What kind of firm are you in (and perhaps more important: country/culture)? I've actively been a friendly pita wherever I worked and always found people to help search for answers, even if the question was not really in the line of work. Have a discussion related to tax and payrolling going on right now. Couldn't make sense of company policy even when reading / quoting the law (ianal). Still the surroundings stay friendly (or I'm in massive bubble). Getting into trouble for having a (truthful) opinion, sounds like a showstopper to me. Just don't email the big shot CEO if you haven't got your story straight, that would be my perferred level of openness.