Here is my video playthrough, but for more specifics:
1. Start the mission, and gain access to the elevator via the receptionist.
2. Go up one floor to the first floor.
3. Talk to the first person.
4. Pick an available clerk and talk to them.
5. When you respond, make sure you respond with Conway's dialogue. This will direct you to another clerk.
6. Go to that clerk, use Conway's dialogue, move to the next.
7. Talk to each three times, doing three loops, thus unlocking the achievement.
* Use Shannon's dialogue to continue on afterwards in the mission.