Office 365 Readiness Assessment: Is Your Business Ready?
25-point interactive checklist covering infrastructure, data, users, security, and planning. Find out if your business is prepared for a smooth Microsoft 365 migration.
Before you migrate a single email to Microsoft 365, there is one question that determines whether your project succeeds or fails: Is your business actually ready? Most migration disasters — downtime, data loss, angry users, emails in spam — trace back to skipped preparation steps.
This interactive 25-point readiness assessment evaluates your infrastructure, data inventory, user preparedness, migration planning, and security posture. Complete it honestly, and you will know exactly what to fix before migration day.
Your Readiness Score
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Interactive Readiness Checklist
Infrastructure
0/8 checkedData & Content
0/6 checkedUsers & Training
0/4 checkedMigration Planning
0/7 checkedSecurity & Compliance
0/4 checkedWhat Your Score Means
0–49% — Not Ready
Major gaps exist. Migrating now carries high risk of downtime, data loss, or post-migration issues. Complete the critical infrastructure and data items first.
50–79% — Partially Ready
Core items are in place but some gaps remain. You can plan migration with these items flagged as risks. Address remaining critical items before go-live.
80–100% — Ready to Migrate
Your business is well-prepared. You have verified infrastructure, inventoried data, planned the timeline, and addressed security. Proceed with confidence.
Email Your Assessment Results
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Top 5 Readiness Gaps We See (And How to Fix Them)
Domain ownership is unclear or expired
CriticalLog into your domain registrar and confirm the registration is active. Ensure you have admin access to update DNS records (MX, SPF, DKIM, DMARC). If someone else manages your domain, get delegated access before migration.
Total data volume is unknown
CriticalExport a report from your current email admin panel showing total mailbox sizes. Add 20% buffer for growth during migration. If total data exceeds 500GB, plan for a multi-day staged migration rather than a single cutover.
No backup exists before migration
CriticalUse a third-party backup tool (like Veeam, SkyKick, or CodeTwo) to create a full export of all mailboxes before day one. Alternatively, export PST files for each user as a fallback. Never migrate without a verified backup.
Users have not been told about the migration
HighCreate a communication plan: announcement email 2 weeks before, reminder 1 week before, daily updates during migration, and a "all clear" email after cutover. Include training dates and a single point of contact for questions.
SPF/DKIM/DMARC records not documented
HighUse MXToolbox or Google Admin Toolbox to inspect your current DNS records. Screenshot or document every record. After migration, these must be updated to reflect Microsoft 365 endpoints or your emails will land in spam.
Frequently Asked Questions: Office 365 Readiness
QWhat is an Office 365 readiness assessment?
QHow do I know if my business is ready for Microsoft 365?
QWhat are the most common reasons Office 365 migrations fail?
QHow much data can I migrate to Office 365?
QDo I need to backup my email before migrating to Microsoft 365?
QHow long does an Office 365 readiness assessment take?
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We conduct full readiness assessments, handle every migration step, and guarantee zero downtime. Get a fixed-price quote within 24 hours.