I had a problem getting this achievement first time round. Like the comment on the previous guide I qualified first in all of the races in a championship, but still no achievement :(
The problem is that you have to officially finish the qualifying session for the pole to count towards the achievement. This is how to ensure that your qualifying position is registered:
Follow these steps for each race in a championship.
- enter the qualifying session, either by playing through the 2 free practices of by using the Session Selection option in the pit menu.
- set a pole qualifying time (duh)
- pause the game and select "return to pit".
- once back at the pit menu, press Y to advance the session clock in the top right of the menu. This counts down to "00:00" then ends the session.
- look at the registered qualifying times.
- press A to advance to the raceday.
Your pole position is now locked in for the cheevo, only 7 more to go.
I got this achievement on medium with penalties off, so it can be achieved without turning them on.