Did I Almost Pass Up My Best Headshots?

As I've been rebuilding my Halligan Media business, originally launched in 2014, one of the first things I knew I needed to do was completely redesign my website. With just about every website comes one unavoidable task: choosing photos of the person behind the business.

Easy enough, right?

Not exactly.

I've spent more than 30 years working in broadcasting, entertainment and communications. During that time, I've spent plenty of hours in front of the camera, behind the scenes and reviewing hundreds, sometimes thousands, of headshots while casting talent for various projects.

I've never been the photographer in these situations, but I've experienced headshots from just about every other angle.

Actors, anchors and other on-camera talent often have agents or managers helping them choose the photos most likely to get auditions or interviews for the right roles or positions. Business owners, executives and entrepreneurs usually don't have that luxury. You're left staring at hundreds of nearly identical images, trying to decide which one represents you best… and that's surprisingly difficult.

Sure, you can easily eliminate the obvious ones. You can star the photos where you think you look your best or the most professional. But are those actually the strongest choices?

Maybe.

Maybe not.

Then comes the inevitable comparison stage. You start flipping between two photos that look almost identical, wondering whether one eyebrow is slightly higher or your smile is half a percent more genuine. Before long, every photo starts looking the same, your vision gets blurry and your brain feels like it’s about to explode.

I know because I just went through it myself.

Despite everything I've learned over the years, I had a terrible time choosing my own new headshots.

Was I conveying what I wanted people to see? Was the outfit right? Should I be looking directly into the camera or slightly off to the side? I loved one photo, but my hair covered part of one eye. Could it be retouched? Was it worth it? Was another image almost as good?

Eventually, I realized I needed to stop looking at tiny details and start thinking about the bigger picture.

How did I want people to feel when they landed on my website?

I wanted them to think, "She seems experienced. She knows communications. She also seems approachable, like someone I'd enjoy chatting with over coffee, a smoothie or an afternoon snack."

Once I focused on the feeling I wanted to create instead of finding the "perfect" photo, the choices became much clearer.

That's because the best professional headshots aren't necessarily the most technically perfect ones. They're the ones that create an emotional connection.

Now, every profession has different needs, and even within the same profession, those needs can vary.

If you're an actor, your commercial headshot may look completely different from your theatrical one. A spokesperson hosting medical content one day may need a very different look the next day to host a comedic competition show. A financial advisor probably wants to project something different than the owner of a daycare center.

Your headshot should match your profession, your audience and your brand.

But across almost every industry, the strongest professional headshots tend to share the same qualities.

1. The Eyes

This is where people connect first.

Do your eyes appear engaged? Does it seem like you're looking at a person instead of simply staring at a camera? Is there warmth? Curiosity? Confidence?

Perfection isn't what draws people in.

Connection does.

As a recovering perfectionist (I’m recovering. I swear!), I can tell you that technically perfect isn't always emotionally memorable.

2. The Smile

Is it genuine?

Does it look like someone caught you in the middle of an enjoyable conversation or does it look like you're smiling big waiting for your cell phone timer to count down?

A real smile reaches your eyes. There's usually a little softening around them. Your cheeks and jaw should be relaxed. It feels effortless rather than performed.

People are remarkably good at sensing authenticity.

3. The Energy

Every headshot communicates something.

Do you appear capable? Experienced? Welcoming? Calm? Trustworthy?

Would someone feel comfortable reaching out to you?

Your energy often speaks before anyone reads a single word on your website or LinkedIn profile. Ideally, your photo should communicate both credibility and kindness.

4. Your Pose

Your pose should look natural and comfortable, not stiff or overly posed.

A slight turn of your body often feels more engaging than standing squarely toward the camera. Good posture communicates self-assurance, while relaxed shoulders and an open stance make you appear inviting. Small adjustments in your posture, head position and angle can create definition without looking forced.

The best poses don't call attention to themselves.

They simply let you shine.

5. Your Expression

Your expression should reflect both your personality and the impression you want to leave.

Whether you're aiming for confident, compassionate, energetic or thoughtful, sincerity matters far more than exaggeration. A subtle expression that genuinely feels like you often builds more trust than the biggest smile in the gallery.

Choose the photo that feels the most like yourself, even if another image seems slightly more "perfect."

People connect with people, not perfection.

If you've narrowed your choices to two photos that are incredibly similar, but you truly can’t decide, try asking yourself these questions:

• In which photo do my eyes feel more alive?
• In which photo does my expression feel more spontaneous?
• In which photo does my personality come through most clearly?

Those answers are usually more valuable than asking which one makes your nose look half an inch smaller.

Ultimately, a great professional headshot makes someone stop scrolling and think, "Who is this person? I'd like to know more."

Of course, getting feedback from family, friends or colleagues can be incredibly helpful. Just remember that your goal isn't simply choosing the photo where you think you look the most attractive or the most polished.

It's choosing the one that makes people feel like they already know you.

That's exactly what a great headshot should do.

After all, communication begins long before we ever say a word.

I wish you all the best of luck and truly hope your headshot selection process involves far less brain pain and blurry vision than mine did.

Ready to create a stronger first impression? I'd love to help. To learn more about Halligan Media or explore how we might work together, reach out to me at Lynda@HalliganMedia.com.