Documents at Scale

Template

A document kept only to be copied, with fixed text, styles that set its look, and fields where each client’s details go. In Word it is saved as a template file (.dotx), and each use starts a new document from it, leaving the template unchanged. A firm that uses its last letter as a form copies the last client’s details, and whatever else that file carries, into the next one.

Mail Merge

Word’s way of producing one document for each row of a data source, such as an Excel sheet whose first row names the columns. Merge fields pull each row’s values into the main document, and a rule (If…Then…Else) includes text only when a value calls for it. Word merges an Excel amount as the number Excel stores, so $2,500.00 can arrive as 2500 unless the field is formatted.

Document Assembly

Software that builds documents from answers to an interview instead of rows in a table. The answers choose which clauses appear as well as filling in names and numbers, and one set of answers can produce several related documents. A mail merge fills blanks, while assembly also decides which paragraphs belong, so an error in its rules repeats in every document it builds.

Electronic Signature

Florida’s Uniform Electronic Transaction Act, section 668.50, Florida Statutes, defines it as an electronic sound, symbol, or process attached to or logically associated with a record and adopted with the intent to sign. Where a law requires a signature, an electronic one satisfies it, but the act applies only between parties who agreed to do business electronically, which their conduct can show. It does not govern the signing of wills, codicils, or testamentary trusts.

Attribution

Under section 668.50(9), an electronic signature is attributable to a person if it was that person’s act, shown in any manner, including by the efficacy of a security procedure. E-signature services record the evidence in an audit trail: the address the request went to, when it was opened and signed, and the signer’s IP address. The trail shows which account signed; whether the right person controlled that account is a question of fact.

E-SIGN Act

E-SIGN, the federal Electronic Signatures in Global and National Commerce Act, bars denying legal effect to a signature, contract, or record in interstate commerce solely because it is electronic (15 U.S.C. § 7001). When a law requires that a consumer receive information in writing, an electronic copy counts only if the consumer consented after specific disclosures. A state that enacts the uniform act may modify or supersede section 7001 for matters of state law (15 U.S.C. § 7002), and Florida’s version is section 668.50.

Remote Online Notarization

Chapter 117, part II, Florida Statutes, lets a notary registered with the Department of State notarize over live audio and video, wherever the signer is. The notary confirms identity by personal knowledge or by a government ID checked through credential analysis and identity proofing, and the session’s recording must be kept at least ten years. For a will and certain other estate documents witnessed remotely, section 117.285 adds screening questions, and remote witnessing does not count for a signer who is a vulnerable adult.

Metadata

Data a file keeps about itself: its author and company, tracked changes, reviewers’ comments, and text formatted as hidden. Under Florida Bar Ethics Opinion 06-2, a lawyer sending an electronic document must take reasonable steps to protect the confidential information in its metadata. A lawyer who receives one should not mine it for what the sender did not intend to send, and one who comes across such information must promptly notify the sender.

Part 1: Read What the Old Letter Carries

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, September 16, 2026. Marcy is out this week, so the new engagement letters are yours. Since March we have made every one by opening Howard Ashdown’s letter and typing over it, and I want that to stop. Build us a real template from it, keep our terms as they are, and run it against the New Matters sheet. No letter goes to anyone whose conflict check hasn’t cleared. Send one of them out for electronic signature so we can see how it works, and tell me in writing why a signature that way holds up. And before anything leaves this office, make sure it isn’t carrying Howard’s business with it.

Download the letter and the workbook, read the workbook’s Start Here sheet, and open a copy of the letter in desktop Word. Before you change anything, find everything the file carries. Show all markup on the Review tab and read every comment and tracked change. Then run the Document Inspector (File > Info > Check for Issues > Inspect Document) and read its report without removing anything, and open the file’s properties, including the Custom tab. Look at the letter itself too, because the inspector does not find everything. For each item, fill in columns B and C of the Metadata Log: what it says, whose information it is, and whether a new client would see it. The Document Inspector runs in Word for Windows; on a Mac, check the properties and the Review tab by hand, and say so in the log.

Part 2: Build the Template

Now take the letter apart. Remove everything the Metadata Log says belongs to Howard Ashdown or to the firm’s private notes. Read what each tracked change and comment means for the terms before you delete it, because the firm’s terms stay as they are. Connect the letter to the New Matters sheet (Mailings > Select Recipients > Use an Existing List), then run the Merge Field Planner on the cleaned text. Replace each client-specific passage with its merge field, and rewrite anything that assumes Dana Whitfield is the lawyer, since Luis Ortega signs two of these letters. The deposit paragraph is the hard one. Anne Pruitt Lowry owes no deposit, so use a rule (Mailings > Rules > If…Then…Else) to write that paragraph one way when the Deposit column is empty and another when it holds an amount. To put a merge field inside a rule’s text, show the field codes (Alt+F9). Save the result as a Word template (.dotx), and fill in column D of the Metadata Log.

Part 3: Merge the Letters

One row on the New Matters sheet has no cleared conflict check. Leave it out in Edit Recipient List rather than deleting it from the sheet. Preview every letter before you finish, and read each one as its client would: every name, greeting, and amount. If an amount comes through as 2500, format the merge field with a numeric picture switch, as Microsoft’s page on currency fields shows, instead of typing over the merged letter. Finish the merge and save the three letters as PDFs, one file per client. Word can copy a document’s properties into a PDF, so check the options when you save. Last, run the Document Inspector on your template and on one merged letter, open one PDF’s document properties, and fill in column E of the Metadata Log and its row for the signed PDF.

Part 4: Send One for Signature

Choose one of the three letters and send it for signature through the service in Resources, or another that gives you an audit trail. You are sending for the firm, and the signer is the client. Send the request to a second email address of your own, never a real client’s, and sign it there as the client. If you choose the Brandts’ letter, add both of them as signers. Download the signed letter and its audit trail or certificate, and fill in part A of the Signature Record from them. Then write answer 1, Dana’s question: why does this signature bind? Run the Signature Challenge with your audit trail and the statute’s text, answer the lawyer it plays, and write answer 2 from what the challenge showed you.

A note from Luis Ortega. Anne Pruitt Lowry asked me today whether, once her will is drafted, she can sign it online the way clients sign our engagement letters now, from her kitchen table. Find out what Florida law requires and write it up for me. I’ll talk to her.

Read sections 732.522 and 117.285, Florida Statutes, on the Legislature’s site, and run the Signing Rules Checker with their text. Check every answer it gives against the statutes, then write answer 3 on the Signature Record in your own words.

Part 5: Post Your Deliverables

Create one new discussion thread. Attach the letter set: your template (.dotx), the three merged letters as PDFs, and the signed letter with its audit trail or certificate. Attach the documents workbook with the Metadata Log and the Signature Record filled in. Add three to four sentences naming the item in Howard Ashdown’s letter that would have done the most harm if it had gone out with the new letters, and why.

Part 6: 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.

Merge Field Planner

Asking for a table breaks the letter into decisions you can check one at a time, and forbidding new columns keeps the model inside the data the firm actually has. Where it flags text that no column covers, the choice between adding a column and rewriting the sentence is yours.

Signature Challenge

Red-teaming turns the model against your conclusion, which tests it harder than a friendly review would. Because it may rely only on the audit trail and the statute you paste, every weakness it finds is one you can check for yourself.

Signing Rules Checker

Source grounding holds the model to the statutes you paste, and the quotation it must give for each answer is what lets you check it. A model answering from memory can borrow another state’s rules for wills, and a missing quotation is a sign that it has.