Geoffrey Brow On Why the Best In-House Lawyers Learn To Fly The Plane With One Engine Burning

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 were no law books to follow, no precedents to cite and sometimes no regulators who fully understood what was being built.

This changes the job.

When Brow worked on Virgin Hyperloop, he wasn’t negotiating familiar commercial models wrapped in up-to-date terminology. He was helping to structure the legal relationships around a transportation system that moved 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 on operations, engineering, product, AI, open source software and technology transactions that continue to evolve faster than the surrounding legal frameworks.

The common ground is not technology. It is judgment under uncertainty.

And that’s where this conversation got interesting.

The lawyer as a builder, not a reviewer

One of the biggest misconceptions about transactional law is that it is procedural work masquerading as expertise. Brow sees it differently. For him, contracts are not documents. They are an operational architecture.

“A commercial transaction contract is really just a description of the agreement,” he explained. “It’s all the things that go with it. When are you going to deliver the thing? What happens if it goes wrong? You have to fill in all the blanks.”

This framing matters because it changes the way you think about legal practice. The lawyer is not sitting outside the business throwing flags. The lawyer is inside the system, trying to translate the ambiguities into an executable structure.

Brow repeatedly returned to creativity during our discussion, which is not a word most lawyers instinctively associate with contracts. However, his career clearly shows this. When you are working on technology that has never existed before, legal drafting ceases to be a precedent exercise and begins to become applied design.

“There’s no precedent. There’s no case law. It’s completely new,” he said describing Hyperloop’s work. “It 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 doesn’t 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 also where it might fail, where assumptions were uncertain, and where the company itself still didn’t quite know the answers.

“It takes a lot of questioning with business and engineering to understand what they want to do, what the risks are, how you can mitigate those risks, and then document it.”

This is modern inner practice in one sentence.

Why in-house lawyers should give up on perfection

One of the strongest parts of our discussion focused on the transition from elite law firm training to 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 the big firms with obvious respect. Significance mattered. Accuracy mattered. 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 wrong. It has to be absolutely perfect.”

Then he went home.

“What you have to understand is that your client’s primary industry is not the law,” he explained. “They want transactions to go through.”

This difference sounds obvious until you experience it. Many lawyers never fully make the psychological transition. They continue to optimize for technical excellence long after the business has moved into operational execution.

Brow described watching lawyers struggle with imperfect formatting, messy negotiations or unresolved drafting nuances because they were trained to believe that any loose thread represented failure.

Working inside the home forces a different pattern of prioritization.

“You have to understand what the core issues are,” he said. “What are the most important weaknesses or goals to achieve?”

This thinking is especially critical in technology companies where speed itself becomes part of the competitive environment. The legal department cannot act as an external review committee detached from operational realities. It should function as part of the decision-making system.

That doesn’t mean abandoning rigor. It means learning proportionality.

Flying the plane as the parts fall

At one point, Brow offered an analogy that perfectly captured the emotional reality of legal work within low-tech environments.

“I think of an airplane flying together,” he said. “All kinds of parts start falling out of the plane. Bolts, sheet metal, what have you. Your job is to get the plane on the ground.”

Then he stopped.

“The plane may look really ugly when you land, but you kept everyone alive.”

This is probably the most honest description of inner practice I have heard in a long time.

Law firms are often optimized around perfection. Internal teams are optimized around continuity. The goal is not theoretical elegance. The goal is steady forward movement in imperfect conditions.

And increasingly, this means making decisions in environments where legal frameworks lag far behind technological reality.

Brow made an important distinction between enterprise transactions and consumer-facing systems. In B2B contexts, sophisticated parties often consciously accept higher levels of uncertainty and experimentation. Consumer-facing products are different. The downstream consequences become materially more severe.

“You can’t really take too much risk” when products directly affect consumers, he said.

This distinction matters more now than ever in the age of AI.

AI will continue to change work. Judgment is even more important.

At the end of our discussion, we moved on to where younger lawyers should focus as AI reshapes legal work.

Brow’s response was notable because it wasn’t focused on technology.

He concentrated on training.

“I would encourage anyone graduating from law school to choose a path where they will have real mentoring and learning opportunities,” he said.

He spoke candidly about the value of tough 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. “This is a real pair of scissors.”

Then he said something that many lawyers forget.

“Write as much as you can.”

Not because lawyers need more beautiful 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 essential mechanisms through which legal judgment is exercised.

This observation feels especially relevant now. AI can speed up drafting. It can summarize. Can synthesize. But lawyers still have to decide what matters, where the risk lies, what compensations are acceptable, and how uncertainty should be distributed.

Technology changes. There is no responsibility.

Thriving lawyers stay curious

One of the last points Brow made stuck with me after the talk ended.

“Keep an open mind,” he said. “You may find an area of ​​the law that you never considered before.”

His career reflects this reality. He didn’t go to law school intending to work on Hyperloop systems, drone delivery frameworks, or AI-enabled product environments. He pursued curiosity, embraced unknown territory, and constantly allowed himself to evolve.

This may be the most profound lesson for in-house lawyers right now.

The future probably won’t lie with lawyers memorizing more rules. It will belong to lawyers who can step into unfamiliar systems, ask better questions, understand how the technology actually works, and help organizations move forward responsibly when a clear roadmap doesn’t yet exist.

This requires technical skills.

It also seeks comfort with uncertainty.

And maybe, once in a while, a willingness to land a single-engine plane 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 reliable under real business conditions. Her work focuses on how legal rules distribute 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 Forensic Informatics. She is the author of several books on legal innovation and technology, has given six TEDx talks, and her insights are regularly featured in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as the essential infrastructure designed for how organizations actually function.