For lawyers, document drafting is a demanding and time-intensive part of the job. The constant pressure for high-quality legal documents in short time frames, especially for a high-volume practice, can be overwhelming. Fortunately, modern attorneys have access to a new way of dealing with this pressure that past generations did not: Word add-ins that assist lawyers with document drafting.

A Word add-in is essentially any program that can be attached to Microsoft Word to give it additional functions. Some of the more common examples of add-ins are macros, toolbars and shortcut menus. 

A major advantage of Word add-ins is that they can automate repetitive tasks for certain commonly used documents. They can also help bring the different components of a document together. And they can allow the user to look up data in internal reference systems, saving her the trouble of opening new apps and performing the copy-and-paste routine. For attorneys trying to maximize productivity while drafting complex documents, these functions can be critical.

As for legal document drafting in Word, an add-in has the advantage of being distributable and shareable throughout the firm, and easily activated whenever Word is opened. The add-ins are also seamless to the user, since they are often part of a tab, task panel, or drop-down menu. This makes the technology more accessible, in both perception and reality, to less tech-savvy attorneys who may be intimidated by having to open another document or program (yes, looking at you, the one who thought an add-in was a calculator function).

And there’s the final added benefit of being able to recover the lost productivity time when toggling between applications. In fact, according to psychologist Gerald Weinberg, every time you switch a task or ‘context’ you adversely affect productivity:

• Focusing on one task at a time = 100% of your productive time available

• Juggling between two tasks at a time = 20% lost to context switching

• Task switching between three tasks at a time = 40% lost to context switching

Here are our recommendations for Word add-ins specifically made for attorney document drafting … tools that every lawyer should know. There’s even a “bonus” recommendation (spoiler alert: it’s us) to round out our list.

1. WordRake

WordRake is an antidote to the all-too-lawyerly trait of writing in language that is overly flowery and difficult to understand. This add-in tightens up your writing by editing for brevity and clarity. The user simply clicks the “Rake” icon on their toolbar, and the program “rakes” the document by suggesting revisions within seconds, which the user can either accept or reject. 

WordRake does not edit grammar or spelling, since Word already has those functions without any add-ins. Instead, the software edits unnecessary words and phrases, making the writing more concise and direct. For example, “we stand in agreement” could be edited to “we agree,” or “the purpose of my letter is to explain” revised to “my letter explains.”

Company founder Gary Kinder, a best-selling author and writing instructor with a law degree, came up with the idea after teaching over a thousand writing programs to lawyers nationwide. Kinder noticed a pattern of signs that showed up in meaningless or dull writing. He worked with software engineers to incorporate those signs and patterns into algorithms, and WordRake was born. The company holds multiple patents on computerized editing. 

Customers can choose from long-term subscriptions of either one year or three years, with a one-year rate of $129 as of this writing. Various volume discounts are also available, with up to 50% off for 1,500-plus orders. And for those who seek email editing, WordRake also offers Outlook add-ins, along with package prices for Word and Outlook combined. 

2. Donna

Donna is a Word add-in designed for contract drafting. It works by identifying and correcting common contract mistakes, focusing on the following contract elements: 

• Definitions: Donna checks for undefined terms and duplicate definitions, also suggesting defined terms when necessary. The user can quickly review if definitions are used consistently and without ambiguity.

• References: The add-in identifies broken and missing cross-references, which is usually an onerous task for lengthy contracts. And Donna streamlines the insertion of cross-references, another cumbersome Word process without add-ins.

• Other Contract Details: Donna checks for issues with formatting and punctuation, as well as small and easy-to-miss details like dates and money amounts. It also highlights placeholders, helping attorneys and legal staff to avoid template mistakes.

For all these benefits, the pricing for Donna is fairly affordable. After a 14-day free trial, a solo user can subscribe for $25 per month, and teams can sign up for a monthly rate of $35 per user.

3. Loio

Another Word add-in for contract drafting, Loio bills itself as a legal document analysis and editing tool. In simplifying and speeding up contract review, Loio uses these three primary approaches:

• Highlights: The Highlights tool scans the contract for key details, such as parties, dates, places, and money amounts, allowing the user to check these details and offering suggested revisions.

• Styling: Loio’s Styling tool can review and edit the contract formatting in seconds. It identifies all styles used in the text and allows the user to re-format styles as necessary, which can be especially useful to fix formatting in documents drafted by the other party.

• Numbering: The Numbering tool deals with another common headache in contract review: numbered lists. Besides checking and fixing numbering issues, the tool also marks all internal references - references to clauses within the same contract - to allow for double-checking.

Loio offers a free thirty-day trial and a standard annual subscription for $199 per year. This package includes 24/7 support to resolve any issue.

4. DocStyle

Just as its name suggests, DocStyle empowers users to manage styles and formatting in Word documents. This add-in focuses on two main objectives: (1) converting PDF files to Word documents, and (2) fixing formatting and style issues in existing Word documents.

Specifically designed for legal documents, the PDF conversion aspect of DocStyle tackles all the common challenges of PDF-Word conversions. It can regenerate tables of contents and footnotes, and even insert a PDF page into a Word document. This streamlines a process that can otherwise take hours or days to complete.

For both Word and PDF files, DocStyle will analyze the document, determine proper formatting, and structure a clean document. The functions tackle some of the common hassles in Word formatting, such as numbering, section breaks, headers and footers.

After a free 14-day trial, users can subscribe to DocStyle for low monthly amounts: $29 per user for the standard edition, $39 per user for the enterprise edition.

Bonus Recommendation: Woodpecker

Sure, it’s our blog, but we would be remiss not to mention the advantages of the Word add-in offered by Woodpecker. (Plus, we told you this was coming!) Woodpecker users can create and store templates for many types of common legal documents, such as pleadings, retainer agreements, non-disclosure agreements, written discovery and more.

The add-in automates the document preparation process, and information for documents can be captured through web-based questionnaires, which can be used externally for client intake forms or for internal data entry purposes. 

All of these add-ins fulfill the ultimate purpose of automating and streamlining of document drafting. Using automation for generating documents is especially critical for lawyers, where even minor document mistakes can have major consequences and client expectations for quality are high. And by being able to use the automation directly in Word, attorneys are able to better maintain uninterrupted focus and concentration, resulting in a higher quality work product.

Mike Robinson is a freelance B2B copywriter specializing in the health tech, fin tech and legal tech industries. After a sixteen-year legal career in business and healthcare finance litigation, he now crafts compelling content for professionals in these verticals to help them better understand the options for technical tools that can move their business forward.