Before You Book, an Executive Headshot edition by Tony Taafe

The Executive Headshot · Preparation

Before You Book

How to find a headshot photographer who’s right for you.

By Tony Taafe

Read the guide below, or click the cover to open the complete illustrated edition.

Look Beyond The Best Photograph

Looking for advice on how to find the right headshot photographer? You’re in the right place.

Choosing a photographer can feel surprisingly difficult. You’re comparing photographs, prices and personalities, often without knowing exactly what you should be looking for.

The aim is to find someone whose work you appreciate, whose approach suits you and whose photographs you’ll feel confident using. Here’s what I would pay attention to before booking.

One great image might catch your attention. Keep looking.

What matters is consistency of quality across the portfolio. Pay particular attention to the light, the color and the overall feel. Do the colors look true? Does each photograph look as though it has received the same level of care?

Some photographers prefer colors that pop a little. Others favor a more muted look. Both can work great. The question is whether the work has a consistent quality and a style you can see yourself in.

If the quality varies considerably, it’s difficult to be sure which images you’ll get. The great ones, or the okay ones?

A strong, consistent portfolio gives you a much clearer idea of what to expect. Then look at the expressions.

Do You Believe The Expressions?

Expression is one of the most important parts of a headshot, and one of the most overlooked.

When you see an image that feels right, you might not stop to work out why. The person looks natural. The photograph feels good. A genuine expression can be a large part of that response.

If someone is smiling, do they look as though they’re actually smiling, or smiling for a photograph? If they look confident, does that confidence feel genuine, or do they simply look serious?

People don’t always consciously notice expression, but they feel it. The same thing happens when somebody sees your headshot. They may not be able to explain what they’re responding to, but the expression helps shape how they see you.

Consistency of quality and genuine expressions. Those are two things I would always look for.

Get comfortable with the person behind the camera

In my experience, feeling uncomfortable in front of a camera is very common. A good photographer should expect that and know how to help.

There isn’t one question you can ask before booking that guarantees the right experience. Ask a photographer whether they’ll make you feel comfortable, and naturally, they’ll say yes.

If you can, have a short phone call instead. It doesn’t need to be a lengthy consultation. A few minutes can give you a sense of how you feel talking to them.

Read the reviews, too. Look for patterns. Do clients regularly mention feeling at ease? Do they describe helpful direction and an enjoyable experience?

Being asked to turn a certain way and smile is only a small part of direction. Helping to direct somebody so they feel so comfortable that the genuine expressions come naturally, that’s where the photographer is really doing their job well.

You won’t know everything about the experience until you’re there. But a brief conversation and some thoughtful reading can help you make a better choice.

Choose For What You Need

Before deciding on a session, think about where your photographs will be used. Then look a little further ahead. Could your needs change over the next six to twelve months?

If you need one image for one purpose, you’re happy to use it for an extended period and you don’t foresee that changing, keep it simple. Find a photographer who can give you one home-run image. Save yourself some time and money.

In my experience, a skilled photographer can produce several strong headshots in less than 30 minutes. The extra time becomes useful when you want different outfits, backgrounds, crops and photographs for different purposes.

A speaker may need images for event programs and publicity. An entrepreneur or executive may need a selection for press features, a website and professional profiles. Others simply appreciate having some variety without arranging another shoot each time they want a change.

If you need that range, take the time and make the investment. Your photographs will represent you in places where you aren’t there to introduce yourself.

Know What The Price Includes

Price is relative. What feels comfortable to one person may be a significant investment to another.

In my experience, price and quality tend to line up more often than not. But the highest price alone is never a guarantee of the best work. Look carefully at the work, speak to the photographer and aim for the best quality within your budget.

Then make sure you understand the complete cost.

Some photographers charge a session fee and sell the images separately. Others include images in a package. The overall value can be similar; it’s often simply a matter of one photographer preferring a different pricing model.

Retouching may be included or charged separately. Different approaches can work well, provided everything is clear before you commit.

Get the details in writing. A preparation guide or a straightforward email confirming the price, deposit and remaining balance can remove a lot of uncertainty.

Before booking, clarify:
• How many finished images are included, if any.
• Whether retouching is included and what additional images cost.
• Delivery time after you make your selections.
• The file formats and resolution you’ll receive.
• Your usage rights and any recurring licensing fees.
• What happens to your deposit if you need to reschedule.

I don’t charge licensing fees for headshots and I grant all usage rights. I also allow clients to move their deposit to a rescheduled shoot date. Other photographers’ terms can differ, so it’s worth checking rather than assuming.

Have The Retouching Conversation

Retouching preferences are personal. Some people want very little. Others prefer a more polished finish.

The photographer should explain what’s included and ask about your preferences before you leave the shoot. If they don’t raise it, make sure you do.

For me, that conversation covers blemishes, uneven skin tone, flyaway hairs, teeth whitening, the under-eye area and heavier lines. Then we discuss the details. Would you prefer those lines softened or removed? Is there anything specific you’d like addressed that I haven’t mentioned?

Without that conversation, the photographer is left guessing.

If a finished photograph looks too heavily retouched, let them know. Explain what doesn’t feel right and discuss a correction. You don’t need to quietly accept a result you’re unhappy with.

A clear conversation before you leave can save frustration later.

Know When To Keep Looking

Your comfort level matters. If you don’t feel comfortable with a photographer, take that seriously. It affects both the experience and how you feel in front of the camera.

Poor communication is another reason to reconsider. So is pricing that doesn’t fit your budget.

Look for consistent work, genuine expressions, clear terms and someone you feel comfortable working with. Whether you need one exceptional image or a considered collection, those are the foundations of a good choice.

I’m here if you have any questions.
Happy headshot hunting!