Sometimes you know that the question you want to ask is unwelcome. You then debate whether you should ask or not. If you ask you'll reap the wrath of those annoyed and angered by the question, but if you don't ask, the information unknown could lead to a troubling lack of awareness and consequences.
The wise ones amongst us generally ask the questions using humor and a bit of self deprecation so that they don't incite those who may be annoyed by the question. Others remain silent and don't ask, and still more may ask abruptly creating dismay.
Not long ago there was a question I wanted to ask, and I remained silent. It wasn't a big deal and I knew that if I asked the question, the result would be annoyance, bother, and perhaps a harsh response. I let it go and I'm watching the situation roll out. I suspect that had I asked earlier, some money may have been saved and there may have been a greater impact with regard to the initiative, however I'm unsure, and as I stated earlier, it's not a big deal and the it may have been the right decision to stay silent.
You always have to weigh the situation of asking versus not asking. If a child's welfare is involved, you have to ask. If it may mean considerable senseless effort, time, or money, you have to ask. If it's a small situation, staying silent might be the best course of action.
Step by step we wander the paths of decision making, and the more we have our end goals and overarching values in mind, the better we'll decide.