The Accidental Roadshow

By Jeffrey Roach posted 12-05-2019 09:37


During ILTACON 2018 I had the pleasure of co-presenting with Sherry Kappel and Donna Payne on a three-part session devoted to Office 365. We invited law firm members and industry experts to participate in each panel and it turned out to be a highlight of my 20 plus years of presenting for ILTA (the artist formerly known as LawNet).

As far as I was concerned, that was the end of my Office 365 shenanigans until ILTACON 2019. Then, I got a call from my friend Cindy in Chicago, asking me if I could just do one presentation for ILTA in Chicago. Five months later, I rolled into Dallas for the last leg of the accidental roadshow with a new perspective and a better understanding of where the legal profession is in terms of adopting Office 365. What did I learn? Here are my big three takeaways, after spending months chatting with firms about their plans for Office 365.

Office 365 is more than just Office, but it’s still mainly just Office. While it might seem shortsighted to look at Office 365 as just a way to update to the latest version of Office on the Windows 10 platform, that’s the approach the vast major of the firms who attended the roadshow are taking. It’s not because they don’t see the value in the other platforms and apps, but the scope of Office 365 is so huge that it’s difficult to tackle the entire thing as a single initiative. The Win 10 platform is a known and obvious target, so that’s where most firms have elected to get started. There were a small number of firms who flipped the paradigm and decided to focus on other products like Teams and Planner. These firms tend to already be on Office 2016 and didn’t have as much pressure to upgrade. And, an even smaller set tried to embrace both the traditional products as well as the cool new apps that are part of the Office 365 service. Generally, these were smaller, more nimble firms who didn’t have to drag thousands of users to a new platform.

Many firms talked about taking a multi-phased approach to 365 but confessed that they were having trouble finding the time and motivation to get past Phase 1. Once the Windows 10 desktops/laptops are updated, the channels are figured out and the updates are being managed, it’s tough to take that second breath and think about what Phase 2 looks like. If you are still planning your upgrade, be sure to take a holistic approach and plan for all phases upfront.

Office 365 is constantly being updated. I know, this seems like an obvious observation, but you don’t really get it until you live it. By now most of us are aware that Office updates are distributed across three different channels. The semi-annual channel is updated twice a year in January and July, has a longer lifecycle, and is the likely candidate for most users in a law firm or corporation. The semi-annual targeted channel is updated in March and September and each update replaces the previous update. This means that anyone in this channel is getting updates twice a year. This is a good channel for the CIO organization and Office champions. The monthly channel is updated each month, which means anyone in this channel is subject to changes both big and small every single month. Here is what the channels looked like at the end of my roadshow:

I’m in the monthly channel. Since the roadshow occurred over a five-month period, I found myself needing to constantly update my presentation. This usually meant the night before each presentation I was holed up in my hotel room reviewing the changes to Outlook, Word, Excel and PowerPoint.

I wasn’t concerned about the updates breaking an integration point, although that’s a reasonable thing to be concerned about. I don’t have as many add-ins to Office as a typical law firm and my integrated apps accommodated the monthly onslaught of changes with grace. The challenge was understanding what changes had occurred and which ones were going to be valuable to law firm users. Further, I needed to identify which changes might be disruptive enough to either delay, suppress or plan some change management around. This is a big job. Especially these days when Office exists across multiple platforms and devices. Does anyone care that you can snap a picture of a table and Excel for iOS was convert it to a spreadsheet? If so, who? How do I make them aware of what’s possible? Yes, Office 365 is constantly being updated and it’s a chore to catalog, analyze and filter these updates. Have a good plan in place before you start, because the updates are coming fast and furious these days.

Office 365 is part of a more complex puzzle. The most feature-rich place to store documents created in Office 365 is OneDrive for Business or SharePoint. For most law firms, that’s simply not going to work. And while the major DMS vendors out there are closing the gap in functionality, they all come with one caveat—you need to move your documents to the cloud. In fact, the cloud and connectivity are two recurring themes in Office 365 and the experience drops considerably if either gets stifled. Stacking a major DMS upgrade on top of an Office 365 upgrade is a tough ask from most IT teams. As a result, sequencing becomes a real headache. Which comes first? How do you sell the dream of an anytime, anywhere user experience when it’s going to take years to put all the moving parts into place? When I interview lawyers, they consistently tell me that mobility and collaboration are key to them working effectively. We’d like to give them those two things, but make sure they do it securely. While it’s exciting to create a future state desk, it’s important to explain how you are going to get there. I like to think of it as the transition state, which occurs between the current state and the future state. The transition period is going to be one of constant and iterative change and that means good project and change management are crucial to put the pieces of the puzzle together without disrupting workflow.

Staying connecting and sharing our Office 365 experiences. Now that it’s over, I must admit that I miss the accidental roadshow. The logistics of being on the road for five months are tough, but there’s really nothing else like it. To keep the conversation going, I’ve created a Yammer group devoted to discussing all things Office 365. Drop me a message at if you would like an invite.