Just because someone doesn't speak up doesn't mean they agree with what you are doing. A culture that discourages open dissent will face surprises and unexpected actions from its participants. Its not enough to wait for someone to speak out, one needs to encourage others to speak up without any fear of retribution. The culture of the Bush Administration, for better or worse does not encourage dissent. Which is why generals may not say they need more troops when they do (and why when administration officials express bewilderment to a general's criticism and say if they had been asked for more troops they would have provided them is not entirely believable).
Former press secretary Scott McCellan's apparant disillusion with this administration is a good example of this.