Tips + Techniques

How Photographers Make Good Portraits in Lousy Settings

July 6, 2020

By David Walker and Conor Risch

© Mackenzie Stroh

Abby Stein, a former rabbi, photographed for London-based Sunday Times Magazine.

In these in-depth discussions, three talented portrait photographers share how they problem-solve and make good portraits in lousy settings, and tackle the bad locations that every photographer dreads—from boring conference rooms and generic hotel rooms dozens of others have photographed to cramped or badly lit homes and offices. 

Saoirse Ronan photographed by Mackenzie Stroh for The Wall Street Journal.
Saoirse Ronan for The Wall Street Journal. © Mackenzie Stroh

Mackenzie Stroh on Portrait Problem Solving

Celebrity and editorial photographer Mackenzie Stroh has shot portrait assignments in all types of lousy settings and environments, from cramped bedrooms to “locations that are super, super fancy.” She tries to scout the locations beforehand, or at least get location photos to help her figure out what she’ll need for lighting. But about half the time, she doesn’t know what to expect.

“You have to brace yourself for the worst circumstances, and go in fully armed and ready to problem solve,” she says. “OK, worst case scenario: What’s the plan B, what’s the plan C?”

Stroh keeps her cool by focusing on her goal. “My mantra is: It’s about the person…you’re here to engage with the subject. It’s not about the space. The space can help, and it definitely is a huge part of a portrait sometimes, but it should never be the focus.”

Among recent assignments in difficult locations and lousy settings was a Wall Street Journal assignment to photograph actress Saoirse Ronan. Ronan was on a press tour for the film Mary Queen of Scots. Stroh had 8 to 10 minutes for the shoot, “in a basement setting” at the Crosby Hotel in New York. The loose assignment brief gave Stroh the freedom to shoot as she wished. 

She had two set-ups in mind: One with soft light, shot wide open, another with hard, specular light. Of the hard-light set-up, Stroh explains: “[Ronan is] so stunning and her eyes are incredible. I thought: Let’s do something more dramatic…. It’s kind of like old Hollywood glamour.” Stroh brought several different colors of seamless. “I knew that I wanted to do something on a dark colored background.”

Saoirse Ronan in lousy setting that's been re-imagined, photographed by Mackenzie Stroh for The Wall Street Journal.
Saoirse Ronan for The Wall Street Journal. © Mackenzie Stroh

Upon arrival, Stroh discovered a low ceiling in a tight space. “I had to move all the furniture,” Stroh says. She managed to squeeze two set-ups into the space, but there was barely enough space to position the lights where Stroh wanted them, or to put much distance between Ronan and the seamless backgrounds. “I had to shoot her tight because the space was tight,” Stroh says. When the actress walked in, she was exhausted. “We chat for a minute, but really she just wants to get through the photos and get out,” Stroh says.

Ronan was gracious—she had even asked Stroh what she wanted, and the photographer showed her some reference images of subjects with intense gazes and subtle gestures: “Things with a little bit of movement, nothing too pose-y,” Stroh says. Then for several precious minutes, she struggled to get something that felt authentic. Finally, with two minutes left, Stroh decided to change the backdrop. She had already tried several different colors but says, “As a wildcard I [used] this orange [seamless].” It complemented the blue sweater Ronan happened to wear to the shoot (there was no stylist on set). Stroh also had a hard Fresnel light on Ronan, and she went in tight. 

“The PR people were like, ‘Oh, this is interesting!’” the photographer says. That helped animate Ronan. “She was super generous in terms of doing what we needed, moving and being lovely in front of the camera,” Stroh says. “I definitely covered it wider as well, but her eyes were so stunning.”

Stroh says she often saves the set-ups she most wants to shoot for last, because it usually takes some time to build rapport with her subjects. “Even though I had only eight minutes [to photograph Ronan], sometimes it takes six minutes for somebody to feel comfortable.”

Gayle King photographed by Mackenzie Stroh for <i>The Hollywood Reporter.
Gayle King for The Hollywood Reporter, photographed by Mackenzie Stroh on a rooftop above CBS studios in New York. © Mackenzie Stroh

Another challenging shoot, Stroh says, a shoot with TV journalist and personality Gayle King for The Hollywood Reporter. King moved up the time of the shoot, so Stroh had no time to scout the CBS studios in New York. She adds, “I didn’t have the time I needed to really pull my ideas together, so I said: Let me just do the best that I can when I get there.” 

Stroh had to shoot several portraits in order to give THR editors options for both the cover and inside spread. Her plan was to start with classic portraits against seamless. She arrived to find 50 chairs set up in the room where she was supposed to do the shoot. “We asked: Can we get these moved? And the answer was like: I have to get the guy who gets the guy who gets the guy to move the chairs.” 

Stroh and her assistant waited 20 minutes, then ended up moving the chairs themselves, in violation of union rules. “I said to my assistant, I don’t care, let’s go, we’re running out of time.”

The room also had little space and low ceilings, making a set difficult to light. Stroh struggled to get enough distance between King, the backdrop and her camera. “It was challenging to get a couple different [portrait] options in a short period of time. Ideally, there’s one set-up on one side of the room, and another on the other side, but there wasn’t space for that,” Stroh says. She resorted to switching out the background to get two different portraits from one lighting set-up.

Then she and her assistant rushed up to the roof to get more portraits of King outdoors, with a Manhattan skyline behind her. They had just a few minutes to move equipment and set up. “It was the most insanely windy day I’ve experienced in New York,” says Stroh. The wind forced her to make do with a fill light and nothing else and she says, “[King] almost shut the shoot down because of how windy it was and her hair was blowing all over the place.” 

Fortunately, King was comfortable enough with Stroh by that point to give the rooftop setup a try. Stroh wasted no time. When she noticed King looking outward, away from the camera, she clicked the shutter. “Probably she looked out, quite frankly, to get the hair out of her eyes,” Stroh says. “That’s a case of, despite everything going wrong, there’s a moment of stillness that worked for the story.”

Good portrait in lousy settings: Abby Stein photographed by Mackenzie Stroh for photographed for London-based Sunday Times Magazine.
Abby Stein, a former rabbi, photographed for London-based Sunday Times Magazine. © Mackenzie Stroh

Not all of Stroh’s assignments are celebrity shoots. She often photographs non-celebrities at home. Clutter and lack of space are frequent challenges. “A lot of times you walk in and people are like, Oh my god, I had no idea you were bringing this much equipment,” the photographer says.

That happened on a recent job for the London-based Sunday Times Magazine. Stroh was assigned to photograph Abby Stein, a transgender woman and former rabbi who had left the Hassidic community to transition. Stein agreed to be photographed at home in Brooklyn after editors asked Stroh to shoot “in an intimate location.” 

Stein hadn’t been able to send location photos of her apartment. “When we got there it was not what we were expecting. It was really tight, there was a lot of furniture in the space, and we needed a full range of portraits, from full body to really tight.” 

To make it more difficult, The Times’ esthetic leans to glamour, Stroh says. “They want people to look good.” They also wanted photographs that were clean, not cluttered. “Sometimes I love a cluttered space, a quirky space, but the whole aim was to show the transition and femininity of this person, and the background wasn’t working with what I was trying to get.”

Stroh went for a minimalist look, removing all she could from the space. “Thank God I brought multiple sizes of seamless, because only the very smallest fit into the room. We shoved everything into the hallway, and had it stacked to the ceiling. The makeup artist was in the hallway as well,” Stroh says. To shoot one portrait of Stein lying on her bed, for instance, Stroh directed Stein to put a white sheet on her bed, and wear a flower print dress.

“[Stein] was game to collaborate, and you don’t always get that. She was [also] a little vulnerable, which is what that portrait called for,” Stroh says. “That’s a small victory to say we made it work in that time, in that space, with that person.
—David Walker

Cayce Clifford on Challenging Office Portraits

Based in the San Francisco Bay Area, Cayce Clifford often shoots editorial portraiture assignments involving executives and employees at major tech companies. The headquarters of these companies may be designed by famous architects and look amazing, but, Clifford says, secrecy and confidentiality frequently prevent her from taking full advantage of the spaces. “You walk in and it’s beautiful, and [the PR rep is] like, ‘But here’s your conference room where you can shoot.’”

Portrait of a woman outside photographed by Cayce Clifford.
Old Navy CEO Sonia Syngal photographed by Cayce Clifford for Fortune. When Clifford showed up to make the portrait, the electricity in the building was off and security was contemplating evacuating the building due to a utilities issue nearby. © Cayce Clifford

Other office shoot challenges and lousy settings include overhead fluorescent lights that you can’t turn off; immovable conference tables; low ceilings; and coworkers who make faces at a subject who is having a portrait made, or who won’t stop playing pool in the next room while Clifford is trying to record a video interview, which happened to her recently on a shoot.

Working with clients such as WIRED, Bloomberg Businessweek, Inc and The California Sunday Magazine, Clifford says one of the things she does to prepare for the inevitable difficulties is ask her editor for images of the location. “They could explain all day what the space is like,” she says, but being able to actually see it allows her to pre-visualize what might present a challenge. On a recent shoot for Audubon, Clifford did not get an image of the conference room where she was supposed to set up a 9-foot seamless. Had she done so, she would have realized there was a 25-foot conference table occupying the big, open space she was told she’d have to work in. If she cannot get an image of the location, she’ll do things like zoom in on a building on Google Maps to learn what she can about thing like the height of the ceilings, or how much natural light to expect.

Author and Transhumanist Hank Pelissier photographed by Cayce Clifford.
Author and Transhumanist Hank Pelissier, photographed by Cayce Clifford on assignment for German magazine Die Ziet. Clifford had to set up a seamless in the author’s backyard, which turned out to be especially difficult because of the San Francisco wind. © Cayce Clifford

On a recent shoot for German magazine Die Ziet, Clifford was sent to the home of writer Hank Pelissier, who is a leading voice in the Transhumanist movement, which advocates for the use technology to transcend human limitations and extend the human lifespan. Though she does not often use a backdrop unless a client requests it, Clifford had preplanned a concept for a shot using a seamless and lighting that would make Pelissier “look robotic in a sense, because he’s trying to extend his life by whatever means necessary,” she explains. She got to the house, and the only place she could set up was in the backyard, which wasn’t attractive, so Clifford set up the seamless. That might have been an easy solution, were it not for the San Francisco wind. “Shooting outside on seamless isn’t such a good thing,” she says. But she and her assistant made it work by lugging five sandbags to weigh down the backdrop and keep it from blowing. 

The fact that she had an assistant was part of her strategy for dealing with the inevitable things that happen on every location shoot. Even if there isn’t a budget for an assistant, Clifford has recently opted to hire one out of her own pocket so she can concentrate on making the images rather than dealing with what she calls “shoot brain,” a condition in which “you can’t focus on anything and you’re just scattered and crazy, and any preplanning you did just goes out the window because you’re worried about some light [falling] over or something like that,” she laughs.  

Another strategy Clifford uses to cope when shooting at a company headquarters is to ask to see the personal office of her subject. “People have a misconception that I want to photograph them in this designed office space” that represents their company, Clifford says, but an individual’s office is sometimes nicer and less hectic, which allows for a quieter moment. If the lighting is bad, she’ll ask to go to a room with natural light. Or she’ll overpower the ambient lights with strobes, or use gels on her lights to match the interior light. If there is no saving an ugly space, she’ll ask a subject to step outside, as she did with the owners of Chinatown butcher shop. On that particular shoot, the outside shot “ended up being the choice photo,” she says.

There are “special” times when she shows up for a shoot and the natural light is beautiful, “interesting and there’s space for me to move around,” she says, “and that’s the most ideal.” But the majority of the time, “when you arrive on location at a place, nothing can really prepare you for everything that could happen,” she says. “Recently I showed up to a shoot and there was a manhole explosion and all of the lights in the building were off and it was being evacuated,” Clifford laughs. “You can’t control everything, so there’s no point in worrying too much about it—it’s kind of a fun challenge.” —Conor Risch

Director Lulu Wang photographed by Cole Wilson.
Director Lulu Wang photographed by Cole Wilson for Soho House, in the bedroom of a Southampton, New York inn. © Cole Wilson

Cole Wilson on Being Candid About Portrait Location Challenges

Brooklyn-based editorial and commercial photographer Cole Wilson goes into portrait assignments assuming he’s walking into a difficult situation. “If I get my hopes up about a space, then I’m probably setting myself up for failure,” Wilson says. “It’s not usually just the location that’s difficult,” he adds, “it’s the subject as well, or the fact that you have five minutes with the person.” Nearly every location presents its own challenges, he says, and his experiences shooting for clients such as The New York Times, WIRED, Bloomberg Businessweek, The New Yorker and The Financial Times among many others have taught him that being candid about those challenges—with himself, with subjects and with clients—can help him get good results from less-than-ideal situations and locations.

Prior to a shoot, Wilson says he’ll ask a lot of questions and get as many details about a location as he can from photo editors, producers or PR reps. But, he says, “Never plan on anything being as it seems.” A recent assignment for Soho House, for instance, took him to an inn in Southampton, New York, to photograph director Lulu Wang. She was there for the Hamptons International Film Festival, and Wilson’s assignment was to make portraits and a video interview with Wang against a nine-foot seamless. When he showed up he realized that the inn, which was also the festival headquarters, did not have open spaces for the shoot, “which wasn’t communicated to us beforehand,” Wilson explains. Fortunately, someone was checking out of a room early, so he had a couple of hours in one of the rooms. Unfortunately, it was “the kind of place where the bed just occupies the entire room,” Wilson says. “It’s one thing to shoot in a hotel room, but it’s another thing to shoot in a hotel room when you have a very specific get that is going to require a little more space.”

Wilson was able to make it work by rearranging the furniture, but it was also important to be frank with Wang and her reps about the situation. When Wang showed up, Wilson asked for a bit more setup time, and she was flexible. “Being able to communicate and ask for what I needed was pretty clutch, rather than just lying and telling people I was ready when I wasn’t,” he says. In similar situations, taking a bit more time to set up, even if it cuts into the shoot time with a subject, can be worth it. “I want to make sure that everything is locked in before I bring someone in there and waste my time on something that isn’t fully formed,” Wilson explains.

Menswear entrepreneur Mark Cho photographed by Cole Wilson.
Mark Cho, menswear entrepreneur and founder of The Armoury, photographed by Cole Wilson for the Financial Times. © Cole Wilson

Wilson says that it’s also important to give himself constant feedback. He’ll ask himself, “Is this working?” And if the answer is no, he’ll analyze what’s not working about a shoot. Early in his career, he sometimes struggled to identify what was off, but experience has taught him what he can change to make a shot work. “If I don’t like the way something is looking I know that I can pull the light back, or try dragging the shutter, or just a slightly different angle on the light, or bouncing another light. A lot of it is thinking really quick, too.” 

On shoots at offices, when a public relations rep offers up a claustrophobic conference room with a massive, immovable table, Wilson says he’ll gravitate towards lobbies or reception desks where there’s more space, or he’ll find an angle that downplays the office setting. “We have the power to edit that bit just by turning and finding a corner rather than having to showcase an entire room,” he says.

Though he is more likely to light a portrait than look for natural light, Wilson says it also helps to “recognize when it’s OK to go off of your own script.” He tries to make himself approachable on set, and assistants and even talent have felt comfortable making suggestions, such as where there’s good natural light to take advantage of. 

Open communication is also important with clients, Wilson says. Being honest about “when it sucks” creates a “better understanding of the reality of the situation,” he explains. Wilson says clients are, from his experience, “more willing to be candid [about difficult shoots] than maybe they used to be, which I appreciate.” For Wilson, “The best assignment is when [the client says], ‘I trust you to be creative in this moment and sort out the best way to do this, given that we don’t know all the variables.’” —Conor Risch