LEAP Software | 4 min

How to Select the Best Legal Software for Your Law Firm

March 30, 2023

lawyer using cloud-based legal software

The software evaluation process can be overwhelming and time-consuming for law firms. As legal professionals are experts in practicing law, they can miss out on asking the right questions or requesting to see crucial features that will make or break the success of the software’s implementation for the firm. Therefore, it is essential to ensure that it addresses the firm’s problem statements across the business to support long-term success and avoid an overcomplicated tech stack.

This blog will cover the core workflows and what questions law firms should ask a software provider before implementing a new solution.

Legal Matter Management Software

The minute a law firm takes on a new client, they are inundated with data, documents, correspondence, due dates, and tasks that all influence the matter’s outcome. Therefore, organized matter creation and management that ensures all staff members related to a matter have access to the most up-to-date information is essential when considering a new legal software solution.

Questions to Ask When Considering Legal Software

  • Does the system offer pre-built matter types for the common areas of law?

  • What details can be entered into a new matter?

  • Can you manage critical matter dates and deadlines?

Legal Document Creation Software

One of the most time-consuming processes is filling out legal documents, forms, and templates. Manually populating court forms, correspondence, and relevant documents takes up several hours a week and law firm staff could instead focus on completing billable tasks or taking on new cases in the same amount of time. Automated document creation frees up this time and reduces the potential for errors that create repetitive work. Additionally, software that can automate existing firm templates can help overcome the initial resistance to change, as staff members can still work using their preferred document formatting.

Questions to Ask When Considering Legal Software

  • Does the software automate form, template, and document creation?

  • Are pre-built, up-to-date forms and templates already available in the system?

  • Can you import existing templates for automation?

Time Tracking for Lawyers

Instant time tracking is a missed revenue stream to support law firm profitability. As a business, fee earners need to be paid for all the work they complete to ensure that the law firm can continue running. Additionally, bookkeepers need to ensure that they have accurate records for when they complete reconciliations to avoid malpractice risks. Instant timekeeping tools that integrate with accounting features can eliminate these risks and ensure that attorneys never miss a billable minute.

Questions to Ask When Considering Legal Software

  • Are instant time-tracking capabilities available? If so, for what software features?

  • Is an electronic timesheet available in the software?

  • Can users record time out of the office on mobile devices and tablets?

Law Firm Communication & Collaboration

Seamless communication and collaboration are essential for a smooth operating law firm and for providing clients with the best legal services. Centralized and secure access to correspondence, documents, and evidence improves a firm’s organization so that attorneys and support staff can always access the most up-to-date information. It also helps eliminate complications IT staff and consultants face when the software already offers additional security measures and encryption features. That’s why attorneys should look for software that offers integrations with tools like LawConnect, a secure online document-sharing and collaboration tool for lawyers and their clients.

Questions to Ask When Considering Legal Software

  • Does the software integrate with email and correspondence applications like Office 365 and Outlook?

  • Do emails and their attachments automatically save to the relevant matter?

  • Does the software integrate with secure document-sharing and collaboration platforms built to meet compliance requirements?

Legal Billing & Invoicing

Frequent and accurate billing is essential for law firms to sustain a profitable business. Accounting features and integrations are crucial in legal software to ensure that invoices are correct, with all billable time captured and funds used correctly.

Questions to Ask When Considering Legal Software

  • Does the system offer accounting, billing, and invoicing features?

  • Does the system integrate with accounting software like QuickBooks Online and Xero?

  • How does the software support compliant legal and trust accounting (i.e., IOLTA, state regulations, etc.)?

Remote Accessibility for Law Firms

Firm staff must ensure they can update matters, upload files and documents, and collaborate internally and externally regardless of whether they’re working from the office, at court, or on the go. Cloud software solutions help support remote accessibility by providing real-time access to data so that partners can offer more flexible working options to their staff while increasing productivity. As the legal skills shortage continues to pose challenges for law firms, flexible work options are necessary to stay competitive with more modern practices so that staff members can establish a strong work-life balance.

Questions to Ask When Considering Legal Software

  • Is data stored in an on-premises server or the cloud?

  • Can the software be accessed from multiple devices through a mobile app? If so, what features are included in the mobile version?

Onboarding & Transition Process

The onboarding and transition process set the stage for how successful software will be for a firm. The average law firm already has limited resources. It cannot be bogged down by long, tedious data transition, training, and adoption processes, so they must ensure that any new software will not cause long downtime periods and offer training options that fit their staff’s schedules.

Questions to Ask When Considering Legal Software

  • How long does the transition and implementation process take?

  • Will the new software provider transition existing data from another system? If so, what data will they transition?

  • Can training be completed in person or virtually?

  • Are training and support options available based on a user’s key role/function?

Support & Training Resources

A software provider should be invested in ensuring that all your firm’s current and future users get the most out of the system with ongoing training and support resources available. If these support features are unavailable, it can create a decline in the ROI the firm gets out of the initial software investment and lead to staff members reverting to inefficient workflows.

Questions to Ask When Considering Legal Software

  • Is ongoing support offered? If yes, what support options are available?

  • Is ongoing support included in the software cost or offered at an additional rate?

  • Can users provide feedback and ideas for software improvements or updates?

Law Firm Data Security

Data security should be the #1 priority for a law firm, whether this is their first software investment or a new system being added to the firm’s existing tech stack. Client data is extremely sensitive and needs to be handled appropriately to meet compliance standards, as data breaches can lead to malpractice, dissatisfied clients, and potential disbarment. Legal cloud software can mitigate these security risks by offering complete data encryption, penetration testing, multi-factor authentication, and 24/7 security monitoring.

Questions to Ask When Considering Legal Software

  • Does the software provider share the security measures they have to protect data? If so, what security measures are in place?

  • If it is a cloud software, what cloud provided do they use to host the application?

  • Is the software provided SOC2 certified?


While these questions provide a starting place for law firms to start the software evaluation process, there will certainly be additional questions that arise in their conversations with software providers. While it might feel like a lot of time and work upfront, it is crucial not to rush the evaluation process. Investing in an inadequate solution can create additional inefficiencies and add to overhead costs in the long run, whereas the right legal software can create streamlined, seamless, and profitable processes that law firms can rely on regardless of how their operations scale and evolve.

Is your law firm ready to start evaluating new legal software providers? Download our e-guide, Everything to Look for When you Switch to a New Legal Software Provider, for a comprehensive document to ensure you pick the right solution for your law firm.

Is your law firm ready to start evaluating new legal software providers?

Download our e-guide, Everything to Look for When you Switch to a New Legal Software Provider, for a comprehensive document to ensure you pick the right solution for your law firm.