Assigning a portrait is far more complicated than you might imagine. Before I can select the photographer, my job as the photo director is to wrangle the subject. How much time can we carve out of his or her schedule? What will the person agree to do for the shoot?
There’s a lot of back and forth with publicists and managers, and if I’m lucky, I can convince them to give us enough time to create something original. In recent years, it has become increasingly difficult to create a memorable situation for portrait photography. Most subjects will offer only a short window of time. Steve Jobs, for example, gave us two minutes for his cover shoot! This means choosing a photographer who can create an iconic image for a TIME cover in a matter of seconds. I have to place my bet on who is going to nail it.
This gallery is a selection of some of my favorite portraits from my years at TIME and The New York Times Magazine. I love working with so many of these pros, especially Mark Seliger, Marco Grob, Peter Hapak, Platon, and Nadav Kander.