Key factors to consider when embarking on a Microsoft 365 rollout

Rolling out Microsoft 365

With a service such as Microsoft 365, it’s tempting to think you need to do little more than a headcount of the number of seats in your organisation and process the order…

It’s certainly possible to do that, but rushed rollouts are a recipe for unnecessary cost, user confusion and poor security…not to mention missed opportunities.

There are all manner of factors to consider before rolling out Microsoft 365 in an organisation, including existing licensing, security, data backup and training staff to use the new apps and services effectively. A partner such as Daisy can help you work through these challenges, leaning on its experience of working with a huge number of organisations in many industries to help find the right solutions for your company.

Here are some of the key factors that should be considered before and during any Microsoft 365 rollout.

Performing an audit

Before the start of any major software or services rollout, it’s vital to perform an audit of the organisation to find out (a) which software and licenses are already within the organisation; and (b) what you’re likely to need in the future.

The bigger the organisation, the more likely it is that there will be legacy software and licenses that are either unused (“shelfware”) or duplicated within the company – pockets of cost and inefficiency that could be eliminated with a full audit.

An audit will also help identify where savings can be made by migrating staff to Windows 365 apps and services that you might already have access to as part of a forthcoming rollout. It can also identify potentially costly pitfalls, such as helping you to put a plan in place for data migrations from one app or service to another.

Daisy’s expert consultants can guide you through the audit process.

Sorting security

It’s tempting to think that you don’t need to concern yourself with security when using a cloud service such as Windows 365, as Microsoft takes care of that. While it’s certainly true that Microsoft is highly qualified and well-resourced to guard the perimeter of cloud services, it’s still down to the organisation to manage access control and other elements of the security mix.

Microsoft 365 can help minimise the risk of data breaches with facilities such as multifactor authentication and by flagging risky user sign-ins. Daisy can help train your staff in best practice with such access controls and help you understand the information delivered on security dashboards. Daisy can also minimise the risk of data breaches, by highlighting which employees have access to what company data.

Daisy can also provide independent advice on third-party solutions that plug in to Microsoft 365 and further enhance your security posture, with additional email security solutions, for example.

Data Backup

Much like security, it’s all too easy to think having your data stored in the cloud negates the need for a separate backup strategy, but that would be tempting disaster.

For starters, if staff aren’t trained to use the new software and apps properly, or the correct policies aren’t enforced, it’s entirely possible that pockets of company data are stored locally and are not properly backed up. Daisy can help with both staff training and ensuring that the correct policies are established at the time of deployment to ensure that no company data slips through the net.

Once again, third-party solutions are also available that can enhance the data backup facilities provided by Microsoft 365, ensuring nothing is lost and that businesses in regulated industries are fully compliant with the legal requirements placed on them.

Migration management

Rollouts are often compromised at the migration stage, when it suddenly dawns that moving data from one service to another is more problematic than first envisaged.

Planning is critical. Pilot testing migrations with different scenarios from across the organisation is crucial, because they can expose flaws or unexpected hiccups in a migration plan before the live users are affected. Likewise, testing with actual users is equally important, as it’s often only the people in those roles who will notice when a critical part of their IT function has stopped working or a necessary piece of data is missing.

Once you’ve tested with these employees, they can then become internal champions for the rest of the organisation, sharing best practice and helping others to overcome difficulties when the system goes live. There will always be some resistance to IT change within organisations, but thorough testing and bringing users with you on the journey can smooth out many of the bumps.

Daisy has a long history of managing Microsoft 365 migrations in organisations from a wide variety of industries, and so can help you implement the processes that will achieve a successful migration with minimal disruption.


The journey doesn’t end when the migration is complete. Even before staff are migrated to the new system, training is essential to ensure that employees feel confident with the new apps and services that are being delivered and that they can continue to perform their roles.

Training may come in a variety of forms, and with employees now more likely to be working out of the office for sustained periods, it’s even more important to think about how this should be delivered. Those internal champions within your organisation may no longer be sat a couple of desks away from co-workers, so planning how colleagues can support one another is just as important as formal training sessions.

While staff are likely to be familiar with Office stalwarts such as Word, Excel and PowerPoint, they may be less so with some of the more recent additions to the Microsoft 365 portfolio, such as Microsoft Teams. Given Teams’ increasing importance in allowing geographically dispersed teams to collaborate and communicate, teaching staff how to get the most out of such software is vital. Daisy has an entire training prospectus devoted to Microsoft Teams, ensuring that employees have the best possible chance of seamlessly adapting to the new hybrid model of office working that is becoming commonplace across a number of industries.

Talk to one of our specialists.
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