How to Avoid the Nine Major Office 365 Migration Pitfalls

By: Thomas Ruden, Senior Solutions Architect, Randstad Technologies

Photo Credit: dennizn /

There are many good reasons companies are migrating to Office 365. For some, it’s more cost effective than traditional licensing, others like offloading the software maintenance and updating tasks, and some find that accessing applications from any Internet-connected computer or device is beneficial.

But, just because it makes sense to migrate doesn’t mean it’s necessarily straightforward. Like most software/infrastructure projects, a little planning goes a long way. Randstad Technologies has over 20 years’ experience in performing mid to large-scale project-based deployments, and we’ve been a long-time partner with Microsoft. Here are nine tips or insights that will help your company think through your Office 365 migration.

  1. Select the appropriate licensing option.

If you’re looking to get more bang for your buck, understand which applications you’ll have access to under each option, especially considering future needs.

2. Upgrade Outlook prior to migrating.

Office 365 uses Outlook 2013/2016 — let users get comfortable using these versions before the migration and you’ll have less user stress.

3. Identify the large mailboxes and reduce their size. 
 Larger mailboxes require longer migration times, which increases the risk of problems.

4. Make sure your version of Exchange is healthy and up-to-date. 
 Most of our clients have required prep work on their infrastructure and email system before their Office 365 migration. In a few cases, the updating was substantial, so consider this when assessing the total migration costs.

5. Research archival/data retention prior to the migration.
If you have mail journaling or an archive vaulting system for email, know whether they are cloud-compatible before the migration. If you’re going to have to pay monthly fees for e-discovery and archiving services in addition to the Office 365 licensing fees, it might be more cost effective for you over the long-term to upgrade on-premises systems.

6. Assess the quality and utilization of your current connectivity and take steps to avoid bandwidth and outage issues.
 Your internet connection is about to become the backbone of your email connectivity. A slow or highly-loaded internet connection will drive your users mad. Many organizations don’t have redundant internet connectivity — so if they lose their connection, there goes their email.

7. Keep disruption of current practices to a minimum.

If the migration is going to dramatically change how your employees work, watch out! Although there might be some apprehension about having such vital applications now in the Cloud, if potential minefields are disarmed before the migration and if the migration goes smoothly, people’s uncertainty will diminish. It is important to get the migration right the first time. Once the internal rumor mill starts churning about a “nightmare” migration, you’ll be hard pressed to salvage it.

8. Slow down. 
 Only so many users can be migrated over a given time, so don’t rush the migration. The size and the number of items in users’ mailboxes will drive migration speed. For planning purposes, expect to see speeds of 250MB to 500MB per hour and assume that 400 gigabytes per day is a practical limit.

9. Don’t bite off more than you can chew. 
 Knowledge of Exchange doesn’t guarantee migration success. Just because it’s Microsoft or just because it’s Office doesn’t mean migration is going to be a snap. It might be — but finding out it’s not as straightforward as you thought can be costly. The majority of clients who engage us to help them with an Office 365 migration have already attempted it themselves. The problem with this approach is that having to go in and correct issues resulting from the DIY attempt can be more costly than had they just gotten help at the start.

Remember that the migration requires not only attention to the technical issues, but to personnel issues as well. For things to go smoothly, adequate attention must be devoted to both.

Learn more about Randstad Technologies migration services here.

Thomas Ruden is a Senior Solutions Architect, combining over 25 years of extensive information technology experience with professional training services and enterprise consulting real world experience. He has been working for Randstad for nine years and is primarily focused on the Microsoft Technology architecture. He is Randstad’s lead architect for Exchange migrations, including Office 365.

About Randstad Technologies: Randstad Technologies has been connecting top companies around the globe with the expert technology talent and solutions that drive their success since 1984. Their deep industry expertise and full-service capabilities — Recruitment, Consulting, Projects and Outsourcing — enable organizations to be agile, productive and ahead in the field with Randstad’s wide network of specialists and flexible solutions. For more information, visit

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