It took Osman Yaya, a 12-year-old from Bennett Middle School in Salisbury, Maryland, and his skilful town hall moderating to tease out details about Obama's early reading habits, his post-presidency plans and his facility with digital media.
Middle schoolers at a Washington library and students watching online may have puzzled over Obama's reference to the Hardy Boys, just like Obama appeared stumped by Osman's mention of Alex Rider.
Obama was at the Anacostia Library in Washington for a "virtual field trip" with students to promote White House initiatives to make free e-books available to low-income students and to get cities to provide access to universal library cards.
"And our first question is from Mrs. Cook's second-grade class at Pinegrove Elementary School in Alabama," Osman began. "They asked: 'As a child, did you enjoy reading?' Well, you said you loved reading, so that question is done. And they also asked: 'If so, what type of books spark your imagination and interest?'"
Obama conceded that the youngsters probably didn't read the Hardy Boys mysteries anymore and said he had been fond of the book "Treasure Island." What did Osman read, he asked.
Osman described the Alex Rider spy books and their gadgets and offered to lend Obama some books. Then, with a bit of sympathy, he added: "To make you feel younger, my best friend read 'Treasure Island.'"
When Osman asked why it was important to have access to electronic books, Obama, a father of two teenage girls, revealed every parents' knowledge of the digital age.
"So you're texting all day and you're looking at Vine and Instagram, and you're looking at Grumpy Cat or some video of your favourite singer, rapper," Obama said. "What that means is, is that we want to make sure that that becomes a tool not just for entertainment, not just for talking to your friends, but also for learning. "
Asked what inspired him to be president, Obama conceded he had once harboured wishes to be an architect or basketball player but was ultimately inspired by the civil rights movement. As for his post-presidency career, the president seemed to suggest he might just return to his old job as a community organizer.
"I'll still be pretty young," he said. "And so I'll go back to doing the kinds of work that I was doing before, just trying to find ways to help people — help young people get educations, and help people get jobs, and try to bring businesses into neighbourhoods that don't have enough businesses."
But when Obama got a little garrulous on a question about how to avoid writer's block, Osman politely stepped in: "Yes. And I think you sort of covered everything about that question."
It was a bold move. White House reporters were taking notes.