"On Obama" is a weekly column about Barack Obama and American politics.

On the morning of Nov. 5, 2008, the day after Barack Obama's election, I sat in the office of my Chicago apartment, filled, like most Americans, with a peculiar sense of hope. It seemed that in electing the country's first black chief executive, we'd finally taken a huge step toward becoming a true meritocracy. My friends -- an educated, well-traveled, multiethnic bunch, very much a reflection of Obama's world -- were convinced that the moment signaled the country's new understanding of the tricky road talented African Americans climbed toward professional success -- the "double consciousness" that W.E.B. Du Bois described.

Post-civil rights era blacks who'd invested years overachieving at the best schools and cultivating key relationships at top firms now had more reason to believe that we'd have a credible shot at making partner. Or becoming senior managers at new-media outlets that had apparently broken from the old guard.

Of all the narratives crafted about Barack Obama's presidency so far, few have seriously explored a richly distinctive vein: What is Obama's tenure teaching America about how black executives -- particularly men -- lead? And what role will race play in his assessment this November?

These are hardly trivial questions. Nearly a half-century after the civil rights movement's peak, senior black executives remain a relatively rare phenomenon. The pot of Fortune 500 CEOs who are black is so small, they can be counted on one hand: notably Ursula Burns, of Xerox; Kenneth Chenault, of American Express; and Clarence Otis Jr., of Darden Restaurants, the $7.5 billion purveyor of Olive Garden and Red Lobster.

In many ways, Obama is like any other senior black executive at a blue-chip firm -- except, of course, his case is extraordinarily magnified. It takes a certain mix of restraint and audacity to believe that one can climb from organizing residents on Chicago's South Side to the corner suite -- or the White House -- and still keep a sense of blackness, however that's defined, intact.