Headshots and portraits have become staples of my livelihood. There are countless photographers that work specifically in this niche, and so it’s difficult to stand out through the work alone.
What really makes a headshot/portrait session special, as cheesy as it may sound, is the experience you have with the photographer. If your photographer is stiff, spending too much time tinkering with settings, or simply awkward it is going to be uncomfortable— and the results will probably reflect that.
The object of a headshot/portrait is to capture the essence of a person so that on some level you can see them through the picture. It should give you an idea of who someone is without needing to read a caption.