A Day-by-Day Test Plan for a Legal Billing Software Free Trial

The trial starts on a Monday. Someone logs in Tuesday and clicks around for a few minutes. A client matter blows up on Wednesday, and nobody opens the software again until the expiration email arrives, when the decision comes down to a general feeling.

A legal billing software free trial is a short window, and it’s easy to spend it browsing. A browse tells you whether the screens look pleasant. A test tells you whether the software can carry one of your matters from time entry to cash in the bank and leave the books right. Here’s a seven-day plan for the second kind, built around one matter, a few people, and a scorecard you fill in as you go. If your trial runs longer than a week, start the plan on day one anyway and keep the remaining days for a second round on whatever the scorecard leaves open.

Before Day 1: set up the legal billing software free trial to answer real questions

Do four things before you start the clock.

Pick one matter. Choose something real but low-stakes: a small active matter, or a recently closed one you can recreate with client names removed. It should have at least one wrinkle, such as a write-down, a partial payment, or a retainer, because sample data never does.

Name the people. You need two working timekeepers, the person who closes the books each month, and the partner who will make the call. Put short blocks on each calendar for the days they’re needed.

Decide which accounting company to use. If you can, connect a sample or test company instead of your live books, and confirm with the vendor what the trial connects to. Some tools are built around a specific accounting system: LeanLaw, for example, runs on QuickBooks Online and requires it, so you’d need a QuickBooks Online company ready before Day 1.

Write the scorecard now. One row per day below, with three columns: worked on its own, worked with help from the vendor, didn’t work. Writing it first keeps the trial honest.

If you haven’t yet narrowed down what matters to your firm, the buyer’s checklist for small-firm billing software is the place to set your criteria before the trial starts.

Day 1: Connect accounting and set up one matter

Connect the trial to your accounting company, then create the client and the matter, with real rates and real billing terms. Note what you had to decide that you didn’t expect (account mappings, tax settings, invoice numbering) and whether the help available answered it.

Score it on one question: could the person who will own this system set it up without the vendor on the phone?

Day 2: Time capture by two real timekeepers

Ask your two timekeepers to enter a normal day’s work on the test matter, in whatever way they’d actually use it. Then ask them separately how it went. The partner who loves software is the wrong tester here; you want the timekeeper who enters time on Friday afternoon from memory.

Time that never gets entered is money left on the table, and it shows up later as weaker utilization. If entering time feels like a chore on Day 2, it will feel the same in month six.

Day 3: Draft an invoice with a write-down

Build an invoice from the time entered, and have a partner write down part of it the way they normally would. Then look at what’s left behind. Can you still see the original time and the reduction? Can you report on write-downs later by matter and timekeeper?

That record is realization (what the firm billed against the value of the time worked). Software that hides the write-down makes it harder for partners to see where billed time comes up short.

Day 4: Take a payment and apply trust if relevant

Record a payment against the invoice, and make it a partial payment so you can watch how the remaining balance behaves. Check what the client would see on the next statement.

If your firm holds client funds, test the trust workflow too: deposit a retainer to trust, apply it to the invoice, and check the client’s trust balance before and after. Under ABA Model Rule 1.15(c), fees paid in advance stay in trust until they’re earned; each state adopts its own version, so check your jurisdiction’s rule. Use test transactions only. A trial is no place to move real client money.

Day 5: Check what landed in the books

Open the accounting company and find everything from Days 3 and 4: the invoice, the payment, and any trust activity. Is each one where you’d expect, against the right customer and the right accounts? Did anyone have to type anything twice? Does the deposit match what the bank will show?

Let the person who closes the books run this day; it’s the one they care about most. They’ll spot in minutes what everyone else would miss, and their answer tells you whether month-end gets shorter or just different.

Day 6: Run the reports partners will ask for

Ask the deciding partner which questions they ask at month-end, then answer them from the trial: what each timekeeper worked versus what was billed, what’s outstanding and how old it is, and what’s been collected on the matter. If a report needs an export and a spreadsheet to answer a basic question, mark it on the scorecard.

Day 7: Decide with a written scorecard

Bring the scorecard to a short meeting with everyone who took part. Go row by row. Anything marked “worked with help” deserves a follow-up question: was that help part of setup, or something you’d need every month?

Then decide one of three things: move forward, run a second round on the open questions, or stop. Write the decision down along with the reason, so the next conversation starts where this one ended.

What a free trial can’t show you

Two things matter a great deal and rarely fit inside a trial window.

Migration of your history. A trial starts empty. Ask the vendor to walk you through how historical clients, matters, open invoices, and trust balances would come over, ideally using a small sample of your own data, and what stays behind in the old system. The cleaner the source data, the easier this goes; this guide to cleaning up your firm’s accounting data before migration covers what to fix first.

Support under pressure. A vendor has every reason to be responsive during a trial. Send support one genuinely hard question during your week, the kind you’d have at month-end, and judge the answer on accuracy as much as speed. Then ask for a reference firm of your size that switched recently, and ask them what support was like during their first close.

What the partners are deciding

At the end of the week, the partners are weighing three things: whether more of the firm’s work will turn into invoices, whether invoices will turn into cash sooner, and whether the books will stay right without extra hours at month-end. A scorecard built on one real matter answers those far more convincingly than a week of clicking around.

If LeanLaw is one of the tools you’re comparing, start with the requirement: it’s built on QuickBooks Online and runs on it, so you’ll need QuickBooks Online to use it. Its free trial runs 7 days, with no credit card required, so this plan maps onto it day for day. Here’s more on what’s worth testing in a LeanLaw trial. Whichever tools make your shortlist for the best legal billing software for small firms, run each one through the same seven days and the same scorecard, so the decision compares like with like.