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The Top Five Admin Challenges of Office 365

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AmyKelly Petruzzella
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Office 365, Microsoft's collaboration platform, is comprised of numerous apps that cover everything from email and chat, to project and task management, to security and automation. The full list of applications includes:

  • Microsoft 365 Apps: Word, Excel, PowerPoint, OneNote, Publisher, and Access
  • Email and Calendar: Exchange, Outlook, and Bookings
  • Meetings and Voice: Microsoft Teams
  • Social and Intranet: SharePoint and Yammer
  • Files and Content: OneDrive for Business, Stream, Sway, Lists, and Forms
  • Work Management: Planner, Power Apps, Power Automate, Power Virtual Agents, and To Do
  • Advanced Analytics: MyAnalytics and Power BI Pro
  • Viva: Topics, Connections, Learning, and Insights
  • Microsoft 365 Groups
  • Microsoft Advanced Threat Protection

Business end users rely on these Microsoft collaboration apps to support their day-to-day work activities as efficiently and effectively as possible. It is crucial that these platforms are available when needed and wherever needed. When Office 365 is not actively monitored, it becomes a significant barrier to end user productivity. To get the most out of Office 365, it is necessary to monitor service availability and review all back-end settings and policies to find the right balance between security and governance and employee productivity.

The Top Five Admin Challenges of Office 365

Because Office 365 is not just a single app but rather an entire suite, there are a variety of different challenges IT teams face when it comes to management and monitoring. These challenges are often compounded for enterprise-sized businesses, because they tend to have complexities that smaller companies do not have to contend with. For example, different organizations within one enterprise may have competing needs or there may be geo-political differences in how features are enabled or disabled.

The top five challenges of Office 365 management are troubleshooting, user adoption, security, IT utilization, and performance.


To say that determining the root cause of an Office 365-related issue can be challenging is an understatement. Because Office 365 is comprised of so many various but interconnected apps, a huge amount of data is generated every day. But deciding what to focus on is just the first hurdle when it comes to troubleshooting — next comes navigating the myriad of native tools to track down the root cause and implement a solution.

User Adoption

Creating buy-in from end users as well as tracking adoption of Office 365 applications can be a resource drain on the IT team, especially when migrating from Exchange to Office 365. If Office 365 is not fully adopted, it can also cause issues when it comes time for IT to show ROI of their cloud investment. While native tools can give IT some insights into adoption, it can still be a challenge to understand the full picture across all environments.


Although Microsoft provides multilayered security for Office 365, many organizations are still concerned about losing data that is stored in the cloud. To add to the confusion, navigating the Microsoft security model is anything but simple and requires in-depth knowledge of at least five different admin consoles. Some security settings for certain apps can be set in one single place, while others have overlapping functionality with other applications. Microsoft offers security-related settings to protect customer data, but many require a heavy handed “all-or-nothing” approach causing significant frustration for end users. For certain apps, this native security and governance functionality just isn’t flexible enough to meet the needs of most enterprises.

IT Staff Utilization

With all these applications and corresponding native tools, the most effective and efficient way to proactively monitor Office 365 can be unclear — especially for small IT teams, often reduced due to outsourcing to cloud services. An ideal team includes an expert in each application or subject area, but this can be cost prohibitive even for large enterprises. No matter the size, every IT team faces the additional challenge of monitoring their existing Microsoft environments while also trying to stay up to date with the pace of new releases, updates, and security patches by Microsoft.


At the end of the day, it is not enough to simply deploy Office 365 and educate your end users — the system must be monitored on an ongoing basis for performance issues, anomalies, and usage. Most often, monitoring performance is an issue of bandwidth for IT. Every application generates thousands of data points that must be combed through to glean insights into performance, and it can take even more time to determine correlations between these points. And that is even before Help Desk tickets are taken into account!

To address all these top five challenges, companies must take a multifaceted approach. It is key to have end-to-end visibility of your entire Microsoft collaboration platform. Leveraging 3rd party tools that provide quick, consolidated views of all critical components in real-time, as well as looking back has tremendous upside, especially when your priorities are uptime, security and usage.


Office 365 End User Experience Monitoring and Reporting

To ensure your Office 365 collaboration goals are met, monitoring usage and adoption is just the start. Put your users at the heart of your monitoring strategy by measuring their ability to perform essential tasks within key Office 365 applications.

ENow’s Office 365 End User Experience Monitoring and Reporting:

  • Mimics end-user behavior with synthetic transactions by proactively testing common actions
  • Visually maps service status for a specific user in a specific remote location
  • Pinpoints issues down to the root cause, decreasing MTTR

Gain true end-to-end visibility into how users experience Office 365 applications with ENow’s Office 365 End User Experience Monitoring and Reporting solution. Access your free 14-day trial today!

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