What questions belong in a legal e-billing and matter management RFP?

Which functional questions actually separate vendors?

The ones that force a demonstration instead of a yes. Every vendor will affirm that it enforces guidelines, manages budgets, and tracks matters. Ask instead how the file stays current, what happens when counsel sends a status report, and how a guideline violation surfaces. The distance between marketing answers and demonstrated behavior is the most reliable signal in the whole process.

• Guideline enforcement: which rule types run automatically on LEDES invoices, and can we watch a violation fire in the demo?
• Matter currency: how does the case file get updated when defense counsel sends a status report, and how much of that is manual?
• Budgeting: how are budgets set, tracked against actuals, and flagged when a matter drifts?
• Counsel performance: what does the system measure about firm and attorney performance, and from what source data?
• Reporting: can our administrators build the reports leadership asks for, or does every new view require the vendor?
• Traceability: for any fact the system asserts, can a reviewer trace it to the source document?

Which integration and migration questions prevent surprises?

The ones that turn later-phase items into priced commitments. Integration with your claims system and your AP or ERP platform, and migration of open matters and historical spend, are where change orders live. Require named scope, a fixed fee, and acceptance criteria for each, in the RFP response itself, so the comparison across vendors includes the costs that usually stay hidden.

• How does the system sync with our claims system, in both directions, and what does that integration cost, fixed?
• How do approved invoices reach our AP or ERP platform for payment, and who builds that connection?
• Which LEDES versions do you accept, and how do you handle firms that submit outside the standard?
• What is your migration methodology for open matters and historical spend, priced with acceptance criteria we define?
• What are our data export rights at termination: format, completeness, cost, and timeline?

Which security and AI questions are non-negotiable?

Litigation data is privileged, so the security section carries contract weight. Require current SOC 2 audit coverage with documentation available to your team, ask where data is hosted and who can access it, and put the AI questions in writing: what the models do, whether your data trains anything, and whether every AI output traces to a source document in your own files.

• Do you maintain current SOC 2 audit coverage, and will you provide the report and security documentation for our review?
• Where is our data hosted, who can access it, and how is privileged material segregated and protected?
• What exactly does your AI do, and is any of our data used to train models that serve other customers?
• Can every AI-generated statement be traced to the source document, page, and line it came from?
• What are your breach notification obligations, and will you accept them as contract terms rather than policy statements?

Treat vendors that claim their AI predicts case outcomes with particular skepticism, and make them put the claim and its basis in writing. CaseGlide's position is the opposite: the AI reads and structures what your counsel already sends, keeps every fact traceable to its source, and leaves the judgment with your team.

How should you structure the RFP process itself?

So the vendors do the proving. Write requirements from your own workflows, force identical pricing scope, and replace the scripted demo with your scenarios: one live matter, one messy invoice, one guideline violation. Score in writing against weighted criteria, check references that match your profile, and carry the winning answers into the contract as commitments, not intentions.

1. Write requirements from workflows, not feature lists: document how a matter moves from assignment to resolution today, and ask vendors to demonstrate each step.
2. Fix the scope: same matter volume, user count, integration list, and migration package for every bidder, priced all-in over the same term.
3. Run scenario demonstrations: your sample matter, your guidelines, a deliberately noncompliant invoice, and a status report the system must process.
4. Check references against your profile: similar portfolio size, similar claims system, and at least one reference that switched from another platform.
5. Score and negotiate in writing: weighted criteria agreed before responses arrive, and RFP answers incorporated into the contract.