Choosing the Right Document Management System

With the accelerating pace of innovation in cloud technology and artificial intelligence, selecting the right document management system (DMS) is no longer just an IT decision—it’s a strategic one. For law firms and legal teams, the consequences of choosing the wrong system can be significant: fragmented matter files, compliance risks, inefficiencies, and even exposure to malpractice. 

Sikich helps firms navigate DMS selection and implementation. The Sikich difference is a thoughtful, criteria-driven evaluation process. Below are some of the key questions Sikich clients consider as part of that journey, drawing on lessons learned from system selection, vendor negotiation, and successful go-lives. 

6 Essential Questions to Ask About the Document Management System Platform Itself 

Implementing a DMS isn’t just about getting the software to work, it’s about making it work well within the firm’s broader technology and workflow environment. Here are six questions Sikich recommends every client ask: 

1. What systems does the legal DMS integrate with? 
   Seamless integration with Microsoft 365, Teams, time & billing, or your case management platform can dramatically improve adoption and workflow efficiency. Sikich encourages clients to look beyond the demo and review real integration capabilities and user experience. 
2. How does the DMS address security and compliance? 
   Legal work demands strict confidentiality. A modern DMS should offer built-in encryption, user-level access controls, audit trails, and compliance certifications. It’s critical to understand how the system will support your firm’s security and regulatory obligations. 
3. Does it support mobile and flexible work environments? 
   Today’s professionals expect to work from anywhere. A DMS should support secure access via mobile devices, eliminate VPN reliance, and provide a consistent experience across desktop, tablet, and phone. 
4. How intuitive is file organization and search? 
   Matter-centric design, robust foldering, and filtered search are no longer nice-to-haves, they’re essential. Sikich encourages clients to validate OCR capabilities for PDF and image files, as well as version control for collaborative editing. 
5. Does the legal DMS allow for secure collaboration with external stakeholders? 
   External sharing shouldn’t require moving files out of your secure environment. The right DMS will let you collaborate with clients, experts, and co-counsel without compromising data security. 
6. What additional functionality or add-ons are available down the road? 
   Whether it’s email management, AI-driven search, or advanced records management, future needs should be considered now. The best-fit system will scale with you. 

5 Questions to Ask the DMS Provider 

Technology is only half the equation, your customer experience with the vendor also matters. When supporting clients in vendor selection, Sikich advises them to go beyond the technical spec sheet and assess the provider’s support model, references, and long-term viability: 

1. How quickly can we launch a proof of concept? 
   A POC is essential to test fit. Cloud-native vendors can often deploy a working environment in 1–2 days, giving you a head start on hands-on evaluation. 
2. What’s your approach to data migration? 
   Data migration is often the most complex and risk-prone part of any DMS project. Sikich helps clients understand how Sikich works with DMS vendors to handle legacy data, maintain security throughout the process, and avoid hidden costs tied to multiple migrations. 
3. Can we review your cloud services agreement upfront? 
   System uptime, maintenance windows, and support SLAs should be transparent before contract signature. A careful review now can prevent surprise disruptions later. 
4. What is your customer churn rate and why do firms leave? 
   No vendor is perfect, but it’s a red flag if many clients are jumping ship. Sikich always recommends looking at user forums, reviews, and peer references to confirm long-term satisfaction and roadmap delivery. 
5. Can we speak with reference clients using the same deployment type? 
   Not all DMS environments are created equal. You want feedback from Sikich clients using the same version and cloud deployment model you’re considering. This is something Sikich regularly coordinates during vendor due diligence. 

Final Thoughts 

Choosing a DMS is about more than checking boxes; it’s about aligning the technology with your firm’s goals, risk profile, and day-to-day workflows. Sikich helps legal teams identify what matters most, ask the right questions, and ensure that the implementation delivers on its promise, not just during the demo, but every day after go-live. 

If your firm is exploring a document management system, or if you’re not getting the most out of your current DMS, let’s connect. A structured, strategic approach can save you time, money, and future headaches.