Some of the key reasons for businesses to move to the cloud are mobility, agility, progressive technology, and a need to stay abreast of the industry trends today. Businesses need powerful solutions that allow them to be more competitive, and there are several options cloud available to them today. Among the alternatives provided by the big three providers including Amazon, Microsoft, and Google, several businesses choose to use Microsoft’s Office 365 offering, since it provides effective functionality and is well integrated with Microsoft Office suite of products that most businesses are already running on.


Organizations can choose to migrate in any of the following methods:

  • Cutover Migration: In this, all data is moved in one big move from on-premise applications to MS 365. An example of where this is used is for Exchange server migration, where all Exchange mailboxes can be moved to MS 365 in one go if the number of mailboxes is manageable.
  • Staged (batched) Migration: In this, the migration happens in stages or batches, in order to break down a larger number of assets into a manageable limit. For instance, if the number of Exchange mailboxes is more than 2000, then a staged migration can be done.
  • Hybrid Migration: In this, while the migration happens, the on-premise version is also maintained in parallel for a period. This is to ensure that the migration is successfully done and tested, and can be relied on, before the on-premise version is discarded. Building a hybrid migration model can be challenging and is in fact one of the key challenges in the migration process.


Building hybrid solutions

If the organization decides to choose hybrid migration, and retain some of the aspects in the on-premise environment, then this calls for a detailed strategy and well-thought-out plan to migration. Typically, organizations may choose to do this when they want to use cloud for their mobile workforce, but also want to retain on-premise for employees at the office desktops. A hybrid solution makes sense for a large organization that needs to maintain data stores for thousands of users.

Organizations typically implement a single sign-on with Active Directory Federation Services to get the best of both Office 365 and the familiar on-premises solutions.

Not all areas are easy to transition

Organizations run several applications and software, and not all of them lend themselves to easy migration. For instance, Exchange migration is fairly easy and straightforward. However, an application like SharePoint Online is more complex and the migration can introduce changes in the way the application is configured and run. Another example is a linked Excel spreadsheet, which can pose some issues when migrated to Office 365.

In order to overcome this challenge, organizations need to set realistic expectations, and keep in mind that like-for-like migrations for legacy systems may not always exist.

Low bandwidth and network issues

Limited bandwidth and slow network can make the migration to Office 365 very slow and painstaking. Also, if the internet connectivity has challenges, it can pose problems even after migration is done, since the operations on cloud can become slow and hampered.

As a solution, organizations can either upgrade network equipment and/or use migration tools to help overcome this problem. Also, organizations need to communicate this problem clearly and involve network specialists as early as possible in the migration process to prevent users from getting hampered.

Security concerns

One obvious challenge is the fear of data security. One of the major qualms enterprises have about making the switch from corporate-owned on-premise applications/servers to something like Office 365 based on the cloud, is the security implication of sharing business information in a public forum.

However, these fears are mostly unfounded because Microsoft has plenty of safeguards in place to ensure that data is safe during the migration process and after the transition. Organizations typically involve stakeholders as early in the migration process as possible and communicate risks and mitigation to them clearly. It also makes sense to discuss if the organization’s legal and compliance policies prohibit the storage of data in the cloud or if stakeholders breed resentments regarding the security concerned with physical access to Microsoft datacenters. These could determine the migration strategy as well.

Active Directory synchronization

When organizations decide to go with the hybrid migration model, the synchronization of Active Directory between on-premises Active Directory and Office 365 (in reality Azure AD) is very important.

A crucial part of the migration preparation is the state of the Active Directory in the organization. A good Active Directory quality is required when setting up Single Sign-on (SSO) using Active Directory Federation Services (ADFS) or Microsoft Azure Active Directory Connect.

As a precaution before the migration, the organization can inspect the Active Directory and try to work out any risks or issues before making the switch to Office 365


Very often, templates in legacy MS applications may not work as expected in the migrated environment. It is likely that organization employees and users work with many templates dating back to the late 90s or early 2000s. It becomes obvious that these templates need to be able to accommodate the changed migration scenarios.

This is a risk that organizations need to anticipate and plan for. Being prepared for changes to be done on templates, and for documents to be updated in the new environment, are vital to make the migration a success.

User adoption

As is the case in any organizational change, one of the key risks is resistance to the change and an eventual acceptance of the change. Same is true in the case of a migration to Microsoft 365 as well.

Users need ample communication, help, and guidance to understand the new environment and its implications. Organization leaders need to reach out to the right stakeholders regarding user adoption as early as possible in the migration process and get in touch with Internal Communications, HR, and the Marketing department. It is crucial to properly inform users about and prepare them for the switch to Office 365, and to keep the communication flowing all through the migration and post-migration process. Microsoft knows that user adoption is key and therefore the Microsoft site provides excellent hands-on material for successful user adoption, including prepared user e-mails, posters, articles for intranet, and much more.


  • Decide on the migration model – Decide whether to choose a hybrid migration or not. This would depend a lot of the type of data and applications you have, and the need for on-premise along with cloud implementation.
  • Audit your data and standardize your sites and libraries – Conduct a due diligence of all the data sites you have. Make sure you know what data is being migrated, and make it standardized so that migration becomes easier.
  • Identify roles and responsibilities – This helps identify who does what during the migration, and brings in traceability and accountability.
  • Handle change management and communication – A good communication plan and applying effective change management is important to the success of the migration project. It is important to let users know what is changing and how, and what they should do to be prepared for it.
  • Have a plan for external users – An organization’s end users may also be impacted by the migration. Make sure to list out external end-users, communicate to them about the migration and let them know what to expect and when.
  • Collaborate for best results – Migration is a collaborative effort, and several teams and stakeholders are involved in the process. It is therefore highly important to understand how the collaboration works, establish the rapport with various stakeholders, and ensure everyone works together for the effective migration.


Moving to Office 365 is a multi-phased project that often requires technical consulting and support. It requires a combined workforce and effort from IT, HR, Change Management and other teams in order to make sure the migration is smooth and easy.