Unless you’re an experienced marketing professional, you probably don’t know how to evaluate photographers.

This step-by-step guide will give you the expertise you need to ask the right questions to help you make the best decisions about your headshots and headshot photographer.

Professional Headshot Tips

Professional Headshot Tips

Table of Contents

Why Hire a Pro?

Controlling Perceptions

Your executive headshots define others’ perceptions of you. A professional photographer will partner with you to craft your image, giving you control of those perceptions and helping you manage their expectations.

Your headshots should help you connect with the decision-makers you must influence to achieve your goals and advance your career. A first-rate headshot conveys a sense of your executive presence in a manner that promotes engagement and builds rapport with those decision-makers by showing that you are ready to take your place at their table.

No matter how good they may be, company headshots or headshots taken at a photo booth aren’t going to give people the impression you need. They will likely leave people with the impression that you’re an imposter, a wannabe, or “also-ran,” rather than a leader with the drive, skills, and expertise needed to help them achieve their goals.

“We hold ourselves back in ways both big and small, by lacking self-confidence, by not raising our hands, and by pulling back when we should be leaning in.”
― Sheryl Sandberg, Lean In: Women, Work, and the Will to Lead

A professional photographer takes the time to understand your goals to discover what they need to do to help you achieve them. They leverage their talent to make you look your best and their expertise to confidently coach you in presenting yourself to the camera without coming off as arrogant, foolish, or frightened.

You’ll look fantastic by investing the time and effort needed to work with a professional photographer. Your headshots will have the professional polish that tells people you’ve got your act together and are ready to seize the next opportunity.

Selecting Your Photographer:

The Wrong Photographer Will Not Give You The Right Headshots.

Choosing your photographer is your single most important decision about your business portraits. Their personality, style, and process all affect the outcome. Making the right decision about who to work with will make the difference between getting good headshots and bad headshots.

Define your needs, and then set your expectations.

To prevent mission creep, write out why you need new headshots: Job search, company website, promoting a book or speaking tour, press release, etc.

Decide how you want to be perceived by the decision-makers who see your headshots: relationship builder, innovative creator, decisive leader, etc.

Explore your options.

Ask a friend who raved about their recent headshots for a referral to their photographer. Past success is a good indicator of future performance.

Search on Google. Limit your search to photographers who specialize in headshots by specifying “headshot photographer” (include the quotation marks), ensuring you’ll get immediate, relevant results.

Photographers show the work they are most proud of on their websites. The style and type of photograph they want you to associate with them.

Photographers put photos on their website to be judged by you. The goal is to help you decide if they deserve your trust.

Review photographers’ websites and shortlist the ones whose work you like the most.

Who you choose to shortlist depends on how you’ve determined you want to be perceived. One photographer’s work may be polished and have a solid commercial feel; another will be casual and down to earth.

Headshots are all about first impressions, and the first impression you get from a photographer’s website should influence your decision to shortlist them or not.

Select three or four photographers who feature headshots of people looking like how you want to look.

Now is the time to look at the price.

  • Never spend more on your headshots than you can easily afford.
  • If you’re looking for a $150K+ position, $2000+/- is appropriate. You’ll spend that much on a suit and get less traction.
  • If you’re in management looking for a promotion to a director, $800 – $1200 might be just right for you.
  • If you’re looking for an entry-level position, $100+/- is about all you should spend.

Interview the photographers on your shortlist over the phone or Zoom to learn if they’re the right kind of person for you.

We all have our personalities, and that influences our approach. As an example, my mentor, Peter Hurley, has a larger-than-life personality. He might be the perfect photographer for you, or you may prefer to work with someone with a nurturing, thoughtful approach.

Ask about the photographer’s process. Put them on the spot and see how they respond. Do they know what they’re doing or making it up as they go along?

Ask about their studio. Choosing a photographer who works on location requires you to be comfortable performing for an audience.

After you hang up the phone or end the Zoom meeting, answer these three questions. Of the photographers you interviewed:

  1. Who do you like the most?
  2. Who respects the value of your professional image the most?
  3. Who do you trust to lead you through your headshot session the most?

All of this requires a good investment of your precious time. The return is headshots that make you look good and work to help you advance your career.

Wardrobe Advice for Your Headshots:

Combining Style with Professionalism

Executives must be prepared to present different aspects of their personalities to suit the culture of diverse workplaces and match the tone of a particular event.

Express yourself

The first rule of dressing well for your headshots is to be comfortable in whatever you’re wearing. The second is that your clothes need to fit you, and the third is to express yourself.

Dress comfortably but well

In an instant, the clothes you wear communicate your social status nonverbally to everyone. A Silicon Valley executive is expected to wear a suit jacket over a t-shirt or an open-collared shirt but no tie. The jacket may be from a $2000 suit and the t-shirt from Lululemon, while an engineer for a startup is expected to wear a hoodie.

The relaxed standards of formality that are common in the Tech Industry do not always apply to women. Even when projecting an air of casual competence, female executives are expected to present themselves more effectively than men.

Clothes

Bring too many outfits to your shoot, consult with your photographer about what works best for you. Suits and ties are great. If you wear sweaters, turtlenecks, t-shirts, bring them, or whatever clothes you feel most comfortable in at work.

I advise women not to wear sleeveless tops unless they’re under a jacket or sweater for two reasons. The first is that your bare upper arm will compete for attention with your face because it’s about the same size as your face. The second is that it’s a very casual look that could undermine your authority. Talk with your photographer about how it works for your unique look.

Neckline

Whether you’re a man or a woman, wear shirts with a neckline that mirrors your jawline because it enhances your natural attributes. If you have a sharply tapered jawline, a V-neck will look great, whereas a rounded chin will be enhanced by the smooth curve of a crew neck.

Women should wear whatever depth of neckline they’re comfortable with in the workplace. The deeper the neckline, the more critical it is to select the right necklace. Bring several options and work with your photographer to craft your look specifically for each outfit.

Subtle Colors and Small Patterns

Subtlety is the rule for colors and patterns in executive headshots.

A heavily textured fabric can be so energetic as to compete for attention with your smile. Pinstripes and patterns smaller than your little fingernail create texture and add interest without taking the focus away from your eyes.

Strong colors or loud patterns overpower the color of your eyes and end up being the most memorable feature of your headshot. Neutral colors or soft pastels are safe.

*Here’s a caveat. Jewel tone shirts alone or under a dark jacket can create an elegant and energetic tone in your headshots.

Jackets

Jackets should be well fitted. A jacket that’s too tight or too loose will never hang properly. It’s well worth your time to have your jackets fitted by a tailor. You’ll be more comfortable in the jacket, and you’ll look and feel confident knowing your jacket fits you perfectly.

Jackets look great over a t-shirt, a button-up shirt, with or without a tie, or necklace. Bring several combinations to your headshot session to display different aspects of your personality. Your photographer will help you select the ones that fit and look best and coach you on projecting the appropriate psychological message for each outfit.

Shirts

There’s a misunderstanding about black or white clothes. There’s no reason not to wear either if you like them and they look good on you. White shirts can wash out your complexion, but this needs to be taken on a case-by-case basis.

Select shirts that complement the color of your eyes and bring several, especially the ones you like the most.

All shirts should be freshly laundered and pressed, regardless of whether you’re going for a casual or formal look. A hand steamer is not a substitute for a professional press.

Ties

Ties are not expected of anyone in Silicon Valley but are expected of professionals in Europe. However, most executives need to wear a tie on occasion. So, bring your favorites, and work with your photographer to choose the ones that work best for you. It’s always a good idea to have at least one formal headshot on hand.

Scarves

Solid color scarves or scarves of a darker tone are great. This depends on your personal and cultural preferences, but a brightly colored and heavily patterned scarf might overwhelm your smile. Bring the ones you like and work with your photographer to craft your look.

Jewelry

The jewelry you choose for your headshots should enhance your features and help you communicate status. It should always be small and conservative. In many cases, it’s best to wear no jewelry at all because it can compete with the sparkle in your eyes for attention.

Earrings should be small: diamond studs or small hoops. Statement pieces should never be worn in your headshots because they’ll be all that anyone sees in your photos.

7 Essential Headshot Tips for Men

Be well-rested for your headshot session. Jet-lagged is not a look that inspires confidence. Schedule your session for a day that allows you to show up when you’re well-rested. It will show.

1. Express yourself

Don’t practice your smile. Be yourself and address the camera with confidence and good humor. Present yourself as a unique individual with character and personality, not the person you think I think you should be, not the person you think your kids think you should be. Just be yourself. Your photographer will guide you in expressing your confidence and approachability.

2. Get your hair cut a week before your shoot

Getting your hair cut several days before your shoot will give it time to grow in and look casually well-groomed.

3. A touch of grey

Don’t be self-conscious of salt and pepper. Men really do look more distinguished with a touch of grey. If you’re going to have your hair colored, even if it’s just a wash to tone down the grey, do it two weeks before the shoot. A little wear on the color will make it look natural.

4. Shave and trim beards, nose, ears, and eyebrows

A friend of mine once joked that as men grow older, we don’t actually lose our hair. It just migrates south. Trim your ears, nose, and eyebrows carefully.

Some men look fantastic with two or three days of beard growth. If you like a little scruff, do a set with the beard, then shave at the studio and do a second set.

5. Exercise the day of your session

You want to be pumped, primed and ready!

6. Moisturize liberally

Moisturize two or three times a day and drink seven to ten glasses of water per day for three days before your session. Well-hydrated skin has a deep, healthy glow and will soften the edges of your smile lines.

7. Don’t put too much pressure on yourself

It’s not your job to look good in your headshots; it’s your photographer’s job to make you look good. Give yourself the time you need to feel comfortable in front of the camera and get into the flow of it, and remember it’s not your job to look good in your headshots. Even experienced actors and models need time to warm up.

9 Key Headshot Tips For Women

As a woman’s career advances, her corporate headshots should project the image of a successful, empowered career woman. It’s inherently unfair, but people have higher expectations for women’s appearance than for men’s. However, you’re not alone in your efforts to look great in your headshots. Your photographer, makeup artist, and retoucher are all highly skilled, talented professionals giving all they’ve got to help you make it look easy to do it backward, wearing heels.

If you need a new top or jacket, go shopping to find the perfect addition to your wardrobe. Keep the tags on in case you decide to return them.

1. Don’t practice your smile.

Your photographer will work with you to capture authentic expressions that showcase your confidence and approachability. Practicing your smile undermines your self-confidence more effectively than anything else you can do.

2. Moisturize.

Most women don’t think to moisturize their ears, throat, and chest, as well as their face. Along with drinking extra water for a few days, this will give your skin a consistently soft internal glow.

3. Groom the day before.

Just as with men, grooming is essential. Tweeze, thread, or wax the day before your session. Your makeup artist will do fine-tuning and some planning if needed, but the best thing is to show up to your shoot ready to go.

4. Makeup artist.

Hire a professional makeup artist experienced with commercial photography to do your makeup for you at the studio. For the best results, your photographer and makeup artist should combine their talents with those of the photographer and the retoucher.

5. Makeup for the camera.

If you’re doing your makeup, bring your supplies and do it at the studio. Makeup for an executive headshot using one of today’s high-resolution cameras does not translate to makeup you’d wear on the street or for a wedding shoot. You’ll look more natural if you go too light with your makeup and have additional work done in retouching. Your photographer will help by offering guidance and advice.

6. Hair color.

Have your hair colored and the roots touched up a few days before the shoot. Your makeup artist should be able to style your hair for your session but not add color. You’ll get the best results if your stylist does it.

7. Retouching.

Don’t go too far with your retouching. Good retouching should remove imperfections but retain your skin’s natural texture. Too much retouching will undermine your authority by making you look self-conscious about your appearance.

8. Jewelry.

Jewelry should be elegant and understated. You don’t want anything competing with the sparkle of your eyes or the brilliance of your smile. You don’t need to wear jewelry at all if you don’t want to. Earrings should be dignified studs, nothing dangling. Necklaces should be small, a solitaire or pear-shaped pendant. Chains should be light and delicate.

9. Remember, you’re a superhero!

Finally, start your day with two minutes doing the superhero pose. Do it again just before you step in front of the lights. It’s a simple thing and makes an enormous difference to how you feel about yourself and your place in the world.

Don’t Sit For It:

Projecting Strength and Confidence in Your Headshots

The purpose of your executive headshot is to showcase your strengths: confidence, approachability, and assertiveness. Being photographed while seated undermines your efforts to project an executive presence by sending subconscious signals of weakness, low status, and anxiety. Our expressions, posture, and how we address the camera speak volumes about our emotional state and social status.

The messages we send change dramatically depending on if we’re looking up at someone or looking them straight in the eye. If you’re seated and looking up at the camera, you’re sending messages of passivity and submission, and that’s never a good look for an executive.

When we sit down, we relax our back, our shoulders slump, and all of our weight rests on our tailbone. That slumped posture sends messages of passivity and submission. You can sit up to correct your posture, but that puts you in an unnatural and uncomfortable position, which quickly wears you out and may be interpreted as anxiety.

By standing up for your headshots, you’ll effortlessly hold a comfortably erect posture that communicates strength and confidence.

Being up on your feet also helps relieve any anxiety you might feel while being photographed by suppressing your fight or flight response because you’ll be able to move freely. While this may be a subtle change, it could help add a zero to your retirement account.

Selecting Your Headshot:

Setting the Stage for Your Next Career Move

Your professional headshots aren’t simply a photo showing your smiling face. Headshots are tools that communicate your desired memorable character traits to decision-makers you need to influence when you can’t meet them face-to-face.

As an executive, some circumstances require you to present yourself as an authority figure or visionary leader. Other times, you’ll want to project decisiveness. And then there are times when you’ll showcase your charm and good nature.

For the evaluation part of your headshot journey, you’ll want to lean on your photographer because they’ve crafted the content of your message using their expertise in body language and nonverbal communication. Your photographer will offer you an objective assessment of the messages your photographs send without being distracted by minutiae or influenced by their own experience of who you are and what makes you tick.

Your photographer is the best person to give you an objective assessment of how you look in your photos. They’re the expert, and won’t be influenced by emotion

Let me introduce you to two concepts to keep top-of-mind that will help you assemble your executive headshot library and make it easy to communicate complex ideas to your photographer in a language they’ll understand. There’s an exception to every rule, but these two concepts provide a foundation upon which you can build a collection of headshots that portray the different aspects of your personality.

Low-key Photographs

Nothing says seriousness and formality quite like dramatic lighting and a dark background. When combined with a thoughtful expression or powerful gaze, low-key photographs communicate decisiveness, strength of character, and authority.

High-key Photographs

High-key photographs are bright and airy. A cheerful smile combined with glamour lighting and a bright or colorful background communicates your wit, charm, and mastery of social skills.

When selecting your headshots, it’s essential that you like your photos and look good in them. However, you also want to think about the messages your headshots are sending. You’re not just picking pictures to show to people. You’re assembling a library of visual communications you’ll be using to advance your best interests and those of the people who depend on you.

Projecting Your Executive Presence:

Promoting Engagement with Your Headshots

Your headshots should project your executive presence and promote a sense of engagement with everyone who sees them, either online or in press releases. To accomplish this, people need to see your expression well enough to read it. That requires a closely cropped photo, with your face filling 40-60% of the frame, rather than the traditional “waist-up” or “head-and-shoulders” professional portrait.

Studies prove people form first impressions of others in the first 1/10th of a second when seeing them for the first time – this includes in photographs. These first impressions influence our interactions and expectations of others long after we’ve already established relationships. Tight close-ups or headshots are the standard online format because they allow people to read the subtle nuances of your expression, helping you influence these first impressions.

Traditionally, professional portraits have been head-and-shoulders or waist-up photographs with lots of negative space above the head. These photos are fine for viewing a framed print hanging on a wall because there are no distractions. The frame focuses the viewer’s attention on the subject, and hanging the photo on a wall communicates that it deserves their time and attention.

However, the online world presents no such opportunity to isolate an image with the trick of positioning it on a wall. Instead, your headshots must compete with the compelling text and attention-grabbing graphics of a well-designed website. Fortunately, headshots can overcome these distractions and command attention because humans are programmed to focus on people’s faces.

Our faces are sophisticated signaling devices that communicate a wealth of information about our emotional state to others in the blink of an eye. People instinctively use this information to determine our intentions and decide how to interact with us.

To ensure your headshots have the desired impact, crop your photos so that your face fills 40-60% of the frame. Filling the frame in this manner ensures others can see your face and can read the subtleties of your expression. A profile photo where your face fills 20-30% of the frame does not have the emotional impact of a close-up headshot.

Professional photographers command the viewer’s attention by showing a tight close-up of a person’s face, the human feature we instinctively turn to for information about someone’s emotional and psychological state. Filling the frame of your headshots with your face allows you to project your executive presence through the screen. People can interpret the nuances of your expression, which, in turn, positively influences the decision-makers who are important to your success.

Download the entire Headshot Success Guide in PDF

This Professional Headshot Success Guide will help you go beyond Googling “business headshots near me” by giving you the knowldege you need make well-informed decisions about your professional headshots.

Download the Guide Here

(Professional Headshots Palo Alto is my former headshots business name. I’m in the process of rebranding. I’ll update the booklet’s branding over the holidays in 2022.)

I make the time to help my clients select their headshots. 

Due to information overload, selecting photos is the hardest part of any photo shoot. I’ve been doing it for 35 years and am very good at it. 

You’re in control.
I’ll offer my unbiased opinion and professional interpretation of any photo if you want.

Working together, we can narrow your choices from 50+/- great headshots to the 8-12 absolute best in about 15-20 minutes.

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