Mike Kelleher, director of the White House Office of Correspondence, said he chooses 10 letters among the thousands sent by citizens everyday and personally delivers the missives in the daily briefing book to the president. Obama then answers them by hand, the Times reported.
"We pick messages that are compelling, things people say that, when you read it, you get a chill," Kelleher told the Times. "I send him letters that are uncomfortable."
The president regularly receives mail from fans offering words of encouragement as well as critics, who have started letters with such lines as "I didn't vote for you."
Kelleher sorts the letters according to addressee (including the First Lady and White House dog), and then selects the ones he thinks best represents what Americans are thinking.
One letter that made it into Obama's hands came from Cynthia Arnold, a Pennsylvania woman whose son Matthew called her to ask who would make his funeral arrangements in the event of his death.
"Please make our troops one of your priorities," Arnold wrote. "I beg you to spare other mothers from taking a call such as mine from their sons and daughters."
Obama responded with a hand-written note, promising to "do everything in my power to make troops like Matthew my priority."
Another letter came from Michael Powers of Tennessee, who lost his father to lung cancer and urged the president to stop smoking.
"Thanks so much for the wonderful letter, and the good advice," Obama wrote back. "I will remember your dad's memory."
The president's senior adviser David Axelrod said he's seen Obama moved to silence by some letters.
"I remember once he was particularly quiet, and I asked him what he was thinking about. He said, 'These letters just tear you up.'"
Obama has referenced the letters during policy meetings, according to White House Chief of Staff Rahm Emanuel. He told the Times he's seen the president turn to advisers to say, "I want to read you a letter I got. I want you to understand."