Why Executives Are the Easiest People I Photograph

Everyone assumes photographing the CEO is going to be the biggest challenge. Big title, no patience, opinions about everything, and probably a long history of hating photographs of themselves.

For me, it almost never goes that way. When I walk into a company to photograph the chief executive and the leadership team, the executives seem to always make my job smooth sailing. However, the hurdles I get entangled in with those underneath them makes me shake my head at times.

What executive headshot sessions are actually like

The attitude I get at the top is almost always some version of the same sentence: “You’re the pro. What do you need me to do?”

Someone on their team brought me in, and I hope they gave them the memo that I’m pretty good at this. Before I’ve even said a word, they’ve already decided I must know what the heck I’m doing. So, in the interest of time, they embrace my method and begin taking direction. Every once in a while, I get a live one who needs settling down a touch, but it’s rare.

That may sound like a small thing, but it can completely make or break my day. When somebody hands me that kind of trust, I can tell them where the chin goes, how to position their shoulders, what to do with their eyes, and when to react, etc. There’s nothing to negotiate, and I never have to fully explain the method to my madness. I capture images directly into my laptop and review them with my client as we go, so the proof really is in the pudding.

I was fortunate enough to photograph Tom Bilyeu, who built Quest Nutrition, sold it for a billion dollars, and now runs Impact Theory. A client of mine whom Tom had interviewed referred me, so I knew he already had a sense of what I did. With that solid referral, he was amenable to whatever we needed to do to get the job done. He stood in front of my camera and said, “Just do your thing. I’ll do whatever you need me to do.” I loved it. I know my direction so well that, with someone who gives me that level of trust, I can push into territory I wouldn’t normally introduce unless I felt completely comfortable. It showed in the work, and I was fired up about the results. I also photographed Tom’s wife, Lisa, and the two of them together. The success of that initial session led to my photographing the cover of Lisa’s book, Radical Confidence.

I can’t stress enough how important it is for me to direct people exactly the way I feel like directing them. No hedging, no checking whether they are going along with it or not and no second guessing. That, in a nutshell, is the difference between a session that flows freely and one that drags on while you are simply hitting the shutter button just to get it over with.

Who actually gives me a hard time on a corporate shoot

The people below the executives are a different story.

When someone hasn’t yet decided that I’m the expert, they can be apprehensive about taking my direction. They hold something back. They take half the direction and keep the other half for themselves. But a session where someone is holding onto control will never go as far as one where they’ve let it go.

I can’t blame them. Almost nobody has been photographed by someone who truly directs them. They’ve been pointed at and clicked, told to say cheese, then left to figure out the rest alone. So when a stranger starts telling them what to do with their jaw, holding back is a completely reasonable instinct. It’s also the thing that puts a stiff, guarded face in the picture.

The executive wasn’t born easier to photograph. Someone gave them permission to trust me before I ever stepped through the door. Nobody handed the person three floors down that same permission.

Why company headshots come back looking mismatched

Now put yourself in the booking seat for a leadership team or an entire company. Your own headshot is the easy part. The hard part is everyone else on the schedule. A VP who’s never been directed in his life. A new hire nobody has ever told where to put her eyes. Give a building full of those sessions to someone who simply points a camera and presses a button, and you get what you’ve seen on a hundred company websites: a leadership row where half the faces look like they were hired by a different company.

One confident executive is an easy shoot. Forty people, most of whom dislike being photographed, who all need to look like they belong to the same organization? That’s a different job. And the whole job is earning trust from people who didn’t walk in offering it. That’s what my group sessions for business and corporate headshots are built around, whether your team is in one office or spread across the country.

That’s why I trained a network of talented photographers rather than shooting everything myself. Every certified associate photographer in my network follows the same system by design, so your office in another city receives the same direction principles allowing us to capture the same look as the people I photograph myself.

Why an executive headshot has to work small

Your photograph is going to live small. On LinkedIn, it’s a circle next to your name. On a leadership page, it’s a thumbnail. In a press piece, it may be one face beside four others. That’s why I shoot tight: chest up, with the face dominant. Even when the image gets small, there is still a face to see.

You can check this yourself. Open your company’s leadership page and lean back from the screen. Some faces still reach you. Others turn into blurs.
Most likely the faces that reach you were shot tight. That’s the difference.

You don’t have to walk in trusting me the way Tom did. Most people don’t. Trust gets built during the session, and building it is most of my job. The camera part is easy.

Whether it’s just you or your entire company, here’s how a corporate session works.