Headshot Tips for Savvy Entrepreneurs – How to Avoid the F-Bomb (Fake Smile)

Headshot Tips for Savvy Professionals - How to Avoid the Fake Smile with Portland Oregon Photographer, Briena Sash
spunky fun relaxed casual portrait dating headshot of young women in 30s for online profile in portland oregon

Hi! Photographer Briena Sash here, creator of Sash Photography. I’m here to empower you with tricks and tips to help you get headshots you love, that will intrigue and captivate your viewers.

I’ve received a lot of compliments over the years about my headshots. People telling me they see something different about the people in my portraits… something deeper. They feel like they actually know the person in the picture, or can “see who they truly are”.

The skill of capturing a person’s personality, or a certain essence about them, is really in the art of connecting with that person… helping them to feel relaxed, and drawing out genuine emotion from them.

Briena Sash is an extraordinarily talented, super creative photographer who has the gift to evoke the Essence of a person in her photography… She captures the vulnerability and heart of her subjects very deeply.

Nicola B.

Arm Yourself Before Going To Your Headshot Session

Look. Let’s be completely honest here. Photography is not as simple as many people want to believe. It takes a lot of technical skill, a trained eye, and… if you’re photographing people… good photography that has the power to captivate viewers takes the skill for connecting with your subject.

And there are too many headshots I’m seeing which have all the technical stuff in place… good lighting and white balance… but which completely lack genuine emotion and personality, and are pretty much just lifeless.

Simply put… they don’t embody the spirit of the subject.

So, answer this question for me…

If you’re up shopping for a new realtor, what’s the first thing that’s going to catch your eye and make you think… “Hmmm… She might be nice to work with”… ?

If you’re like most people, it’s going to be her headshot. And that’s not shallow. You’re looking for someone you feel you can connect with. It’s going to be how genuine and personable she looks. It’s going to be the energy she’s projecting. It’s going to be that discernment as to whether you think you’ll be able to jive with her. (Pssst… this is why it’s especially vital for a realtor to have a killer headshot… and why realtor headshots tend to be the running joke… over-the-top cheese smiles! I don’t know who started the rule in Realtor-land that your headshot has to be a stiff-necked Glamour Shot on a blotchy 90’s backdrop, but I know you know what I’m talking about! Wait… what? You’re a realtor and you have a headshot like that? Oh dear lord.)

Arm yourself with these tips and secrets that I personally use in my headshot sessions. Whether or not the photographer you choose is skilled at connecting with you as their subject, and drawing out your genuine personality, you’ll have the skill to make sure you get the results you want.

See The Difference

I want you to see and feel the real difference between a fake, or forced (“say cheese!) smile so that you can understand the magnitude of importance a genuine smile has, and how to achieve it in your session.

I’ll go over all that in the video, but I just want you to take a look at these two images below. Take a moment to evaluate both images. Disregard the background, just look at her face. Can you see a difference? Do they effect you differently? Which one makes you feel like you know more about her?

The first photo was taken at the very start of our session, before I began really getting her comfortable with me and guiding her through the steps I’ll go over in the video.

The second photo (BAM! Right?! Huge difference!) was taken towards the end of our session, after I had the chance to connect with her and guide her through my process.

Headshots by Sash Photography https://sashphotography.com/headshot
beautiful natural smile headshot by Portland Oregon Photographer

Watch The Video

In this video, I’m going to awkwardly show you the difference between the fake “cheese” smile, and a genuine smile. (I say “awkwardly” because… holy cow, I’m awkward in video… Embarrassing! But I’m toughing it out for you). And, I’ll give you my secret on how to draw out the genuine smiles in my clients. It’s super easy, and you can easily do this for yourself in your next headshot session.

Watch it here:


Now that you’ve learned my little secret tricks to drawing out a genuine smile, go practice in the mirror! It might sound embarrassing, but no one has to know and I give you permission to feel ridiculous. It really helps to understand how these tricks work, how they actually make you look, and how to get the genuine look and feel that you want to be projecting to your potential clients.


I hope this helped! If you have any questions or comments, I’d love for you to connect with me by leaving a comment below!

Love, Briena xo