Great question Jordan Gross and you are right — context is very important. My first reaction is that Simon Sinek can afford to wait — he is fucking cool. But in all seriousness (and I may write a post about this question) as the answer may be too long for a comment (thanks for that) — In a group setting listening and thinking may be best as if you make a well thought on comment you may get remembered more, but when it comes to people you walk by everyday on the street going first is never a bad idea. Every time I do this I am reminded of how interesting each person is and have met a few people I did not know where “important” by doing this — Editorial Director for GQ — dude who ran a marathon on all 7 continents to build schools etc and this came by seeing a T-shirt that interested me and saying something about it.
As an introvert in the world of sales I tend to go first to hide my introvertism (if that is a word) and ask questions and listen to take the pressure off of me which works in my favor as I am good at recognizing peoples needs. I kind of fake confidence to get to my strenghts if that makes sense.
Really appreciate the question and if I get the time to go into this deeper I will let you know. Keep asking these kinds of questions — best one I have gotten in a while.