Most lawyers are trained to avoid uncertainty.
Then there are lawyers like Geoffrey Brow, who spent years helping companies build technologies so new that there was no legal playbook to follow, no precedent to cite, and sometimes no regulator who fully understood what was being built.
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That changes the job.
When Brow worked on Virgin Hyperloop, he was not negotiating familiar commercial patterns wrapped in updated terminology. He was helping structure legal relationships around a transportation system moving hundreds of miles per hour through vacuum tubes. Before that, he advised on drone delivery systems at Google. Today, as assistant general counsel at Roku, he works across operations, engineering, products, AI, open source software, and technology transactions that continue to evolve faster than the surrounding legal frameworks.
The common thread is not technology. It is judgment under uncertainty.
And that is where this conversation became interesting.
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The Lawyer As Builder, Not Reviewer
One of the biggest misconceptions about transactional law is that it is procedural work disguised as expertise. Brow sees it differently. For him, contracts are not paperwork. They are an operational architecture.
“A commercial transaction contract is really just a description of the deal,” he explained. “It’s all the stuff that goes with it. When are you going to deliver the thing? What happens if the thing goes wrong? You have to fill in all the gaps.”
That framing matters because it changes how you think about legal practice. The lawyer is not sitting outside the business throwing flags. The lawyer is inside the system, trying to translate ambiguity into an executable structure.
Brow repeatedly returned to creativity during our discussion, which is not a word most lawyers instinctively associate with contracts. Yet his career makes the point clearly. When you are working on technology that has never existed before, legal drafting stops being a precedent exercise and starts becoming applied design.
“There’s no precedent. There’s no case law. It is completely new,” he said while describing Hyperloop work. “That requires you to be creative and think about the risks and rewards of those transactions and how to best serve your corporate client.”
That creativity does not happen in isolation. It requires deep integration with engineers, operators, and product teams. Brow described long conversations with engineers to understand not only what a technology was supposed to do, but where it could fail, where assumptions were uncertain, and where the company itself did not yet fully know the answers.
“It takes a lot of questioning with business and engineering to figure out what they want to do, what the risks are, how you can mitigate those risks, and then document it.”
That is modern in-house practice in one sentence.
Why In-House Lawyers Have To Unlearn Perfection
One of the strongest parts of our discussion focused on the transition from elite law firm training into in-house practice.
Brow spent years in New York and London doing traditional corporate work before moving into technology transactions. He described the training at large firms with obvious respect. The rigor mattered. The precision mattered. The intensity mattered.
But eventually, some of those instincts became obstacles.
“In the Biglaw environment, the performance level has to be a thousand percent,” he said. “Nothing goes out with a typo. Nothing is incorrect. It has to be absolutely perfect.”
Then he went in-house.
“What you have to realize is that the primary industry of your client is not law,” he explained. “They want transactions done.”
That shift sounds obvious until you live it. Many lawyers never fully make the transition psychologically. They continue optimizing for technical perfection long after the business has moved on to operational execution.
Brow described watching lawyers struggle with imperfect formatting, messy negotiations, or unresolved drafting nuances because they were trained to believe every loose thread represented failure.
In-house work forces a different prioritization model.
“You have to realize what the core issues are,” he said. “What are the most important vulnerabilities or goals that need to be achieved?”
That mindset is especially critical in technology companies where speed itself becomes part of the competitive environment. The legal department cannot behave like an external review committee detached from operational realities. It has to function as part of the decision-making system.
That does not mean abandoning rigor. It means learning proportionality.
Flying The Plane While Parts Fall Off
At one point, Brow offered an analogy that perfectly captured the emotional reality of in-house legal work inside lean technology environments.
“I think about an airplane flying along,” he said. “All sorts of parts start to fall off the airplane. Bolts, sheets of metal, what have you. Your job is to get the plane on the ground.”
Then he paused.
“The plane might look really ugly when you land, but you’ve kept everyone alive.”
That is probably the most honest description of in-house practice I have heard in a long time.
Law firms are often optimized around perfection. In-house teams are optimized around continuity. The goal is not theoretical elegance. The goal is sustainable forward movement under imperfect conditions.
And increasingly, that means making decisions in environments where legal frameworks lag far behind technological reality.
Brow drew an important distinction between enterprise transactions and consumer-facing systems. In B2B contexts, sophisticated parties often knowingly accept higher levels of uncertainty and experimentation. Consumer-facing products are different. The downstream consequences become materially more serious.
“You can’t really take too much risk” when products affect consumers directly, he said.
That distinction matters more now than ever in the age of AI.
AI Will Keep Changing The Job. Judgment Still Matters Most.
Toward the end of our discussion, we shifted toward what younger lawyers should focus on as AI reshapes legal work.
Brow’s answer was notable because it was not centered on technology.
It was centered on training.
“I would encourage anyone graduating from law school to choose a path where they are going to get true mentorship and learning opportunities,” he said.
He spoke candidly about the value of difficult environments, especially early in a career. Not because suffering is inherently valuable, but because repetition, observation, and exposure build instincts that cannot easily be replicated elsewhere.
“You’ll learn how to draft. You’ll see how partners act on conference calls, how they negotiate,” he said. “It is a true crucible.”
Then he said something many lawyers forget.
“Write as much as you can.”
Not because lawyers need prettier prose. Because drafting is structured thinking. Contracts are operational logic expressed through language. If lawyers lose the ability to think clearly through writing, they lose one of the core mechanisms through which legal judgment actually gets exercised.
That observation feels especially relevant right now. AI can accelerate drafting. It can summarize. It can synthesize. But lawyers still have to decide what matters, where risk sits, what tradeoffs are acceptable, and how uncertainty should be allocated.
The technology changes. The responsibility does not.
The Lawyers Who Thrive Stay Curious
One of the final points Brow made stayed with me after the conversation ended.
“Keep an open mind,” he said. “You might find an area of law you never even considered before.”
His own career reflects that reality. He did not go to law school intending to work on Hyperloop systems, drone delivery frameworks, or AI-enabled product environments. He followed curiosity, embraced unfamiliar territory, and repeatedly allowed himself to evolve.
That may be the deeper lesson for in-house lawyers right now.
The future probably will not belong to the lawyers who memorize the most rules. It will belong to the lawyers who can enter unfamiliar systems, ask better questions, understand how technology actually works, and help organizations move forward responsibly when no clear roadmap exists yet.
That requires technical skill.
It also requires comfort with uncertainty.
And maybe, occasionally, the willingness to land the plane with one engine on fire.
Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to operate, and more trustworthy in real business conditions. Her work focuses on how legal rules allocate power, manage risk, and shape decisions under uncertainty. A serial CEO and former General Counsel, Olga previously led a legal technology company through acquisition by LexisNexis. She teaches at Berkeley Law and is a Fellow at CodeX, the Stanford Center for Legal Informatics. She has authored several books on legal innovation and technology, delivered six TEDx talks, and her insights regularly appear in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as essential infrastructure, designed for how organizations actually operate.