Apple’s top software executives decided early last year that Siri, the company’s virtual assistant, needed a brain transplant.

The decision came after the executives Craig Federighi and John Giannandrea spent weeks testing OpenAI’s new chatbot, ChatGPT

. The product’s use of generative artificial intelligence, which can write poetry, create computer code and answer complex questions, made Siri look antiquated, said two people familiar with the company’s work, who didn’t have permission to speak publicly.

Introduced in 2011 as the original virtual assistant in every iPhone, Siri had been limited for years to individual requests and had never been able to follow a conversation. It often misunderstood questions. ChatGPT, on the other hand, knew that if someone asked for the weather in San Francisco and then said, “What about New York?” that user wanted another forecast.

The realization that new technology had leapfrogged Siri set in motion the tech giant’s most significant reorganization in more than a decade. Determined to catch up in the tech industry’s A.I. race, Apple has made generative A.I. a tent pole project — the company’s special, internal label that it uses to organize employees around once-in-a-decade initiatives.

Apple is expected to show off its A.I. work at its annual developers conference on June 10 when it releases an improved Siri that is more conversational and versatile, according to three people familiar with the company’s work, who didn’t have permission to speak publicly. Siri’s underlying technology will include a new generative A.I. system that will allow it to chat rather than respond to questions one at a time.

The update to Siri is at the forefront of a broader effort to embrace generative A.I. across Apple’s business. The company is also increasing the memory in this year’s iPhones to support its new Siri capabilities. And it has discussed licensing complementary A.I. models that power chatbots from several companies, including Google, Cohere and OpenAI.