I always try to set a top10 lap before entering a race. More often than not, I get pole - I have ~50% or something but in the beginning I wouldn't care so much about the starting position because I didn't even though I could make it into the top10.
I don't enter a lot of races though, even if I have lots of fun practicing and setting flying laps by myself. I avoid tracks and cars I don't like so much or don't know yet as well as some others - on S/S level, not getting a sector right means you won't win a race at all.
Do you win all the races you start on pole? Do you leave the lobby is you see you're not on pole?