Editor’s note: Billy Warden is a writer, marketing exec and multimedia producer based in the Research Triangle, where he co-founded the p.r. agency GBW Strategies.  He writes a column exclusively for WRAL TechWire which is published on Mondays.


Photo by Bill Reaves: “I try to photograph a little of the person’s soul in every portrait.”

RESEARCH TRIANGLE PARK – What does “cosmic mojo” look like in a headshot? When photographer Bill Reaves invited me to sit for a portrait, I found out. 

The resulting shot, seen above, was a wham-bam glam-slam. Granted, Bill was there to capture the essence not of the ‘me’ who co-founded marketing shop GBW, but of the ‘me’ who still performs with funk’n’punk band, The Floating Children. 

Still, the experience – and the resulting groove-licisous eye candy – got me thinking about headshots. In this digital age, they’re often our first impression of a new colleague, business associate, candidate etc. 

And yet, even with piles of advice on corporate and personal branding out there, many headshots amount to, in the words of globetrotting photographer Justin Kase Conder, “a guy in a blue suit and a white shirt and the same tie posed against a gray background looking like he’s been stamped out of a machine.”

So I asked Bill, Justin and other consummate clickers to offer some snap judgements and advice. 

Getting started

Bruce DeBoer: “There is no set way to take business photos. When done well the photos are well crafted but also fit the brand of the company. They should help to tell the story of the individual AND the company.”

Jillian Clark: “I always tell people you want it to feel approachable and trustworthy, but (like) no one’s gonna mess with you, either! It’s a balance, a weird dance.”

Justin: “I like to work with companies that see people as unique and contributing important things. I don’t want to work with companies that see staff as cogs. Each person has a story. Let’s do something interesting to make them individuals.”  

Photo by Justin Kase Conder: This teacher-scientist’s connection to NASA instantly elevates her credibility and intrigue-factor.

Common mistakes 

Kelsey Kemp: “People using poorly cropped photos to stand in for a professional headshot. It can be fine for a placeholder or for something like a company newsletter, but not for the long-term.”

Justin: “Sometimes an approach can seem like it’s trying too hard; it feels overdone. It’s about authenticity. If you’re trying to be a character, OK – but if when people actually meet you, you don’t live up to it, that’s a problem.” 

Jillian Clark: “Too many people shoot headshots from way high up on an angle to try to quell any body issue fears. And too many people wear things that are either too distracting or don’t have enough character. and it falls flat.”

Kelsey: “Just as there’s a way to be too formal – I’m picturing some where someone has folded arms and a serious expression on their faces. We get it. You mean business! – there’s also a way to be too informal. Having your staff in t-shirts for their professional headshots – why?”

Bruce: “Generally, poor quality dragging down the company brand. Poor quality may mean no attention to wardrobe, hair and/or makeup (this doesn’t mean a professional necessarily), lighting, background, etc. Even if the headshot is taken by an administrative assistant, it can be of high enough quality to meet brand expectations.”

Bill: “In my opinion it’s better to have no headshot than a boring one.”

The right look

Bill: “I empathize with a subject having a professional photo. I try to psychologically take the camera out of play by just having a light conversation to calm and get to know them. I always go in with the concept, “THIS IS GOING TO BE THE SHOT OF MY LIFE.” It might sound weird, but I try to photograph a little of the person’s soul in every portrait. It’s too cosmic to explain.”

Justin: “My go to is saying something that’s entertaining. A lot of these people are not initially comfortable. They might have gotten the memo 15 minutes ago that this is happening. I b.s. with them. Take down barriers.”

Jillian: “With any good photographer, you should walk away from a session with a few different moods or expressions to choose from. Something comfortable and confident that feels like ‘you’ is most important.”

Kelsey: “Any photo where you force someone to smile in a way that they normally wouldn’t will look stilted and wooden. Some people smile big. Some people are more comfortable not showing their teeth. A photographer should always check with the client to see if they’re comfortable, how they’re feeling. I always try to show my clients a couple of photos as I’m going to make sure we’re both on the same page.”

Bruce: “Keep the session relaxed and as fun as possible. It can be a challenge to help people who hate having their photo taken feel willing to show their authentic selves. It’s the photographer’s job to find a way to pull what they can from their subject.”

Jillian: “My best trick is to ask the subject to look as if they “‘know something I don’t know.’” 

Photo by Jillian Clark: “My best trick: ask the subject to look as if they ‘know something I don’t.’”

About the author

Billy Warden is a writer, marketing exec and multimedia producer based in the Research Triangle, where he co-founded the p.r. agency GBW Strategies.