The first time this achievement can be earned is in The fallen Idol mission on the Traffic Desk
As your finishing your visit to the Hospital a short cut scene will play showing June leaving with her lawyer. The Dectectives decide to follow her to see where she goes.
Things to note:
If the icon starts to fade you're to far away.
If the icon starts flashing you're to close.
Also don't use the siren
Try to avoid crashing into cars
Once you've followed her around for a short time, she'll come to a stop outside a cafe and go inside. Cole will jump out the car. What your want to do before going in is use
to take cover by the door so you can see in. Once the person in front of June has hung up, wait until she turns to use the phone, at this moment press
again and walk inside, the second booth on the left has a newspaper on it, press
to interact with it. Cole will sit down and listen in on the conversation. After she's finished the call wait for her to leave first before getting up from the booth. Your be given your next objective and the achievement.