This achievement occurs during Episode 1 - It's About Time.
Once inside Edna's apartment do the following:
• Walk to the left side of the room.
• Interact with Pictures.
After 1-3 times you will select the picture of Marshal Strickland, Edna will then give dialog about Marshal Strickland and the achievement will pop. (Picture order is random)
Here's a video
Credit to T_l_M_B_0 of PST