Few technology decisions shape a law firm's daily life as much as where matters, documents, and billing live. Switching later is expensive, so it pays to choose with a clear set of questions rather than a vendor demo and a gut feeling.
Clio, NetDocuments, and iManage are three names that come up constantly, and they are not interchangeable. Clio is best known as cloud practice management for small and mid-size firms, covering matters, contacts, time, billing, and client intake. NetDocuments and iManage are document and email management platforms, widely used by mid-size and larger firms, centered on organizing, securing, and versioning work product. Some firms use a practice-management system and a document-management system together. Check each vendor's current feature list, since products change.
Start with how your firm actually works
Before you look at features, write down:
- How many timekeepers and staff you have now, and in two years
- Whether you bill hourly, flat fee, contingency, or a mix
- How many matters are open at once and how long they stay open
- Whether lawyers work from home, court, and client sites
- What the firm does today that frustrates people most
A five-attorney estate planning practice and a seventy-attorney litigation firm will answer these very differently, and so should their software.
Evaluation criteria
Matter and document structure
Ask how the product organizes a matter, what metadata it tracks, and how easy it is to find a document two years later. Document-management systems tend to be strongest on version control, check-in and check-out, and workspaces. Practice-management systems are typically stronger on billing and client communication.
Security and access control
- Does it support multifactor authentication and single sign-on with Microsoft 365?
- Can you restrict a matter to specific people, including ethical walls for conflicts?
- Is there an audit log of who opened, edited, or exported documents?
- How is data encrypted at rest and in transit, and who holds the keys?
Ask for the vendor's current security documentation and independent audit reports, and have your IT or security advisor read them. Do not rely on a sales summary.
Integration with Microsoft 365
Most firms live in Outlook, Word, and Excel. Test how the product handles saving email to a matter, opening documents in Word, and co-authoring. A tool that fights your email workflow will be quietly abandoned by the attorneys.
Billing and trust accounting
If you evaluate a practice-management system, look closely at trust accounting, three-way reconciliation support, and how it fits your state's rules. Confirm these details with your state bar's guidance and your accountant rather than assuming.
Total cost
Price per user per month is only part of it. Include implementation, data migration, training, add-on modules, integrations, and the staff time spent on cleanup. Ask what happens to pricing at renewal.
Run a real pilot
A demo shows the best case. A pilot shows your case.
- Pick a small group, such as one attorney, one paralegal, and one billing person.
- Load a few real, anonymized or consented matters.
- Ask them to do a week of normal work: intake, drafting, filing, billing.
- Collect written feedback on what slowed them down.
Plan the exit before you enter
Ask how you export your data, in what format, and whether metadata, version history, and audit logs come with it. A system you cannot leave gives the vendor leverage over you at every renewal.
Migration is the hard part
The software choice is often the easier half. Moving years of documents with intact folder structures, permissions, and naming conventions takes planning. Decide what to migrate and what to archive, clean up duplicate files first, and schedule the cutover away from filing deadlines.
Common mistakes
- Choosing for the partner who shouted loudest rather than for the people who use it daily
- Skipping the security review because the vendor is well known
- Underestimating training time
- Copying a messy folder structure into a new system unchanged
Getting a second opinion
Counsel Cyber supports firms running Clio, NetDocuments, iManage, and Microsoft 365, and we can help you evaluate security settings, integrations, and migration plans. We do not sell these products, so our advice is about fit and safety rather than commission.