Microsoft 365 Adoption Trainer & Facilitator

We are looking for an experienced Microsoft 365 Adoption Trainer / Facilitator for a short-term freelance assignment supporting a large international organization in Italy.

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Ideal candidate location : Lombardy region

Travel required: Onsite delivery mostly in the region of Milan

Target delivery: First two weeks of November 2026

Language: English

Contract: Freelance / Consulting

The assignment involves preparing and delivering practical, interactive Microsoft 365 adoption events, helping employees collaborate more effectively and get greater value from Microsoft 365.

We are particularly interested in profiles combining Microsoft 365 expertise with training, adoption/change management and facilitation skills.

Key expertise includes Microsoft Teams, SharePoint Online, OneDrive, Outlook, Microsoft Loop, meeting/collaboration tools and Copilot Chat.

Candidates should have proven experience delivering instructor-led Microsoft 365 training, engaging audiences with different levels of digital maturity, creating practical live demonstrations and translating real business needs into Microsoft 365 solutions.

Experience delivering adoption programmes within large international, manufacturing, laboratory or frontline environments would be advantageous.

Goals and deliverables

• Training preparation
  • Review the existing Microsoft Days programme, materials, demonstrations, and learning objectives.
  • Prepare or improve presentation materials, facilitator notes, demonstrations, exercises, and participant resources.
  • Adapt examples and terminology for an Italian audience.
  • Work with the project team and local contacts to understand site-specific requirements.
  • Help select up to three or four locally relevant business use cases.
  • Prepare realistic demonstrations using Microsoft 365 scenarios.
  • Validate that demonstrations can be delivered reliably in the available technical environment.
  • Participate in preparation and rehearsal sessions before the onsite event.
• Onsite delivery
  • Deliver a full-day Microsoft Day in Italian.
  • Facilitate sessions on Teams, SharePoint, OneDrive, meetings, Loop, knowledge sharing, Outlook, Copilot Chat, and other Microsoft 365 productivity capabilities.
  • Use live demonstrations and practical examples rather than feature- only presentations.
  • Encourage participant interaction and answer functional questions.
  • Facilitate the “Ask the Experts” session and help translate employee needs into potential Microsoft 365 solutions.
  • Adjust the level of detail to accommodate participants with different levels of Microsoft 365 experience.
  • Promote continued adoption through internal Microsoft 365 resources and Boosters network.
• Follow-up
  • Capture recurring questions, adoption barriers, and potential use cases.
  • Provide the presentation, facilitator notes, and reusable training content after the event.
  • Submit a concise post-event report covering participation observations, frequently raised questions, improvement opportunities, and recommended follow-up actions.
  • Incorporate agreed feedback into the reusable training package.
• Required profile
  • Demonstrated experience delivering instructor-led Microsoft 365 training.
  • Strong practical knowledge of Teams, SharePoint, OneDrive, Outlook, Microsoft Loop, meeting collaboration, and Copilot Chat.
  • Ability to build and deliver reliable live demonstrations.
  • Ability to connect Microsoft 365 capabilities to real employee and business scenarios.
  • Excellent facilitation, presentation, and audience engagement skills.
  • Native or fully professional Italian.
  • Experience supporting Microsoft 365 adoption or change-management initiatives.
  • Ability and willingness to travel within Italy when required.
• Preferred experience
  • Microsoft certification related to Microsoft 365, adoption, training, or Copilot.
  • Experience delivering onsite learning events for international organizations.
  • Experience with manufacturing, laboratory, office, or frontline-worker environments.
  • Experience training audiences with mixed levels of digital maturity.
  • Experience gathering feedback and measuring training usefulness.
• Assignment format
  • Short-term freelance or consulting assignment.
  • Preparation and rehearsal before the event.
  • Onsite delivery at one or more Italian locations.
  • Possible travel between locations. xysqume
  • Exact dates and sites to be confirmed.
• Expected skills
  • Microsoft Sharepoint – Expert
  • Microsoft Teams – Expert
  • Microsoft Onedrive – Expert
  • Microsoft Workplace – Expert

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