A Software Buying Checklist

You’re the office manager or managing partner of your firm and you have been tasked with selecting new financial software (i.e. timekeeping, billing, reporting, and accounting) for the firm. You know you have significant due diligence ahead of you. There are not many resources out there and essentially, you are inventing the wheel for your law firm’s financial workflow. Regardless of whether you opt for LeanLaw + QuickBooks Online or not, we would like to help you get clarity on your task.

We asked a law office administrator from a mid-sized law firm (30+ attorneys) to see her list from her search. This list might not exactly match what you need to consider, but it is a great start and truly enlightening on how broadly you must consider how you want your new law firm software to enhance and expand your firm’s efficiency and profitability.


When you think about timekeeping, if you buy a software that is well-integrated, you’ve just streamlined the process. Flexibility is the other big consideration. A larger firm is likely to need multiple timekeeping options including web-based, desktop, and mobile (including iPads, tablets, and phones), calendar view, timers, and shortcodes. You’ll also need to think about whether you need fixed fee and hybrid timekeeping in addition to hourly, how to set up the client/matter entries and the importance of interfacing with Outlook, Google, or whatever online platforms you use.


You’re not only charging for time, but also for expenses. What about late fees? How is the invoice being presented? Do you have to mail it, physically (egads!) or can you send it online? (Yes, you should!) What sort of invoice review workflow is provided? Does it keep the lawyers out of the accounting software (think of the mess they might make!) Does it allow for pre-bill review and appropriate segregation of roles?

Trust Accounting

What about billing from a retainer? How does the software handle that and the associated trust accounting? Is it easy to accept trust deposits? Pay an invoice from trust? Reconcile the trust account? Trust accounting can be a pain in the neck, so make sure your software makes the process easy.


If you don’t understand your law firm’s financial data in real-time, you cannot understand the efficiency and profitability of your firm. Does the new software create reports with the time entry, expenses, trust transactions, and billing entries that you create? It better—otherwise, you’re going to pay someone to spend a lot of time manually entering data, which is a colossal waste of time. You should be getting reports on your timekeepers, on originating attorneys on accounts receivable and work-in-progress, trial balances, and more.

These are just some of the issues and data points you should be thinking about as you prepare for a new software era in your law firm. Also included in the list:

  • Client/matter considerations
  • Receivables
  • Trust and retainer updates
  • Accounts payable
  • General ledger
  • Conflict checks
  • And much more

Remember to do your due diligence. It’s hard work to integrate new financial software into a law firm. You don’t want to make a mistake and do it again, another time. Make sure you have all your questions answered.

Understanding the software features you need is just part of choosing new financial software. Before you ever use a checklist, you should understand your users’ needs and the types of software available to meet them. And once you decide, you need a robust onboarding process to make the transition as painless as possible. Stay tuned for more posts on those topics. Meanwhile, the checklist is a starting place in your journey.

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Best-in-Class or All-in-One?

Ultimately, the answer is different for each firm and situation.