• Comparison of PDF Software for Lawyers [chart]

Electronic documents are now a part of a lawyer’s everyday life. Although file formats such as Microsoft Word, WordPerfect, and Excel are ubiquitous and used daily by every lawyer and firm, easily sharing these documents with other people who might not have WordPerfect or a Mac is a huge issue in today’s technological society. The goals of finding a solution to this interoperability issue and creating a standardized format to store accurate representations of electronic and paper files created a race to develop such a file format. By the end of the 1990s, one format had risen to the fore: the portable document format (PDF) created by Adobe Systems Inc.

“Invented by Adobe Systems and perfected over 20 years, Portable Document Format (PDF) is now an open standard for electronic document exchange maintained by the International Organization for Standardization (ISO). When you convert documents, forms, graphics, and web pages to PDF, they look just like they would if printed. But unlike printed documents, PDF files can contain clickable links and buttons, form fields, video, and audio – as well as logic to help automate routine business processes. When you share a PDF file, virtually anyone can read it using free Adobe Reader^® software or the Adobe Reader mobile app.”

The key fact in this statement from Adobe is that PDF is now an open standard. This means that lawyers and their employees are not limited to using only Adobe products to create, edit, and view a PDF. The PDF also has the benefit of being an electronic duplicate of the document, whether it is created on a computer in a word-processing program or scanned from a paper document. Think of a PDF as an electronic photocopy that provides the ability to limit changes and can be digitally secured and authenticated.

PDF has moved from being the de facto standard for storing and sharing electronic documents in the legal world to the de jure standard based on its adoption for use by federal and state courts and governmental agencies. Because electronic filing is required for lawyers in the federal courts and many state courts, understanding the tools available to create PDF documents is a necessity.

Core Functionality for Lawyers

When it comes to tools to create, edit, and view PDF documents, not all products and services are created equal. Generating a basic PDF file can be done with many products, including Microsoft Office, WordPerfect Office, and a number of other free and low-cost PDF creation tools; however, these solutions do not include some capabilities that most lawyers need. Lawyers face unique challenges, from the filing requirements of courts and other governmental agencies to the need to maintain confidentiality of client information and prevent unauthorized changes to documents. At a minimum, a PDF solution for lawyers and law firms should include the following capabilities:

• Create PDF files from multiple sources, including within commonly used word-processing, spreadsheet, and presentation programs;
• Create searchable PDF files;
• Add comments;
• Add Bates numbers;
• Convert PDF documents to Word, Excel, or even WordPerfect formats;
• Incorporate a typewriter function to allow lawyers and their employees to type directly onto a PDF document that does not contain form fields;
• Redact not only the image portion of a PDF but also any text layer;
• Remove metadata;
• Impose security to limit changes such as printing, adding comments, making changes, and completing form fields;
• Create stamps including images of your signature;
• Use (and, ideally, create) digital IDs and certificates for authentication and security purposes;
• Integrate with other products and services, such as document-management systems, cloud storage, Microsoft’s SharePoint, and others; and
• Create PDF/A files (the PDF version for archiving) and also check for compatibility for compliance with this standard.

The ability to fully redact PDF documents, add Bates numbers, and work with digital IDs and certificates usually is lacking from free and low-cost PDF creation tools. Every lawyer or firm needs to have at least one copy of a PDF tool that includes all these capabilities. The four tools reviewed in this article contain these capabilities and are from commercial enterprises with a track record of producing tools that are both functional and widely available.

This article reviews Adobe Acrobat XI Professional, Nitro Pro 8, Nuance PDF Converter Enterprise 8, and pdfDOCS. All are PDF tools for Windows-based PCs and are used in law firms and other types of businesses. Several of these products also have versions for the Mac platform, but the article does not address those tools.

These products have in common several features, including the ability to add Bates numbering, headers and footers, and page numbers to documents. They all provide redaction tools of varying sophistication, which can help lawyers remove confidential or privileged information from a PDF. They will all convert a PDF document into a Word, Excel, or other useable format such as rich text format (RTF), WordPerfect, or even PowerPoint. All these products can create PDFs that comply with at least one of the PDF/A standards and add tool bars or other functions within Microsoft Word, Excel, and PowerPoint programs. All of these programs also install as a printer so that you can generate a PDF from almost any program that you can print from.

A detailed side-by-side comparison of important features and capabilities appears in the accompanying chart. How each program implements these common functionalities plus any additional features are what differentiate the programs from each other and thus may make one tool more suitable for a particular practice or need than another.

For this article, testing was done with each product using a combination of sample documents provided by several of the companies as well as some of the author’s actual seminar materials in MS Word and PowerPoint formats and actual Outlook messages.

Adobe Acrobat XI Pro

Adobe Acrobat, which created the PDF standard, is the granddaddy of PDF creation, editing, and viewing software. Of the four tools compared in this article, Acrobat Pro probably is the best recognized and most widely used within the legal community. There are two versions of Adobe Acrobat XI: Standard and Professional. To get the law-field-specific core functionalities, including Bates numbering and redaction, you must have Adobe Acrobat XI Pro. Although many lawyers will not regularly need these features, all lawyers will need them on occasion, either for their designated purpose or to add information similar to Bates numbers. In any event, you should have Bates numbering and redaction capabilities on at least one computer in your office.

Some highlights of the new features in Acrobat XI include:

• The ability to edit text and images directly on a PDF without having to find the original document.
• The ability to insert, edit, or delete text and have it automatically reflow to adjust to these changes.
• Improved combine-files feature.
• Improved conversion of PDF files to Microsoft Word, Excel, and PowerPoint formats.
• New form-creation tools.
• Integration with EchoSign for electronic signatures.

The ability to directly edit PDF documents means that the days of searching for an original document, making changes to it, and then generating a new PDF may be over. Editing text on a PDF in Acrobat now works very much like working in a word processor with spacing and lines automatically adjusting for changes in the body of the text. Another significant improvement is that users creating a PDF from multiple files such as Word, Excel, Images, and so on now have the ability to manipulate not only the order of the documents but also individual pages within those documents themselves. This allows you to reorder both the documents and the pages in the documents before creating the PDF. This is possible because the thumbnail views of each file to be included in the new PDF are now “live,” allowing you to preview not only each document but the individual pages in each document as well.

Other functionality includes 5 gigabytes of free PDF storage via Acrobat.com. Unfortunately, this is the only cloud integration that is provided. Unlike several of the other products, Adobe does directly connect to other cloud storage services, such as Evernote and Dropbox. Acrobat XI Pro has added new PDF and Web form-creation tools that are “best in class” for the products reviewed here. Acrobat moved rapidly to integrate its recent purchase of the EchoSign online-document-signature service.

Carryover features from prior versions include Acrobat’s ability to archive Outlook emails, either individually or by folder and including attachments, into a searchable PDF; this remains one of the outstanding tools in Acrobat Pro. The attachments to archived Outlook emails remain in their native format and when clicked, they open in the file’s native program, such as Word or Excel. However, Acrobat Pro still lacks the ability to convert attachments to PDF when archiving emails.

Acrobat’s ability to compare two PDF documents to identify differences remains, as does the Action Wizard from Acrobat X. The Action Wizard allows you to automate repetitive tasks and standardize procedures for multistep processes throughout an organization. You can use the prebuilt actions or customize your own.

While Acrobat does not perform as well as the other products when converting a PDF file to Microsoft Word or Excel format, its conversion of a PDF file to Microsoft PowerPoint works very well. The user interface first introduced in Acrobat X eliminated the heavy reliance on menus and tool bars and introduced Task Panes. The new interface places the majority of tools into the three disappearing panes on the right-hand side of the Acrobat screen. Users’ reactions to this redesign have been similar to reactions to the introduction of the Microsoft Office Ribbon: some people like it, and others request the return of the old menu and tool bar structure. The Acrobat interface uses a paradigm entirely different from that of the more traditional menu and tool bar structure still used in Nuance PDF Converter Enterprise and pdfDOCs. It is also unlike the Microsoft Ribbon and the ribbon-like interface found in Nitro Pro.

After using the new interface daily in both Acrobat X and Acrobat XI, it at times still seems to require more steps than prior versions to accomplish the same tasks. The Acrobat interface is less cluttered than those found in Nuance PDF Converter Enterprise and pdfDOCS. Recognizing that the new interface may not be for everyone, Adobe has provided the capability to customize the tool bars by adding regularly used individual tools, thus allowing you to bypass the Task Panes.

Acrobat still has the most features when it comes to working with PDF files; it also has the largest base of supporting blogs and online videos and tutorials, including TV.Adobe.com. Of the products reviewed here, Acrobat XI Pro is the most expensive, at $449 for a new license. Upgrade pricing is better at $199 from Acrobat version 7 (Standard or Pro) or newer. But even with the (reduced) upgrade price, Acrobat XI Pro remains at the higher end of the price range.

Nitro Pro 8

Nitro Pro 8, the latest release of the flagship product of San Francisco-based Nitro PDF Pty. Ltd., includes several features found in the other products reviewed here, such as redaction, Bates numbering, and metadata removal. Nitro PDF also produces the free Nitro Reader, an alternative to Adobe’s free Reader software. Unlike Adobe Reader, NitroReader includes the ability to create PDFs, type on flat PDF documents using a typewriter tool, and more. Nitro Pro is the full-featured big brother to the free product.

Nitro adopted a ribbon interface similar to that found in Microsoft Office. This presents an uncluttered aesthetic, and for people accustomed to the Microsoft office ribbon, using Nitro Pro will pose little in the way of a learning curve. A Nitro Pro add-on inside Microsoft Word, Excel, and PowerPoint allows you to generate PDFs from the ribbon and to control creation functionality, such as applying security, creating bookmarks, and more.

Nitro Pro allows you to edit text and images and to reflow text as with the more expensive Acrobat XI Pro. Nitro Pro complies with PDF standards, including one subset of PDF/A, allowing you to create documents that comply with the PDF/A-1b standard. It also includes a snapshot tool to select and copy content from a PDF to your clipboard. Nitro Pro allows you to create PDFs from your scanner and create searchable text layers. While you can create forms with Nitro Pro, it lacks the automatic field-recognition capabilities found in Acrobat XI Pro and Nuance PDF Converter Enterprise, but does permit auto alignment of fields and objects when creating forms.

When you use Nitro Pro to open a scanned PDF that has not previously been made searchable, Nitro Pro prompts you to run optical character recognition (OCR) on it. When converting a PDF to a Microsoft Excel spreadsheet, Nitro Pro was faster and more accurate than Acrobat XI Pro and pdfDOCS. (This may be a direct result of Nitro’s integration of technology from the I.R.I.S. Group, a long-time provider of OCR and scanning technology (http://bit.ly/12M7RPP).) Nitro Pro also allows you to batch convert multiple PDF files to word or Excel.

Although there is much to like about Nitro Pro, the product has several shortcomings that may make one of the other tools more attractive as the primary PDF tool for a lawyer or firm.

Nitro Pro lacks the capability to combine multiple files into anything other than a single PDF document. Unlike Acrobat Pro, PDF Converter Enterprise, and pdfDOCs, there is no function for creating portfolios or creating binders to contain not only PDF documents but also Word, Excel, PowerPoint, and other files. While you can view individual files in a portfolio using the attachments panel, that does not offset the lack of ability to create a portfolio. There is also no way to manipulate files or the contents before combining them, like Acrobat Pro’s live tiles. Nitro Pro does not include any Outlook capabilities other than allowing you to print an Outlook email as a PDF using the printer menu. There is no capability to insert a new page into an existing document, either from an existing file or from a scanner. Nitro Pro also lacks the ability to monitor specific folders to see if documents have been placed in them and then automatically convert the documents to PDF, which capability is beneficial in a multiuser environment.

Despite these shortcomings, the tools Nitro Pro does include are robust and easy to use. At $119, Nitro Pro is the least expensive of the four tools reviewed and is a great choice for lawyers who are on a budget or prefer a slightly smaller set of features; it is also less complex with a good user interface and short learning curve.

Nuance PDF Converter Enterprise 8

Nuance PDF Converter Enterprise 8 is produced by the same company that makes PaperPort, OmniPage, and Dragon NaturallySpeaking. PDF Converter Enterprise 8 is a full-featured PDF tool that is second only to Acrobat XI Pro in the number of features. Although Nuance also sells PDF Converter and PDF Converter Pro, these products do not contain the core law-field-specific functions, that is, Bates numbering and redaction. Thus, lawyers should purchase PDF Converter Enterprise if they decide to use a Nuance product.

PDF Converter Enterprise has several stand-out features, including Dragon Notes, which allows you to insert notes using the online Dragon speech-recognition engine. It also adds tool bars in Microsoft Office applications and Internet Explorer. It is the only product other than Acrobat XI Pro that archives Outlook messages and folders. As with Acrobat XI Pro, PDF Converter Enterprise allows you to retain Outlook message attachments in their native file format. Adding to this capability, Nuance PDF Converter Enterprise also allows you to convert attachments to Outlook messages into PDF files as well, something that Acrobat XI Pro does not do. PDF Converter Enterprise includes a wizard, based on legacy technology from Nuance’s retired OmniForm program, that automatically recognizes form fields in a flat PDF. This means that if you download a court form that does not have embedded form fields, the wizard will do its best to automatically detect the fields.

PDF Converter Enterprise 8 shares a number of other capabilities with Acrobat XI Pro, including the ability to combine multiple files into a single PDF or into a portfolio (which allows you to package PDFs and native files such as Excel spreadsheets, Word documents, and PowerPoint files into a PDF container). Like Acrobat XI Pro, PDF Converter Enterprise allows you to assemble documents using live tiles, which means you can rearrange documents and pages before creating the combined PDF. Like Acrobat XI Pro and Nitro Pro, PDF Converter Enterprise works in conjunction with your scanner to create PDFs as well as placing tool bars in Microsoft Office and installing as a printer. In addition to converting PDF files to various Microsoft Office formats, it is the only product reviewed here that can convert a PDF to a WordPerfect file. PDF Converter Enterprises includes cloud connectors for Evernote, Dropbox, Box.com, and Google Drive (using the Nuance Cloud Connector).

Like Acrobat XI Pro, PDF Converter Enterprise allows you to compare two PDFs and then goes one step further by allowing you to also compare a PDF to a Word document.

On the negative side, PDF Converter Enterprise had the most cluttered menu and tool bar structure of the four products, which, for a new user, can make finding features and settings a challenge. PDF Converter Enterprise also does not provide any capability to watch folders and automatically convert files placed into them to PDF, as does pdfDOCS. Although PDF Converter Enterprise 8 improves on Acrobat XI Pro’s Outlook archiving features by providing for conversion of attachments to PDF, it does not include Acrobat Pro’s ability to append a message or messages to an existing Outlook archive. This forces you to create a new PDF each time rather than appending one or more messages to an existing Outlook archive.

Nuance has a five-license minimum-purchase requirement to purchase PDF Converter Enterprise from its website. Even at the Nuance website price of $149 per user, this is a financial disincentive for solo practitioners and small firms. However, Nuance has created an open license program, allowing vendors, such as CDW and others, to sell PDF Converter Enterprise in single-license quantities. A check of the CDW website shows a single-user license priced less than $149, which makes this a very attractive product, even for a solo attorney.

pdfDOCS

Australia-based DocsCorp takes a slightly different approach to PDF tools, based on the belief that different people within an organization may have different needs and that while one staff member may need all possible PDF tools, coworkers might not. With this paradigm in mind, users can purchase from DocsCorp only the features they need, thereby minimizing the cost. If you only need to create PDFs and add comments, annotations, or stamps to them, create searchable PDFs, or convert a PDF to Microsoft Word, Excel, or another format, then the base pdfDOCS product may be all you need. If you need to be able to compare two documents, adding compareDocs will provide this functionality.

Unlike the other products reviewed here, which work from a document-centric perspective, pdfDOCS allows you to work from a matter- or file-centric perspective. Using organizers and projects, you can have multiple projects open at the same time, and each project allows you to organize all documents regarding a specific matter or file in a single location. Projects can then be saved either locally or on the network and can be shared with other people in the firm.

pdfDOCS uses a traditional menu and tool bar structure for its interface. The pdfDOCS desktop is akin to a work-in-progress area, where you can organize and work with documents before creating final versions. pdfDOCS installs an add-on in Microsoft Office, which, by default, allows you to send documents directly to pdfDOCS and the current organizer within the desktop. pdfDOCS allows you to change this default so that when you send a document to pdfDOCS, you are prompted to enter the project where you want the document to be placed. This alleviates the concern about having to determine, before sending a document to the program, which project is open in pdfDOCS.

The pdfDOCS desktop consists of three working areas. The Navigation Pane is on the left of the screen, the Document List is on the top left, and below the Document List is the Editor. Any two of these three areas can be turned off to gain more workspace. Selecting one or more documents in the Document List and then right clicking opens the Document Menu, providing access to much of the program’s functionality. pdfDOCS takes the concept of combining PDF and non-PDF documents to a new level with its Binders. Binders can combine PDF files to a folder that contains mixed PDFs and native documents similar to Acrobat’s portfolios. pdfDOCS automatically creates a table of contents for the files placed in the binder, including indexes, bookmarks, and links across documents.

pdfDOCS allows you to create one or more watched folders, which the program automatically monitors. When a document is placed in any watched folder, pdfDOCS automatically processes that folder, converting the file or files to PDF and placing them into the current Organizer. pdfDOCS is the only one of the products reviewed here that monitors outgoing Outlook email for attachments and prompts you to automatically convert the attachments to a PDF before sending. Strong integration with document-management software is also a plus for this product. For lawyers and firms considering WORLDOX, the pdfDOCS Productivity Suite is available at a significant cost savings.

pdfDOCS lags behind the other products in this article in several important aspects. While pdfDOCS has the capability to automatically watch Outlook emails for native attachments, there is no capability to archive Outlook emails other than by dragging and dropping an Outlook email to pdfDOCS or printing the email using the pdfDOCS printer. Outlook attachments must also be processed separately, and there is no way to leave the attachment linked to the Outlook email when converted to PDF. pdfDOCS metadata removal tools also contain fewer features than do the metadata removal tools of the other three products. Although pdfDOCS can secure a PDF from changes, edits, and comments, to use a digital certificate or digital ID, you must obtain it from another product or provider, unlike the other products, which allow you to create your own digital certificate and ID or use one provided by a third party. The ability to scan directly to pdfDOCS is also missing. pdfDOCS relies on the software that came with your scanner or multifunction copier. While this is a negative, it is partially alleviated if you configure your scanner or multifunction copier to scan directly to a pdfDOCS watched folder. When a document is scanned to the watched folder, pdfDOCS automatically converts it to PDF. Another negative is that to view a final PDF using pdfDOCS, you must have Acrobat Reader installed on your computer. While pdfDOCS’ features work without Acrobat Reader, the first time you go to view or open a PDF from an Organizer, you receive an error message and will have to install it.

pdfDOCS can be obtained either on an annual subscription basis or as a one-time license purchase. The annual per-user license cost of pdfDOCS with the OCR module and compareDocs is $250.

If you are looking for tight integration with a document-management system such as WORLDOX and the ability to tailor the software for the specific needs of the user, pdfDOCS may be your best choice in a multi-user environment.

Summary

If you have a Fujitsu ScanSnap S1500 or iX500 (both of which come with Adobe Acrobat X Standard), it makes sense to upgrade to Acrobat XI Pro (for $199). Acrobat has the most free training and support resources of any of the products in this article.

If you need full functionality including the ability to interact with a scanner other than a Fujitsu ScanSnap, it makes sense to purchase Nuance PDF Converter Enterprise, so long as you can buy only the copies you need. While PDF Converter Enterprise provides almost as many features as Acrobat XI Pro at a lower cost, it suffers from having the fewest free training and support resources of any of the reviewed products.

If you’re looking for a product with most of the functionality of Acrobat XI Pro that you can afford to place on multiple computers in your office, then Nitro Pro 8 is a terrific selection at a reasonable price. You can easily and quickly get up and running with Nitro Pro 8, which sports the cleanest, most user-friendly of the interfaces and has terrific documentation. Nitro sends you a series of emails when you sign up to help you get started, along with a newsletter, but still lacks the depth of tools available for Acrobat.

For firms that have multiple users that use a document-management system such as WORLDOX, or have a large multifunction copier as the primary scanning tool, pdfDOCS has much to offer, from its watched folders and its ability to create a specific table of contents with links and bookmarks for binders, to its model of allowing purchase of as few features as you need. If you want to organize your files from a matter-centric perspective or be able to work on multiple projects simultaneously, you should seriously consider purchasing pdfDOCS.

Ratings

The accompanying chart is a detailed comparison of the four products’ features. Each product was evaluated in four categories using a 10-point scale, with 1 lowest and 10 highest. The categories are ease of use; feature set; value for cost; and manual, help, and online resources.

To my surprise, my top choice is Nuance PDF Converter Enterprise 8. While having the same score overall as Nitro Pro, PDF Converter Enterprise’s shortcomings are concentrated in the somewhat less significant area of less impressive help and online resources. From a feature perspective, PDF Converter Enterprise 8 has a richer feature set that strikes a good balance between advanced functionality and price.

NitroPDF scored very high for its ease of use and price, although its inability to create portfolios and lack of Outlook tools kept it from taking top honors. For users who want key features such as redaction, Bates numbering, and ease of use, with a clean interface and short learning curve, Nitro Pro is a solid product with a nice interface at a great price.

Acrobat XI Pro has a great feature set and comes from the company with the most experience with PDF products. Acrobat has the most extensive training resources and online support community. However, its lack of cloud connectivity, PDF to Office format-conversion results, watched folders that only work with postscript documents, and relatively high price keep this otherwise excellent program from taking top honors.

pdfDOCS fits best into a multiuser firm that relies on network scanners and needs the ability to organize documents by project. Its strong multidocument editing capabilities, watched folders, and PDF/A compliance do not offset its other feature limitations, including the high cost to get document-comparison capabilities. According to pdfDOCs, a new version with updated features is due out by the end of 2013, so keep watch for an improved version that could make this product suitable for more offices.

• Comparison of PDF Software for Lawyers [chart]