Whatever you think of the book, I found (always find) Frank Rich's observation's worth a read. New York Magazine:
I have sympathy for [Obama], too, and I have heard him express that (charming and genuinely modest) amazement that he ended up sitting in the White House, the most unlikely president imaginable. His turning to Rubin during the transition — as he hired his economic team — may have been out of some understandable human insecurity. Or was it because he's too easily impressed by the type of elite he met at Harvard? Whatever. But beyond the bad hiring choices, it was also a bad meta-policy choice, period, to put jobs on the back burner for eighteen months while pushing health care.
Suskind also nails, I think, Obama's intellectual blind spot. Indeed, Obama himself nails it, telling Suskind that he was too inclined to search for "the perfect technical answer" to the myriad of complex issues coming at him. What he'd end up with instead is, as Suskind astutely summarizes it, "clever" answers that were "respectfully acknowledging opponents' positions, even those with thin evidence behind them, that then get stitched together into some pragmatic conclusion — but hollow." That said, could someone else have done better? Not the out-of-it McCain, not Hillary (an equivocator in her own right and one who would have embraced the same Clinton administration alumni and Wall Street crowd that Obama did). I still believe Obama was our best hope, and I still hope, however quixotically and self-deludedly, that he might learn from his mistakes.