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Why are CEO photos so weird?

A Forbes photo director explains.

Apple CEO Steve Jobs with his LISA computer in 1983.
Ted Thai/The LIFE Picture Collection/Getty Images
Rebecca Jennings is a senior correspondent covering social platforms and the creator economy. Since joining Vox in 2018, her work has explored the rise of TikTok, internet aesthetics, and the pursuit of money and fame online. You can sign up for her biweekly Vox Culture newsletter here.

There is a reason nobody in the world ever sits on a radiator. It’s because a radiator is made of big, poky chunks of metal that, even when not turned on and hot, will still jab ruthlessly into the sitter’s ass.

That is, unless the sitter is a cool, young-ish CEO getting his or her portrait taken. While CEOs and founders command millions or billions of dollars and are among the most high-profile people in our society, when it comes time to take a photo for a magazine, they’re forced into some of the most uncomfortable, least humanlike positions in existence.

Maybe they’re told to crouch on a radiator. Maybe they’re perching on a flower box, or the arm of a couch, or a conference table at a strange angle opposite their co-founders. (Regardless, they are definitely putting their butts on something really hard.) Maybe they’re curled up on the floor in the corner or, more likely, crossing their arms and leaning against an exposed brick wall with one foot up. You know, like people do!

For many, the CEO portrait is one of the few glimpses into the lives of society’s most powerful people. There are the corporate kind, those that show up on company websites and in annual reports and are, for the most part, incredibly boring because they attempt to convey “I am an important business person, so please trust me with your shareholder dollars.” And there are the editorial kind, produced by an artist or independent publisher and art-directed in whatever way the photographer wants.

It’s those kinds of photos that are, naturally, the most interesting. A good photograph can convey the attitude behind how businesses are run, as with Mark Zuckerberg’s inexpressive and often awkward stare depicted by Wired or Evan Spiegel looking like a frat bro in Vogue (and possibly leading Snapchat like one).

When Albert Watson shot Steve Jobs in 2006, he reportedly told him to “imagine you are across the table from four or five people who don’t agree with you, but you know you are right.” The resulting picture has become the most iconic image of the late CEO, and in 2011, Apple asked the photographer if they could use it on their website for the announcement of his death.

So why, given the artistic possibilities, are so many of them so awkward-looking? “You cannot underestimate the influence of the Sears portrait gallery,” Robyn Selman says. She’s been the photo director at Forbes magazine since 2012, and directs 200 to 300 photoshoots of CEOs a year. “It’s what everybody thought of when they thought of a picture. Making a photograph was a special-occasion thing. It took quite a long time to get away from that.”

Microsoft founder Bill Gates in 1985.
Deborah Feingold/Getty Images

Photography trends also change with the times. Compare the portrait of the young direct-to-consumer, venture capitalist-backed founder of the 2010s leaning against exposed brick to those of the early ’80s tech whiz. While often also positioned in extremely non-human shapes, like Steve Jobs looking like a newscaster in an intro sequence (above) or Bill Gates lying down on a desk and cradling a computer, the older photos have an intimacy on top of what we’ve come to see now as cheesiness.

“I actually find it a little Playboy-influenced. It seems kittenish to me that he’s canoodling with the technology,” says Selman on the photo of Gates. “When we see people, for instance, sitting on a radiator — a radiator isn’t a comfortable thing to sit on — they lack the intimacy of that Bill picture.”

Today’s Silicon Valley CEO portraits, meanwhile, rather than focusing on the actual thing said CEOs created are more concerned with conveying the casual, uber-chill (no pun intended) aesthetic of the capital of innovation. That’s why we get so many strange-looking, radiator-sitting CEO photos — nobody wants to look like the stuffy executive taking a standard yearbook photo in a bespoke suit.

“It’s a great photograph — beautifully constructed, beautifully lit, beautifully retouched,” says Selman. “Who would have ever thought Kylie Jenner would be on the cover of Forbes?”
Jamel Toppin/Forbes

Like those in other artistic practices, photography trends tend to trickle down from the avant-garde. Richard Avedon’s groundbreaking “In the American West” photo series from 1979, for example, has largely influenced the way we conceive of street photography.

In photography, the avant-garde is often set by those who photograph celebrities. Selman calls it “artificial realism” — the clearly staged, yet still fly-on-the-wall capturing of “the beautiful life,” common in, for instance, Vanity Fair spreads — which has since found its way into corporate photography. “That’s what I think we’re attempting to see when we put somebody on a radiator,” she says. “We’re trying to find a comfort in that environment.”

This presents certain challenges, not least of which is that corporate environments are generally not the most visually enticing backdrop for a photo shoot. As New York Times contributor Cole Wilson told Racked of photographing CEOs, “I’m in these really shitty spaces where you don’t have a lot of control over anything. They have low ceilings and really boring office furniture. There’s nothing to work with that feels aesthetically inspiring.”

“I think my favorite of [this series] is T. Boone Pickens,” says Selman. “There’s such an openness to that man’s face and it’s fantastic. I very much like shooting the senior guys, that demographic. I love looking into those faces.”
Martin Schoeller/Forbes

One way to combat that blandness is by implementing lighting techniques. Wilson uses direct-flash photography to create a blast of light that makes the portrait appear heightened, and, as writer Eliza Brooke noted in the Racked story, “can also give the unromantic appearance of putting its subject under a microscope, which fits the bill when the story is about corporate America.”

Another challenge in making compelling CEO photos is that these are people with some of the most micromanaged schedules in the world, and so photographers may only have a few minutes to work.

Selman offers one former CEO who was a notable exception to that rule, however: “The last time we took a picture of President Trump, he had to leave. We were in the Oval Office and he had to go into a meeting ‘with some of his generals.’ He was only gone for about 10 seconds before he came back, because he couldn’t resist going through the take on the computer and picking out more pictures that he liked. He knows what he wants it to look like, and he will not leave the room until you have flagged for him to see the image that he wants.”

“Anytime you can shoot Oprah Winfrey is golden,” says Selman. “Wonderful.”
Martin Schoeller/Forbes

With these photos, as with any photos, really, the worst thing a photographer can do is fail to make a connection with the subject. Because even if powerful CEOs create are responsible for much of damage in the world, they’re still like everyone else: vulnerable in front of the camera.

“We think of the portraiture as less a portrait of the powerful CEO and more a portrait of a person,” Selman says. “The best Forbes images, you’re getting a feeling. Somehow that image should make you feel something, whether it’s interest or curiosity or, ‘Gee, they look nicer than I thought they would.’”

Ultimately, the subject cares about what the photo looks like just as much as the photographer. “Everybody wants to feel attractive and look good,” Selman says. “We once did a portrait of Carl Icahn, who’s got a pretty notorious reputation in this world — some say that that movie Wall Street is based on him — [and he] called my home no fewer than three times over a weekend to ask that we not make him look like a son of a bitch. They’re all just people.”