Sharepoint Migration - The Pilot Group Manifesto November 07,2019

When migrating your company’s files, websites, data and other content to Sharepoint, you must keep in mind that you’ll have to also migrate people. Their level of buy-in into the platform will drive both the success and speed of your overall your migration and of your return on investment.

We’ve seen that the best way to both launch and accelerate Sharepoint buy-in is by leading a pilot group as the official first adopters in the organization. Our implementations teams have learned from both raging successes and unflattering failures at this.

Before getting into the main guiding principles, it’s important that you realize that Pilot Group participants will not naturally prioritize this effort atop their own day-to-day duties, nor put a lot of extra work into playing their part in your cultural migration to Sharepoint/O365. So you’ll want to guide a pilot group like you manage a project, complete with tasks, schedules, deliverables, milestones, and delegation. And if you can have your pilot group track all this perhaps on their own Sharepoint site(s), and maybe eventually use Planner and Teams on Office 365, they’ll get that much more out of the overall effort. They’ll be much more likely to succeed within the overall time limits that you set. (And you WILL set time limits.)


Our overall takeaway from our Office 365 and Sharepoint pilot groups has been this general guidance:

  1. Pick the right people
  2. Lead them down the path via training and mentoring
  3. Parade their accomplishments through the company.


1. Picking the Right People

Ideal participants are those employees doing work that:

     - Has Potential for Broad Relevance

            The organization has to already see this group’s work as relevant to them. Who owns and produces information necessary to most of the company, or distributes a lot of content? Who does the company wish would better disseminate their messaging and work? A graphics department, an internal communications group, an HR department, are all good examples of groups most likely to use Sharepoint to build communication sites and otherwise share their work through the platform.

     - Is Heavy on Procedure

     Who gets a lot of forms submitted to them? Who guides or owns many processes that would benefit from automation and workflows? Accounts Payable, Human Resources are often good examples.

     - Requires Teamwork

     Pilot groups should already be actively working together. Having a getting-acquainted period for the group only adds to your timeline for rollout, and to your risks of mismatching. And obviously, using an existing team would also be critical for leveraging all the sharing, collaboration, and project-friendly features of Sharepoint and the rest of Office 365.

     - Is Heavy on File-Tracking

     Who stores lots of files and would benefit most from metadata and Search? Groups storing digital assets (although large video content is not a great candidate), departments that have modernized a lot but inherited highly disorganized folders in their network shares, or groups who regularly ingest or ouput lots of documents associated with customers, vendors or employees, are all ideal.


2. Modeling Training

     - Train Beyond The Basics

     Your pilot group will be both the first-trained, and likely the best-trained. This is critical to the group’s own buy-in and the prospects of having an impressive road show to offer later. Meanwhile, the company’s end of the deal is to show the group more interesting features that they could use to substantially aid in their productivity. Leverage direct mentorship by IT, or consultants who tailor the training agenda to features most useful to the group’s current work.

     - Regular Training Sessions

     Who doesn’t want more training? Or to be ahead of everyone else? True, but don’t forget that these folks have jobs, whose description doesn’t include riling up their colleagues about the latest software. So set a clear schedule of digestible training sessions for the training they’ll need to thrive with Office 365.

     - Build a Training Template

     The mentor guiding the pilot group’s training can use it as a laboratory to come up with a template for the rest of the organization’s Sharepoint/Office365 training, post-pilot. It could also provide insight as to where the company would need outsourced help and services down the road, in case some tasks are of a scale that can’t be handled internally. We found this to be the case with tasks like migrating old versions of Sharepoint, large-scale file movement, and complex Flow workflows, etc.

3. The Road Show

The Road Show starts well before the Pilot Group finishes its experiment. Build anticipation amongst all employees by identifying plenty of opportunities to talk about what the group is doing, all throughout the pilot. Regularly feature the pilot group on your most popular internal communication platforms. Perhaps permit the whole company to view the actual project tracking being done with the O365 tools (tasks in Sharepoint or Planner, channels in Teams, Sharepoint communication sites under construction, etc).  This serves to also arouse curiosity about the platform.

As soon as the pilot group’s original goals are accomplished, as they’ll never really feel that their work is completely finished, they are ready to share their accomplishments with the company. Make the end of this experiment and the coming presentations to the company into a big deal. Make sure that the faces, support, and words of the highest-ranking (non-IT) employees available are included with announcements of the pilot group’s demonstrations and stories.

We’ve seen success with a couple of different styles of road show, depending on the personality and size of the company. If your organization is large and spread out geographically, your pilot group could go on a virtual “world tour”, doing videoconferencing/Teams demonstrations to single or groups of offices at a time. Or they could visit departments or other focused groups at a time, leveraging the intimacy of the session to be able to act as consultants to their audience during the session.

Remember that IT should be on the sidelines throughout these presentations, available for policy and technical questions, but not there to explain the technology or take any credit. The focus must be on what the pilot group was able to accomplish on their own. That’s your path to widespread buy-in.

General Group Management Tips

We often solicited brainstorming at the end of each training session, to have the pilot group dream up and record specifically how they will apply the skills they’ve learned to their day-to-day work habits.

Be wary of a lone member within the pilot group having the whole project dumped on them. This runs counter to both the training and the collective buy-in that’s necessary. The Road Show would also suffer, as too few people will be able to testify to their experiences.

Identify Super user/champion for each group. Have this person be the main contact to keep up with new features, participate in Meetup groups or company user groups, look for good training opportunities & online material, and just generally explore outside resources. They’ll turn into a fountain of additional ideas during your regular training sessions.

Document your Pilot Group’s story, probably on a Sharepoint page. Consider making one participant the “scribe”, to post blog entries about the group’s work and progress.


This is a very compacted account of our lessons learned with pilot groups we’ve run for customers. With this approach we’ve seen most groups really run with the project as of the moment they start putting their hands on it. Lay out the entire piloting process with these tips in mind, and you’ll have plenty of departments and users beating down IT’s door to assure their share of opportunities to take advantage of Sharepoint and Office365.

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