Welcome toLegal Ops Briefs—inspired by the mot-r mindset, this blog series of 3-minute reads gives in-house Legal Ops quick, operational insights. Each post will explore the tech, trends, and tactics that boost operational effectiveness and ease legal team stress—without adding to the noise.
Why So Many LegalTech Projects Fail Legal departments are under pressure—staffing is tight, workloads are rising, and tech investments often promise more than they deliver. According to research, 77% of in-house lawyers have experienced failed legal tech projects.
It's not because the tools themselves are inherently flawed. It’s because the process used to choose and implement them is broken. Too often, decisions are led by IT teams unfamiliar with legal's day-to-day realities, or worse, rushed without a deep understanding of operational needs.
That’s where premortems come in—a deceptively simple but highly effective tool to prevent poor decisions before they happen.
What Is a Premortem? A premortem is a forward-looking strategy that helps teams predict failure before it occurs. Think of it as a “prospective postmortem.” You gather your decision-making team, and before any final choice is made, you ask each person to imagine the project has failed—badly—and to list all the possible reasons why.
Unlike a standard risk assessment, this process encourages candor, removes groupthink, and reveals vulnerabilities that might otherwise go unspoken. It's structured, introspective, and inclusive—an antidote to the top-down, checklist-based processes that dominate many legal tech buying decisions.
How to Run a LegalTech Premortem Here’s how it works:
Set the stage: Present a hypothetical scenario—“It’s two years from now. Our legal tech investment failed. What went wrong?”
Individual input: Each participant writes their answers in private, without influence.
Round-robin reveal: Each person shares one reason at a time, creating a master list of failure risks.
Strategize: As a team, identify the most likely or dangerous failure points.
Prevention planning: Develop specific, actionable strategies to reduce or eliminate these risks.
The power of the premortem lies in its timing. By using it early—before commitments are made—you dramatically improve the chances of selecting tools that truly serve your team and avoid common traps like under-resourced implementations or poor adoption.
Real-World Impact: From Insight to Action Let’s say you’re considering a new contract management system. In a premortem, someone might say: “We rushed the selection process, and didn’t get GC buy-in.” Another might add: “Training was minimal, so no one used the system.” These insights allow you to redirect resources, improve communication, and design a phased roll-out that addresses adoption from day one.
Premortems also help flag second-order effects—like the creation of new data silos or user fatigue—that don’t show up in feature comparisons but can seriously derail long-term value.
A Culture of Foresight, Not Firefighting Premortems are more than a one-time exercise—they build a culture of anticipation and accountability. They encourage legal ops professionals to speak up, share concerns, and actively shape solutions, rather than passively inherit them. They help teams own the outcome of their decisions, and avoid the trap of buying tools that look good on paper but add complexity, not clarity.
Chime In. Be Heard.
Join the conversation. Have you used a premortem—or wish you had? What failure scenarios have you seen play out in your legal tech rollouts? Your insights could help other legal ops professionals avoid the same missteps. Let’s build a smarter approach together. Because the best way to fail less is to learn more—from each other.
mot-r is the Work Management System for General Counsel. It is designed to reduce overwork and elevate legal service quality of small to medium sized teams. With workflows, dashboards and granular reporting, it improves operational effectiveness and client service quality. Created by a team of enterprise software experts—who have a passion for reducing the human cost of legal work—mot-r is a trusted supplier to general counsel teams in financial services, healthcare, real estate, sports management and more. When you're ready to modernize how your in-house team works, we're ready to help.
Mike Tobias: Jun 10, 2025 10:45:58 AM