Ask Olivia
Verified Oct 15, 2026 ActiveAI workplace coach that gives real-time, personality-aware advice on handling a colleague or a tricky message.
Listed on EffectHub ·
Pricing
- Pricing model
- Freemium
- Paid options from
- $9.50/mo
- Billing
- Monthly
Cheapest paid option is $9.50/month for either unlimited coaching or unlimited email alone; both together are $14.50/month. Annual billing is 20% off ($91 a year per module, $139 for both). The Business tier for managers is quote-based with a trial on request.
Use tool ↗About Ask Olivia
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.
- Platforms
- Web
- API
- Not confirmed
- Last verified
- Oct 15, 2026
Verified sources
- Pricing page: Starter free with limited coaching; Pro Unlimited Coaching or Unlimited Email $9.50/month each, both $14.50/month; annual $91 or $139 a year (20% off); Business on request, footnote 'no API access to Bots' (15 October 2026)ask-olivia.com ↗
- Home page footer: registered in UK, company number 14128948 (15 October 2026)ask-olivia.com ↗
Is Ask Olivia legit?
We don’t label tools safe or unsafe. Below are the records we checked ourselves, each with the date we read it.
- Domain registered
- Jun 20, 2025 (1 year ago)Registry record (RDAP), registrar IONOS SE, looked up Sep 11, 2026
- TLS certificate
- Issued by Google Trust Services, valid until Jan 10, 2027Seen in our own connection to the site on Oct 15, 2026
- Last checked
- Oct 15, 2026The site answered
- Operated by
- Personality Wise, United KingdomOur research, card verified Oct 15, 2026
Pros & cons of Ask Olivia
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.
Pros
- Separate low-cost tiers for coaching-only or email-only use
- Free Starter tier includes some real coaching, not just a demo
- Integrates directly with Microsoft and Google accounts
- Business tier adds organization-wide conflict and engagement insights
Cons
- Business-tier API access is described inconsistently on the pricing page
- Coaching quality depends on how well the tool has profiled the people involved
- No published pricing for the Business tier
Best for
- Managers wanting quick guidance before a difficult conversation
- Individuals drafting a sensitive message to a colleague
- Teams already using Microsoft or Google workplace accounts
Not for
- Organizations wanting a dedicated HR case-management system
- Anyone needing licensed therapy or formal HR-compliance advice
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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