Making Good Headshots With Levi Sim

In Master Photography Roundtable by Jeff Harmon2 Comments

Everyone needs headshots. It used to only be those at high positions in bigger companies were the only people who needed professional headshots, but thanks to social media it is something everyone needs. Here is how a photographer can get started into meeting some of that demand.

Headshots Are About People

The first thing you have to do is work with people. You can’t get great headshots if you are a jerk. You can’t be selfish and make good headshots are any portrait really.

It takes a mindset that you are doing a service and are honored a person is putting their confidence in you to make a photo of them that will become one of their memories. Clients can tell very quickly if your heart is in this or not and they respond accordingly.

Most people would rather go to the dentist than get in front of your camera. They would seriously rather get a root canal that have a camera pointed in their direction. If you want to make a good headshot for them you have to help them overcome this hesitance.

Develop Your People Skills

For some this comes very naturally. With all of the photographers I have talked and worked with over the years, very few of them have said this has come naturally for them. Don’t feel bad if this is a struggle for you!

The word “develop” was chosen very carefully here. Working with a person to get them comfortable in front of a camera is a skill you can develop. For most photographers it is all about two things:

  1. Taking a real interest in the client
  2. Practice, practice, practice

If this is something really hard for you, the bad news is it doesn’t get a lot easier over time. The good news is this is a skill you can absolutely develop so that it becomes something you can do effectively. Even the most introverted of photographers!

You don’t have to wait for a headshot client to be in front of you to start practicing. Practice every day. Every time you are around people. Take a genuine interest in the people you come in contact with and practice breaking the ice until you get them talking with you comfortably.

This is not a “fake it until you make it” thing. People can tell so easily when you don’t actually have interest in them. You have to be genuine. This is a “do it until you are good at it” thing. Don’t let being introverted be your excuse, practice it until you can do it effectively in spite of it being difficult for you.

Try a Name Tag!

Here is a really different way to develop this skill. Start wearing a name tag! Levi Sim has been wearing a name tag for years and it has helped him to develop this skill. With a name tag people practically beg you to talk to them.

This doesn’t have to be anything super fancy. Very simple bar you can pin to your shirt that has your first and last name. It is magical. It draws instant attention to you and screams at people that you are legit wherever you are.

Sporting a name tag, you will see that contacting people on the street changes. There is a certain level of trust that people automatically assume when you have a name tag on. It breaks the ice almost immediately with anyone and they talk to you differently.

Headshots Need Directional Light

Headshot training usually starts off with an experienced photographer in a huge studio space with a lovely backdrop and softboxes on light stands. They often have their own brand of equipment that they would be happy to sell you and photographers leap at the chance because it is the easy button. Photographers constantly make the mistake of assuming if they have the same gear they will get the same results.

Yes, all of that gear can really help you make great headshots, but you can also make them without having to spend thousands of dollars on lighting gear you may not know how to use.

Light From The Side

Directional light means that it doesn’t come from above, like from the sun. Light from the sun can be changed to be very flattering, but without any modification a mid-day sun on a model is not flattering. We see it every single day of our lives and we are looking for something different from that lighting in any professional portrait.

Just going to a light source you can control and having it be overhead is the same problem. That will produce shadows under the nose and mouth that we all associate with snapshots or non-professional portraits. To make something look professional, those shadows need to have a different direction.

Be careful here about eliminating shadows. That isn’t the goal either, although it is different from the single source above the model and therefore can look professional. But really the character of someone gets lost and photographers refer to that kind of light as being flat. It is a little bit lifeless.

What we are looking for in a professional headshot is light coming from the side that has smooth transitions from light to dark so that it is hard to say exactly where the light ends and the shadow begins. This kind of lighting shows off the shape of the face. It adds depth and defines the face of the model. It makes EVERYONE look their best.

Directional Lighting Without Gear

Yes, you can create the light with flashes, light stands, and softboxes. But for those starting out here are a few ways to get that directional lighting without all of that gear.

  • Delivery Truck
    If you can arrange to meet a model near sunset in front of a big white delivery truck, like say a FedEx truck, you can make great headshots with just the model and your camera! Have the model stand with their back to the sun and let the reflection of the light off the truck light the front of your model.
  • Large Light Blocking Structures
    You can do this very well using building structures that block the sunlight coming from above the model and use light reflecting off the ground back to them. Something like an alley, a garage, or a stairwell. Get your model completely covered by the shade of the structure but as close to the light just outside of the structure as you can get them.
  • Shelter Canopy
    With a minor investment in a shelter canopy (like this 10×10 E-Z Up for about $150) and a reflector (like this Neewer 5-1 for about $25) you can get the flexibility of a light blocking structure anywhere and anytime. Setup the canopy and have your model stand under it so that they are entirely covered by the shade and then put the reflector on the ground just in front of them.

Minimal Gear For Directional Light Indoors

To create this directional lighting indoors the minimal kind of setup is two lights, one in a softbox modifier, and a reflector.

  • Main Light: Also called a “key light” by a lot of photographers. Flash (see below) on a lightstand inside a softbox (plus this S-Type bracket). Softbox should be at least 30 inches. Set it up left of the camera. Have the middle of the softbox even with the eyes of the model. Get it as close to the model as you can without having the softbox in the frame. Have it left enough of the camera so that it comes back toward the model at about a 45 degree angle.

    Check out my flash budget gear recommendations page for details o a really good option that is also inexpensive.
  • Rim Light: Same kind of flash on the same light stand. If budget is a concern this light can be the bare flash, but it is better to have it modified with something like a strip box (you will need that same S-Type bracket here too). The modifier helps prevent some of the specular highlights that happen on people. Set it up opposite the main light and put it behind the model. It should be roughly the same height and positioned so that it is just out of the frame.
  • Fill Light: A white reflector attached to a third light stand. This goes right of the camera to fill in the shadows on the face a little.
  • Background (Optional): If you are going to buy a background, get gray. White is actually pretty tough to use. White reflects so much light you can’t get it to be any other color besides white and you lose some of the directional light you have tried so heard to create. The Westcott 5×12 X-Drop is a very good and portable options. Less portable but offering a lot more room for portraits other than headshots is the Westcott 9×10 with this backdrop stand.
  • Tripod: Can you shoot headshots without a tripod, sure. But don’t! You can’t do a good job of directing a client and holding the camera at the same time. It is one or the other. You should let a tripod hold the camera. This doesn’t have to be a really expensive tripod, something pretty basic will do the job. There are some great and inexpensive options here.

Positioning the Model For Headshots

Now we are to the hardest part of making great heashots. Positioning the model is a challenge and learning how to direct the model so that you can make a headshot that best represents them is a skill you have to develop.

Here are some basic things to start with.

Get the Light Close

It doesn’t make sense to anyone when a photographer first starts using directional light in portraits. Entirely counter-intuitive as everyone feels like the further the lights are from the model the better. It is entirely the opposite, you really want to get that light as close to the model as you possibly can – with a couple of caveats.

First caveat is you also need to make the light source as big as you possibly can. If you are using the “free” light suggestions above then you want to get that model as close to that surface that is reflecting light as possible. If you are using flashes you need to attach light modifiers so that this tiny surfaces where the light comes out of the flash gets transformed into a big light source.

The second caveat is that you need to keep the source of the light out of the frame. The “free” light sources won’t be an issue or will make a great element in the shot for the most part. This really applies only to using flash. It is better to get everything right in camera as much as possible so don’t fall into the trap of cropping the light stand leg or edge of the softbox out of the frame if you can help it.

Shoot the Broad Side, Light the Short Side

Have the model point their nose toward the main (key – the one in front of the model) light. Maybe not at exactly the center of the light, that might be a little too far, but between there and your lens somewhere. May be a little different for everyone.

This should make it so that the person is turning to their right such that the camera cannot see the model’s right ear. You should still see their right eye and cheek, but if you can see their right ear then you should probably try turning them a bit more.

With the model in this position their left side (camera right) is now the “broad side” of their face and their right side (camera left) is the “short side”. You want to light the short side with the key light and the broad side with the reflector plus the rim or back light.

Use a Contrapposto Position

Just having the model position their head this way isn’t usually enough without also putting them in a “contrapposto” position. Contrapposto is an italian term that means “counterpoise” and is the position used most often in art by sculptors and painters. It tends to make the human body look its best.

If your key light is camera left, you have them point their nose to their right (camera left) and then point their toes to their left (camera right). This puts their hips and shoulders in contrast to each other. It is slimming and engaging.

Shoot Their Good Side!

Without question everyone has a good and bad side. The ladies tend to figure that out before the guys, but everyone has a better side. This is something you should ask the model as you are about to start shooting. Which is your good side?

Look back at the instructions on setting up your lighting. The light is setup camera left, which means the person turns their head to the right, and that puts the left side of their face toward the camera while hiding the right side of their face a bit. This was done on purpose because 60-80% of people have a left side that is their better side!

If they know which side is better and your your lights aren’t setup for that side, switch them up quickly if you have the time. Switching the lighting is a skill you should practice so that you can accommodate a different side when it comes up. If you have an assistant, this is a great thing they can do while you give some beginning instructions on posing (see next).

If they don’t know which side is their good side, they will definitely know when they see the photos. Take both sides and then let them choose which they like best. It will be their good side. Now you made headshots they are happy with and they can know going forward which side is their good side.

The one time you just can worry about this is if you are making headshots for a large group of people. You can’t hold up an entire line of people to switch up lights for a good side. In that case, take the normal shot with the “bad” side showing and then have them straighten up more than you would normally. That takes a minimal amount of time and gives them a couple of of options.

Professional Direction

So many photographers spend too much time on the technical aspects of headshots. They mistakenly believe that their primary job is getting the exposure and light right. While this does play a role in making a good headshot, this is not your primary job when hired to make a headshot for a client.

Your primary job as a headshot photographer is getting a client comfortable enough in front of that camera to look like they aren’t in front of a camera. There are very few people who are so used to cameras that they can act normal in front of them.

Here are some suggestions on how you can help a person overcome the anxiety most bring to a headshot shoot.

Tell Them You Will Tell Them What To Do!

You have a golden opportunity to put the person at ease immediately by addressing their top concern. They don’t know how to stand, where to put their hands, or how to position their head and they are worried about it.

Let them know that the only normal thing about this exercise they are going through is feeling apprehensive. Everyone feels that way about making headshots. There is nothing “normal” about making headshots but you know how to do this

Then take a few seconds to let them know you are going to direct them through this. You will tell them where to stand, how to stand, how to position their toes, their face, and their eyes. You will repeat a lot of the same directions several times. That too is all very normal.

Use A Tripod

This was mentioned above, but it is so important it is worth repeating. While this headshot shoot is happening that camera may as well be a life-threatening weapon. The person you are making headshots with is nervous at just being with you, you don’t want to be waiving your camera in your hand.

With the camera on a tripod you will be better able to provide direction. Not only does it lower the intimidation a little with your being able to distract them away from the camera while providing direction, you are able to move without restriction when you don’t have to worry about holding that camera.

When the camera is in your hand they know that a you can press that shutter button to take a picture at any second and they are constantly on guard preparing for that. You are far more likely to get unnatural poses this way.

Don’t Waste Smiles

Another thing to tell them up front is that they don’t have to spend the next couple of minutes smiling the entire time. Your job is to get them to look their best and you know how to do that. Their job is to be as natural as they can be and that means not forcing a smile on their face.

Avoid asking them to smile. At least not using that keyword “smile”. That is something they have heard their entire lives from family and friends when taking photos and they instantly go into that traditional and entirely unnatural smile they have used for years.

Let them know that you have done this thousands of times (even if you haven’t) and as you are working together natural smiles will come without having to ask for them.

Avoid Giving Negative Directions

Think of what happens when you have told a child not to do something. What happens next? They do the very thing you told them not to do. If you want a person to stop doing something, don’t tell them to stop doing that thing.

You need to tell them where to stand, how to stand, how to position their head and shoulders. You need to exude confidence as you are providing this instruction but you need to do that while avoiding negative directions.

Avoid that command to “smile” as already discussed, but there are other phrases to avoid using. You don’t tell them “shut your mouth” or even “close your mouth” because that is used in negative situations so much in our lives. Instead use phrases like “close your lips for me”, or “put your lips together”.

Another phrase photographers tend to use is “open your legs” when trying to get them to have a more open stance. Again, negative connotation to that phrase and a better one would be “open up your stance for me”. This can be even more effective with you doing a bit of a demonstration that is possible because you aren’t holding the camera.

Avoid “Left”, “Right”, and “Little” Directions

Asking someone to do something to their right or left makes them think. For just a second they have to work through which is their left and which is their right. Then they wonder if you meant their left or your left. Instead ask them to look “over there” at something and even include your hand/arm pointing in that direction.

This direction is most commonly needed when the person isn’t tilting their face well. It can be a real challenge to get them in the right spot by asking them to move “a little”. Instead, have them move their head well beyond where you want them to go and then have them come back.

For example, if you are needing them to move their face a little more camera left (to their right – see how hard it is to keep left and right straight), direct them to look at something camera left and then ask them to look back at you.

After looking beyond the mark, when you ask them to look back at you, they nearly always end up just where you want them to be without giving them a direction that is not simple or clear. Plus, they got a second to get that camera out of their eyesight.

Jam Forehead, Turtle

For getting their head to look their best, there are two kinds of directions that work well with most people. It feels entirely unnatural for the person, but everyone looks better with their forehead and face slightly closer to the camera than their neck, shoulders, and hips. The challenge is how to direct them there using simple, positive direction.

You want to avoid directions like “tilt your head forward”. That generally gets them looking down. Peter Hurley is famous for his direction to “jam the forehead forward”, which tends to work really well. Another is to ask them to put their head forward like a turtle coming out of its shell.

The action you are looking for is to push their forehead towards the camera without pushing their chin toward the camera. The chin movement destroys the pose. So never tell them to stick their chin out or forward. Best to not mention the chin at all really, but if necessary just tell them to lower their chin after they have done the turtle.

It looks ridiculous from the side, which you may want to include in the direction. Stating something like I know it is going to feel funny, but you promise you that they will look amazing if they will listen to your direction. Trust you to make them look great.

Sneaky, Serious Look

A great way to get a really natural look is to direct them to give them a “sneaky” look. Everyone instantly knows what a sneaky look is. At worst you get a sneaky kind of look that works really well in a headshot. At best it makes them have a natural smile because they weren’t expecting you to say that.

Another one is to try and get them to have a serious look. You could say it just that way, give me a serious look, but something like “give me a Clint Eastwood look” works well on anyone over 30. Again, at worst you will get that serious kind of look that tends to work well, and at best they give you that natural smile.

Smile Phrases

You have already seen a few ways you might be able to get a natural smile to happen without saying the word “smile”. Here are a few more suggestions you can try out.

  • If they have a child, ask them the name of their oldest child
  • If they have children, ask them which of their children is their favorite
  • Ask them which is their favorite movie, singer, video game
  • Tell them to not look so miserable (this one works REALLY well)

Use Your Language

You have been given a few suggestions here on phrases you can say as you provide direction for this headshot. You can try those out, but if this just isn’t the way you speak then it will fall flat and feel forced.

You need to find your own directing voice. It needs to be something natural to you but convey in simple, positive terms what you need them to do. Adopt these phrases for a bit until they become your own or you can find some of your own that feel more natural.

The biggest thing that will help you to get to your own language is practice. The more people you can get in front of your camera for headshots, the more you will be practicing your direction technique, and the more you will develop what works for you.


Jeff: Tripp Lite AVR750U UPS ($90).  My UPS started having problems a couple weeks ago.  The battery was giving up and it meant providing inconsistent power to my desktop computer that made it turn off.  Never good to have your computer power off suddenly.  Fortunately, no harm done.  I looked into replacing the battery, but it was a really old model so I decided to buy a new one.  After doing some research, this is the one I landed on as a good balance between price and performance.  Working extremely well thus far.

Levi: The Headshot ($40) by Peter Hurley. Angler Parabolic umbrella ($50).



  1. Hi Jeff
    During the heads shots you were chatting to your guest about time lapse
    If you are interested I have done some time lapse with a canon 600d and a hahanal Gigi pro 2
    Current cost 65 gbp on amazon
    Hope you do do a pod cast on time lapse

    1. Author


      It isn’t the timer that is the expensive part. I wanted to have a camera sit inside some kind of weather proof container and be powered up to take a frame every 30 minutes for 3 months as my house was being built. There is gear that facilitates that but it is very expensive especially when I am doing this as a personal project and not something where there is a commercial client paying for it.

Leave a Comment