relationships with outside counsel are brand new. The institutional memory simply does not exist like it did in previous technology litigation Michael has worked on.
"These are brand new companies doing brand new things, trying to train an LLM, with brand new relationships with lawyers,” he said. “Companies are doing things that maybe more established companies would have different procedures governing. In the Fujitsu IBM case, there was a guy who was responsible for that line of code. He had been working with the company for 10 years. "
His advice for in-house lawyers at rapidly growing tech companies who want to protect their organizations? Build the relationships with outside counsel before you need them, document the decisions and your reasoning behind the moment, and please, read the contracts.
Read all of the rules. Read the rules about the rules.
Note from CZ: The pace of adoption for new technology has completely changed the landscape of tech litigation. ChatGPT reached a billion users faster than any product in history. In an era where “move fast and break things” is the status quo, institutional memory is essentially nonexistent.
Why Humans Are Still Talking to Humans in an AI World
In Michael’s opinion, AI has forced law firms to deliver a service demonstrably better than online legal tools. Most AI tools are as capable as a second or third year associate. They still require quality control, strategic oversight, and a senior lawyer who can review the output and improve it. What legal AI cannot do is bring a human voice to a human audience.
"The job of the law firm now is to deliver a product that's better than the AI product and to be demonstrable about that,” he said. “I'd like to see what you got and then I'd like to see how you improved it."
At the end of the day, the work of a lawyer is humans talking to humans. Great legal AI can handle the research, the drafting, the document review, and the first-pass analysis so that the lawyer who needs to walk into a courtroom, a boardroom, or a mediation can spend their time on the thing Michael has spent four decades refining: translating something complex into something a human can understand, act on, and trust. Try the AI built for in-house lawyers for free.
