{"id":134102,"date":"2025-09-29T14:26:51","date_gmt":"2025-09-29T22:26:51","guid":{"rendered":"https:\/\/xira.com\/p\/2025\/09\/29\/tyler-quillin-on-why-speaking-eighth-grade-can-transform-your-contracting\/"},"modified":"2025-09-29T14:26:51","modified_gmt":"2025-09-29T22:26:51","slug":"tyler-quillin-on-why-speaking-eighth-grade-can-transform-your-contracting","status":"publish","type":"post","link":"https:\/\/xira.com\/p\/2025\/09\/29\/tyler-quillin-on-why-speaking-eighth-grade-can-transform-your-contracting\/","title":{"rendered":"Tyler Quillin On Why Speaking \u2018Eighth Grade\u2019 Can Transform Your Contracting"},"content":{"rendered":"
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When I first heard Tyler Quillin, principal corporate counsel at Microsoft, say that he asks engineers to \u201cexplain it to me like I\u2019m an eighth grader,\u201d 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\u2019ve been there.<\/p>\n

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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\u2019t fully understand, Tyler has learned to slow the conversation down deliberately.<\/p>\n

\u201cSometimes I\u2019ll ask them to say it again, slower, or explain it like I\u2019m 10,\u201d he told me. \u201cThen I\u2019ll work my way back until I can really grok it.\u201d<\/p>\n

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.<\/p>\n

Why This Matters In Contracting<\/strong><\/p>\n

If you have ever read your own company\u2019s 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.<\/p>\n

Tyler put it plainly when we discussed regulatory interactions. \u201cThe disconnect often comes when regulators don\u2019t entirely understand how the industry or product functions. So it\u2019s critical to open up those conversations, educate them on what the product does and doesn\u2019t do, and find a path to meet their goals.\u201d<\/p>\n

That is equally true for contracts. If the words do not clearly convey the deal, you are asking for trouble.<\/p>\n

The In-House Counsel As Translator<\/strong><\/p>\n

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.<\/p>\n

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.<\/p>\n

Making Simplicity A Strategic Advantage<\/strong><\/p>\n

Clarity is not just a kindness. It is a competitive advantage. If your contracts are easier to understand than your competitor\u2019s, 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\u2019s eighth grader. \u201cIt is not about being the dumbest person in the room,\u201d he said. \u201cIt is about making sure we can all speak the same language because that is how you actually get things done.\u201d<\/p>\n

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.<\/p>\n

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Olga\u00a0V. Mack<\/em><\/strong><\/a>\u00a0is the CEO of\u00a0<\/em><\/strong>TermScout<\/em><\/strong><\/a>, 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.\u00a0Olga\u00a0is also a\u00a0<\/em><\/strong>Fellow at CodeX, The Stanford Center for Legal Informatics<\/em><\/strong><\/a>, and the Generative AI Editor at law.MIT. She is a visionary executive reshaping how we law\u2014how legal systems are built, experienced, and trusted.\u00a0Olga\u00a0<\/em><\/strong>teaches at Berkeley Law<\/em><\/strong><\/a>, 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\u00a0<\/em><\/strong>Virtual Gabby (Better Parenting Plan)<\/em><\/strong><\/a>,\u00a0<\/em><\/strong>Product Law Hub<\/em><\/strong><\/a>,\u00a0<\/em><\/strong>ESI Flow<\/em><\/strong><\/a>, and\u00a0<\/em><\/strong>Notes to My (Legal) Self<\/em><\/strong><\/a>, each rethinking the practice and business of law through technology, data, and human-centered design. She has authored\u00a0<\/em><\/strong>The Rise of Product Lawyers<\/em><\/strong><\/a>,\u00a0<\/em><\/strong>Legal Operations in the Age of AI and Data<\/em><\/strong><\/a>,\u00a0<\/em><\/strong>Blockchain Value<\/em><\/strong><\/a>, and\u00a0<\/em><\/strong>Get on Board<\/em><\/strong><\/a>, with\u00a0Visual IQ for Lawyers\u00a0(ABA) forthcoming.\u00a0Olga\u00a0is 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\u2019s relationship with law\u2014making 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\u00a0<\/em><\/strong>Spotify<\/em><\/strong><\/a>,\u00a0<\/em><\/strong>Apple Podcasts<\/em><\/strong><\/a>, and\u00a0<\/em><\/strong>YouTube<\/em><\/strong><\/a>), 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\u00a0<\/em><\/strong>LinkedIn<\/em><\/strong><\/a>\u00a0and X @olgavmack.<\/em><\/strong><\/em><\/strong><\/p>\n

The post Tyler Quillin On Why Speaking \u2018Eighth Grade\u2019 Can Transform Your Contracting<\/a> appeared first on Above the Law<\/a>.<\/p>\n

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<\/figcaption><\/figure>\n

When I first heard Tyler Quillin, principal corporate counsel at Microsoft, say that he asks engineers to \u201cexplain it to me like I\u2019m an eighth grader,\u201d 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\u2019ve been there.<\/p>\n