Describe a situation when you convinced an adversary of something.
If Obama wasn't naive about the political reality, he may have had too much faith in the play he kept running: Look reasonable so people will see that Republicans are overstepping. It didn't really work. It didn't cow Republicans. Their approval ratings sank, but their positions didn't change, and Obama's status with voters didn't improve as he'd hoped it would by using the GOP as a foil.
The president also probably had an outsize opinion of his own powers of persuasion. "One of the things I'm good at is getting people in a room with a bunch of different ideas who sometimes violently disagree with each other and finding common ground, and a sense of common direction," Obama told "60 Minutes' " Steve Kroft. "And that's the kind of approach that I think prevents you from making some of the enormous mistakes that we've seen over the last eight years."
This was a theory largely untested by reality. Obama had worked with Republicans in Illinois, but that was a much smaller playground and he'd only done it for eight years. In the United States Senate, there was virtually no evidence of his persuasive powers on any meaningful issue. In the early days of his presidency, Obama couldn't even get his own economic advisers to agree, let alone Republicans.
Mitt Romney propagates a similar notion. It's the myth of smart people in a room and the ability to wrangle a way forward from knowing how to conduct them. But what if the smart people in the room don't want to agree with you? If they're members of Congress, you can't fire them. You can't engage them in collective action for the good of the share price. They are trading on an entirely different market.