Choosing Legal Tech

Needs Assessment

The written account of what the firm needs a tool to do, gathered from the people who will use it before anyone looks at products. Each requirement names a task and who needs it, such as reconciling the trust account each month, never a product or a feature label from a vendor’s page. Must-haves are the requirements a tool cannot fail; nice-to-haves only add to its score.

Evaluation Rubric

A fixed set of criteria, each with a weight, against which every candidate is scored on the evidence. The firm sets the weights before anyone watches a demo, so a smooth presentation cannot change what matters, and a tool that fails a must-have is out whatever its total. A score is only as good as its source: a feature seen working in a trial counts for more than a claim on a marketing page.

Vendor Due Diligence

The research a lawyer must do before trusting a provider with client information. Florida Bar Ethics Opinion 12-3 asks whether the provider is bound to keep the data confidential and to report a subpoena, and how it protects and recovers the data. It also asks what the agreement says about the forum for disputes, the limits on the provider’s liability, and the firm’s access to its data once the relationship ends.

Technology Competence

Rule 4-1.1 requires competent representation, and its comment says that staying competent includes understanding the benefits and risks of technology, including generative AI. The comment adds that competent representation may involve retaining a nonlawyer advisor of established technological competence. Rule 6-10.3(b) gives the duty a number: 3 of the 30 continuing legal education hours a Florida lawyer must complete every three years must be in approved technology courses.

Data Portability

Whether the firm can get its own records out of a tool, complete and in a form another program can read, both while it subscribes and after it leaves. Some records must outlast any vendor: Rule 5-1.2(f) requires trust records to be kept for six years after each representation ends, and Opinion 06-1 advises that files kept electronically must stay readily reproducible. An exit plan says what comes out, in what format, who pulls it, and what the vendor does with the rest.

Total Cost of Ownership

Everything a tool costs the firm in its first year, not only the price per user. It adds the plan that actually covers the must-haves, the add-ons, setup and migration fees, any payment processing, and the hours people spend moving records and learning the tool. A price page often quotes the annual rate, so the budget states the plan, the billing term, and the number of seats with every figure.

Implementation and Training

The work of putting a chosen tool into use: moving the records, setting who may see and change what, training each person on the tasks that person does, and deciding when the old way stops. A plan names a go-live date, a period when the old and new records run side by side, and who answers questions afterward. Rule 4-5.3(b) has the partners make reasonable efforts to put measures in place that keep the staff’s conduct within the lawyers’ duties, which is hard to do with a tool the partners never learned.

Generative AI Features

Features that draft, summarize, or answer questions from what a user puts in, now built into many legal products. Florida Bar Ethics Opinion 24-1 lets lawyers use them while protecting client confidences, which starts with researching the program’s policies on data retention, data sharing, and self-learning. It recommends the client’s informed consent before confidential information goes into a third-party program, and it has lawyers develop policies and practices so the use meets their ethical duties.

Part 1: Read the Firm’s Needs

Temko & Eden, P.A. A three-lawyer firm on Beach Street in Daytona Beach. It still carries the names of its late founders. Dana Whitfield, the managing partner, handles civil litigation and real estate closings. Luis Ortega, a partner, handles family law and probate, and Kim Nguyen, an associate, handles personal injury. Marcy Cole is the legal assistant, Ron Pike is the bookkeeper and office manager, and you are the firm’s paralegal.

An email from Dana Whitfield, Monday, October 5, 2026. The partners have agreed to pay for one technology change next year, and we’ll pick it at our November meeting. Two parts of this office run on workarounds. Ron keeps the trust records in a spreadsheet because our practice management system can’t, and that system’s contract ends December 31. Marcy has been sending engagement letters from a free e-signature account in her own name. Take one of the two. Compare two real products, recommend one, and tell me what the first year costs, what could happen to our clients’ information, and how we’d get our records back if we ever left. Everyone’s notes and the budgets are in the workbook. Don’t let a demo make this decision for us.

Download the evaluation workbook and read its Start Here and Firm Profile sheets. Choose billing and trust accounting or electronic signatures, and enter your choice on the Requirements sheet. Then turn the notes for that function into requirements. Some notes name a product or a wish instead of a need; write down the task underneath it. Add anything the rules in Resources require that no one at the firm mentioned. Mark each requirement Must-have or Nice-to-have, and run the Requirements Interviewer on the ones you are unsure about.

Part 2: Weigh Before You Look

Pick two real products for your function. Resources lists some with a free trial or a free plan, and you may choose others that offer a trial, a free plan, or enough public documentation to judge them. Before you open either one, set the weights on the Scorecard so they total 100, and record the date. A weight set after a demo can be bent to fit the tool you liked. Then run the Trial Script Builder to turn your must-haves into tasks you will try in each trial, each with what counts as passing.

Part 3: Read What the Vendor Promises

Work through the Security Review for both tools. Start from each vendor’s security or trust page, then read its terms of service, privacy policy, and help articles. For every answer, record the page and whether it binds the vendor; a promise on a security page is marketing until the agreement repeats it. Opinions 12-3 and 24-1 explain why each question is on the sheet. For the breach record, search the California Attorney General’s list under the vendor’s name and its parent company’s, then search the news. The Security Page Reader can check your reading of a long page, but find each quotation it gives you on the page itself before you rely on it.

Part 4: Try Both Tools

Run your trial script in each tool, with made-up names and figures only, never a real person’s information. If a trial asks for a credit card, skip it, score that tool from its documentation and the vendor’s own demo videos, and say so in your evidence. Fill in the Met columns on the Requirements sheet as you go. Try the export too: pull out whatever the trial allows and open it in Excel or a PDF reader. Then score both tools on the Scorecard, with the evidence for each score.

Part 5: Price the Year and Plan the Exit

Fill in the Cost sheet for the plan each tool needs to meet your must-haves, which may not be the cheapest plan on the page. Count seats by who needs to sign in, check whether the price assumes annual billing, and look for any add-on a must-have depends on. The Bar’s member benefits page shows discounts the firm’s lawyers can claim. Then answer the Exit Plan for both tools from their help articles, their terms, and your test export. The rules in Resources say which records must outlast the tool, and for how long.

Part 6: Write the Recommendation

Write Dana a memo of 800 to 1,200 words that recommends one tool. Open with the recommendation and the criterion that decided it. Then give the first-year budget, what the security review found, and the questions still open for the vendor. Add the exit plan, and a training plan that names who learns what and by when, lawyers included, with a go-live date. Write one paragraph of policy on the tool’s AI features: which ones staff may use, with what information, who checks the output, and when a client must agree first. Then paste the memo and your Scorecard into the Counter-Recommendation. End the memo with a short section that states the strongest point it made and answers it, or change your recommendation if you cannot.

Part 7: Post Your Deliverables

Create one new discussion thread with a headline-style subject line that names the tool you recommend. Attach the workbook with every sheet filled in, and the memo as a PDF or Word file. In the post itself, write two or three sentences on the requirement that did the most to separate the two tools.

Part 8: Share Chat Link

Include one AI chat link with a 1–2 sentence explanation of what the conversation shows and why you chose to share it.

Requirements Interviewer

Socratic elicitation makes you defend each requirement instead of accepting a list the model wrote for you. The rule that the model may ask about the Bar’s rules but not state them keeps the legal answers in the rule text, where you can check them.

Trial Script Builder

Breaking each requirement into a task with a pass condition is decomposition, and it turns a trial from a tour into a test. The model does not know how these products work, so try each step in the tool before you trust the script.

Security Page Reader

Grounding the answer in pasted text, with a quotation, makes every claim checkable, and the instruction against filling gaps keeps the model from supplying a promise the vendor never made. Find each quotation on the page yourself before you record it, because a model can change wording while it quotes.

Counter-Recommendation

Red-teaming asks the model to attack your conclusion, which brings out weaknesses a request for feedback tends to smooth over. Holding it to your own materials means every objection is one you can test against your evidence.