How to Prepare for a Legal Case Management Software Demo

In our latest Legal Case Management Jam Session, Confido's Emery Wager spoke with Lea Wold, CEO and founder of Checkmark Projects. With more than fifteen years of experience in operations, Lea shared her insights into the often-overlooked science of preparing for software demos from the buyer's perspective. While most of us sit through software demos to be sold, Lea proposed a more proactive approach that ultimately saves time and reduces the chances of picking the wrong software.  


When to Start Looking

Lea explained that the decision to explore new software solutions often arises when law firms face challenges in the form of disorganization or poor communication within the firm. The first step is deciding if the the problem requires an operational or a software solution. If it's a software problem, it's time to start the process of evaluating new systems. 


Cost vs. Value

A key theme of the conversation was that the decision-making process goes beyond mere cost considerations. Instead, she urged law firms to focus on the potential value a system could bring in terms of time saved, reduced errors, and increased efficiency.


Proven Process for Software Selection

Lea's approach to software selection starts with getting clear about the firm's pain points and priorities. These considerations are then ranked in order of importance. This is the starting point. 

The next step is doing research to determine which systems are good candidates. There are several resources to help you get started, including Capterra or our legal case management research hub and software database. Once you have built a list of systems, rank them and pick your top three to run the demo process. Diving deep into more than three systems can be overwhelming, and Lea recommends against it. Lea also highlights the benefits of involving team members in the demo process to garner support and excitement for the potential improvements. 

In preparing for the demos, Lea suggests defining your goals and coming up with questions ahead of time. Once in the demo, make sure to push the sales rep and get clear answers to your questions. Don't tolerate "hand waving." Make sure to probe, not just on the software, but on the support you'll get and the data migration process.

Once you have completed your demos, select the top choice. Now it's time to push forward building the implementation plan (a topic for another day). If none of the solutions appear to be right for your firm, go back to your longer list and evaluate if it makes sense to start the demo process with other systems on that list. 


Making the Right and Wrong Software Choice

The conversation concluded with the acknowledgment that while choosing the wrong software can have significant consequences, it is a mistake you can recover from. Lea encouraged law firms to view the decision-making journey as an opportunity for growth and improvement, emphasizing that the right choice can lead to substantial leaps in efficiency and productivity. 



Lea emphasized the importance of running a clear software selection process and proactively preparing for demos. She discussed the value of maintaining control in the demo process, ensuring you don't end up just buying from the smoothest talking sales rep. Although it takes more time and thought early in the process, she's seen this approach ultimately save time and many headaches down the road.

If you're considering an upgrade and need expert guidance, visit Lea's website at

To receive a free legal case management software consult and to view a database of legal case management software, visit our case management center.

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