PWPM Wiki

Microsoft 365 Migration Lessons Learned

This is a practical guide to building a lessons learned for a microsoft 365 migration project — what went well and badly, captured to improve future projects, adapted to the realities of migrating email, files and collaboration to Microsoft 365.

What a Lessons Learned is

A lessons learned is what went well and badly, captured to improve future projects. For the full concept and how it works in general, see Lessons Learned. On a microsoft 365 migration project it plays the same role, tuned to this kind of work.

Why it matters for a Microsoft 365 Migration project

Microsoft 365 Migration projects live or die on migrating email, files and collaboration to Microsoft 365. A well-built lessons learned gives the team a shared, explicit reference for exactly that — reducing ambiguity, aligning stakeholders, and making problems visible early enough to act. Skipping it, or doing it generically, is how microsoft 365 migration projects drift into avoidable delay and cost.

What to include

  • What happened
  • Impact
  • Root cause
  • Recommendation

Microsoft 365 Migration-specific considerations

Tailor the lessons learned to the risks that most often derail microsoft 365 migration projects:

  • Mailbox and file migration errors
  • User adoption and training
  • Security and compliance configuration

Example

On a real microsoft 365 migration project, the lessons learned would be shaped by migrating email, files and collaboration to Microsoft 365. In particular, it should explicitly account for the project’s biggest risks — mailbox and file migration errors, user adoption and training, security and compliance configuration — rather than treating them as afterthoughts.