When you talk to Diego as part of the main quest, if you pick the right dialogue choices you can unlock this achievement. You want to appear to his ego, more or less.
The options you want to choose are:
1. Appease
2. Direct
3. Deflect
4. Bait
It can probably also be gotten with the social augmentation mod, but there is little reason to waste Praxis points on it in the game.