To me this is the fundamental question of the 2016 election.
For some reason this is a sensitive question. I'm not sure why. Maybe Robby Mook sucked. Maybe misogyny as a voting influence is deeper than racism as a voting influence. Maybe voters weren't happy with the results of 8 years of Obama. Maybe 25 years of media attacks on Clinton did their job. Maybe Clinton was a horrible campaigner. Maybe her proposed policies sucked. Maybe the media didn't talk about policy (they never do, so of course). Maybe CNN becoming "The Donald Trump" show for 10 months or so did it. Maybe Clinton's ad campaigns sucked. I actually don't have any answer, and of course one can invoke any and all of these things to throw the necessary couple of hundred thousand voters in the right places to Clinton.
Whatever the reasons, Hillary Clinton lost to Donald Trump in part because people who voted for Obama once or twice didn't vote for her. Figuring out why matters if Democrats want to win.