If he can't pick a reliable deputy to manage a single IT project how could he possibly manage a government? The President has to delegate well: Mitt either couldn't or didn't place a key service under someone reliable.
If Romney has to pick n reliable deputies for various things, then for sufficiently large n, he's inevitably going to make a mistake you can pounce on, even if he's really good at picking out people. Good judgement is not an all-or-nothing dichotomy.
Oh, certainly - I would just have thought that getting out the vote is so widely recognized as a key factor in modern campaigns that he'd have put his best people on it. Would we be talking about leadership at all if, say, many of his ads were a little ham-handed?