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The Hidden Reason Legal Tech Fails.

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Welcome to Legal 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.


Rethinking Legal Tech: Build Solution Evaluation Teams that Deliver

In-house legal teams are drowning in complexity, overwork, and burnout. Technology promises relief—but too often delivers more frustration. Why? Because legal tech evaluation is still being driven by role-based teams using outdated checklists—not by strategic thinkers who actually understand the problem. If Legal Ops wants better results, it’s time to reinvent the evaluation team.


Why Traditional Legal Tech Teams Fail

Most legal tech decisions are made by role-based committees—Legal, IT, Procurement—assembled out of habit more than strategy. These teams are often disconnected from the day-to-day challenges of in-house legal work and lack shared accountability for the outcome. The result? Muddled decisions, misaligned expectations, and costly tech failures.

According to the Avoiding LegalTech Failures report, 77% of in-house lawyers have experienced failed tech projects. Many of those failures can be traced back to poorly composed evaluation teams that didn’t understand what success looked like—or how to get there.


Competency-Based Teams: A Smarter Structure

Instead of roles, start with competencies. What skills and insights are essential to evaluate a legal tech solution effectively? The report suggests a broad spectrum, including:

  • Legal operations know-how

  • Service quality and legal process expertise

  • Change management and organizational strategy

  • AI tools and API/integration fluency

  • Evidence-based decision-making

  • Deep understanding of current and future enterprise architecture

You may not have all of this in-house—and that’s okay. Generative AI can supplement gaps by simulating expert reviews or pressure-testing assumptions. The key is assembling a team that can collectively see the full picture and challenge each other’s blind spots.


Understand Each Person’s Circle of Competence

Even with the right competencies at the table, be aware of the "circle of competence" principle: people gravitate toward topics they know. If your IT expert dominates the conversation with technical specs, you may end up over-indexing on features and underestimating real-world usability. Legal Ops needs to steer the team’s attention back to what matters—operational outcomes.

Guard the group’s focus, elevate overlooked voices, and align your process with the people who will live with the daily consequences of the tech decision.


Use Premortems to Prevent Failure

A powerful technique covered in the report is the premortem—a strategic way to avoid disasters before they happen. Here's how it works:

Imagine it’s two years from now and your tech implementation has failed. Ask each team member to write down what went wrong. Gather the reasons, rank them, and build strategies to avoid them. This prospective hindsight prevents groupthink and surfaces risks that might otherwise stay buried.

It also signals to your team that failure prevention is everyone’s responsibility, not just a project manager’s afterthought.


Align Around What the Work Actually Requires

The best tech doesn’t just check boxes—it removes friction. To get there, teams must define evaluation criteria based on "Jobs to Be Done." What are the actual problems legal teams face? What slows them down? What impedes client satisfaction or service delivery?

By focusing on these operational realities instead of generic features, evaluation teams can spot real solutions—and reject ones that just add complexity.


Don’t Just Evaluate—Anticipate

Tech doesn’t exist in a vacuum. Team turnover, workflow shifts, KPIs, integrations, and even regulatory changes will impact your platform's long-term fit. Competency-based teams are better equipped to ask hard questions: How will this solution scale? What happens when the org changes? Will this platform create new silos or break down old ones?

Good decisions come from anticipating ripple effects—not just reacting to them.


Chime In and Be Heard

Join the conversation. Let's build legal departments that work better. 

What’s one competency you wish had been in the room during your last legal tech purchase? How did its absence shape the outcome? What else would you have done differently? Share your experience and insights—save others the hassle and frustration.

 



 

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.

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