In Document Management
Software Deployments

I love finding patterns and creating formulas for nontraditional situations. I want to share a pattern I’ve noticed when it comes to software. This applies at both a micro, single workstation deployment and a macro, new document management solution (DMS), level. Over time, I’ve created a list of the dangerous “D”s of software deployment.


This is surprisingly common. Many firms deny the cause of the actual problem. Perhaps my favorite example is that of DMS rollouts. I’ll talk to a firm and ask what their most significant issues are. The usually list the following items:

  • Naming Convention
  • Versioning
  • Folder Structure
  • Remote Access

I could go on, but when I ask if they have problems accessing or finding documents, they list document access and the ease of finding them as pros of the current system.

So, I send a survey to the entire firm. “What do you love about your current system?” Everyone says they love how easy their current system makes to find documents, they merely want a managed structure and filtering options.

Well, the very next survey question is “What is the most difficult part about the documents are managed?” Ninety percent or better say they can’t find documents. Once I have the survey results, I show the firm. During the reveal, you can hear an audible giggle. That is the giggle of enlightenment.

Why is this example important? Well, I’ve worked with many firms now. Each time I speak to a partner or office manager, I’ll ask about problems I see.

“It looks like you guys do a lot of printing. Maybe you could benefit from going paperless?” Or, “Your office seems to share documents a lot by printing them and placing them on each other’s desks. Perhaps you could benefit from targeted training to assist with collaboration?”

To which I have heard

“We tried going paperless, but for the style of law we practice we need to print.” Or,“We don’t collaborate here.”

To this day, I don’t know what makes a workflow so unique that it requires printing, nor do I see how drafting a document and giving it to someone else to edit is not collaboration. I realize this may sound arrogant, but that is not my intent.


This is usually the other side of the denial coin. Firms will deny their dysfunctional workflows. Here is another example:

I was working with a firm that wanted to integrate Clio with OneDrive. While I like both products, the integration is not stable because of the way OneDrive is designed. The design is not conducive to large-scale sharing.

Anyway, this firm wanted to use OneDrive without the local sync option. They also did not like the idea of downloading a document for editing from the internet and then reuploading when they were finished making changes. Their justification was security. At this point, I mentioned that they have severely limited the functionality of OneDrive while over applying security. Encrypted drives and 2FA along with a few O365 security settings would have done the job and allowed people to work effectively.

We planned training for OneDrive using only the WebApps. While the web app for Word is beautiful, it’s limited when compared to the desktop app. Upon seeing these limitations, they decided that the web app was no good. Again, we discussed their plan, and they did not want to budge on any of the items.

If you’re following along, the firm can’t download files to open in Word nor can they use the web app. Well, we found a third clunky option that allows OneDrive act as a mapped drive if you use the IE web browser. Needless to say, the project ended badly because they insisted on a dysfunctional workflow.


Every law firm that I have ever worked with has said they are unique. While they differ with different specialties, they are not so unique that they all need something that is “one-of-a-kind.”

Nearly every DMS deployment for firms with more than 15 people thinks that the “best practice” structure is insufficient. The best practice for DMS is a client folder with matter subfolders. Then each matter subfolder has a subfolder for document types, which I call Client Matter DocType. But each firm proceeds to tell me that this does not work for them. They request more folders like practice areas, document status, or a hundred different document type folders per matter.

It is at this point; I begin the project discovery process which involves workflow interviews and a document structure review. Then we create a few sample folder structures and discuss. Can you guess which structure their workflow yields? Yes, Client Matter DocType.


I mention these examples because they are the most extreme that I have encountered. While I do want to get some entertainment from them, I do not intend to make fun of anyone. I realize that some firms need to go through the journey to understand. After all, I’m sure I have looked less than intelligent more than my fair share of times.

My point here is to help firms identify some of the obstacles (Denial, Dysfunction, and Different) that make projects more difficult and can hold them back from embracing technology. Changing a workflow to better leverage technology can be difficult, but in the long run, it will make you more efficient.

As you look at your firm, do you recognize any of the three “D”s in your environment?

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