My last article (July 21, 2025, issue of Pennsylvania Bar News) provided a brief history of the evolution of computing at law firms. I also provided some insights into the challenges of our current computing environment:
• An ever-increasing threat landscape
• Forced migrations as software packages reach end-of-life
• Forced hardware replacement as software continues to outrun hardware capabilities
• Secure access for telecommuting, virtual and hybrid workers
• Integrating applications provided through various cloud servers
• Finding comprehensive —and affordable—support for the increasingly complex environment; one that has surpassed the capability of many boots-on-the-ground IT companies
Once lawyers only had to worry about risk management for their clients. Nowadays, we have an intricate web of ethical requirements that create a high level of risk management for the firm:
• Maintaining client confidentiality
• Ensuring security of client property
• Securing communications with and about client matters
• Utilizing evolving technology tools to handle matters efficiently and cost-effectively
I concluded that the only realistic and affordable solution for the majority of law firms that cannot afford their own IT staff is to return to a relatively simple and inexpensive workstation, including laptops, notebooks, iPads etc., along with a cloud-based service provider who provides everything:
• Documents storage, including security, organization, secure transmission and receipt, backup and restoration
• Creating seamless integrations between various software packages
• One provider for all levels of IT support
• No more big cash outlays – pay as you go
• Flexibility to scale up or down as needs dictate
• Security at a level most firms can’t afford, covering email, documents, texts, voicemails, all connections between users and data from any device or location
I did my research before I started my search for the right vendor solution. First came a thorough review of PBA Formal Ethics Opinion 2011-200 [Ethical Obligations for Attorneys Using Cloud Computing / Software as a Service While Fulfilling the Duties of Confidentiality and Preservation of Client Property]. I also reviewed a document my colleagues from other state bars created back in 2006, “Questions to Ask Online Storage Vendors.” It’s a basic due diligence outline we created back in the day when law firms were just beginning to use the cloud for backup purposes. It still contains relevant bullet points to consider.
I next outlined all the software functionality I needed. I also decided I should look at more sophisticated solutions for two areas: document management and file sharing.
I maintain a detailed and consistent file hierarchy to organize my files. And I use the search and navigation features of Windows File Explorer to quickly access target documents. However, with the passage of time, the number of files grows exponentially, while memory dulls. It’s frequently difficult to remember in what folder the document I want is stored. If you experience the frustration of muttering to yourself, “Who the heck was the client I wrote that brilliant motion for?” but search in vain, you know what I mean.
To enhance my ability to efficiently use prior work products despite my memory limitations, I started using Copernic Desktop Search as my document management solution shortly after its creation in 1996. It provides the ability to do full text search for words, phrases, and by using Boolean operators, on a variety of file formats including all Microsoft products, WordPerfect, PDF (with a text layer), and more. This solution lacks versioning capabilities. More importantly, it offers no secure file sharing capabilities. This is especially problematic for the very large resources I frequently provide PBA members. Using a document management solution like NetDocuments or WorkSite NT would solve these issues, among others. (Many case management systems include this functionality, too.)
I also decided to explore sophisticated file sharing tools like ShareFile, Egnyte and TitanFile. (I know lots of attorneys use Dropbox or Box, but I am not satisfied with their security.) I have been using Hightail (originally YouSendIt), for this purpose for about 20 years. But since it’s purchase in 2013, the application has become increasingly complex, without a corresponding increase in functionality. So, exploring file sharing apps was my “plan B” in case document management was too costly.
As it turned out, the document management solutions were far too costly. These are not tools designed for the budgets of most solo or small firms. However, I’m sure that the cost would be irrelevant if practice areas require sophisticated document versioning, an audit history, collaborative development, ethical walls, secure file sharing or other capabilities only true document management can provide. In exploring my “plan B” file sharing applications, I discovered that most were designed for much more sophisticated and demanding use and priced accordingly. They were surprisingly complex and expensive. So, I decided to continue to use Copernic and Hightail.
Lastly, for those of you who are long-term QuickBooks users, and really use its many features, you understand why I refuse to switch from Intuit’s desktop version to their cloud version. Their cloud version is not as robust. I was delighted to learn that I did not have to change, despite moving all my computing to the cloud.
I interviewed several of the service providers included on the resource I maintain for PBA members. I asked about their infrastructure; I wanted to know that they were in a location with redundant sources of power, internet connectivity, and servers. I wanted to know that if a regional disaster happened, they had one or more co-locations that kicked in so quickly, customers wouldn’t know. I wanted to know how they monitored customer usage to proactively avoid issues and interruptions, and how they kept their infrastructure to proper scale with customer growth. How did they screen employees; what were the credentials and number of people? What were their security measures internally and externally. Were they adequately capitalized? What software were they going to use for backup and security and more.
Next came proposal review. After my interviews I invited only two vendors to submit proposals. The difference between the two was night and day. Two experienced providers; one would think the proposals would be very similar. Nope. One was clear and flowed from point to point in a logical and comprehensive fashion, with detailed pricing for each point. The other was so vague and disorganized that I couldn’t get a clear picture of exactly what they were providing, let alone imagine how they would effect a smooth migration. And the price was much higher. So, my vendor selection was made.
Next came migration. I knew from experience that nothing of this magnitude happens without a hiccup or two. I was prepared for the worst but my anxiety levels were high. I worked with Chris, my migration expert. This person is key because there were so many programs to migrate, and so much data, and the possibility of real disruption in workflow . . . it was the mountain of complexity that had prevented me from making the switch sooner.
When I started to work with Chris, the clarity of his vision for the orderly migration of my information made it seem simple. I remember several times thinking, “When does this start to go sideways? Surely, we’re missing something!” But I am thrilled to tell you that it really was simple.
Chris dialed in and spent adequate time with me to see how I organized all my data, what software and utilities I used and how, and even how I organized data across my three screens. Then, while I continued to work on my current system, he built my computing environment on my virtual server. All the software pieces were made to play nice in the new sandbox with each other. My desktop QuickBooks was reinstalled on the server, ready for the data transfer. Even the smallest detail, like the timer built into Microsoft which would no longer be available in Office 365, was tended to. Chris found a replacement that was a substantial improvement, at no cost.
Occasionally, Chris would ask me whether I wanted something to work one way or another, and show me the options if necessary. Because of the size of my data storage in Outlook (well over 11,000 contacts alone), he migrated my data over a holiday weekend, so we had an extra day. I still used my system that week. The next weekend he migrated all my files and QuickBooks data.
On Monday I came in to find an electronic note on my desktop that told me how to log in. It was short and simple. He also told me to expect a call in an hour to tour my new computing environment. I was amazed. The tour was brief. Everything pretty much worked exactly as it did before. I was able to get to work immediately, and I’ve had very few issues since. In fact, I recently presented a webinar on the new system without a hitch.
Don’t be afraid to leap into the cloud. Unlike a lot of software migrations, moving my computing environment was easy and the learning curve was minimal. Now, I have no IT responsibilities or headaches, and no security concerns. And I can work securely from anywhere 24/7/365. Any PBA members considering this solution for your firm are welcome to reach out to me with any questions, or for my resources on this topic.
A version of this article originally appeared in the August 25, 2025 issue of Pennsylvania Bar News.
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