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Olivia AI Communication Coach

by PersonalityWise

Adapts Communications to Your Colleagues' Personality for Better Collaboration.

Olivia: Effortless Tailored Workplace Communication Powered by AI

Communicate smarter, collaborate better, and strengthen workplace relationships—all from your Outlook inbox. Olivia uses advanced AI and data science to tailor emails and messages to each colleague’s personality, giving you real-time guidance, actionable advice, and insights about yourself and your team.

Why Olivia?

  • Make every email or message count —create, rewrite, or reply in a way that truly resonates with each recipient
  • Handle tricky conversations with confidence —feedback, conflicts, or sensitive topics.
  • Boost teamwork and collaboration across your team or organization.
  • Gain insights into your own work style and the dynamics of your workplace.

Key Benefits:

  • Save Time: Fast, personalized communication assistance.
  • Expert Guidance: On-demand advice for meetings, messages, and interactions.
  • Real-Time Support: Tips and coaching exactly when you need them.
  • Seamless Outlook Integration: Works in Outlook for Mac, Windows, and Web.
  • Team & Organizational Insights: Managers can foster stronger communication, trust, and productivity.
  • How It Works:

    1. Install the Ask-Olivia Microsoft 365 Add-in.

    2. Open Outlook and access Ask-Olivia in your Apps section.

    3. Pin it to your Ribbon or sidebar for instant access.

    4. Connect with colleagues to tailor emails and advice.

    5. Use Communications Assistance to draft, rewrite, or reply to emails.

    6. Use Ask A Question for guidance on working with colleagues.

    7. Use About You for self-insights to maximize workplace success.

    How to Register & Pricing:

    Free to use.

    In order to use this app you need to have an active account or register with Ask-Olivia.

    You can do this by installing Ask-Olivia from here in the Microsoft store or by going to https://app.ask-olivia.com where you can create an account, you will be prompted to return to the Microsoft to Install and finish your On-Boarding.

    Compatibility:

    Supports Outlook Web App and Office 2016+ across Windows and Mac.

    Feedback, Support & Issue Reporting

    Need help or want to share feedback? Please go to: https://ask-olivia.com/other/contact-us

App capabilities

When this app is used, it
  • Can send data over the Internet
  • This app can access personal information on the active message, such as phone numbers, postal addresses, or URLs. The app may send this data to a third-party service. Other items in your mailbox can’t be read or modified.

At a glance

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