The other day, Democratic and Obama campaign officials were caught badly off guard by the question everyone knew was coming: “Are we better off than we were four years ago?” Why weren’t they prepared?

I caught up with Dem messaging chief Chuck Schumer in Charlotte today and asked him why Dems were caught flat-footed by such an obvious question. He demurred, and said: “To me, it’s not a hard question to answer. I can’t tell you what happened with them, but it’s a pretty easy question.”

Here’s how Schumer himself answered that question:

“We’re clearly better off. You compare January 1, 2009 to today: 600,000 jobs lost versus more than 100,000-a-month jobs gained. 4.5 million new jobs created.”

“January 1, 2009: Financial services paralized; businesses large, medium and small, can’t get any loans,” Schumer continued. “Now, financial services are in much better shape, and you can get loans. Chrysler and GM, ready to go under? Saved.”

“The average American knows we’re better off than we were the day the president took office,” Schumer concluded. “They wish the progress could be quicker. But the way America works is an optimistic, futuristic thinking country. It’s: What can you do for me in the future?”

Schumer said the convention had been carefully planned to lead up to a discussion of the future in his speech tonight.

“It’s sort of had a rhythm to it,” Schumer said. “Michelle Obama talks about who the president is, and what he believes. Bill Clinton talks about what happened in the past, and where we are up to now. They’ve teed it up perfectly for the president to talk about the future.”

Clinton did an excellent job last night taking on the “are you better off” question, and also showed that it’s possible to make a strong case for another four years in the face of a tepid and disappointing recovery.

But it still remains to be seen how much specificity Obama will bring to the task tonight of spelling out what his second term will look like. Specificity will be imperative if voters are to see this election as a choice about the future, rather than voting on the “are you better off” question or on disgust with the status quo.

By the way: Along those lines, the Romney campaign rolled out another argument today: The economy is getting worse. His new ad says: “As the economy gets worse, Barack Obama calls on Bill Clinton to help his failing campaign.” Perhaps some enterprising reporter will ask Romney or his campaign what metrics he’s using to reach that judgment.