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3.8 min to readDigital WorkplacePublisher Advisory Services

Master 5 major Office 365 migration challenges

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Jeroen EngelanderSenior Cloud Solutions & Business Consultant
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In recent years, consultant Jeroen Engelander has frequently encountered organizations who were keen to take the step into the cloud, or that had already made tentative progress. But there may be some obstacles that need to be overcome during migration, for instance to Office 365. Our Cloud expert has put together the five most common challenges and explains how Cloud Management can help to overcome them.

Quite a few early users found themselves in a bit of a pickle once they noticed that implementing a frequently hybrid cloud environment is not so simple and actually comes with a fair degree of complexity. For instance, take the dependence on Internet connections, the intricacy involved in providing and managing a hybrid environment and the interdependencies between the various Office ProPlus-Plugins and Office 365.

Top 5 Office 365 Migration Challenges

Most companies are now switching to Office 365. My cloud colleagues and I notice that our customers encounter a number of recurring challenges. We have assigned them to five main categories.


Microsoft provides a flood of information about Office 365 that generally focuses on implementation and new features. All the same, we observe that plenty of questions remain in regard to hybrid identity and exchange implementation. Many conversations revolve around issues of support and the performance of Office 365. What’s more, new features are added to the Office 365 service every quarter. 155 features have already been added, 81 are currently being rolled out and another 170 are in development. Office 365 reduces the administrative workload, of course, but however hard you try, it will still be difficult to keep an eye on how all the new features impact the company.

24/7 availability

Many companies are expanding their working hours to keep pace with the standardization of the modern workplace. Many companies have offices all over the world. How can you keep track of the performance and availability of Office 365, which company is afflicted by malfunctions, who will you call, and at what price?

User adoption

Most users will feel confident about working in Exchange Online. After all, their e-mail accounts are available in the familiar Outlook application. But if we consider the use of Skype for Business, SharePoint, OneDrive for Business or Microsoft Teams, it may well be sensible to consider organizing user training to ensure that the investment in Office 365 pays off as much as possible. This is a continual process, so it is advisable to keep pace with the steady stream of new features and to monitor adoption of all available solutions. In our experience, many of the features in the purchased Office 365 Suites remain unused, despite the availability of detailed TechNet documentation.


With its roughly 500 different settings spread over 11 portals, Office 365 is a handsome but nevertheless fairly extensive platform. How can you make certain that the Office 365 device satisfies organizational regulations like the ISO or NEN standards? Changing just one of the 500 available settings can have significant knock-on effects for security if you’re not precisely aware of the implications, for instance allowing external content items without restrictions, e.g. in the HR or accounting departments.

Cost optimization

There is no need to fear a lack of licenses once you have switched to Office 365. The tricky part is keeping an eye on their actual use. In practice, many licenses remain unused, or only parts of the purchased Office 365 Suites are adopted. We can help you to gain insight into which licenses are used, so you can tell at the press of a button where you can save money.

As you can see, using Office 365 comes with a number of challenges. Our managed service solution for Office 365 is called 365Simple. It can help you overcome these challenges. The service consists of three modules:

  • Support (Problem Management)
  • Optimize (Adoption)
  • Manage (Change Management)

Service Manager

A Service Manager who acts as a consultant and primary contact is in charge of all our services. We work together as partners to ensure your use of Office 365 is successful. The Service Manager is responsible for the following:

  • Collaboration with the company to prepare a roadmap for roll-out and alignment;
  • Management of the onboarding process;
  • Development of a long-term strategy with company representatives to ensure continuity and added value of the service;
  • Single-point-of-contact to coordinate all resources and to keep communication lines as short and simple as possible;
  • Escalation manager with responsibility for the escalation team;
  • Audit report with all Office 365 configurations changes (each month);
  • Provision of monthly SLA reporting with an overview of all support tickets, status, solution and customer satisfaction. The report contains a section on the availability of the Office 365 environment.


We give you the opportunity to select a 30-day trial of our managed service at a small fee, before deciding on whether it’s right for you. This Proof of Value is available in two versions.

1. If you want to migrate, we can use our Proof of Value to ensure that you take the first step toward Office 365. We offer the following in this variant:

  • A Cloud Readiness Assessment to smoothen the bumps on the path to migration;
  • Implementation of Azure AD Connect;
  • Basic configuration of the Office 365 tenant;
  • Migration of the first 25 pilot users;
  • Organization of a Customer Immersion Experience session to get the first 25 users set up and working with Office 365 features in their own live environments (Office Pro Plus,
  • SharePoint, Skype, Yammer, Teams, Delve etc.).
  • Access to all modules for 30 days;
  • Configuration of the Adoption Dashboard and Service Health Monitoring Dashboard
  • User access to our online training platform;
  • Access to our 24/7 support line for all technical and functional issues relating to Office 365.

2. We proceed as follows if you already use Office 365:

  • Review and advice on the currently implemented environment;
  • Access to all modules for 30 days;
  • Configuration of the Adoption Dashboard and Service Health Monitoring Dashboard
  • User access to our online training platform;
  • First Adoption Roadmap;
  • Access to our 24/7 support line for all technical andfunctional issues relating to Office 365.


You have migrated your business-critical applications (e-mail etc.) to Office 365. Things work a little differently with Microsoft compared to beforehand, when you could switch the server and then use monitoring tools to keep an eye on the status of your e-mail environment. Although Microsoft offers a 99.9 percent up-time guarantee with its SLA, it is still possible that you will encounter a couple of bugs. You have less control over the availability and performance of the environment. You can rely on the basic support provided by Microsoft if something happens, or can decide to conclude a Premier Support contract. If you opt for basic support, you and hundreds and thousands of other customers throughout the world will be directed to the Tier 1 Support Desk, without any guarantee that the problem will actually be solved. You may also incur additional costs, and in the worst-case scenario will have to accept a response time of 72 hours. Another option is to conclude a costly Premier Support contract. But that is too much of an investment for many organizations.

We offer unlimited support 24/7 to answer technical and functional questions. We are also able to monitor the Office 365 environment and the matching on-premises components. We simulate user activity in Office 365 every 60 seconds, which allows us to identify the source of the performance glitch. We also compare response times with those of other customers. In cases of malfunction, we will inform you proactively and cooperate with you to decide on how to proceed. Our Monitoring Service provides an overview of the entire environment, so we can quickly determine where the problem lies and which responses are necessary. This is practical, because if Microsoft happens to be the problem, we can forward the call directly to the right point of contact at the Microsoft Premier Support Desk and escalate as necessary. We have an unlimited Microsoft Premier Support contract and can therefore offer targeted problem analysis and ideal solutions.


In the Optimization Module, the Service Delivery Manager ensures that an Adoption Roadmap is prepared in collaboration with the key stakeholders in the company. Our Adoption Monitoring Service measures acceptance of the Office 365 products to ensure an optimum adoption outcome. We offer live users webinars for all Office 365 solutions and provide access to our online training platforms, where you can watch short videos to learn how to use Office 365 products. The successful rollout of new technologies requires more than just a good amount of gear.

Providing knowledge to employees that use technology is just as important at least. Many projects fail because the staff are unable to work with the new solution, which leads to dissatisfaction. And given the wealth of new features and online services that are added continuously to the Office 365 platform, it is important that employees using the system get special attention. We join with you to decide whether the many allowed features are relevant to the company and whether user training is necessary.


The Manage Module is a combination of the Support and Optimization Modules. Additionally, we handle complete administration of the Office 365 client, including change management for all conceivable Office 365 settings.

We maintain your company’s security policies like the NEN7510 and ISO standards in Office 365 to let you focus on your core business. We also provide information on use of the Office 365 licenses and offer tips for optimization.

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Prepare your remote workers for change

Our Adoption Change Management team can help your remote workers learn to love new technology.

Prepare your remote workers for change

Our Adoption Change Management team can help your remote workers learn to love new technology.


A man in a suit and tie is posing for a photo.

Jeroen Engelander
Senior Cloud Solutions & Business Consultant

Microsoft P-Seller and Specialist in Microsoft 365