What if the biggest blocker to legal transformation isn’t tech—it’s the words on the page? Today, most conversations around legal innovation focus on automation, AI, and end-to-end platforms. But those tools can only accelerate what already exists. If your contract content is unclear, outdated, or overly complex, no technology can fix that.
That’s exactly what Chris Simkins believes. As a legal operations leader and expert in contract strategy, Chris joined Notes to My (Legal) Self to spotlight a foundational (and often overlooked) truth: contract content transformation is where real legal evolution begins .
Watch the full conversation with Chris Simkins here:
Why the First Step in Transformation Is Content, Not Code
Before you plug into new systems or platforms, ask: what content are you feeding into them? Contract transformation isn’t just about digitizing old workflows—it’s about rethinking what’s inside the contract itself.
That includes how ideas are structured, how terms are explained, and how understandable the document is for business users. Chris emphasized that stakeholders outside legal—sales, procurement, ops—are often the ones reading and using contracts. If they can’t follow the content, the whole process breaks down.
Clear, purposeful contract content is what makes automation effective, not the other way around.
Where Drafting, Design, and Process Meet
Traditionally, contract drafting was siloed within legal, and design was treated as decoration. But that’s changing. Chris advocates for blending content strategy with process and layout—bringing legal, design, and ops into the same conversation.
When contracts are rebuilt around user experience, they don’t just protect—they perform. Sales closes faster. Procurement runs leaner. Legal gets fewer escalations.
And it’s not about polishing old templates. Real transformation often means starting fresh—questioning every clause, cutting legalese, and building from the user’s point of view. It’s not always easy, but the payoff is speed, clarity, and stakeholder trust.
From Complexity to Clarity
This isn’t theory—it’s already in motion. Legal teams that invest in content transformation are seeing measurable impact: faster deals, lower legal spend, and fewer back-and-forths during negotiation.
Chris shared how modular content models are changing the game. Instead of managing dozens of versions across departments, teams maintain one source of truth. Updates cascade. Risk is contained. Version roulette disappears.
Clarity reduces friction. Simplicity saves time. And best of all, teams can adapt contracts quickly—without reinventing the wheel every time a clause changes.
Looking Ahead: Content as Strategy
Looking ahead, two big shifts are reshaping contract content.
First, more legal departments are treating content as infrastructure—not just output. That requires new skills: product thinking, knowledge management, UX sensibility. Legal isn’t just drafting anymore—it’s building systems people rely on.
Second, there’s growing energy around standardization. Shared language, common templates, and industry-wide frameworks could redefine how contracts work across organizations. It’s early—but the momentum is real.
Chris encourages teams not to wait. Start with one contract. Rethink it from the user’s perspective. Test, learn, evolve. Treat content like a product—and make it usable without a translator.
So, the Big Takeaway?
Contract content isn’t just paperwork. It’s a lever for transformation. When legal teams focus on clarity, structure, and usability, they unlock speed, trust, and long-term business value. That’s the kind of transformation technology alone can’t deliver—but content can.
Watch the full conversation here: Notes to My (Legal) Self: Season 4, Episode 2 (ft. Chris Simkins)
Join the Conversation
At Notes to My (Legal) Self®, we’re dedicated to helping in-house legal professionals develop the skills, insights, and strategies needed to thrive in today’s evolving legal landscape. From leadership development to legal operations optimization and emerging technology, we provide the tools to help you stay ahead.
What’s been your biggest breakthrough moment in your legal career? Contract content transformation is one approach. Let’s talk about it—share your story.
