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Headshot Photo Mistakes That Diminish Career Potential

Why your headshot photograph sets the tone before you speak

 

By Chris Gillett

 

In business, first impressions often happen before a word is spoken. Your headshot is more than a picture; it’s a visual handshake, a silent introduction that conveys confidence, likability, and professionalism in a single frame. Like a handshake, it can be firm and reassuring, or limp and forgettable. The difference often lies in small but critical choices.


Why the Headshot Matters

 

A headshot lives everywhere your reputation does—LinkedIn, firm websites, pitch decks, press releases. Before colleagues, clients, or hiring managers meet you, they meet your image. That photograph carries cues about how trustworthy you appear, how engaged you seem, and whether you project authority or warmth. Research in psychology consistently shows that people form judgments of competence and likability in milliseconds. Your headshot is the first test of that instinct.


Outcomes of a Strong Personal Brand

 

If you have a face, you have a brand. People do business with who they trust and remember. A strong brand puts you in control of the story others tell about you, instead of leaving it to chance. That is one reason I hate when I see people post multiple headshots online and ask the online masses which one they like best. I would NEVER outsource my online image to a bunch of people, even people I trust. I am making that decision. I have even seen marketing professionals appeal to the herd, and I think it betrays the fact that they don’t really know why they are posting headshots in the first place. “Hey gang, which one do you like?” That’s pretty weak. I know the image I want to project, so I am selecting the shots that accomplish that goal.

 

You make your own luck, and if you have a strong personal brand, opportunities are more likely to find you. I’ve had executives get speaking invitations, media features, and even board seats because someone saw their headshot and profile and thought, this person looks like a leader.

 

First impressions are formed almost instantaneously, and a good online image can establish faster trust in business.

 

One client told me, “Before I walk into a pitch, people already feel like they know me.” That confidence comes from a consistent image across LinkedIn, the website, and press features.

 

A strong executive brand adds “career insulation.” Executives who invest in their brand aren’t as vulnerable when companies merge, restructure, or downsize. Their name and presence carry weight beyond the logo on their business card.

 

Finally, a strong personal brand doesn’t just win clients. It helps draw in ambitious people who want to work with YOU, not just for the company.

 


If you want to stand out in a crowded market, don’t try to look like everybody else. That’s camouflage, not branding.  Ladies, your business blazer, high crewneck top, bold lip, and fake camera smile make you look like a zillion other women. That’s a great recipe for not standing out.

 

Perhaps surprising is the fact that likability beats credentials. Executives assume their résumé, degrees, or track record are what set them apart. But in reality, people do business with those they like and trust, and that perception is built in seconds.

 

Figure out what you want to be known for, then make sure everything from your words to your photos point in that direction. If you can’t figure out why you are different, damn. That’s depressing. Contact me, and we’ll go on a vision quest and figure it out.

 


Do’s: Making the Most of Your Visual Handshake

 

  • Do use genuine expression. Confidence is communicated through the eyes; likability through the mouth. Together they create the balance of authority and warmth that makes people lean in. Forced smiles or stiff stares fail that test. If your smile doesn’t reach your eyes, it is fake.
  • Do consider the message you want to send. A law partner may want gravitas; a startup founder may want energy. There is no right answer other than the one you decide on. The headshot should serve that purpose, not just “look good.”
  • Do refresh periodically. If your appearance has changed meaningfully, update your headshot. Mismatched expectations can erode trust before you’ve even said hello. A ten year old shot or an AI shot is professional catfishing.

 

Don’ts: Pitfalls That Undermine Presence  

 

  • Don’t rely on selfies or casual snapshots. What may work for personal social media rarely translates into professional credibility.
  • Don’t over-edit. Excessive retouching may erase authenticity and make you look like you lack confidence. A headshot should present the best version of you, not an unrecognizable one.
  • Don’t ignore body language. Slight posture cues—a tilt, crossed arms, leaning too far back—can signal defensiveness or disengagement. Tilting your head towards the shoulder closest to the camera makes you look weak.

 

5 Things to Successfully Build Your Brand

 

  1. Own Your Voice. Don’t water yourself down to please everyone. My website is unapologetically in my voice. Some people hate it, but the people who love it become lifelong clients. You can’t build a brand on beige.
  2. Invest in Your Image. Executives who show up online with blurry iPhone selfies or, worse, AI-generated headshots are basically saying, “I don’t take myself seriously.” I’ve watched clients flourish after updating their professional headshots because perception creates opportunity. While you are at it, get clothes that fit you well and flatteringly, and GET IN SHAPE. This is a HUGE lifehack. It makes everything better. Start yesterday. If you don’t know where to start, talk to me.
  3. Be Consistent. Your brand isn’t just a headshot or a LinkedIn post; it’s the sum of all your signals. I’ve had clients who looked like leaders online, then showed up in person looking like they just rolled out of bed. That inconsistency kills trust. The executives who win are the ones who match the message across every touchpoint. You can’t half-ass this. You need to make it a habit.
  4. Differentiate or Disappear. Crowded markets punish sameness. I had a client whose peers all used the same generic corporate headshots and jargon-filled bios. We rebuilt his brand around clarity, confidence, and personality. Now he’s the first call when people think of his specialty. Standing out isn’t optional; it’s survival.
  5. Stand for Something Bigger Than Your Title. If your brand is just “I’m a lawyer” or “I’m an executive,” you’ll blend into the noise. If you are in energy law, you can be just “another litigator,” or you can be the guy who makes complex disputes simple for business leaders to understand. That positioning may get you quoted in industry publications and bring in clients because you stood for something bigger than just your job title.

 

The Broader Impact

 

A strong headshot doesn’t just open doors; it can also align a team’s brand. When a firm or company presents cohesive, polished headshots across its leadership, it communicates unity, credibility, and attention to detail. Conversely, mismatched or outdated images suggest inconsistency and a lack of care and resources. In an age where clients, investors, and partners often vet online before meeting, those subtle cues matter.

 

Think of your headshot the way you’d think of a handshake in a critical meeting: intentional, practiced, and aligned with the impression you want to leave. Done well, it can become one of the simplest yet most effective tools in your professional arsenal.

 

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Chris Gillett is a professional headshot photographer and expression coach based in Houston. He helps executives, attorneys, and entrepreneurs master the visual handshake” by combining confidence and likability in every image. Connect with him at www.liketherazor.com.

***Some or all of the accommodations(s), experience(s), item(s) and/or service(s) detailed above may have been provided at no cost and/or arranged to accommodate this review, but all opinions expressed are entirely those of Merilee Kern and have not been influenced in any way as per the disclosure policy on our “Legal” page***

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