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The problem is he's running against several people with experience who could argue they have good judgement as well. For Obama to argue he has good judgement means nothing. He has to show it, not say it. Show it by explaining his policies, his beliefs. Show what he can do, don't tell it.
He's really showing his political inexperience. He's lasering in on every criticism, trying to prove his critics wrong. He's under the impression that he has to convince people the experience isn't a big deal, but every time he brings it up, he makes people think about it. It's a classic mistake in politics (and in sales, incidentally). Rather than focus on people's objections to him, he needs to focus on his strengths, steer the conversation away from his weakness. Make people want him for what he has. When he began campaigning, his numbers were high, but he was no more experienced than now. It isn't the experience that people liked, and they didn't miss it. It was his passion, his focus, his insight, his optimism for the future. That's his strength, and every time someone steers him away from that, he needs to ignore them and get back to it. When Clinton calls him "naive," he shouldn't get upset, he shouldn't object. He should just show he isn't. "It's naive to take nukes off the table," she says. He should respond "I will not be the president who launches nuclear weapons at an innocent population. America can and will find a better solution when I'm president." That cuts off her point, makes her look less idealistic, and makes him look like a leader.
Instead, he argued that he wasn't naive, that experience wasn't everything, that Clinton's policies were Republican-lite, that Rumsfeld and Cheney had experience and were still bad. None of that showed what he can do, none of it sold anyone on anything positive about him. He's becoming defensive, and that never looks like leadership.
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