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.
Why Document Management System Projects Fail in Legal Departments
A Document Management System (DMS) should make your legal team’s life easier. Centralized access, faster search, fewer version control nightmares—what’s not to love?
Yet for many in-house teams, DMS projects fall short. After months of planning and investment, the platform is met with lukewarm adoption, limited functionality, and a creeping sense of “we’ll never fix this.”
Sound familiar? You’re not alone. These five common mistakes could be holding your DMS back.
1. Treating Legal DMS Go-Live as the End Goal
Legal teams often sprint to implementation but forget to plan for the marathon afterward. Go-live should be the start of your adoption journey, not the end.
When you treat the launch like the final milestone, you risk losing momentum—and your users. Sustained engagement, feedback loops, and post-launch training are what turn a tool into a team habit.
2. Delivering Generic Training for DMS Users in Legal Ops
Many DMS rollouts rely on one-size-fits-all webinars or pre-recorded demos. While convenient, these generic sessions don’t meet the nuanced needs of different roles across legal, compliance, or operations.
Instead, tailor onboarding to your actual users. Offer role-specific walkthroughs and hands-on sessions based on real workflows. And make training continuous—not just a one-time event.
3. Failing to Assign Internal Ownership for Your Legal DMS
A system with no internal champion quickly becomes orphaned. Who’s tracking adoption? Who fields questions? Who’s refining access permissions or approving folder structures?
Without a clearly designated system owner—or better yet, a cross-functional working group—your DMS loses its strategic anchor. Assign ownership and give that person (or team) visibility, authority, and support.
4. Not Communicating the Business Value of the DMS Rollout
People don’t resist change—they resist change they don’t understand.
If your rollout is driven purely by IT or compliance without showing how it benefits the end user, you’ll face resistance. Frame the rollout in terms of value: “fewer email attachments,” “faster reviews,” or “clear audit trails.” Lead with benefits, not just requirements.
5. Overlooking Metrics to Measure Legal DMS Success
If you don’t track adoption, how will you know if it’s working?
Define success metrics upfront: usage rates by department, reduction in email-based sharing, time saved in document retrieval. Build dashboards that spotlight wins and illuminate gaps. Reporting isn’t just for leadership—it’s how you keep momentum alive.
What to Do If Your DMS Implementation Failed
Even if your DMS launch stumbled, recovery is possible. Begin by acknowledging what’s not working, then re-engage with users through listening sessions and re-onboarding. Many teams see greater impact from their second wave of training than their first.
Legal tech success isn’t about a perfect rollout. It’s about continuous improvement and empathetic leadership.
Chime In. Be Heard.
Has your legal team experienced one of these pitfalls—or sidestepped them with smart planning? What lessons would you pass along to others preparing for their DMS rollout? Share your insights with the Legal Ops community. You might help someone else avoid a painful misstep.
mot-r is the next-generation Enterprise Legal Management software. As a trusted supplier to general counsel teams in financial services, healthcare, real estate, sports management (and more) it reduces overwork and elevates legal service quality of legal teams of all sizes. 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. When you're ready to modernize how your in-house team works, we're ready to help.
Mike Tobias: Jul 22, 2025 8:45:00 AM