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AI workplace coach that gives real-time, personality-aware advice on handling a colleague or a tricky message.
Ask Olivia is a workplace communication coach built by Personality Wise, a UK-registered company. It offers guidance on day-to-day workplace situations such as giving feedback, resolving conflict, or wording a tricky message, tailored to what it knows about the personalities involved, and it connects to Microsoft and Google accounts rather than requiring a separate inbox. The free Starter tier covers basic coaching and limited email help; paid personal plans unlock unlimited coaching, unlimited email assistance, or both, billed monthly or at a discount yearly. A separate Business tier for managers adds directory-wide insights, conflict analysis, and reporting at custom pricing.
Cheapest paid option is $9.50/month for either unlimited coaching or unlimited email alone; combining both is $14.50/month, with roughly 20% off on annual billing. The Business tier for managers is quote-based.
Use tool ↗Ask Olivia gives on-demand workplace-communication coaching that adapts to what it knows about a colleague's personality, aimed at everyone from individual contributors to managers and executives. The free tier is real but limited, and the more useful unlimited coaching and email help sit behind a low-cost personal subscription.
Watch out: The Business-tier listing both advertises API access and separately states there is no API access to bots, so confirm that detail with sales before assuming it is included.
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