Choosing a new court management system (CMS) is one of the most consequential technology decisions a court will ever make. The system you select will shape how your staff works, how cases move through your jurisdiction, and how well your court can serve the public for years to come.
The move to cloud-based, software-as-a-service (SaaS) CMS platforms has accelerated significantly in recent years, and courts across the country are actively evaluating their options. But the vendor landscape is crowded, and every vendor will tell you they are the best fit. Marketing materials look polished. Demos are rehearsed. References are pre-selected. Without a structured framework to guide your evaluation, it is difficult to distinguish genuine capability from well-packaged promises.
We have put together 10 questions that any court should ask any vendor in any conversation, regardless of which system you are considering. These questions are designed to surface the things that matter most and that are most likely to be glossed over in a standard sales process: long-term costs, implementation realities, data ownership, security posture, and what a vendor’s behavior looks like when things get hard.
A note on our perspective: equivant is also a court technology vendor, and we believe these questions should be asked of us, too. It’s important to evaluate the software you choose to implement, but it’s equally important to evaluate the people you will be working with. We have built our approach around the idea that courts deserve more than a product; they deserve a partner who invests in their long-term success. This list reflects that belief.
Question 1: What automation and integration capabilities does the system support and how do you plan to grow them?
A modern CMS should do more than store case data. It should actively reduce the manual burden on your staff by automating routine processes and connecting with the other systems your court depends on.
When you ask this question, push past the general answer. Almost every vendor will say they have “robust integration capabilities” or “open APIs.” What you want to understand is the specifics: Which workflows can be automated out of the box? Can the system trigger automated notifications when a case status changes, calculate fees without staff intervention, or route documents through approval workflows without manual steps? Does it connect with your justice partners (law enforcement, corrections, prosecutors) and how are those connections maintained over time?
Equally important is the forward-looking piece. Integration is not a one-time project; it is an ongoing investment. Ask whether integration development is part of the vendor’s core product roadmap or whether it is treated as a custom engagement each time. Courts that choose a vendor with a strong integration foundation today will be far better positioned to take advantage of emerging capabilities, including AI-assisted workflows in the years ahead.
What to listen for: Specific examples, not generalities. A vendor with real integration depth will be able to describe your exact use cases — not just tell you it is possible.
Question 2: How do you protect court data and what is your approach to AI-related privacy risks?
Courts handle some of the most sensitive information in the public sector. Criminal histories, juvenile records, sealed filings, victim information, etc. Security is a core requirement.
Start with compliance frameworks. Does the vendor meet CJIS Security Policy requirements? Are they StateRamp authorized or working toward authorization? Have they achieved SOC 2 Type II certification? Then go deeper. Ask specifically who owns your court’s data. If your contract ends or you transition to another vendor, how will your data be returned to you, and in what format? Courts that do not ask this question upfront sometimes discover that their own records are effectively held hostage by a vendor’s proprietary format or retention policies.
The AI dimension of this question is increasingly important. Many vendors are incorporating AI features into their platforms (document summarization, predictive scheduling, workflow recommendations, etc.). These capabilities can be genuinely valuable. But courts should understand exactly how those features work: Is your court’s data being used to train the vendor’s AI models? Who has access to AI-processed outputs? What governance and oversight exist around AI-generated recommendations?
Ransomware attacks on court systems have increased significantly in recent years. Ask every vendor what their incident response protocol looks like, and how they have communicated with customers when something has gone wrong in the past. A vendor’s history in a crisis tells you more about the partnership than their behavior during a sales process.
What to listen for: Specific certifications, clear data ownership and exit policy, and a thoughtful, honest answer to AI governance. Vague answers here are a red flag.
Question 3: How configurable is the system and who does the configuring?
No two courts operate exactly alike. Workflow differences, local rules, document templates, fee schedules, case type structures — the variation from one jurisdiction to the next is significant. A CMS that cannot adapt to your court’s specific processes forces your staff to adapt to the system instead, driving workarounds, reducing adoption, and ultimately costing more in lost efficiency than you saved on the contract.
This is why configurability matters, and why the word itself deserves scrutiny. There is an important distinction between a system that is “configurable” and one that is “customizable.” Configuration means adjusting the system using built-in tools, without touching the underlying code. Customization means modifying the code itself. Customization is expensive to build, difficult to maintain, and often breaks during system upgrades. True configurability (where administrators can adjust workflows, forms, document templates, and case type structures without vendor involvement) is far more sustainable over the long term.
Ask specifically who can make those adjustments. Can your court administrators update a form or modify a workflow on their own, or does every change require submitting a support ticket and waiting on the vendor’s development queue? The answer has significant implications for how quickly your court can respond to new legislative requirements, local rule changes, or operational needs.
What to listen for: Ask the vendor to demonstrate configuration live, in the product. A system with genuine flexibility should be able to show you how an administrator would make a change.
Question 4: What does the pricing model actually look like, including what comes after go-live?
SaaS pricing can be difficult to evaluate, and that difficulty is sometimes designed. A subscription price that looks reasonable in year one can look very different by year five once you factor in the cost of integrations, additional user licenses, premium support tiers, training services, storage overages, and annual escalations.
Ask every vendor for a full multi-year total cost of ownership projection, not just their base subscription rate. Walk through each line item: What is included in the base price? What triggers additional charges? If your court grows and you add users or case volume, how does pricing scale? If you need a custom integration with a partner agency, what does that typically cost?
What to listen for: Willingness to provide detailed multi-year projections and transparency about what drives cost increases. Reluctance to answer these questions directly is informative.
Question 5: What kind of partner will you be and what are your values?
This may be the most important question on this list, and it is also the one most likely to be answered with polished, rehearsed language. Every vendor will tell you they are committed to your success and that they view the relationship as a partnership. What you want is evidence, not a talking point.
Start with governance. Who owns the company, and how does that affect their decision-making? Ask about the formal customer relationship. Is there a customer advisory board or council? Do customers have meaningful input into the product roadmap, or is that process internal and opaque? How does the vendor communicate when something goes wrong, like a bug, an outage, or a security incident? Do they reach out proactively, or do you find out when staff start calling the help desk?
Then ask for references. Ask specifically to speak with courts that have been on the platform for five or more years, courts that have gone through a difficult implementation, and courts that have had to escalate a support issue. Those conversations will tell you more than any demo.
What to listen for: Specificity about how the partnership actually works day to day, and a willingness to connect you with customers who have experienced the relationship at its most challenging.
Question 6: What is your implementation track record and how do you handle things when they go off course?
A CMS implementation is a major undertaking. Even when everything goes well, it requires significant time, resources, and change management from your court. When something goes wrong (and in any complex technology project, something usually does) the vendor’s response makes all the difference.
Ask for documented implementation track record data: What percentage of implementations are delivered on time and on budget for courts of comparable size and complexity? What are the most common causes when a project runs long or over budget? How does the vendor typically handle scope changes that emerge mid-implementation? These questions are meant to help you understand what you are signing up for and whether the vendor is honest about the realities of the work.
The follow-up question is the one that really matters: What will you recommend when issues arise that could impact our budget or schedule? A vendor who tells you implementations always go smoothly is not being straight with you. A vendor who can walk you through how they have navigated difficult situations, including what they communicated, what tradeoffs they presented, and how they worked with the court to find a path forward, is demonstrating the kind of partnership that holds up under pressure.
What to listen for: Honesty about challenges, specific examples of how difficult situations have been handled, and a clear picture of who is doing the work.
Question 7: How will our historical data be migrated and what happens if we ever need to leave?
Data migration is consistently one of the most underestimated and most consequential parts of a CMS implementation. The complexity of moving decades of case records, document attachments, financial transactions, and event histories from a legacy system to a new platform is significant.
Ask every vendor for a detailed data migration methodology. How is legacy data inventoried, mapped to the new system’s data model, cleaned for quality issues, and validated before go-live? What happens to records that do not map cleanly — are they flagged for manual review, migrated as-is, or lost? How is migration testing structured, and what is the court’s role in reviewing and approving migrated data before the system goes live?
The data portability question (what happens if you need to leave) is one that many courts avoid asking because it feels awkward in a sales conversation. Ask it anyway. You should know, before you sign, what format your data will be provided in if you ever transition away, whether there are exit fees associated with data extraction, and how long the vendor retains your data after contract termination. A vendor who is confident in their product and their partnership should not have any discomfort answering this question clearly.
What to listen for: Detailed methodology, not vague assurances. Specific answers on data format, exit terms, and retention policy. A vendor who is uncomfortable with the exit question may be telling you something about how easy it would be to leave.
Question 8: What ongoing support and maintenance do you provide, and who will I actually talk to?
Go-live is not the finish line. The ongoing support relationship is where the day-to-day reality of a vendor partnership becomes clear. Ask for a clear breakdown of support tiers: What is included in your base subscription, and what triggers additional cost? Is there a dedicated account manager or customer success contact assigned to your court, or does every interaction go through a general support queue?
Ask for specifics on how software updates and patches are handled. Can your court control the timing of updates, or are they pushed automatically on the vendor’s schedule? In a court environment, a system update during a busy court calendar can create serious operational disruption. Understanding who controls that process matters.
Ask about resolution time commitments for critical issues: How does the vendor define “critical,” and what response time is contractually guaranteed? What happens if those commitments are not met? If your court operates in a non-standard time zone or has coverage needs outside standard business hours, ask specifically about how those needs are accommodated.
What to listen for: Named contacts, not just queues. Specific SLA language, not general assurances. A vendor who cannot clearly explain what support looks like after go-live is telling you something important.
Question 9: What training and change management support are included both at launch and long-term?
Technology implementations succeed or fail largely because of adoption. A system that is technically excellent but poorly adopted by court staff will not deliver its promised value. That failure will often be attributed to the technology, rather than the implementation approach. Training and change management are core to whether the investment pays off.
Ask specifically what training is included in the base contract and what is billed additionally. In projects that run long or go over budget, training is often the first thing to get cut or compressed. Ask how that is protected and whether there are contractual minimums around training hours or milestones that must be met before go-live.
Long-term training is equally important and often overlooked. Courts experience staff turnover. New employees need to be trained months or years after go-live, often without the vendor’s active involvement. Ask what self-service learning resources are available (knowledge bases, recorded training sessions, user documentation) and whether those resources are kept current as the system evolves.
What to listen for: Workflow-specific training, long-term learning resources, and a vendor who treats change management as part of their responsibility.
Question 10: Where is the product headed and how much of that roadmap is driven by customer input?
The CMS you select today will evolve significantly over the life of your contract. Technology is changing quickly because of AI capabilities, new integration standards, evolving security requirements, and shifts in how courts interact with the public. The question is not just whether a vendor has a good product today, but whether they have the vision, the resources, and the customer relationships to keep that product moving in the right direction.
Ask how the vendor decides what to build next. Does investment direction come primarily from internal product decisions, from the priorities of their largest customers, or from a structured process that gives all customers a meaningful voice? Courts treated as partners in product development tend to get systems that actually fit how they work.
The AI question deserves specific attention. Vendors across the industry are adding AI-powered features, and not all AI is created equal. Ask what AI capabilities the vendor has built or is developing, how those features are governed, and what guardrails exist to ensure AI outputs are used appropriately in a court setting. Responsible AI in the justice context is not just a technical question, it is an ethical one, and the vendor’s answer will tell you how seriously they take it.
Ask also how the vendor stays current with court technology standards. Standards exist to ensure interoperability and data quality across justice systems. A vendor who is actively engaged with standards bodies and incorporates those standards into their development process is building a more durable product than one who treats compliance as a box to check.
What to listen for: A roadmap that reflects genuine court priorities, a clear and honest answer on AI governance, and evidence of active participation in the broader court technology community.
Ask These Questions of equivant, Too
We wrote this guide because we believe courts deserve vendors who are willing to be held to a high standard, and that includes us.
equivant has been working alongside courts for decades. We have built our products, our services, and our culture around a single purpose: simplifying justice. We are not the right fit for every court, and we would never claim otherwise. But for courts that are looking for a partner with deep expertise in court technology, a team that picks up the phone, and a track record of implementations built on honesty rather than optimism, we believe the conversation is worth having.
Bring these 10 questions to that conversation. Ready to start the evaluation process? Contact our team and bring your toughest questions.
