This heavily relies on the right RNG to trigger multiple events in a row. You will want to restart the day by returning to the main menu and then selecting “Continue” if you fail to trigger any of these events.
You need to do this before day 15. You will need to send out expeditions with a single character and purposefully get them lost by running out of action points. This will trigger a random event; however, you need to trigger the "Listen To Them, The Children Of The Night" event and choose the second option to return to camp, beginning the process of unlocking this achievement. Then send another single survivor expedition and get them lost to hopefully trigger the "Wolf Scout" event, selecting the first option to save yourself and earning “Cry Wolf”.
See the video below for more information.