Learn how to combine the strategic insights of AI with the robust migration capabilities of ShareGate to streamline your Exchange Online migration.
We’ve all heard about how much time generative AI can save us. But you need to know how to prompt Copilot, ChatGPT, or your LLM of choice to really reap those benefits.
Similarly, ShareGate can make your mailbox migration smoother, faster, and just plain easier than doing it manually. Knowing a few expert tips on how to leverage can make it even more efficient.
So, today I want to give you a leg up by sharing some of the prompts I use to simplify the migration process, ensure data integrity, and reduce the risk of data loss while ensuring a seamless transition.
My name’s Jasjit Chopra, and I’m a Microsoft MVP and the CEO of Penthara Technologies, a proud ShareGate Partner. I have 22 years of consulting experience in SharePoint, Microsoft 365, and Azure, and right now I’m focused on AI-driven automation for healthcare and pharma, as well as enterprise security.
Table of contents
Leveraging generative AI in migration
Traditional Microsoft 365 migration strategies relied heavily on project management tools, but AI and automation now streamline the migration plan. Now, generative AI is the de facto solution for virtually any problem, so let’s look at how we can marry generative AI in the field of migration planning.
AI-powered automation enhances the migration strategy by optimizing workflows, improving scalability, and ensuring real-time data protection.
Below are ready-to-use Exchange Online migration prompts for key Microsoft 365 workloads. Simply feed your ShareGate reports into an LLM (like Copilot) and use these prompts to generate step-by-step migration plans aligned with Microsoft best practices.
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Exchange Online migration prompts
You can start with a broad request for a migration plan, like this one:
“You are an Exchange Online migration expert. I have attached an exported report from ShareGate that includes detailed information about the source platform. This report contains mailbox discovery data, group configurations, domain details, and user identity mappings. Based on this information, provide a detailed migration plan that ensures data security, minimizes downtime, and adheres to Microsoft best practices”
But you can also dig a little deeper. In my experience, Copilot does better with smaller, more specific asks. So let’s break this down a bit into the 9 different stages of a migration.
1. Discovery and inventory analysis
Ask Copilot to summarize the discovery of mailboxes, shared mailboxes, distribution lists, and groups found in the exported file. Ask it to include:
- Total number of mailboxes ({number_of_mailboxes}).
- Identification of mailboxes exceeding ({size_threshold}, e.g., 50GB or 100GB).
- Primary and archive mailbox sizes.
- List of domains to be migrated ({domains_list}).
2. Stakeholder and client engagement
Upload department and title data, then ask Copilot to identify the key stakeholders for discovery validation and overall migration planning using their titles and department data.
Then, ask it to outline a plan for client engagement, focusing on:
- Migration timelines for {start_date} and {end_date}.
- Expectations around migration timelines.
- Dependencies on integrations or business-critical applications.
- Setting clear expectations for data that will and will not be migrated (e.g., oversized mailboxes).
Make sure to create and assign tasks to your team to gather this information before reaching out to clients.
3. Environment preparation
Ask Copilot to detail the actions required to prepare the destination tenant:
- What do we need for the configuration of destination licensing for all accounts?
- How should we create new identities in the destination platform?
- How should we create an identity mapping file between source and destination accounts?
- Outline the domain preparation steps:
- Steps to verify and move domains ({domains_list}) between tenants after cut off.
- Pre-migration validation of UPNs, email addresses, and secondary aliases and SMTP services.
4. Migration tool configuration
Tell Copilot that you’ll be using ShareGate to migrate Exchange Online, and ask it for advice specific to ShareGate. Include how the ShareGate aligns with best practices for Exchange Online migrations.
Or, if you’re using another migration tool, ask it for a comprehensive checklist for provisioning and configuring the licenses required.
5. Data migration preparation
First, you need to do an audit of the data you already have in your source tenant. The ShareGate Source Analysis report can help you out with that.
Ask Copilot for help deciding which data should be moved and where and which should be left behind and archived.
You can also ask it to provide steps to ensure critical mailboxes, shared mailboxes, and groups are included in the initial sync as well as to provide recommendations for recreating distribution lists and groups at the destination tenant.
6. Sync and validation
Outline procedures for:
- Internal validation and remediation during the initial sync.
- Client/business validation and sign-off after the initial sync.
- Provide recommendations for delta sync if the time difference between the initial sync and final sync exceeds two weeks.
7. Cut off planning
Tell Copilot to detail the steps for preparing the final sync and cut-off phase, including:
- Confirmation of cut-off date and time for domain moves.
- Adding secondary SMTPs to all users at the destination.
- Validation of Pre2K format for third-party integrations and ensuring only one SIP and one SMTP in caps lock per user
8. Post-migration steps
To get ahead of any issues that might pop up, ask Copilot to provide guidelines for internal validation and remediation after the cut-off.
Ask it to create a checklist for client smoke tests and final sign-off that includes best practices for post-migration support and monitoring.
9. Check for limitations for Exchange Online
To avoid errors while migrating, ask Copilot to sift through your ShareGate reports and ensure that the plans it provides you are tailored to your specific data and uses Microsoft-recommended best practices.
Make sure it uses your reports to extract all critical data points, such as mailbox sizes, domains, and user details, to ensure everything you want to migrate is within the prescribed limits.
Here’s what I use:
- Match the license type to the mailbox size to avoid exceeding the storage limit.
- Ensure no single folder contains more than 1 million items to prevent migration errors.
- Ensure the current and archive mailboxes do not exceed 100GB; if they do, request Microsoft to pre-expand the target mailbox.
- Verify that the maximum message size limit (150 MB) in Exchange Online aligns with source environment policies.
- Ensure total mail items per folder and per mailbox stay within Exchange Online’s permissible limit of 10 million items.
TIP: If you have an LLM that can create Word files, you can use the following prompt instead of the above prompts:
“Ensure that the migration plan is tailored to the specific data from the attached file and provides actionable insights based on Microsoft-recommended best practices. Create the plan as “Exchange migration plan for {Customer Name}.” Make sure it uses all the extracted critical data points, such as mailbox sizes, domains, and user details, in this plan. “
Integrating ShareGate into the migration strategy
I love ShareGate because it’s designed specifically for Microsoft 365, and it offers powerful migration services and functionalities to simplify complex migrations.
These are a few of my favorite ShareGate features:
- Limitless data migration: No matter how big, how many users, or how many mailboxes, you can do it all with ShareGate at the same predictable, flat price.
- Pre-migration reporting: If it wasn’t already clear based on how many times I mentioned it already, I love ShareGate’s Source Analysis report and other pre-built reports. They identify potential issues, suggest potential solutions, and help you stay on top of your source and destination tenants.
- Granular data selection: It’s great to have precise control over what gets migrated so that I can reduce clutter and optimize workflows.
With its user-friendly interface and transparent pricing, ShareGate minimizes technical complexities, enabling smoother transitions to Microsoft 365.
Combining generative AI with ShareGate
Combining artificial intelligence with ShareGate optimizes the Microsoft 365 migration process, automating key benefits like data loss prevention and post-migration validation.
The biggest benefit of using the two together is leveraging ShareGate’s detailed and customizable reporting and real-time monitoring to ensure that Copilot is working with the best information when it gives you its recommendations and timely interventions if problems arise.
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Want more prompt suggestions? Check out our articles on SharePoint migration prompts, Microsoft Teams migration prompts, and OneDrive migration prompts.
