Ask Olivia

Ask Olivia is an AI workplace coach that adapts guidance to each colleague's personality, helping managers and individuals give feedback, handle conflict and write messages that land. It targets onboarding, 1:1 preparation and day-to-day collaboration, with executive-level culture insights. Pricing is not shown on the homepage.

Ask Olivia is a workplace coaching tool built around personality awareness. It pairs an AI coach with profiles of how each colleague prefers to communicate, so advice on feedback, conflict and everyday messages is shaped by the actual person on the other side of the conversation. The product is made by Personality Wise, a UK-registered company, and is pitched as a way to help teams understand each other rather than a generic writing assistant. In practice, Olivia sits where work already happens. The site stresses tailoring messages inside existing workflows, and there is a dedicated integrations page, so the intended pattern is drafting an email or preparing a difficult conversation without leaving the tools a team already uses. Users can ask Olivia for guidance at any time, with pre-1:1 preparation and key collaborations named as the moments where quick, actionable answers matter most. There is also onboarding use, where new colleagues learn each other's communication styles and ways of working from day one. The audience runs from managers and team leaders who want to give feedback that lands and resolve friction, to individuals who want stronger working relationships with peers and managers. Executives get a separate pitch around organizational insight, culture and employee relations risk, supported by a business benefit page and testimonials from a first-time manager, a lead developer and a CEO, plus a Cambridge-linked research post claiming most workplace emails were improved with personality-aware AI. Competitors here are broader writing assistants and generic coaching chatbots; Olivia's difference is the personality layer rather than raw text generation. The homepage does not publish prices, plan tiers or a free trial, so cost has to be settled through a demo request or the pricing page. The platform is a web app reached through a login portal, with no desktop or mobile client described.