Seven Secrets to a Great Headshot & Why You Need One


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Portrait photographer Lisa Rayman Goldfarb and I met as co-presenters at a networking event geared toward women re-entering the workforce.  Branding Yourself to Compete in the Millennial Marketplace was the theme, and Lisa convinced me that a good headshot is a brand essential in an era where the new first impression is that thumbnail photo of yourself on social media.   I hired Lisa to take my headshot and along the way she shared some of her secrets.  As you can see from my headshot above, Lisa has some serious talent!

Step 1.  Find a Portrait Photographer.

If you’re going to invest in headshots, go with a photographer who specializes in portraits.  You wouldn’t ask a podiatrist to conduct brain surgery, right?   And make sure you find “the right” portrait photographer.  Having your portrait taken is surprisingly intimate.  Talk to the photographers you’re considering and review their work to make sure your personalities mesh.  

Step 2.  Create a Mood Board and Consult with Your Photographer.

Before the photoshoot, Lisa asked me to create a Pinterest board with portraits that appealed to me.   If you work with a photographer who doesn’t ask you to create a Pinterest board, I highly recommend creating one anyway and sharing it with him or her to make your expectations clear.  Discuss your vision and your board to make sure the photographer can meet your expectations.  Here’s the Pinterest board I created and shared with Lisa.

Step 3.  Wear Minimal Makeup.

Lisa advised me to focus on my eye makeup—mascara, eye liner, a little eye shadow.  On the lips she recommend Vaseline or natural gloss.  Other than that, she asked me to keep it simple.  Wearing too much make up can make it harder for her to do fabulous things like edit photos to minimize wrinkles.  I also used a brow pencil.  Don’t overdo it.  Just fill in bare spots to give your brows a natural, uniform shape.

Step 4.  Dress Like Yourself.

Lisa advised me again to keep it simple and not to overthink my outfit.  She told me to dress the way I normally would, so that my comfort with myself would shine through.  As a general rule, choose simple necklines and solid colors that complement your eyes and skin tone.  Trendy patterns or necklines may eventually make your headshots seem dated.  For about half the photos, I wore a simple blue crewneck sweater and my favorite jeans, making these photos fairly timeless.   

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If your photographer gives you the option of additional outfits or looks, as Lisa did, I would recommend using this opportunity to showcase more interesting pieces and accessories.

I love this headshot Lisa took of our mutual friend and Coldwell Banker realtor Jessica Estreicher, wearing her signature leather jacket.  If I were looking to hire a realtor, this photo would give me a nice sense of her personality.  She looks competent and fun at the same time.  

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I wear glasses on an almost daily basis, so it made sense to take some photos with my glasses on.  People often remove glasses for photos, but if you like your glasses and they convey something about your personality, keep them on.  I’ve always had a thing for funky glasses and love my current Warby Parker metal frames!  I also often wear my hair in a topknot secured by a pencil, so Lisa snapped a few photos with my hair up.

Step 5.  Find the Right Light.

A good photographer knows how to find and use the right light for your portraits.  Light is everything in photography and your portrait photographer should know how to use light to create the right mood for your specific session.    Lisa taught me that each light source has a different color temperature.   Early morning sun gives off cooler blue light and late afternoon sun—the “golden hour”—is perfect for warmer portraits.  

My friend and Product Development Executive Carla Moreale has a golden personality, so this photo Lisa took of Carla during the golden hour perfectly conveys Carla’s inner warmth.

 DSC_4645 sunlight big smiles FINAL for amy h wm

For photos in direct sunlight, Lisa asked me to close my eyes and then open them up right before she snapped the shot to prevent squinting.

Step 6.  Strike a Pose.

I can’t give away all of Lisa’s secrets, but I’ll share one go-to position that worked well for me.  To combat the appearance of a double chin, she advised me to lengthen the back of my neck and tilt my chin down slightly.   She guided me with other gentle posing tips and positions to bring out my best features.  Sometimes the position or angle felt slightly funny or forced in the moment, but Lisa convinced me that through the camera lens the angles would work.

Step 7.  Trust!

If you’ve done your due diligence and found the right photographer, communicated your vision for what you want from your session and your portraits, it’s time to trust your photographer to deliver!  Relax and enjoy the session, don’t stress about looking or being perfect.  Lisa says, “it’s just photography, not brain surgery.”  😉

To view more of Lisa’s work, visit her website.