Short answer
Ask a Microsoft 365 migration company how many migrations like yours they have done, what discovery covers, who will do the work, how cutover and rollback work, how mail flow and identity are handled, whether the price is fixed and what is excluded, and what support and documentation you get afterward. Ask for written answers so proposals are comparable.
Key facts
- Ask for evidence of your exact migration type, not general Microsoft experience.
- Ask who does the work and whether any of it is subcontracted or offshored.
- Ask how cutover, rollback and user communication are handled.
- Ask what is excluded from the fixed price.
- Ask what documentation and knowledge transfer you receive at handover.
Experience and evidence
General Microsoft credentials do not prove migration skill. Ask for specifics that match your project.
- How many migrations of this type have you delivered in the last two years?
- Can you share an anonymized case study or reference of similar size?
- What went wrong on a recent project, and how did you handle it?
- Can we see a redacted runbook or cutover checklist?
Discovery and planning
Good answers here predict an accurate price and fewer surprises.
- What does discovery cover, and what do we receive at the end of it?
- How do you find apps, scanners and devices that send mail through our server?
- How do you assess identity: UPNs, Entra Connect, MFA and Conditional Access?
- How do you size data: mailboxes, archives, OneDrive, SharePoint and file shares?
- How do you decide waves and pilot groups?
Cutover, risk and rollback
This is where migrations succeed or fail, so press for detail.
- How is data pre-staged so cutover only syncs recent changes?
- Which DNS records change at cutover, such as MX, Autodiscover, SPF and DKIM, and when?
- What is the rollback plan if a wave fails?
- How do users learn what to expect, and who supports them on the first morning?
- How are shared mailboxes, delegates and calendar permissions verified?
People, pricing and contract
Make sure you know who you are hiring and what you are paying for.
| Question | What a good answer looks like |
|---|---|
| Who will do the work? | Named specialists, no undisclosed subcontracting |
| Is the price fixed? | Fixed price for a written scope set after discovery |
| What is excluded? | A clear list of exclusions and assumptions |
| How are changes handled? | A simple written change process with pricing up front |
| How often will we hear from you? | Structured check-ins with a set cadence and status report |
After the migration
The project does not end at cutover. Ask how long hypercare lasts, what documentation you receive, whether your team gets knowledge transfer sessions, and whether ongoing support is available as a separate agreement. Ask what security settings are reviewed after migration, such as MFA, Conditional Access and legacy authentication.
Also ask how old source systems are decommissioned and when, so you are not paying for two platforms longer than needed.
How to use the answers
Send the same written questions to every firm you are considering, along with a one-page summary of your environment: source platform, user count, data volumes, domains, identity setup and devices. Ask for answers in writing so you can compare them side by side.
Score answers on specificity. A firm that names the tools it would use, explains why, lists assumptions and identifies risks in your environment is showing how it will run the project. Generic answers that could apply to any client usually mean the real planning has not happened yet. Follow up on any answer that sounds like a promise without a method.
How Accred Consulting approaches it
Accred Consulting expects these questions and answers them in writing. Discovery produces an inventory and risk list, and the Proposal sets clear scope, assumptions, a fixed price and a timeline. Clients work directly with the US-based specialists assigned to the engagement, with no offshore handoffs. Delivery includes structured check-ins, and Handover includes documentation and knowledge transfer, with optional Support retainers. Anonymized case studies covering tenant-to-tenant, Google Workspace, Exchange, SharePoint, security and Intune work are available for review.
Track record: 400+ client projects, 2,000+ migration workstreams and 150,000+ users migrated by a US-based team. Company facts · Case studies
Related questions
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