This achievement will unlock regardless of which lifepath you choose. It is however missable.
During story and side missions you will have various dialogue options. When either the Nomad, Streetkid or Corpo option are available, choose them.
The tracker correctly monitors these so you can see how many are left to do. There are many more opportunities to use different dialogue options than just the 10 that are needed.
You'll more than likely unlock this around halfway through the story, assuming of course you don't finish any side missions.
Below I have added what the dialogue option looks like.