Top 6 Takeaways from "Windows 10/Office 2016 Pre-Flight & In-Flight Checks"

Kenny Leckie and I spent Friday morning in New York with the Professional Legal Trainers Group (PLTG), discussing how to train and support a Windows 10/Office 2016 migration. The tech-fair style format allowed participants to engage in discussions centered on six key areas, and these were my top takeaways:

  1. Needs Assessments: Take time to assess your current state and determine your future state. By performing a gap analysis, a learning roadmap can be constructed to guide the learning journey. Align your learning program with the business objectives of the firm, ensure you are solving the right problem with the solution being deployed, and build a compelling story.
  2. Voice of the End User: It is important to get a seat at the table early in the planning process so trainers can advocate appropriately for the end users. Conduct focus groups to identify needs. Trainers should be involved in testing –– and deeper than just opening an application. The best pilot groups will include users with various workflows and personality types. Solicit and incorporate feedback.
  3. Training Approaches and Strategies: View learning through the lens of a change agent. The training strategy should be integrated with both an intentional communication and reinforcement strategy. Remember that just because you build it, doesn’t mean they will come. If you want to bring about sustainable change, you must reinforce learning. Strategies discussed were diverse, ranging from assigned to self-selected learning paths; training by traditional roles to personas; and traditional installation/deployment to self-installation of upgraded programs.

    Training delivery ranged from in-person, instructor-led to virtual instructor-led and recordings coupled with Q&A sessions to a flipped classroom approach (eLearning coupled with learning labs).

    Overall, the length of sessions as well as the number of days of floor support is less than in previous rollouts. Training approaches discussed were push vs pull vs a blend; what’s new and what’s different; need to know vs nice to know; and using the “running with scissors” litmus test to determine if content should be included in the structured learning session or if it should be included in a reinforcement learning opportunity. 

  4. New features and use cases: Take time to point out when a feature has moved. Customize when it makes sense, for example, the default “Tracking Display is Simple Markup,” which is likely not the best option in most instances. Take time to consider standard formatting options used by different people groups, and ensure you know where to locate them. The group noted that in PowerPoint, the “Number slides from” option is challenging to locate: Design | Customize | Slide Size | Custom Slide Size
  5. Training scope: When deciding what should be included in the structured learning session, highlighting “What’s New and What’s Different” was a common approach. Design learning in a workflow manner rather than focusing on features. The “Tell Me What You Want To Do” Office feature was popular. Most agreed on the following:
    • The majority of training time should be spent in Outlook
    • Share the improved functionality in a few key features in Word
    • Highlight a few features in Windows 10 that can improve productivity
    • Include a light touch on key changes to the third-party tools that must be upgrade
  6. What NOT to do: The biggest theme was to be mindful to break content into short, targeted sessions rather than offering one long session. Suggestions included offering short, application-specific sessions and reinforcing best practices in separate sessions.

The session ended with a sneak preview of Office 2019, which was a great reminder that the next big adventure is just around the corner. To learn more about the PLTG, visit