how will this work? is this proven to be effective? cuz this sounds really strange to me. how will you compensate when you accidentially pick someone with similar problems like you have? or just some aggressive idiot. i would react quite beside my normal self if someone i don't know comes along and tries to engage me in a conversation for no reason. don't get me wrong, but people approaching me and start chatting out of the blue normally want to sell me something or are trying to distract me in order to cover that guy that tries to steal my wallet. especially in coffee shops or bars or the like. this happened twice to me already. i've grown quite suspicious to behaviour like that, since i've been too friendly with most people. many of my friends did as well. dunno if this is just a problem with bigger towns but i think a better way would be that the professional you're talking about accompanies you for maybe a week and watches you in situations that simply happen and you have to face in everyday life and does not try to get his impressions from forced engagements from your side like the 'start conversation' you mentioned. dunno if you get my meaning..
One of the major differences which you have to take into account is the cultural background. In Germany it is quiet unusal to engage in a conversation with a total stranger. Katie please correct me if I'm wrong, but in Canada people tend to be more open to such conversations. So it might be a natural thing to practice this.