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This achievement is easy to be done in the case The fallen Idol.
You have to tail June to a cafe during this tail an icon will be shown on the map if the icon starts to fade you're to far away. If the icon starts flashing you're to close. She'll stop at an cafe to make a phone call. Take cover at the door entrance of the cafe. Before entering make sure she has started her call. Walk in and walk to the 2nd booth with the news paper on it. Go sit there and use the newspaper as cover. As soon she left the cafe this achievement should pop up. If not press quit and than Resume. The game will resume from the last checkpoint wich might be at the start of the tailing but also might be when she walks into the cafe.