Piloting your Office 365 rollout


If you’re just beginning to plan your Office 365 rollout (or are in the process of rolling out additional Office 365 applications), it’s important to consider the benefits of running a formal pilot program. A pilot enables a subset of users to access Office 365 prior to its rollout to the entire organization. There are many benefits to running a pilot, including:

  • Road-testing your communications and training. I host weekly Q&A calls for my pilot testers. The calls enable pilot participants to provide feedback on their experience, highlight favorite features, identify gaps in our training materials, recommend new methods for engaging business teams, etc.. This feedback is key because it comes from the business. Whenever possible, I like to test out the pilot users’ training ideas during the pilot itself. If they request a What is Office 365 training session, I’ll assemble a training curriculum and offer the new class to the pilot group. Taking this extra step during the pilot enables me to gather more feedback and puts me in the best possible position for my org-wide rollout.
  • Building a knowledgeable set of pilot users that can support your rollout and (hopefully) recommend Office 365 to their colleagues. Giving users early access to Office 365 and offering them the opportunity to impact your rollout builds rapport. This enhanced sense of community engagement will help you build momentum for your rollout, enhancing user adoption.
  • Testing your license enablement and support processes. As part of your pilot, you’ll need to enable Office 365 applications for your pilot testers. You’ll also need to provide support as they begin using the products. This is an excellent opportunity to test (and improve) your licensing and support processes. After all, pilot testers are more likely to forgive enablement issues and support delays. And learning from your mistakes during a pilot will ensure the same mistakes don’t occur during your org-wide rollout!
  • Identifying use cases and success stories. Ideally, your pilot testers will be leveraging the new capabilities they’ve received. Consider setting up time for them to show off their results. You may find unexpected use cases for Office 365 and success stories that highlight key value-adds. Leverage these use cases and success stories to tell the story of Office 365’s business value.
  • Validating your governance and compliance policies. A pilot program enables you to see how Office 365 performs in your environment. Your networking team can validate network traffic is flowing smoothly. Your information security team can validate all appropriate risk requirements have been met. If you have compliance or legal record hold requirements, those teams can validate to ensure data is being scanned, stored, and supervised appropriately. If there are issues, you have time to correct before Office 365 is rolled out to your entire organization.

Pilot Planning
But how big should your pilot be? And how long should it last? The scale of your pilot should reflect the size of your organization and the level of governance and compliance controls you need to implement.

As a general rule, I recommend building a pilot program that is roughly 3% of your overall user base. If you’ll be rolling out Office 365 to 10,000 users, that would mean having a pilot group of 300. If you have a user base of 50,000, you’d want to build a pilot group of 1,500. While this 3% target may sound large, it affords the best opportunity for user feedback. Keep in mind that you cannot expect strong participation from all pilot users. No matter how well-intentioned, there is always a percentage of pilot testers that contribute minimally or not at all. Targeting 3% of your user base ensures you will have a viable set of pilot testers to try out your products.

Your pilot program will also enable you to test key governance and compliance controls (e.g. archival and supervision of Outlook email, record retention, SharePoint hub site governance, etc.). In order to run a valid test, you will need a sufficient data sample size. If 3% of your user base will not give you enough data to work with, increase the size of your pilot group accordingly. It is always best to adjust any necessary governance policies or security and archival controls before your org-wide implementation.

Now that you have a rough idea of your pilot size, it’s time to start planning who should be part of the pilot. Ideally, you should target:

  • Highly engaged users from across multiple business lines (not just IT).
  • Green dot and yellow dot users that are quick to adapt to change.
  • Volunteers. Always engage those who want to be part of your pilot. These users are more likely to engage, will dedicate more time, and are much more likely to provide feedback. While it may be more work to amass a set of volunteer resources, they will be more engaged and provide better feedback than voluntold users.
  • Strong communicators. Feedback is an essential part of the pilot process. You want to engage those that are willing to provide written or verbal feedback.
  • A variety of personality types. Ideally, you want to include technology optimists and pessimists in your pilot group. Technology optimists have a good impression of IT and are generally enthusiastic about trying out new technologies. Technology pessimists have a stronger “what’s in it for me” mentality and need to see or hear something compelling before they decide to jump on board. Incorporating both technology optimists and pessimists in your pilot will give you the best opportunity to validate your Office 365 messaging and training.

How long should your pilot last? While many companies have intense pressure to roll Office 365 out quickly, I’m a firm believer in meaningful pilots. The more time spent piloting and refining your approach to governance, training, and license enablement, the more successful your rollout will be. A pilot period of 3 weeks is incredibly tight, but can generate value. A pilot period of 1-2 months will generate more user data and enable you to refine your training offerings.

There is one exception to this “lengthier is better” rule for pilots. If you work for a company with a strong technology innovation culture and most of your users are very comfortable with technology change, a longer pilot may not be necessary. If your organization is facing a great deal of technology debt in the workforce productivity space, a longer pilot will better enable you to build momentum for the upcoming change.

Pilot execution
Now that you’ve completed your pilot planning, it’s time to execute your vision. Plan to launch your pilot with a formal series of kickoff meetings, brown-bag lunches, and/or targeted pilot communications. The goal is to celebrate this important stage of your Office 365 rollout efforts. And the more positive noise you can generate, the more pilot user engagement you’ll see.

You’ll also want to make it easy for pilot users to learn about Office 365 and provide feedback on their experience. A few ideas I’ve seen work well:

  • Share “getting started” scenarios. Many users may feel intimidated when they first open a new Office 365 app. Providing quick, easy-to-follow “getting started” scenarios for each app gives your pilot users a running start. If you’re going to pilot OneDrive for Business, for example, you could create getting-started scenarios that explain how to:
    • Create files in OneDrive
    • Save Microsoft Office files to OneDrive
    • Share a OneDrive file (or folder) with someone
    • See OneDrive files that have been shared with you
    • Open files using the OneDrive sync client
    • Edit files in the OneDrive mobile app
  • Host weekly Q&A sessions. As I mentioned previously, I host weekly Q&A calls for my pilot testers. The calls enable pilot participants to provide feedback on their experiences and ask product-related questions.
  • Schedule “Show & Tell” events where pilot users can share Office 365 tips and demo solutions they’ve built. Provide an opportunity for your pilot users to shine. Schedule a recurring meeting where the pilot users come together to share cool new tricks they’ve learned and demo solutions they’ve built in Office 365. For best results, keep this a peer-to-peer sharing meeting. Having a pilot user demonstrate a new Microsoft Flow they’ve built is powerful stuff. Their excitement and confidence in using Office 365 will motivate other pilot users to follow suit.
  • Build a private Yammer group for your pilot users. Yammer is a great “thinking out loud” app that supports discussion and sharing of ideas. I recommend creating a private Yammer group where pilot users can share insights, ask questions, etc. Add all pilot testers to the group before your pilot begins and send them the group URL for easy reference. As the pilot coordinator, it’s important you actively participate in the Yammer group. Share Office 365 tips, provide links to appropriate training resources, and answer pilot user questions.
  • Track your pilot user Yammer sentiment. If you’re providing your pilot users with a Yammer group for sharing ideas, use Microsoft Flow and Azure Cognitive Services to perform sentiment analysis on the pilot Yammer posts. The sentiment data gathered may provide insights into your pilot group’s overall satisfaction with Office 365 and help you identify solution use cases.
  • Stay in touch. I always want my pilot testers to feel like they are part of a valued community. Connect with pilot users that are in your geographic area by hosting meet-ups or coffee chats. Communicate with geographically-distributed pilot users via Yammer or Teams. And share an “Office 365 tip of the week” for all pilot users.

Want to learn more?
Asif Rehmani published a great article on the key reasons to include an early adopter program in your Office 365 rollout. Check it out–it’s well worth a read!

It’s not about the technology. It’s about the use case

This week, I participated in a REgarding 365 debate about use of org-wide Microsoft Teams. Not surprisingly, the Microsoft Teams versus Yammer question was raised multiple times. Here’s the thing–there are uses for Microsoft Teams (including org-wide teams) and there are uses for Yammer. In the end, it’s not about which tool myself or the other REgarding 365 panelists prefer. The valid questions are:

  • What are your organizational use cases and content needs?
  • What is your company culture?
  • Which technologies best fit your use cases and culture?


Use cases are practical business needs (aka requirements) that need to be met. Examples of use cases include:

  • Sharing organization-wide HR policy changes
  • Sharing strategy and content updates from the company’s CEO
  • Providing newly-onboarded employees with a resource center for frequently asked questions
  • Enabling employees to instant message, chat, and screen share with their peers
  • Enabling employees to quickly engage with other employees and members of IT on technology support questions

As collaboration strategists, our first job is identifying and documenting the unique use cases for our organization. Next, we need to assess our organizational culture, including: company values and norms; technology adeptness (aka how well our users adopt new technologies); and readiness for change (e.g. do our users welcome change or do they fear it?).

When we view our use cases alongside our company culture, we’ll be able to determine which technologies are best-suited to meet our needs. There is no one-size-fits-all model or one Microsoft 365 capability that wins the day. Let’s look at our organizational use cases and culture and determine what tool works best for our specific needs.

SharePoint hub sites: How do you know when you need one?

As SharePoint enthusiasts, we’ve eagerly anticipated the arrival of hub sites. Hubs provide a new means of logically grouping our SharePoint sites, changing the way many organizations will manage their intranet and information architecture. But the use and management of hub sites also brings up key questions. How should site owners determine when a hub site is necessary? And what processes should organizations put in place to manage the provisioning and use of hub sites? This blog post provides an introduction to hubs and explores key criteria for the evaluation of hub sites.

What are hub sites?

Hub sites enable logical grouping of SharePoint Online sites with a common navigation and branding experience. In a March 2018 Tech Community article, Mark Kashman calls out 4 key elements of hub sites:

  • Cross-site navigation (navigation that spans multiple sites without requiring manual creation for each site)
  • Content rollup (automated aggregation and display of news content from multiple sites)
  • Consistent look and feel (common site theme and branding that drives familiarity and make sites feel connected)
  • Scoped search (ability to search all sites in a hub quickly and easily)

While there is no limit to the number of sites you can associate with a hub site, you cannot associate a single site with more than one hub. (In other words, there is no opportunity to “parent” a site under two different hubs.)

Enterprise governance of hubs

If you work in a large enterprise, be prepared to govern your use of hub sites. While Microsoft hasn’t provided much guidance on what should constitute a hub site, they initially capped the usage of hub sites to 50 per tenant. In August 2018, Microsoft announced they were doubling hub site capacity, enabling a maximum of 100 hubs per tenant. In May 2019, Microsoft announced another increase–this time to a maximum of 2,000 hub sites per tenant. No release date has been provided for this 2,000 hub site limit, so stay tuned for more information. In the meantime, we’re all living with the current 100 hub site limit.

In order to ensure your hub sites are being leveraged appropriately, I recommend putting key questions and criteria in place to govern what constitutes a hub site. Since sites are elevated to hub site status via Powershell, tenant admins can establish governing principles and/or processes to manage the creation of hub sites. If you are a SharePoint administrator, you will need to determine how hub site promotions will take place. Will you require your site owners to submit request forms for new hub sites? How should they justify whether the hub site is needed? And how much rigor will your enterprise team go through in validating these hub site requests?

To get you started, here are a few hub site questions. The questions are intended to guide site owners through the process of justifying the need for elevating a site to a hub site. You’ll want to modify these questions to suit the specific needs of your organization.

  • Do you need to centrally control the branding theme for multiple SharePoint sites?
  • Do you need to relate multiple disparate sites together with a similar branded look and feel?
  • Do you need a common visual experience for 2 or more sites so users view them as “belonging together”?
  • Do you need to apply the same navigation settings to many different sites?
  • Do you need to update your navigation settings in one location and have it automatically applied to many other sites?
  • Do you need to aggregate news from multiple SharePoint sites into a single aggregate feed for a specific audience of users?
  • Do you need a targeted search function that searches across multiple disparate SharePoint sites quickly and easily?
  • Do you have multiple sites that fall under a logical business area (e.g. Human Resources, Legal, Corporate Communications)?
  • Do you have a functional business reason to link your sites together into a hub site?
  • What value will a hub site provide to your site users?
  • What value will a hub site provide you as a site owner? (In other words, do you have a clear business objective for your hub site?)

You should also consider what operational standards are required for the management of your hub sites. With only 100 hubs to work with, you should consider:

  • Who can approve use of a hub site?
  • Will hub sites be reviewed or audited to ensure they’re still being used? At what interval will auditing take place (e.g. 6 months, annually)?
  • Will you set up thresholds for hub site management (e.g. when you reach a total of 30 hub sites in use, will additional reviews be required?)
  • Will certain key business units (e.g. Corporate Communications, Information Security, etc.) be provided a hub site right away?
  • Should hub sites be “public” by default (e.g. be viewable by all employees)? If not, why not?
  • Will you set up a required minimum number of modern sites that will be joined via a hub? (e.g. you must have a minimum of 5 modern sites to qualify for use of a hub site)

Enterprise governance of hub sites is in its infancy. Most of us are just scratching the surface, trying to determine how much (or how little) governance will actually be required. If you plan to use hub sites, start having open dialogue about hub management now. As you continue learning more about how your site owners (and your organization) engage with hubs, you can build in appropriate governance processes and checkpoints to ensure effective management.

Keynote video: Earning the right to seek executive SharePoint support

I’m starting a new blog post series to share some of my favorite keynote speeches from past conferences/events. First on the list is Michael Sampson’s session Success with SharePoint: Earning the right to seek executive support, which was presented at the 2012 SHARE conference held in Atlanta. Michael did a fantastic job on this presentation–he explains why pleas for executive SharePoint support fail and provides guidance on how to change your approach. Some of my favorite one-liners from the session are:

  • “Success is 90% people, 10% technology.”
  • You have to build credibility with your executives. Stop being the excited teenager.
  • You have to earn the right to talk to your executives about SharePoint.

The formal session abstract and speaker bio are included at the bottom of this post. Enjoy!

[vimeo w=500&h=280]

Here’s the abstract for this session:

Many IT departments have installed SharePoint and are now wondering how to make the technology deliver business value. A quick answer is often to seek executive support, but before rushing to do so, there are a number of critical disciplines that need to be put in place to earn the right for making this approach.

The keynote will present the roadmap to success with SharePoint, and the role of executive support in transforming SharePoint into a place where great business gets done.

Lessons: – Having the technology available is a common place to start, but you can’t stay there forever – Success with SharePoint involves following a roadmap to success, including vision, governance, engagement, and user adoption – Executives have a role to play in the roadmap to success, but you have to earn the right to seek their support

And here is Michael’s speaker bio:

Michael Sampson is a collaboration strategist. His passion is helping organizations to make collaboration work, when their employees have to work together effectively and efficiency while separated by distance and time. Michael advises end-user organizations in New Zealand, Australia, the United States, and Europe.  He holds an MCom with first class honors in telecommunications-based IT, from the University of Canterbury in New Zealand.  Michael is the author of four books on collaboration strategy—Collaboration Roadmap, User Adoption Strategies, SharePoint Roadmap for Collaboration, and Seamless Teamwork.  His blog can be found at and you can follow him on Twitter: @collabguy

Don’t miss your chance to win the Golden Lifeguard Award

If you’re a SharePoint governance pro, you have to check out Axceler’s new Golden Lifeguard Award. The award “honors an individual or a team that has conceived, developed and defined best practices around governance that resulted in a notable increase in security and compliance within their SharePoint environment.”

All award submissions will be evaluated by a team of judges, including myself, Michael Pisarek, Susan Hanley, Ruven Gotz, Veronique Palmer, David Rubinstein and Owen Allen. The winner will be unveiled at a gala event on November 14th at the Tryst nightclub in the Wynn Resort during the SharePoint Conference 2012 in Las Vegas.

To submit an award nomination, go to: There is no cost to submit, and you do not have to be an Axceler customer to participate.

The nomination deadline is October 18, 2012.