When I first heard Tyler Quillin, principal corporate counsel at Microsoft, say that he asks engineers to “explain it to me like I’m an eighth grader,” I had to laugh. Not because it was funny, although the image of an Xbox hardware engineer breaking down technical specs like a middle school science project is objectively charming, but because I’ve been there.

Tyler supports Xbox hardware devices and accessories, meaning his daily work involves translating between engineers, executives, and, increasingly, regulators. It is a role where technical complexity is the default. Instead of nodding along to words he doesn’t fully understand, Tyler has learned to slow the conversation down deliberately.

“Sometimes I’ll ask them to say it again, slower, or explain it like I’m 10,” he told me. “Then I’ll work my way back until I can really grok it.”

I have used a similar trick for years, but my go-to is eighth grade. The reason is simple. U.S. consumer protection rules often recommend that critical disclosures be written at about an eighth-grade reading level. When I tell engineers this, they stop seeing my request as a confession of ignorance and start seeing it as a shared goal: making our language work for the people who will actually use the product.

Why This Matters In Contracting

If you have ever read your own company’s end-user license agreement and felt your eyes glaze over, you already know the problem. Contracts are too often written at a level that requires a law degree and a strong pot of coffee to understand. That is not just a usability issue. It is a compliance risk. When customers, partners, or even internal stakeholders cannot grasp the meaning of their contractual obligations, the chance of misunderstanding, delay, or outright breach skyrockets.

Tyler put it plainly when we discussed regulatory interactions. “The disconnect often comes when regulators don’t entirely understand how the industry or product functions. So it’s critical to open up those conversations, educate them on what the product does and doesn’t do, and find a path to meet their goals.”

That is equally true for contracts. If the words do not clearly convey the deal, you are asking for trouble.

The In-House Counsel As Translator

The job of in-house counsel is not only to get the deal done or make the language airtight. It is to make the deal and its terms understandable to everyone who has to operate under it. That means using plain language where possible, avoiding internal jargon that only makes sense inside your department, and anticipating where a regulator, counterparty, or internal team might misunderstand a term so you can clarify before it becomes an issue.

Your audience might not be one group. You are often speaking to multiple stakeholders at once: engineers building the product, regulators shaping its market, customers buying it, and executives approving the deal. Each has a different starting point of understanding, but they all have to walk away clear on what the words mean.

Making Simplicity A Strategic Advantage

Clarity is not just a kindness. It is a competitive advantage. If your contracts are easier to understand than your competitor’s, you will close faster, reduce post-signature disputes, and build trust with both counterparties and internal teams. And if you ever need a real-world example of how simplifying the message opens doors, just remember Tyler’s eighth grader. “It is not about being the dumbest person in the room,” he said. “It is about making sure we can all speak the same language because that is how you actually get things done.”

The next time you are drafting or negotiating, ask yourself if an eighth grader could explain this back to you. If not, your work is not finished yet.

Olga V. Mack is the CEO of TermScout, an AI-powered contract certification platform that accelerates revenue and eliminates friction by certifying contracts as fair, balanced, and market-ready. A serial CEO and legal tech executive, she previously led a company through a successful acquisition by LexisNexis. Olga is also a Fellow at CodeX, The Stanford Center for Legal Informatics, and the Generative AI Editor at law.MIT. She is a visionary executive reshaping how we law—how legal systems are built, experienced, and trusted. Olga teaches at Berkeley Law, lectures widely, and advises companies of all sizes, as well as boards and institutions. An award-winning general counsel turned builder, she also leads early-stage ventures including Virtual Gabby (Better Parenting Plan), Product Law Hub, ESI Flow, and Notes to My (Legal) Self, each rethinking the practice and business of law through technology, data, and human-centered design. She has authored The Rise of Product Lawyers, Legal Operations in the Age of AI and Data, Blockchain Value, and Get on Board, with Visual IQ for Lawyers (ABA) forthcoming. Olga is a 6x TEDx speaker and has been recognized as a Silicon Valley Woman of Influence and an ABA Woman in Legal Tech. Her work reimagines people’s relationship with law—making it more accessible, inclusive, data-driven, and aligned with how the world actually works. She is also the host of the Notes to My (Legal) Self podcast (streaming on Spotify, Apple Podcasts, and YouTube), and her insights regularly appear in Forbes, Bloomberg Law, Newsweek, VentureBeat, ACC Docket, and Above the Law. She earned her B.A. and J.D. from UC Berkeley. Follow her on LinkedIn and X @olgavmack.

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