The Admin That Never Ends: Dilani Kahawala on Building Anna

Georgie Healy talks to Dilani Kahawala, who built Anna, an AI assistant for parents. Anna connects to your emails and calendars and surfaces what needs your attention through iMessage or WhatsApp, like a change to the swimming carnival instructions.

They open on the admin that never stops. Georgie shares the day she completely forgot to pick up her son from school, and Dilani explains the mental load, why she carries her husband's admin in her head too, and the guilt of letting other volunteer parents run the school WhatsApp group.

Dilani describes building Anna, from hundreds of hours of data labeling so an AI trained mostly for coding learns that soccer matters and a Pilates discount doesn't, to the nine experiments and the pivot from enterprise to consumer. She also covers privacy, saying Anna never sells data and doesn't train on it.

The second half turns to kids and AI. Dilani has already introduced AI to her eight-year-old, but doesn't want him using it to get the answer, and argues that learning to think critically is the skill that matters most. She says waiting until kids are 15 isn't the answer, supervision is, and she's honest that she doesn't know how humans stay in control once they stop understanding what AI does. The episode closes with a round of What's Harder, from theoretical physics versus the school pickup to naming a startup versus naming a child.