Ask Olivia

Personality Aware AI to Improve 1:1 & Team Communication

?·Published on Oct 5, 2026·0 reputationReputation invested into this product to boost its ranking. Anyone can spend the reputation they've earned here — recent investments count for more and lift the product higher on the leaderboard. This is separate from community upvotes.

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About Ask Olivia

Ask Olivia uses personality-aware AI coaching to help individuals and teams communicate and work better together. Any two people can connect, creating limitless pairing opportunities allowing Olivia to scale in ways traditional coaching or generic tools can’t.

Think of Olivia as the coach on everyone’s shoulder, providing real-time guidance right in your email, chat, or through a standalone app.

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 and colleagues work style and the dynamics of your workplace.

✦ Good to know

Starter plan is free and includes unlimited co-worker connections and Microsoft/Google integration with limited coaching.
Business plan offers unlimited coaching and communication assistance with organizational insights and conflict analysis.
Provides personality-based guidance tailored to each team member for feedback, conflict resolution, and communication.
Integrates into existing workflows through Microsoft and Google integration with email and message rewriting assistance.

Taken from the product's own website and re-checked automatically.

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