#CareerGoals: Old School vs. New School: 6 Ways a Modern Headshot Will Elevate Your Career

Guest post by Brian of BRIAN DESIMONE PHOTOGRAPHY

Modern headshots: Current & Classic (Photos: Brian DeSimone Photography)

The first impression is a lasting impression

What words would you use to describe your current headshot? Acceptable, average, nothing special, good, pleasant, classic, good enough for my needs? Think about that. Are those the same words that you would use to describe yourself and your success? What if you could instead describe your headshot as stylish, memorable, current, beautiful, modern, artistic, compelling, interesting, stand-out, new-school?

We all know that being successful in business doesn’t come from being average and doing the bare minimum. Your headshot is a direct extension of your accomplishments that holds up to the same logic. The picture you choose to share with the world is going to be your first chance to make a strong and lasting impression.

That outdated or average photo you’re using isn’t actually doing you any favors; in fact, it might be holding you back. There are lots of successful and talented people in your field. In theBoardlist alone, you’re competing against 1300+ amazing, accomplished executive women with backgrounds similar to yours. How will you stand out? Is your headshot helping you get attention and connect with the right boards? Or are you being overlooked?

(Photo: Brian DeSimone Photography)

Your photo is the first thing potential clients, employers, employees, and investors see. Why? Because they’re looking for you on Google, LinkedIn, Facebook, theBoardlist, and they’re seeing photos of you immediately. To be taken seriously in today’s work culture, you need a photo that works for you, not against you. Finding the right photographer for the job isn’t always easy, but it’s critical.

I’d like to share 6 reasons why you need far more than just an OK photo, taken by an OK photographer, to represent you.

Reason 1: You are your brand (so look like it)

Good brands evolve with the times. They appeal to their audience. And they not only know how important their image is, but they take ownership of it. (A great case study: Modcloth.)

But I’m complicated, you’re thinking. I’ve got this traditional and honestly conservative image to uphold in the corporate banking world where I make my bread and butter . . . and on the side, I’m a consultant for a bunch of hipster tech companies. And I have no idea what either of those things really look like, anyway . . .

Let me stop you right there. This is where a professional, and more importantly, a modern professional photographer can really help.

While you might think in spreadsheets and sums, photographers think in color, depth, image, style and presentation. With an understanding of lighting, aesthetic and composition, an ability to channel different audiences, and great retouching skills, the right photographer can create a versatile image that encompasses all aspects of your brand — meaning all aspects of you.

Which of these image grabs your attention? Which image are you going to remember? Whose resume are you more curious about? Imagine these 2 gentlemen had identical resumes. Which person is going to get a call back for an immediate interview?

What is it about the image on the left that makes it so special? It’s the result of a clear conversation between the photographer and client beforehand to discuss the look, vibe and desired outcome. Not only is the end result professional, intentful and confident, the stylistic retouching elevates the image to give it a very modern feel.

Reason 2: Your look impacts who you’ll work with

I’m not talking about how you look (we’re beyond that, right?) — but rather, the image you convey. Yes, your LinkedIn is full of accomplishments, committees, and testimonials touting your sheer awesomeness, but you need to draw the right attention.

Here’s the deal: boards are looking for someone exceptional. They’re looking for people who have a proven track record of excellence in very specific things — and really only those who are in the top 5% of whatever thing it is they’re looking for. When they’re scanning the bios of multiple accomplished executives with similar backgrounds, they’re often making quick decisions about whether someone’s interesting enough to learn more about based on that person’s image. And just like your website, portfolio, and Twitter feed present you in a certain light, so does your picture.

A current image produced with modern styling and boutique retouching elevates your look, and changes how you’re perceived. Choose to stand out!

Lesley Grossblatt, COO & VP of Product at theBoardlist (Photo: Brian DeSimone Photography)

Reason 3: Your photo needs to tell not just your story, but the right story

Notice how body language, slight movements, loosened collars, certain colors, and facial expressions send a distinct message. It’s important that the message you are sending is the right one. There’s a lot to consider, and unless photographing people is your area of expertise, it’s hard to get it all right.

Pro tip: Speak with your photographer ahead of time. A good photographer will coach you through the process, helping you understand what image you want to convey, and choosing what to wear (extra pro tip: you’ll want a few different outfits/accessories).

Example: Images Tell a Story

Here are two different images of the same woman that tell two very different stories:

Same woman, same outfit, very different headshots. (Photos: Brian DeSimone Photography)

The first image (on the left) has a lot of energy. It is very inviting and exudes personality. She has her body turned towards the viewer with her jacket open with a natural smile in her eyes and mouth. This image very clearly reads as friendly, approachable and full of energy.

The second image (on the right) her body is turned slightly away from the viewer, her suit jacket is buttoned and her expression is confident and maybe borderline intimidating. This image reads to me like she means business and is not to be underestimated.

What story do you want to tell?

Light-hearted or serious — how do you want your headshot? (Photos: Brian DeSimone Photography)

Reason 4: A good picture is worth a thousand words . . . and so is a bad one

  • Light matters — Professional photographers literally study light to learn how to manipulate it and change the appearance of a subject. Good lighting can make a person seem strong and powerful, bright and energetic, open and honest, badass and worthy of respect, or even dark and evil. Bad lighting can make you look like you just crawled out of a cave after a year.
  • Express yourself — Imagine a world where no one has to ask “Who are you?” They look at your photo, and they know. That’s the magic of a killer photo. Expressions are how we connect with, and interpret, the people we meet — it’s human nature, after all. A good photographer captures the right expression to tell your story.
  • Angles — The right angle can accentuate your features and make you look strong while the wrong angle can make you look wide or distorted. A good photographer has the experience and know-how to work with all shapes and sizes. It’s their job to coach you into your best angles and capitalize on your unique features.
  • Style — A quick chat and a little forethought will insure that the clothing you choose to wear for your headshot keeps the attention on you and keeps your photo feeling current. (No 80’s shoulder pads or neon yellow hair scrunchies!)
  • Post-processing — Actually, this requires its own point. Let’s move on.

Reason 5: Post-production can turn a great photo into a jaw-dropping, comment-gathering, fantastic photo

With retouching, the goal isn’t to try and make the image perfect but to play with different elements and colors to make the image pop and dance a bit. There is no silver bullet or photo filter for this. This is the part of the process that separates an average photograph/retoucher from a professional one.

Do you want to look basic? Or brilliant? How you come across says a lot about you — so make sure it says the right thing.

Post-processing can take a good photo and make it outstanding. (Photos: Brian DeSimone Photography)

Example: Before and After Post-Processing:

Post-processing can make a huge difference, check the before (left) and after (right). (Photos: Brian DeSimone Photography)

Reason 6: You have to spend money to make money

Ahhh. An adage as old as time, and continually true. Good photography costs a little dough. But it’s an investment in yourself. I like to think of it like buying jeans. Sure, you can purchase discount denim at Costco. They almost fit, and the price keeps money in your wallet for a hot dog and Coke on your way out the door. Except . . . you don’t love them, they’re not nice enough to wear to work, they don’t make your legs look killer so you don’t wear them on dates . . . and soon you’re trying to figure out where to sell them. But when you buy great jeans — the pricey kind — you never want to take them off. They go everywhere with you, and frankly, you only need that one pair. Oh, and they last forever.

Photography is like that. You can skimp on a budget headshot photographer and the final image might work for while. But it’s not quite what you had hoped for and you will quickly outgrow it, or realize it’s not great, and want to move on. Get it done right the first time and choose your photographer wisely.

Bonus! What to expect from an awesome photographer

Finding a photographer can be intimidating, especially if you’re not sure what to expect. Here’s a quick checklist — make sure your photographer’s process includes all of these points, and you’re likely in good hands:

  • Examples — You should be able to see previous work before you book a photographer.
  • Consultation — Before you meet, your photographer should communicate with you about your needs. Think of it like any other creative service: the creative should listen to your wants, do some research, and have time to prep.
  • Direction — Your photographer should not only tell you how to prepare for the shoot, but plan on directing you during the shoot to help you get the right look.
  • Options — Make sure you know about how many photos you’ll have to choose from for your final image — a good photographer will give you options.
  • Post-production— Any photographer worth their salt is also a master retoucher, and will work with you to decide how “perfect” you want to look and how stylish they should take the image.

Stay Memorable

Okay, enough with the lists. Let me end by quoting Colleen McKenna of Intero Advisory: “LinkedIn is about people connecting with people and it’s much easier to do that when you can see the person you are connecting with. It’s a pretty human reaction and most of us are visual. Seeing a person creates an immediate connection.”

If you’re on LinkedIn, theBoardlist, or any number of websites, the implication is that you’re making an impression whether you want to or not. Whether you’re trying to land a board seat, make new connections, get a better job, find a partner — you’re trying to connect with another human. As McKenna points out, most humans are very visual, and how they see you relates to how they’ll remember you.

It’s time to book that photographer. Stay memorable, friends.


Brian DeSimone is a professional portrait and editorial photographer currently living in Oakland, CA but will travel to take photos (including yours!). Brian will be at theBoardlist’s Holidays & Headshots in San Francisco on December 14 creating amazing new headshots. See his work at www.briandesimone.com

Brian had editing help on this piece from one of his favorite clients, writer Alicia Ostarell, who believes no one should write alone.

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