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DIY Legal Tech: Do More, Work Less

Using document automation to speed up much of the routine work of lawyering

In the average solo or small firm, 40 percent of the hours that lawyers work aren’t billed. You can buy yourself extra time by automating documents used regularly in your practice—on your own or with the help of software packages. But don’t underestimate the commitment of time it will take to get started. Here’s how.

0916-DYI-Legal-TechAt the end of the day, are you left with that nagging feeling that you are not quite as efficient or profitable as you could be? If so, you are not alone; data shows that for the average small law firm, 40 percent of the hours worked are not billed.1 Look, the problem isn’t that you’re not a great lawyer (you are), the problem is that over the course of a week, you’ve spent two days not being a lawyer. So if you’d like to add another day (or two) to your work week, you need to offload those non-lawyer things you are currently doing.

Not surprisingly, there’s technology that can help. And given that paperwork seems to be an integral part of every lawyer’s life, reducing the time spent creating and managing documents seems like a good way to start to reclaim some of that 40 percent. The options range from virtual typists to document assembly software and document management systems with price tags running from free to thousands of dollars. There are cloud-based solutions, desktop applications, server-based systems, and application plug-ins. There’s even some robust, mature open-source software available.

What you’ll find here are some simple time-saving approaches to document creation and management. All are based on things I’ve tried in my own practice—some with more success than others, but all can be easily and (relatively) inexpensively implemented by even a solo practitioner.


The first step toward more efficient document creation is to stop spending your time typing. The fact of the matter is, unless you are an extraordinary typist, you can talk faster than you can type; the generally accepted (and most likely apocryphal) statistics say that speaking is seven times faster than writing long hand and four times faster than typing. So, to paraphrase the productivity consultant David Allen, if you want to move information out of your head and transform it into something usable,2 learn to use dictation and offload the typing onto someone else.

Now, don’t think that dictation is just about producing documents faster. Unless your practice is radically different from mine, there is a whole world of administrative typing occupying that non-billable 40 percent of your day—stuff like calendar entries, case notes, time entry, and contact information. All of which can be dictated. Think of it this way: Dictation is simply a structured way to ask someone to enter keystrokes for you so you can spend more of your time doing billable work or even (dare I say it) head home a little early.

The good news is that, once you get over being self-conscious about talking your writing, it’s not hard to learn to dictate; it just takes practice and organization. Don’t try to speak off the cuff; take some time to pull your thoughts together and to create an outline. Once you start to dictate, wait a couple of seconds before speaking and be sure to start with a description of just what it is you are dictating (a letter, a memo, time keeping notes, etc). Once you are done, wait a couple of seconds before hitting the stop switch. Having a little dead time at the beginning and end of each dictation will help your typist cue everything up as well as ensure that your words aren’t accidentally cut off.

Be sure to speak clearly and to enunciate (as well as spell) any name, unfamiliar words, or terms of art; the best practice is to say the word, spell the word, and then say the word again, being careful to clearly articulate (or use the phonetic alphabet equivalent) letters that sound similar such as ‘m’ and ‘n’ or ‘b’ and ‘p’. You will want to speak your punctuation and your formatting rather than relying on someone to interpret that pause in your words as a comma, a period, a new paragraph, or simply a moment when your brain left the room.

So, for instance, to dictate a letter to a client, you would say:

Start a letter, Dear Jim Smith comma new paragraph I am enclosing the documents you requested period If you have any questions comma please call me period sign as cordially Bob Jones end letter

While dictation used to require expensive recorders and transcription machines, these days there’s an app for that. For around $20, you can buy an app that will turn your smartphone into a full-function digital recorder. Unlike voice recognition and voice-based note-taking apps, digital dictation apps won’t scan your files for content or send your data to a remote server for processing. When it comes to dictation apps, my first recommendation would be “Dictate + Connect”; this app will not only turn your smartphone (iPhone, iPad, or Android) into a full-featured digital recorder, but can also encrypt your recorded files and securely transfer them to your transcriptionist. Other options are: Dictadroid (for Android systems) and PocketDictate (for IOS).

Notes from the Field: I use a virtual typist service for my dictation. Because my need for a transcriptionist is not consistent, using a virtual service allows me to avoid adding a staff position. And because the service guarantees a turn-around time, there is the added benefit of knowing that my documents will be ready when I need them without the worry that a staffer might be out sick when a deadline approaches. There are a number of such services out there, including LegalTypist, Virtual Gal Friday, and The Virtual Paralegal.3  While setup fees vary widely, transcriptionist services typically run about $0.75 per minute (a 10-minute minimum is common), so a one-page paper will cost about $7.50 while a 10-page contract may be on the order of $20. While my needs are relatively simple, these services can act as a personal assistant and, in some cases, a business consultant; expect to pay $45 – $150 per hour for these additional services.

While there were a few initial issues in transferring my voice files to the service (I had failed to read the instructions carefully enough and had saved my files in the wrong format), the only real hurdle to implementation was learning to have the discipline to talk when what I really wanted to do was type.


Document automation is simply a system that takes pre-existing segments of text and assembles a new document from them. The assembly process is governed by a set of pre-determined rules and variables, and the final document is the result of parsing the rule tree. Now, if all the documents you produce are completely unique, then document automation is not for you; the underlying assumption of any document automation system is that at least some of your documents will reuse pre-existing text.

Let’s say you want to draft a will. It’s unlikely you’ll start from a blank piece of paper; you’ll probably use some base document (a previous will, a form-bank will, etc.) and proceed to modify that base document until it suits your needs. Over the course of time, your base document will come to include a number of optional paragraphs, clauses, sentences, etc. each blocked out from the others by some sort of tag that tells you when to include or exclude that particular block of text. There will be blank spaces to indicate places where you need to supply additional information.

Eventually, writing a will becomes an exercise in cutting and pasting blocks of text into and out of your base document based on your knowledge of the matter (your rule tree) and filling in the blanks where necessary (variables). At this point, you’ve created a simple, though somewhat labor-intensive, document automation system.

The problem with this form of document automation is that it relies on us somewhat-less-than-infallible humans to preserve the base document as inviolate and to catch and correct errors during the modification process.

The first flaw inherent to this type of system is often called a “Save As” error, since there is the possibility that the base document could be overwritten (and thereby lost) should someone forget to use “Save As” (or create a copy of the base document) the first time they create a new document from the base document. While making the base document read-only can address this particular error, a read-only base document is a static entity and becomes difficult to modify should changes in the law require changes in the base document’s clauses. (This leads to a versioning problem: If you create a new read-only base document, you then have to make sure that everyone who might use the base document uses the correct base document.)

The second flaw, the cut-and-paste error, is the more dangerous of the two. While overwriting your base document will result in a few hours of annoyance as you retrieve a copy from your backup, a bad job of cut-and-paste (or its evil twin, search-and-replace) can lead to serious embarrassment or even malpractice. The fact that your base document will contain stuff that has to be removed leads to the risk of accidentally removing too much (or not enough), so that you may end up referring to per stirpes inheritance in one paragraph and per capita in another. Add to this the fact that you have to make sure pronouns match genders, verb tenses are correct, and all the rest of those pesky grammatical rules are met, and it becomes fairly easy to see that avoiding these problems might make for happier clients.

The solution is document assembly software. These software products start from the same place you do, a database (or base document) containing all the textual elements of a document, a template of what the final document should look like, and a set of rules for everything from selecting the correct text to matching pronouns and plurals. The systems even maintain a set of variables so that matter-specific information (client name, gender, address, etc.) can be tracked and correctly applied. The beauty of these systems is that once the initial setup is complete (base documents created, rules set, etc.), the systems are simple to use. Most are based on a question-and-answer format, and there is a dramatic time savings to be had. In fact, a recent study shows that document automation can reduce the time it takes to get to a first draft of a document by up to 75 percent.4

Where to Start Automating

No matter what approach you take, all document automation starts with the same initial steps: identifying the documents you want to automate and creating clean, up-to-date digital templates. The typical approach is to take a look at all the documents your practice generates and group them by their frequency of use. You don’t have to be terribly exacting; four groups (“used daily,” “used weekly,” “used monthly,” and “special occasions”) are generally sufficient. You’ll use these groupings as a way to determine which files you’ll be automating first (hint: it’s those in the “used daily” pile) and which will bring up the rear (those “special occasion” documents).

Once you know which documents you need to automate, it is time to clean them up. Take a close, critical look at them: Can you make the language more precise? Can you tighten things up? How’s the spelling, punctuation, and grammar? Do they comply with current law?  Is the formatting clean and legible? Is all the information in them accurate? (Be sure to check your contact information; it’s easy to overlook the simple stuff.) And are they the best possible examples of your work?  Once you have a set of clean, up-to-date, perfect forms, save them to a directory as templates5 and you’ll be ready to start digging into the technology.

Use What You Have

The least expensive way to get into document automation is to leverage the features built into your word processor. When it comes to supporting document automation, Word is the word. Now, you may have good reasons for not using Word, but when it comes to hacking together a little DIY document automation, Word stands above the pack.

The place to start is with Word’s AutoCorrect (by the way, any word processor spell-checker can do this trick). AutoCorrect is normally used to find and correct common misspellings and simple typographical errors, but it can be taught to expand a nonsense word (like QED) into a phrase (like quod erat demonstrandum). The key here is to be sure your nonsense words follow a deliberate pattern and are unlikely to be used accidentally. The best practice is to limit the use of this hack to simple pieces of text like your attorney number (“myatno” correcting to “Attorney No.: 0000000”), common court districts (“dcrt1” correcting to “First Judicial District”), and the like.

From here, you can branch out into using Quick Parts6 (which has been renamed AutoText in newer versions of Word). For those of you who’ve never explored Word beyond the Home menu, there is a world of useful stuff already built in, and Quick Parts is a little gem sitting on the Insert Menu.

Quick Parts is just what its name indicates, a library of pre-built text segments. While the out-of-the-box Quick Parts is fairly limited (featuring simple, general purpose business phrases), there is nothing to keep you from adding to the library. Again, it is best to use some restraint when adding to your Quick Parts library: The best practice is to limit yourself to blocks of text that won’t require additional editing in order to fit into your document. A notary block, a severability clause, or a signature block would make ideal additions to a Quick Parts library, but remember to avoid using pronouns or making reference to gender or other parts of a document (such as a specific numbering scheme), etc. When it comes to Quick Parts, the more generic the better.


The next step up in performance is to use a document assembly plug-in for Word like Pathagoras or The Form Tool.7 The good news is that these plug-ins offer about 90 percent of the functionality of a desktop document assembly application at substantially less cost. The bad news is that these plug-ins only work with the desktop versions of Word running on Windows,8 so if you are using Word on Macs—or Office 365—this option won’t work for you.

Both plug-ins install as Word toolbars and allow you to turn your standard forms into automated documents without programming experience. Even though both offer the advanced user powerful options (like stored clauses, drop-down lists, conditional assembly, math functions, and metadata removal), the novice user can create useful automated templates in under an hour with either tool. The chief distinction between these two is that Pathagoras has a slightly shorter learning curve (if you can place square brackets around a word, you have all the skill necessary to create a basic document with this plug-in) than The Form Tool. On the other hand, The Form Tool offers a more graphical user interface, which tracks the data that went into creating the document from the template (this is useful in tracking data entry errors when proofreading).

The downside to these plug-ins is that the creation aspect and the document generation aspect are one and the same; neither offer a “player” type application, so anyone needing to produce documents from automated templates needs to have a licensed copy of the complete plug-in added to their copy of Word. This makes it difficult to share automated forms with others outside of your practice. Distributing your templates is not the issue (they are Word documents after all), but you can’t share the automation that makes these forms valuable.


For those who need the very best, stand-alone applications are the gold standard for document assembly. Based on its market share, highly developed ecosystem, active user community, available knowledge base, and extensive consultant community, the reigning king of standalone document assembly software is HotDocs (an MSBA partner who powers the association’s mndocs doc assembly system), but there are other contenders worthy of consideration, such as: RapidDocs, GhostFill, SmoothDocs, Exari DocGen, ContractExpress, XpressDox, TextPlan, and ProDoc.9 System choice often comes down to a decision between going the DIY route or buying a turn-key library of pre-fab automated forms.

These systems all operate in a similar fashion. The document to be automated is turned into a template10 complete with variables, conditionals, formulas, and some programming logic. A questionnaire is associated with the template, and when all the questions have been answered, the template and the answers are merged together to create a completed document.

The chief advantage of the DIY route is its flexibility. You have complete control over the entire process from content creation to document formatting and, for simple documents, template and questionnaire creation is not all that complex. Most systems provide tutorials that should get you to the point where you can start implementing basic documents in a few hours. The problem is that the time commitment (learning and implementing) grows as the documents become more complex. On the other hand, what turn-key systems may lack in customization, they more than make up for it in time savings, since they are ready to go from the moment they hit your desktop.

The reality is that adoption of document assembly systems tends to be a short-term affair and it tends to follow a fairly specific pattern regardless of the approach chosen (be it using Quick Parts, a Word plug-in, or a desktop application). There will be some initial success as you work through a few tutorials and create a few basic documents. Then the demands of the practice will begin to impinge on your schedule and, despite your good intentions, the conversion to automated forms get pushed to the back burner, where progress slows, dwindles, and dies.

It is best to remember that document assembly systems require regular care and feeding. You’ll have to commit to really learning the system, which means reading all the tutorials and doing all the exercises (even the blazingly obvious ones). When you know how things work, you have to commit to developing your automated templates, so be prepared to block out the time you need to churn out a new form on a regular schedule (perhaps you can take a page from the NaNoWriMo folks and dedicate 30 days to churning out an initial form set). Then, once you have your forms, commit to using them. Set a cut-over date and commit to using only your automated forms from that point forward.

Finally, remember that it will take a bit of thinking to get everything integrated and running smoothly and, unless you are using a turn-key set of forms, it’s more than likely your first attempts are not going to work the way you want—so give yourself permission to throw them away. Just be sure to take notes as you go so you can learn from your mistakes.

Notes from the Field: In my practice, I use The Form Tool/Doxsera as my principle document assembly platform and have found that, with a little practice, creating a single automated document does not take much time. But creating a useful, functional set of documents takes a significant amount of planning and preparation, and it is really important to have those clean, up-to-date templates in place before you start automating: It’s far easier to proofread a document before it is marked up for automation than afterwards.

I have also found it helpful to decide on and stick with a common naming convention. By using the same names in all my documents, I know that information in one will be carried across to the others when groups of documents are assembled simultaneously. Experience has taught me to use the planning stage to look for blocks of text, such as notary blocks, that are common to multiple documents. These can be stored in their own template, automated once, and then included by reference in an entire set of documents (Doxsera will automatically insert the appropriate text wherever it is referenced). It is far less time-consuming to automate these common bits of text this way than to automate them separately in each individual document. (I should note that it’s taken me a half-dozen false starts and the investment of a couple dozen hours for these lessons to sink in.)

Finally, please be aware that no matter how good your starting documents are, you should never assume that what comes out of a document assembly system is a final draft. At best, the assembled document is a remarkably good first draft. At worst it can be an unreadable mess (remember the old computer adage: garbage in, garbage out). The reality is that because every matter is unique, it is inevitable that your assembled documents will need a little tweaking. The power of document assembly lies in the fact that you can get to that 99 percent-correct first draft in a matter of minutes rather than hours.


If you’re like me, your document management strategy most likely uses a BOF (bunch of folders) scheme. There will be a set of top level folders (Forms, Clients, Business, etc.), then a set of subfolders (Forms/Estate, Forms/Divorce, Clients/Smith, Clients/Jones, etc.), then a set of sub-subfolders (Clients/Smith/Estate, Clients/Smith/Divorce, etc.), then a set of sub-sub-subfolders (Clients/Smith/Estate/Letters, Clients/Smith/Estate/Documents, etc.) which is all well and good as long as everybody knows the system, knows the distinction between Letters and Documents, and uses the system in precisely the same way.

Then comes the day when someone forgets or simply finds that the system just doesn’t work for them, so they make a few tweaks and now you have two document management strategies to contend with. Which means finding the Judgment and Decree for the Rodgers divorce just got a bit more complicated (unless of course your new helper is out sick; then things get really interesting).

Fortunately, there is a simple solution. With a document management system, you can store, track, and manage your documents electronically without relying on those fallible humans in your office to remember where they filed the most
recent version of your retainer agreement, or if the Rodgers’ Judgment and Decree was filed under Motions, Documents, or ThankGodItsOver.

In its most basic form, a document management system simply stores and organizes documents. It allows users to check documents in and out of the system, provides version control (so that there is a trail tracking the changes made to each document from its first instantiation to its present form), provides an audit trail (showing who did what to the document over the course of the document’s life, from creation to deletion), and allows all the documents to be searched using a wide variety of criteria (author, creation date, tags, name, text, etc.).

Document management systems will vary in size, feature set, and content support. They run the gamut from small desktop solutions to enterprise-wide behemoths and can be found as server-based systems or cloud-based apps. They may support almost any type of document (from digital images to voice recordings to plain text documents), or they may be limited to a few common word processing formats. Given the great variation in cost and feature sets, it is important to determine your needs before running out to buy a system. Will you need it to integrate with your current practice management system or your customer relations management system? Do you need to learn Boolean search capabilities? Do you want to have document approval workflows? Do you need any advanced features like document encryption, access control, or storage control?

The leading legal document management system is Worldox, but there are a number of other options out there, including: NetDocuments, OpenText, Smokeball, and eFileCabinet.11 For the adventurous, there are a couple of free open-source document systems (OpenDocMan and OpenKM)12 out there as well. Both offer similar feature sets and both are supported by fairly active user communities.

Notes from the Field: In my practice, I use OpenKM as my document management system. Since my needs did not warrant the power or the expense of a commercial system, I was willing to take a chance on an open-source product. Prior to choosing OpenKM, I installed and tested both OpenDocMan and OpenKM, storing, editing, and deleting about a dozen files in each system. While I found OpenDocMan’s interface was a bit more intuitive (you can be moderately productive even if you only skim the quick start guide), OpenKM was far easier to install and far simpler to update and maintain.

Transitioning to a document management system brought with it the realization that I (a) keep way too many out-of-date documents and (b) have way too many copies of the same document. It also offered an excellent opportunity to do a little housecleaning along the way.

Here too, planning and preparation go a long way. It helps to outline the basic document classifications, tags, and divisions you’ll be using before you start loading files into the system (not that it is all that difficult to move things about, but why make extra work for yourself?). It also helps to review your documents and toss out the old, useless, and redundant before starting. Not only will you reclaim disk space; you will streamline the process of populating your management system.

Typical Features

When shopping for a document management system, you will inevitably find that the system’s list of features will be written in tech-speak rather than common English. Here’s a list of some of the common features and what they should mean to you:

  • Auditing (or Audit Trail): The system will provide a list of who is working or has worked on a document, when they started, when they ended, and whether the document is currently checked out or available to other people.
  • Versioning: The system will track all the different versions of each document and will permit you to revert to older versions without losing or altering the most recent version. Some systems are capable of comparing versions so that you can see the edits made to each version.
  • Full Text Searching: The system will allow users to search the full text of each document rather than limiting searches to system metadata (file name, author, date, file type, etc.).
  • Document Retention: The system is capable of automatically archiving old documents, thus freeing space for current documents.
  • Security: The system will permit you to limit document access so that you can determine who may read, edit, and delete documents.
  • Lockdown (or Workflows): This prevents users from circumventing your document management policies. It forces users to follow an explicit methodology when inserting, deleting, or modifying documents.
  • Email Integration: This means the system can interface with your email system and allow you to save your emails directly in the system.
  • Scanner Integration: This means the system will directly interface with your document scanner, allowing automatic storage of the scanned documents.

BRUCE CAMERON operates Cameron Law PLLC and practices Estate Planning, Collaborative Family Law, and Mediation. He blogs at and, and is the author of “Becoming a Rural Lawyer: A Personal Guide to Establishing a Small Town Practice.”

The author wishes to thank Andrea Cannavina and the staff of Legal Typist for teaching him how to dictate and for their help in preparing this article.


1 LexisNexis (2012) “LexisNexis Law Firm Billable Hours Survey Report,” Retrieved from:

2 Allen, David, Getting Things Done, Penguin Books (2002).

3 For more information, see:,, or I will note that I am a happy LegalTypist customer and, should you contact them, feel free to tell them I referred you.

4 Epoq, An Assessment of the Savings Possible from Using Document Automation Technology, Retrieved from

5 In this context, the term “template” refers to a specific file format. Most modern word processors have a special read-only document format commonly referred to as a “template.” When a template is opened, the word processor creates a copy of the original document and all editing is done on this copy, leaving the original intact. The word processor will ask the user for a file name the first time the copy is saved, thus preventing the original document from being overwritten.

6 For a far better treatment of Quick Parts direct from the source see:

7 A free 90-day demo of Pathagoras is available from and The Form Tool, including the free basic tool, can be found at

8 Pathagoras and TheFormTool work with Word versions 2007 through 2013/365.

9 The relevant websites are:, (RapidDocs), (GhostFill),, (Exari DocGen), (ContractExpress),,,

10 In this context, the term “template” has a slightly different meaning than my previous usage. While it is still going to be a read-only document, it is not going to be something you’d want to open with your word processor as it contains a fair bit of programming code along with your form’s original text and is not something you’ll want to edit manually.

11 For more information, see:,,,, and

12 See: and

One Comment

  1. Roy Lasris
    Jan 03, 2017

    Just wanted to (1) thank you for the mention of Pathagoras in your article and (2) to advise that we have released a cloud (i.e., ‘platform-less’) version of our program. We call it ‘Pathagoras On Cloud’. While the editor is not as robust as her earth-bound sibling, it is pretty dynamic, allowing drag and drop assembly, full variable replacement controls and plain text setups as the earth version. Once assembly is complete, it is easy to share document with others or download to self for final touches.
    Check it out at
    Call me if any questions or if you would like a tour.

    Innovative Software Products of Virginia
    1-866-PATHAGOras (1-866-728-4246) (tollfree)
    (757) 877-2244 (Virginia, USA -day)
    (757) 898-7374 (Virginia, USA -eve)

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