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...art made primarily to display technical virtuosity is often beautiful, striking, elegant... and vacant.
When you're shooting head shots, "vacant" is about the last thing you want to produce. In the context of head shots, the word "vacant," of course, refers to expression and emotional projection, i.e., the lack of it. That's not to say technical virtuosity is a bad thing or a thing that has little worth, but it's not the only thing that counts in terms of head shots that don't suck. In fact, technical virtuosity counts for far less than filling those potential vacancies: vacancies which might result when expression and emotional content are given too little care and attention because so much care and attention was focused on technique. (Especially, when people are the subjects of the photos)
Peter Hurley, a New York City-based head shot photographer, one who has gained quite a bit of recognition as a head shot shooter in recent years, didn't become the #1 go-to head shot guy in NYC because of his incredible skills with lighting and composition coupled with an all-around technical virtuosity that is nearly peerless. Trust me when I tell you there's plenty of shooters in NYC, indeed everywhere, who can light, compose, and process a shot as well as Peter Hurley can do so. Instead, he's become that go-to guy because of his abilities to fill the potential vacancies of expression and emotion via his skills at getting appropriate and engaging expressions and emotions out of his clients and recorded by his camera.
Technical virtuosity is achievable by anyone who picks up a camera and is willing to engage in the process of learning and practicing with an eye towards achieving such virtuosity. There are many, many photographers these days who have achieved a high degree of technical prowess, both in their production and post-production skills alike. We see their (technical) virtuoso photos posted on social media regularly.
But if you think those sorts of skills alone are the skills that will make you a stand-out head shot shooter, you're missing the point about head shots. Head shots are, above all else, intended to say something about the subject. Something that fulfills the purpose of the head shot. Something that reaches out and touches the photo's viewers in ways that "sell" the subject. You don't need super-exceptional technical skills, special wardrobe or props, or cool shooting locations to achieve the goals of head shots that don't suck. What you need are the right sort of people skills, that is, skills and abilities at drawing memorable expressions, attitudes, emotions and more out of your head shot subjects.
What are some of those abilities and/or how do they manifest themselves when you're shooting?
You access them by creating confidence via rapport with your subjects: confidence in you as a photographer and in themselves as the subject of the photographs. If you're unable to create confidence in themselves as the subject of the head shots -- and frankly, some people aren't ever going to be confident while posing in front of a camera -- then you do whatever else you can to "trick" the right expressions and emotions out of them; be it with jokes (they don't even have to be good jokes), with personal anecdotes or stories about yourself, by asking your subjects to recall certain events, feelings, whatever from their own lives... in other words, whatever you need to do to extract those expressions and emotions out of them for that very small fraction of a second, i.e., the duration of your shutter as needed to capture a well-exposed photograph.
Terrific head shot pics are rarely the products of a timid, overly quiet, barely interactive photographer even when that sort of photographer has notable technical virtuosity. You need to communicate. You need to use your words and actions to sometimes drag the right, make that the best expressions out of your subjects. (Best in terms of them being best for the head shot's primary purpose.) Head shot subjects aren't simply relying on you to produce technically superior photos. Yeah. They want that too. But they're also counting on you to help them deliver the right expressions and emotions. Not only help them, but to make it easy or easier for them to do so.
Anyone who thinks head shot shooting is all about photography has another think coming. It's as much about psychology and human interaction as it is about photography. In fact, it might very well be more about those non-photographic skills than it is about actual photography skills.
So, by all means. Develop your technical skills and continue working to make beautiful, striking, elegant head shot photos. But don't do so at the expense of emotions via expressions or in ways that produce "vacant" head shots. In other words, head shots that lack the sorts human elements which truly make them shine (i.e., not suck) no matter how technically superior they might or might not be.
The pretty girl in the head shot at the top is Daisy. I snapped it in daylight, adding a single, off-camera flash-- a strobe modified with a 5' Photoflex Octo. Canon 5D1, ISO 200, f/9, 125th, 135mm focal length. Very little post-processing because, with some models/subjects, not much post is needed when you get it right in the camera. Daisy is very experienced in front of a camera but that doesn't mean that when I'm shooting models with the sort of experience models like Daisy has I'm not doing/saying whatever I can to get the right sorts of engaging expressions out of her. In fact, sometimes it's even more difficult with experienced models because they often go on auto-pilot, only giving you the sorts of expressions and poses they already know work well for them, even when those poses and expressions may not work for purposes other than the sorts of photos they are normally (or mostly) featured in.