My buddy Adam Marelli just presented a talk at the B&H Photo Space talking about feeling more comfortable approaching strangers and photographing them while incorporating compositions and more. Definitely recommend the in-depth 1 hour and 50 minutes.
Also to learn more from Adam, check out his other talk on how to incorporate design & composition into your work (one of the finest out there). If you want to learn more from Adam, check out his upcoming workshops here.