When it comes to shooting casual portraits on location, I try to respond as naturally as possible. My process for finding places where I can meet with a model quite often is the result of taking a photo walk in a park or practicing street photography. If it's a place where I never worked before, I make sure to arrive an hour in advance to register the environment and explore..
Getting a solid understanding of the place often times add layers to my vision. Previsualizing portraits when I work on location don't always give me the shot I have in mind. Nonetheless, I don't beat myself up if I end up getting a completely different shot that I anticipated. Taking time to create a sort of blueprint for a specific image can offer good benefits. In my case, it allows me to maximize my time a lot better by helping me give out clear directions and also may serve as inspiration for the model to make a creative contribution to the idea.
When I met with Magdalene for our first portrait session, I knew the different areas where I wanted to photograph. I think having shared details from the location, including scouting pictures days before our first collaboration, made the process feel spontaneous, allowing me to be more responsive and create a comfortable situation for the subject during the photo-taking process.
Building experience in portrait photography comes with getting unexpected results, and becoming familiar with the location can set results in the right direction.