Upgrading to Windows 10 and Office 2016 for Law Firms

With security moving to the forefront for legal IT departments, upgrading the core Operating System and Microsoft Office suite are necessary steps to improving security.  Microsoft stopped mainstream support for Windows 7 in 2015 and will stop issuing security patches for it in 2020. Mainstream support for Office 2013 ends in 2018.  Although the upgrade process is time consuming and costly, there are ways to mitigate the impact on productivity for both end users and the Information Technology Department.

Before Beginning the Upgrade

Review Document Management System and Other Core Software Applications

Unless the law firm is using a web-based Document Management System, it is likely that the DMS must be updated in order to be compatible with Office 2016 or Office 365. Even with a web-based DMS, extensive testing is needed for Office add-ins prior to a full rollout. If a DMS upgrade affects customers significantly through interface or method changes, consider completing this upgrade first. Customers will have a chance to acclimate to this change before the Windows and Office upgrades. Word add-ins can also be affected by both upgrades. Some of these challenges may not be industry specific and may be pre-empted or resolved through Microsoft hot fixes.

Consider a Hardware Refresh

Consider a hardware refresh at the time of the upgrade. If customers’ computers do not exceed minimum requirements, slowness and Operating System crashing can result. This negatively impacts customer confidence in the software product and, by extension, the IT department as a whole.

Select Pilot Group Participants

A carefully selected pilot group is an important tool when facing a firmwide upgrade or implementation. Although it seems more efficient to pilot new software in one small office, or a single floor of a larger office, this approach leaves gaps in testing that could be avoided. Consider setting up a pilot group that represents all roles and practice groups throughout the firm. This approach is more complex but stands a greater chance to reveal incompatibilities and customer issues. If these customers volunteer for the pilot group, that is even better. They will offer more constructive feedback and be patient during the inevitable growing pains. Take advantage of power users, especially for Office add-ins. They may use shortcuts and other features that most other customers do not.

Train IT Support Staff

IT familiarity and confidence are key to a successful technology upgrade or rollout. The personnel supporting the product should be well-prepared, confident and knowledgeable when working with customers. To this end, early pilots and training for IT support personnel are a key component of success. You can secure a high level of familiarity by retaining the services of a third party support provider, such as Intelliteach. For them, your law firm is not the first to perform this upgrade; their support technicians are well versed in common customer issues and their resolutions and Intelliteach also offers additional input from other past projects.

Advertise the Change to Customers

When facing a sweeping change to user experience, customers prefer being kept in the loop as much as practically possible. They want to know why the firm is making this change and will appreciate that IT is keeping up with modern security requirements. Attorneys may have clients who have specific security needs that are met through the upgrade. Customers also appreciate advance notice of software upgrades.

During the Upgrade

Customer Training

E-learning, especially micro learning can be a valuable tool to assist customers through the transition. It can be difficult to convince busy partners and support staff to take time out of their already full days to attend classroom training. Classroom training requires a large amount of resources like trainers, classroom space, and maintenance of training computers. With micro learning products like Intelliteach’s Skillbuilder, customers can access targeted, on-demand video tutorials lasting 30 to 90 seconds covering only their chosen topics. From the customer’s perspective, they have made a similar time investment as a call to the firm Service Desk without explaining their needs to IT staff. And as an added incentive for the customer, they can bookmark the Skillbuilder video tutorial for later use. The use of micro learning not only reduces workload for the training department, it frees up IT personnel to focus on tasks and issues with the rollout as they arise rather than answering customer questions.

Floor Support

Floor support, whether provided by a third party or existing internal staff, is essential to a major rollout or upgrade. The presence of roaming assistance increases efficiency and provides immediate feedback on follow up issues. Regular meetings of floor support personnel allow for information transfer back to the IT team, who can then work on solutions.

Additional Phone Support

Customers always have questions and requests for the support team, even when an upgrade goes smoothly from a technological standpoint. A law firm’s normal Service Desk staff can be overwhelmed by the increased customer calls. A successful rollout can increase call volume by 50-75% during the course of a rollout and for 2-3 months after, or about 1 to 1.3 additional calls per firm employee. Engaging additional support from a third party support provider such as Intelliteach maintains adequate response times, even during periods of higher volume. As mentioned earlier, Intelliteach has already helped law firms successfully navigate this transition and Intelliteach analysts offer the benefit of expertise gained through experience.

Common Customer Issues

Missing the Upgrade

By leveraging the millions of historic law firm client tickets in our IQTrack incident management system, Intelliteach identified that common issues during an upgrade to Windows 10 and Office 2016 are similar across firms regardless of firm size or applications used. One of the more inconvenient of these is for customers whose computers are not on the network during the upgrade. They do not receive the software pushes at all. These customers must be tracked down and encouraged to receive the upgrade. A mix of hands off or silent deployments and hardware swaps is sometimes the most successful method of ensuring that all customers receive the upgrade.

Outlook Mail and Calendar Settings

The most common customer requests after an Office upgrade, relate to how an application worked previously. Change can be challenging for some customers and they sometimes reject the change entirely. The Service Desk is most often asked to recreate the Outlook or Calendar interface and settings to resemble their former application. The impact can be mitigated by carefully capturing customizations and preferences during the planning stages. In addition, making customers aware of how it worked vs how it works today can be quite helpful during training and floor support follow up.

Printer and Monitor Setup

Another common issue that arises during an OS upgrade is restoring monitor and printer settings. This issue arises even more frequently when hardware is refreshed at the same time. These issues can be quickly resolved by a remote team by connecting to a customer’s machine and adding back a favorite printer or adjusting the primary monitor settings. This is significant for some customers, because the missing printer or printer settings are not evident until printing is needed. Customers with these issues are eager to return to work as quickly as possible.

In Summary

Hardware and Software upgrades are a necessary task for the modern Information Technology department.  Preparation is a key to the success of a technology rollout, from reviewing software and hardware, to educating customers, to anticipating common needs.  Intelliteach has many years of experience with rollout support and can partner with your firm to improve the customer experience from start to finish.

About the Author


Craig Friedl joined Intelliteach in 2014 and is responsible for all aspects of day-to-day operations for the IT Support Services division. Mr. Friedl oversees approximately 200 Help Desk and Document Handling employees across three locations – Atlanta, St. Louis, and London, and serves as the key point of contact for clients in ensuring customer satisfaction.

See Craig Friedl’s bio