Migrating to Cloud Practice Management Apps

Vol. 30 No. 5


Benjamin K. Sanchez (bsanchez@sanchezlawfirm.com, 713/780-7745) is a commercial and collection litigation attorney in Houston, Texas. Given that he is in court three to five times a week and has a home office, he relies on cloud practice management technology to easily and reliably manage his practice. Wells H. Anderson (info@activepractice.com, 800/575-0007) works directly with small firms and solos across North America via virtual meetings to implement practice management, timekeeping, billing, and mobile applications. Through his website (activepractice.com) he regularly publishes new technology tips and articles.

It seems as if it was only yesterday that legal professionals were coping with typewriters and carbon copies. In the blink of an eye, we have dashed through copy machines, computers, facsimiles, scanners, and e-mail. Despite the fast pace of technology, the legal industry has tended to lag behind the times, approaching change conservatively at the risk of running afoul of our ethical duties. Yet, here we are, at the doorstep of a new age in legal practice and legal practice management.

This article focuses on cloud practice management (CPM) services, which let us use software-as-a-service to manage our legal practice—from calendaring, contacts, and matters to documents, e-mails, tasks, and billing. What is CPM, how does it work, how do we get there, and how do we keep it secure? In the sections that follow and in an extensive comparison spreadsheet (activepractice.com/cpm), we offer advice, information, and perspectives on CPM and its major features.

Pros and Cons

To begin, let’s briefly review the pros and cons of CPM.

The biggest benefit of CPM also happens to be its biggest obstacle for many attorneys: reduced need for expensive hardware, software, and maintenance. CPM software runs in someone else’s data center, so you don’t have to maintain a powerful server or workhorse workstations for the software. But moving these burdens to the CPM provider means you have less direct control over your data and must rely on the uptime and security of someone else’s operation. This idea makes some attorneys uncomfortable.

In our experience, however, vendors who provide CPM have delivered on strong uptime guarantees and security, so there is no need to worry about access and security. (The caveat is that you must have Internet access whenever you want to use your CPM.)

Another benefit of CPM is mobility; now your software and files are accessible wherever you have Internet access, and many programs have an app for your mobile device as well. Whether you are in your office, in a conference room with a client, in your home office, or traveling, you can resume work wherever you previously left off. Your calendar, files, and information are all immediately accessible and up-to-date.

Another downside to CPM is that you must pay to access your data on a monthly or yearly basis, and when you decide to stop paying, you lose access to the software (although you can retrieve your data in one form or another). The CPM monthly subscription may end up costing you more money than if you had paid for a desktop/server-based program, but you should make up for that cost by lowering your hardware and maintenance costs.

Perhaps the biggest benefits of CPM are the reduction of psychological stress and “soft” cost. You spend less energy and valuable, unbillable time addressing software problems and dealing with computer downtime. You avoid “upgrade fatigue,” having to install yet another upgrade that may malfunction or break links to other software. With CPM, you outsource the burdens and problems of updating and maintaining your practice management software. One of the authors of this article (Benjamin Sanchez) transitioned his practice first from paper files to server-based programs, and then to CPM software, with no hesitations. The other author (Wells Anderson) is also enthusiastically using CPM as well as other cloud services.


The most common question lawyers ask about moving to CPM applications is “How safe is my client information?”

Most fears about trusting client information to “the Internet” are misplaced. One misconception is that client information may be intercepted as it travels across the Internet. Modern encryption has progressed to the point where it is unbreakable. The only way to decrypt information in transit across the Internet is to break a weak password or obtain the cloud subscriber’s password or pass phrase.

The real dangers to confidential client information lie in using unsecure passwords or in failing to follow important security precautions. These dangers apply to everyone: your law office, cloud service providers, and non-cloud companies alike. You face them even when you don’t use cloud applications. Hackers can break into the computers in your office if you don’t use strong passwords, maintain a good firewall, and protect against new viruses and malware. Poorly implemented security precautions could threaten your information stored by both cloud and non-cloud businesses such as banks, credit card companies, law firms you communicate with, and your own law office.

The keys to meeting your ethical obligation to safeguard your confidential client information in a CPM system are:

  1. Use strong passwords or pass phrases.
  2. Select cloud services from companies with solid reputations and documented, appropriate security precautions.

Cloud companies understand that their reputations for protecting customer information are crucial. A single security breach would cost them dearly. Your client information is more secure stored on a reputable, professionally managed cloud server than on your office computers.

Backup and Downloading

The second most common question lawyers ask when considering cloud services is “Can I get my information back if I end my subscription?”

The answer to this one is “yes . . . but.” There are two methods to get back the information you have imported or entered into your CPM system. The best way is direct, unassisted access to an easy method for downloading your practice management data and files. The other alternative is delivery of your data and files either as a downloadable ZIP file or on physical media, but with this method you must submit a request to the company, wait for the vendor to respond, and perhaps pay a shipping fee. Certainly you would rather have the power to retrieve your information yourself and be able to test the system to ensure you can get what you need.

Another “but” is that you can get your information back, but it may not contain some of the many links between various data, such as links from document to matters. This should not be a deal breaker. Typically there are techniques to relink information in a new practice management system; still, these techniques can be time consuming and expensive. Understand that it can be difficult to switch from one practice management system to another, whether cloud-based or not.

CPM companies regularly back up your information. Nevertheless, Wells, a backup zealot and founder of an online backup company, recommends that you periodically download your data and documents. That way you have your own, local backups of your vital client information, and you know that you really can get your information back.

Main Features

Now that you’re comfortable in knowing that your client information is safe while you are using CPM software and that you can get the data back if you stop using it, we’ll highlight the common features of CPM software: calendaring, contacts, matters, documents, e-mail, task management, and timekeeping/billing/accounting. Although most CPM vendors implement these features in their software, how they go about it varies greatly. For a comprehensive spreadsheet comparing the leading vendors, see Cloud Practice Management Comparison, available at activepractice.com/cpm. The leading CPM services include ActionStep (actionstep.com), AdvoLogix (advologix.com), Amicus Cloud (amicus-cloud.com), CaseFox (casefox.com), Clio (goclio.com), Firm Central (firmcentral.com), HoudiniEsq (houdiniesq.com), LexisNexis Firm Manager (firmmanager.com), MyCase (mycase.com), and Rocket Matter (rocketmatter.com).

Calendaring. All lawyers—not just litigators—need a reliable calendaring system. Most of what we do is driven by deadlines, whether these deadlines are imposed by courts, clients, or the opposing sides of a case or transaction. Most CPM software programs integrate with either Google or Microsoft Outlook. The integration is not necessarily robust. The calendaring features may let you keep personal and firm calendars within the CPM software, but most of the time the calendar will be exported into Google or Outlook as a single calendar. Thus, a good calendar entry protocol is necessary in order to name the event with enough detail that you can know what the event is without having to open the CPM software every time. Referencing the file number, type of event, and location will make your calendar far easier to use when out of the office.

Contacts. As with calendaring, most CPM software can integrate contacts with Google and Outlook. Be forewarned, however, that integrating contacts could lead to a lot of hassle if the integration is knocked off balance. Who hasn’t had the experience of double-entries in our contacts or not quite knowing where the source contact is in order to make changes?

Benjamin uses Google business services and has broken free of the Microsoft Exchange server, but he keeps his contacts within his CPM, which also has a mobile app for his iPhone and iPad. Just to be safe, Benjamin doesn’t sync his CPM software contacts with Google. It’s not that he couldn’t, but for him the pain of having to deal with a contact list nightmare is much greater than any potential pain of not having access to contacts in Google. And there is no such pain because the contacts are accessible in the CPM mobile app.

Matters. The heart of any true CPM software and what makes legal software different than other contact management and calendaring systems is matters/cases. This is the part of the program that brings it all together so that we can review each matter or case and get a good understanding of its status.

CPM software can vary widely in how much information is included in matters, as some have pre-built matter templates for specific types of matters, while others have a bare-bones matter template with the ability to add custom fields. The latter requires more thought and effort on your part, but it will allow you to truly tailor the program to meet your specific practice.

What separates some CPM software from others is the ability for clients to have access to their own cases (in other words, a client portal). This particular sub-feature is relatively new, and CPM vendors are rolling it out with varying degrees of success. Benjamin happens to like the client access feature, which eliminates monthly reports for most clients. Our advice is to think about how you want to execute your practice and relate it to clients, which will then help you understand whether or not a particular CPM software package meets your specific needs.

Documents and e-mail. Document and e-mail features vary widely from one CPM system to another. When evaluating competing services, focus on the features that are most critical to your law practice.

Every service has a method for uploading and organizing documents, but only some of them support integration with popular online storage services such as Google Drive, Box, Dropbox, and NetDocuments. These services can provide powerful options for organizing, finding, and exchanging documents.

It is extremely important to be able to save files quickly to the cloud document management system. Too many services require that you first save a new document to your computer and then browse through your computer folders to select and upload your document. A better feature (which nevertheless is time-consuming) is to drag and drop files from a folder on your computer onto a folder in your cloud system. The most efficient features let you “round trip” a document from your CPM to Microsoft Word and back again or create and edit documents entirely in the cloud.

Document templates and automatic document creation features can significantly reduce busywork for you and your staff. Most cloud-based systems include document assembly features that range from basic to advanced. When well integrated with the document filing system and word processing applications, these features streamline the process of creating letters, contracts, and other legal documents.

E-mail is often a weak link in any cloud-based practice management application. E-mail is such an important part of a law practice that you should carefully consider the strengths and weaknesses of this feature in any cloud application. Desirable features include compatibility with Microsoft Outlook, e-mail templates with variables, and any easy method for linking incoming e-mails with contacts and matters.

Task management. Task management (or to-dos) is an underused feature in many practice management systems, both traditional and cloud-based. This feature has great potential for giving you a sense of organization, efficiency, and peace of mind. Efficiency gurus such as David Allen, author of Getting Things Done, encourage us to clear our minds of our many to-dos and organize them in a system. Cloud practice management systems all offer some sort of task management feature, but often they are limited.

Important task management features to look for are:

  • Pop-up reminders
  • E-mail reminders
  • Task delegation and follow-up
  • Priority classification
  • Field for type of task
  • Reusable template or outline of tasks
  • The ability to set a task X days before or after another chained task

Timekeeping, billing, and accounting. Most CPM systems include timekeeping and billing. Selecting financial systems for your law office requires examination of more “must have” features than we have space for here, but a few aspects of timekeeping and billing stand out when comparing CPM systems.

Look for a service that automates timekeeping as much as possible. Valuable options include prompting you to enter time records and displaying total billable time by day, week, and month. Look for flexible invoicing features or strong links to a cloud accounting service such as Xero, FreshBooks, or traditional software such as QuickBooks.


Expect to pay from $45 to $60 and up per user per month for a CPM system. Allow another $30 to $50 per month for an online accounting system for your office or for each entity that you manage in your office.

It can be difficult to compare the overall cost of a cloud-based service versus a traditional desktop/server practice management system. Rather, the attractions of the cloud are reduction of technological hassles, elimination of unpredictable expenses, and easy, immediate access to all your information and documents anywhere.

In your office, you probably still need a central computer operating as a file server, but you don’t need the complexities and expense of a pricey server that runs Microsoft Exchange, Microsoft SQL Server, and other expensive networked software.

Even though your CPM system includes perhaps a week or two of cloud-based backups, we recommend that you back up all your cloud-based information and files and periodically download them to your computer. Then automatically back them up using an independent, professional-grade online backup service. This is not an extra expense. Using an online backup service is something you should do in any case. You are well advised not to rely entirely on a single onsite backup system, whether or not you use cloud-based services.


Hosted desktops, hosted servers, and hosted networks are rather new alternatives to CPM systems. It is now both practical and reasonably affordable to outsource your network to a cloud-based company.

When you subscribe to a hosting service, your network server and all your personal computers are virtualized and run on a professionally managed server farm far from your location. You connect across the Internet and work on your hosted computer desktop using Microsoft Windows and all the traditional software programs that you are used to. It is a bit like using GoToMyPC, LogMeIn, or another remote access program. The difference is that you don’t buy and maintain a server and you don’t pay for everything up front. The virtual desktop computers provided by the hosting company are fast and powerful. You need laptops or personal computers to work on, but they can be inexpensive.

Companies that specialize in hosted servers and desktops for law offices include Uptime Systems (uptimesystems.net), AirDesk Solutions (airdesksolutions.com), and Cloud 9 Real Time (cloud9realtime.com). They specialize in working with law offices and are familiar with legal practice management software such as Time Matters, Abacus, and Worldox.

Advantages of this approach are (1) highly predictable monthly costs and (2) outsourcing of the hassles, updating, and maintenance of not only your server but also most of your desktop programs. No large initial investment for purchasing a new server or replacing an old one is required.

Disadvantages include (1) significant subscription costs in the range of $100 to $150 per user per month and (2) the complexities of traditional law office programs linked together. In contrast, CPM software tends to include almost everything together—contacts, calendars, matters, documents, notes, tasks, timekeeping, billing, and trust funds.


So you’ve decided to take the plunge into the world of CPM software, but now you have to ask yourself, “How do I do it?” Not knowing how to migrate an existing practice into CPM software prevents many attorneys from ever making the change. But it’s not as difficult as it may seem, as long as you give it some good thought beforehand and possibly invest in a good consultant to help you specifically for the migration. Whatever you spend to migrate your practice will be well worth it if you know the migration is being done securely and correctly.

What issues should you think about when it comes to migration? Two important ones are how much information you should migrate and how long you should maintain the legacy systems before relying totally on the CPM software.

The problem with any migration is that you’ll have some double-costs for a while, whether it’s a month, three months, six months, or a year. It really is up to you and how comfortable you feel in letting go of the old. Do you move just active cases over to the new CPM software or all legacy data? Part of this decision may depend on whether you’ll have the ability to access your legacy data if the need arises, but we would advise moving over all active cases and any legacy cases that may have potential questions from particular clients.

When you are ready to migrate, you should take the precaution of exporting your legacy information into spreadsheet or database files that are accessible without the legacy software if possible. Cost also plays a role because you may not be able to afford two practice management software programs for any length of time.

All in all, it is helpful to think about your most important clients, your most troublesome clients, and any legacy matters that may need to be addressed in the future. Rather than worrying about migrating all your legacy matters, you may think about putting your legacy cases on disks or thumb drives for each client and then sending those to your respective clients with a cover letter letting them know that you are moving to a new software and will not be migrating old cases to such software.

You can inform your clients that the enclosed disk or thumb drive contains the documents from their cases, and that if they have any specific questions regarding old matters, you will leave your legacy software open until a specific future date (30 to 60 days) to answer such questions. This will allow you to migrate without having to move legacy data and cover your assets should a question arise once you have closed the legacy software. You should do this only for those clients and matters that are within your malpractice limitations or tax audit period.

Well ahead of time, do some testing of the method for importing information into the new CPM software. Experiment with the functions of the new system with some of your own clients and matters. This testing process will allow you to fine-tune the importing process and allow you to more accurately set your expectations for what it will be like working in the new CPM environment. Migration should run smoothly as long as you think and plan ahead and don’t overkill on moving legacy information.


We hope you found this overview article helpful in thinking about CPM and how you can introduce it into your practice. We expect that CPM services, having greatly matured over the past five years, will become the dominant legal practice management solution within the next five years. 


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