Last week, I made an argument for how dangerous it is when we don’t talk about people we work with or for, or when we don’t write about them in a way that honors their complexity. I drew a sharp distinction between characters who are powerful vehicles for nuanced understanding, and caricatures that only entrench our dualistic, often dehumanizing take on whole groups of people.
So how does one avoid caricature? Here are a few thoughts.
Obsess over (the right) details. It’s hard to turn someone into a stereotype in your mind when you know a few specific and seemingly incongruous things about them: the kinds of shoes they wear, their favorite drink on a hot day, some wonderful turn of phrase that they always fall back on. It’s amazing how much dignity you imbue people with just by including details about them. Novelists know this. The rest of us need to know it far better.
This kind of nuance often comes from listening, not just to what people say, but how they say it. Jon Mooallem, a truly great contemporary journalist, gives a perfect example in his book Wild Ones, when he describes a local in Churchill, Manitoba:

“His name is Dennis Compayre. People called him Dennis the Bear Man. He had longish, sandy hair, and resembled a thick-set Dennis Hopper. He was imposing, but enunciated all of his words perfectly with the breathy, faintly patrician voice of a Haverford comp-lit professor.”

You’re not going to confuse that guy with anyone else, and he also doesn’t fit into any of the schemas you might have had about wilderness tough guys. In just four sentences, he became real.
Or consider Andrea Elliot’s award-winning profile of one girl experiencing homelessness in New York City. She writes:

“Dasani speaks with certainty. She often begins a sentence with ‘Mommy say’ before reciting, verbatim, some new bit of learned wisdom, such as ‘chamomile tea cures a bad stomach’ or ‘that lady is a dope fiend.’”

You can almost hear her, and though she may, indeed, say some things that might fit your stereotype of what a poor girl says, she also has a surprisingly sophisticated knowledge of herbal remedies. It makes you wonder what else this girl knows that you wouldn’t assume she might.
Get curious and pay attention. To write like this, of course, you have to really watch and listen to people, rather than being in automatic pilot mode. You have to be interested in them outside of the “transaction” at hand. Ask questions out of left field. Listen beyond the words. Take copious notes, not just about what’s said, but how it’s said — facial expressions, body language, loaded silences.
As journalist James Parker writes,

“Keep your flaps ajar, brother; lower your filters, sister; and you’ll get more data, more details, more stuff to write about.”

Assume less. Yes, there is something fundamentally human at the core of each one of us — some shared brokenness and hope — but that isn’t an excuse for jumping to conclusions about what the person across the proverbial table is experiencing. Empathy is good, but assuming you understand someone’s motivations or dreams or emotional experience of a particular situation is a missed opportunity for surprise and delight. Instead, ask them. Don’t be in a hurry to relate; it’s less satisfying, ultimately, than earning unexpected understanding.
Related, this requires asking open-ended questions. Parker Palmer and The Center for Courage & Renewal, the best teachers of this lost art that I know of, instruct:

“The best single mark of an honest, open question is that the questioner could not possibly anticipate the answer to it. Ask questions that are brief and to the point rather than larding them with background considerations and rationale — which make the question into a speech.”

This means, ask “How did you feel?” rather than “I can only imagine that was a humiliating experience. Were you pissed off?”
Use real names. Sure, Shakespeare said it, but so did rapper Kendrick Lamar:

“If I’m going to tell a real story
I’m gonna start with my name.”

By which he means that names mean something. Even if you don’t love yours, it comes from somewhere, it says something nuanced about who bore you, where you were raised (possibly), how your lot in life has been influenced by that significant combination of letters — whether you’ve embraced its resonance or pushed back against it at every turn. Inversely, when you leave someone anonymous (which, granted, is sometimes necessary for ethical reasons), you strip them of that embrace or push, that contextualization of source and geography.
Go for possibility, not pity. Even those in the most destitute of circumstances, those most cursed by violence or shitty systems, those with the saddest stories you’ve ever heard — especially those — deserve to be translated with a tone of possibility. Look for the sliver of light in people’s journeys. Usually it’s wider and more promising than you think. Look for the post-traumatic strength born of tragedy. Look for their own dreams, in their own words. This doesn’t mean romanticize. It means to write and speak in a way that honors the full range of the human condition as seen through one messy human. That intricate art, not the flattened rush-job of hero worship or victim pity, is a gift.
Again, Andrea Elliot’s portrayal of 11-year-old Dasani honors the girl with nuance:

When Dasani looks into the future, she sees who she won’t be. She won’t be a dropout. She won’t do drugs or smoke or drink. She won’t get married, unless she finds “a gentle man, not a harsh man.”

She won’t have children unless she can support them. She won’t end up on the street.
“Spare some change?” she says, mocking a panhandler. “Nuh-uh. Not me.”
It is harder for Dasani to imagine who she might become. She has been told she must reach for college if she wants a life of choices, but who will pay? Her mother is quick to ask that question whenever Grandma Sherry tries to encourage Dasani with the shining example of a niece who graduated from Bates College in Maine on scholarship.

Other children talk of becoming rap stars or athletes, escaping their world with one good break. Dasani subscribes to the logic of those fantasies. Her life is defined by extremes. In order to transcend extreme poverty, it follows that she must become extremely rich or extremely something. What exactly she cannot see. To dream is, after all, an act of faith.