Articles

What Is an AI Contract Playbook? From Tribal Lore to Machine-Grade Judgment

Discover how AI contract playbooks transform institutional knowledge into real-time, rule-based guidance. Learn the evolution from tribal lore to machine-grade precision—and why automating your playbook cuts review time, boosts consistency, and turns contract friction into a competitive advantage.

Is AI Contract Review Secure? (A Legal Deep Dive)

AI contract review security isn’t about buzzwords; it’s about clear protections. Learn how data privacy, confidentiality, model exposure, vendor liability, and regulations shape trust in AI tools—and what legal teams should demand to ensure sensitive contracts stay private and secure.

How AI Contract Review Works - From Raw Text to Actionable Redlines

AI contract review breaks contracts into clauses, aligns them with your playbooks, and suggests edits you control. It’s not a black box — it’s a transparent, defensible workflow that speeds up reviews while keeping lawyers fully in charge.

Manual vs. AI Contract Review: A Side-by-Side Comparison

Compare manual vs. AI contract review side by side. Discover key differences in speed, accuracy, and cost—and see why AI is essential for modern legal teams.

What Types of Contracts Are Best Suited for AI Review?

Discover which contracts are ideal for AI-powered review, from NDAs to complex SaaS agreements. Boost efficiency and reduce risk with the right approach.

What Is AI Contract Review? How It Transforms Legal Workflows

The way legal teams review contracts is undergoing a seismic shift - and at the center of it is AI Contract Review. Learn what AI Contract Review is, how it works, and why it’s transforming legal teams’ contract processes. Cut review time by up to 70%.

2025 Transactional Skills Award Goes to Connor Vasile

Award honors Miami Law 3L for excellence in client-focused contract drafting, negotiation, and real-world legal training.

Legal Ops 2.0: From Back Office to Business Engine

Legal Operations is evolving from a behind-the-scenes support role into a strategic leader, driven by the rise of AI and intelligent systems. In this new era, Legal Ops designs and governs the interconnected tools, workflows, and data that power modern legal service delivery at scale.

Are you still babysitting your contracts?

Legal teams are bogged down by repetitive contract reviews due to a lack of trust in business users. Like HR’s transformation, Legal is shifting from hands-on execution to system-based governance. By embedding rules into AI-powered tools, Legal can scale its expertise, enabling teams to handle contracts within set boundaries. This reduces bottlenecks, speeds up workflows, and positions Legal as a strategic enabler—not a gatekeeper.

What Happens When Legal Expertise Stops Being Rare?

Your legal knowledge - once your moat - is now table stakes. What’s left is what you build with it.

❝Is CLM Dead? Or Finally Becoming What It Was Meant to Be?❞

The all-in-one “CLM platform” is fading - and that’s a good thing. See how CLM is becoming a flexible, intelligent toolkit built to fit how people actually work, and evolve as they do.

Prompt Engineering Is the New Drafting

A personal take on how legal tech is reshaping the lawyer’s craft—and why we need to start talking about it.

Prompt Engineering: The Skill Every Lawyer Needs in the Age of AI

While everyone talks about “AI tools” and “automation,” prompt engineering remains the most under-discussed (and arguably the most important) skill lawyers can learn today. It's the foundation that enables AI to actually deliver useful, context-aware insights. Without it, AI is just another black box.

How to Prompt Engineer for Lawyers: Get Better AI Contract Reviews

Lawyers who understand prompt engineering can significantly improve the quality of AI-driven contract analysis, making reviews faster, more precise, and more actionable. In this guide, we’ll break down how lawyers can master prompt engineering to get better AI contract reviews every time.

Law Insider Brings AI-Powered Contracting to 1.2M Legal Users Worldwide

Law Insider, a pioneer in legal technology and the trusted contract resource for 1.2 million registered legal users worldwide, including solo attorneys, small law firms, and in-house counsel, is launching its AI-powered contract drafting, review, and redlining tool across Microsoft Word and its web-based platform.

Why AI Contract Review Won’t Replace Lawyers (But It Will Replace This Task)

In the ever-evolving world of legal tech, one question keeps coming up: Will AI replace lawyers? The short answer: No. The better question: What tasks will AI replace?

AI in Contracts: The Real Value Is Speed, Not Just Accuracy - So Why Are We Only Measuring Accuracy?

AI in contract review is often judged by accuracy—but is that the right metric? In this article, Electra Japonas explores why speed is just as critical, how AI can accelerate deals without sacrificing quality, and what we should really be measuring.

How AI + Standardization Will Change Contract Review Forever

The rise of AI in legal tech is being hailed as a turning point for contract negotiations. We’re told that AI will make contracting more efficient, reduce friction, and speed up the review process. The assumption is that if we can process contracts faster, we will negotiate faster. But speed has never been the fundamental problem. Contracts don’t take too long because we lack processing power. They take too long because we lack consensus.

Why Larger Organizations Should Embrace Contract Standards: It’s Not About Power, It’s About Profit

For larger organizations with significant market power, adopting standardized contracts may seem unnecessary. After all, if your agreements rarely face pushback and counterparties are eager to accept your terms, why bother?

oneSaaS: Standardizing SaaS Agreements for Efficiency, Collaboration, and Impact

The SaaS industry is thriving, with over 30 million SaaS agreements signed annually. Yet, these contracts are plagued by inefficiency, inconsistency, and unnecessary complexity. oneSaaS is here to change that. This paper outlines the problem, our approach to solving it, and why adopting oneSaaS is essential for modern SaaS companies as well as buyers of SaaS and their legal teams.

The Power of Standardization: Lessons from Other Industries and the Legal Sector

Standardization is a concept as old as civilization itself. From the earliest measurements used in trade to the modern-day protocols governing the internet, standardization  has driven efficiency, reduced costs, and fostered collaboration across industries. So, why hasn’t the legal industry embraced standardization for contracts?

The Future of the Legal Industry: Why Standardization is the Key to Progress

The legal industry is undergoing a quiet revolution. Long seen as a field resistant to change, it is now facing pressures to adapt to new technologies, business demands, and societal expectations. In this transformation, one idea stands out as a cornerstone for the future: Contract Standardization.

Our 2025 Predictions

Whether you’re leading a legal team, navigating the latest tech, or simply curious about what’s next, these insights will help you prepare for the challenges and opportunities ahead.

The Importance of Standardization 

Contracts are everywhere, but here’s the problem: there are too many of them, they’re often too complex, and they demand more time than anyone has. Contracts are broken.

Law Insider Taps Chris Handy for VP of Product Marketing to Expand B2B Offerings

Law Insider hires Chris Handy as our new Vice President of Product Marketing. Chris is set to lead the go-to market strategy for new intuitive, state-of-the-art tools that promise to redefine efficiency and effectiveness for legal professionals worldwide.

The Best Learning Resources to Understand Software Contracts

We share 12 resources recommended by experienced practitioners in technology contracts. You can also learn about our upcoming virtual workshop on SaaS licensing agreements.

The Rise of the Modern Knowledge Practitioner: A Mike Whelan Blog Series

In the space of eight short posts, we’ll uncover truths about expertise and consultation that will make you more competitive and more confident.

The Cheapening of Knowledge

Availability has made knowledge cheaper, complexity has made knowledge infinite, and demand has made knowledge transparent.

Your Latest Transaction

Before we get to the method of the True Counselor, let’s look to the past for why we interact with information the way we do.

The Legal Knowledge Business

We’ll dig into this question, recognizing that it is not merely academic. If you can’t justify high rates using exclusive access to knowledge, you’ll need to come up with an alternative explanation.

Knowledge Management

If you’re not familiar with the concept of knowledge management, it is a relative newcomer to the legal environment, at least formally.

Making Experts Out of Employees

We’ll explore the difference between traditional legal knowledge management and a more modernized way to leverage knowledge in your firm.

What Clients Want

“A problem is to reality what an atom is to a table. People experience tables not atoms.” - Dr. Russell Ackoff

The Advisor's Burden

As crucial as that habit is for knowledge-driven firms like yours, it ignores the other core competency that any expert must develop: the creation of new knowledge.

The Modern Knowledge Firm

As we close this exploration, I hope it starts you on a journey. You have an incredible opportunity to build a firm on knowledge assets rather than the churn of daily practice.