Can we truly empathize with someone whose life experiences differ dramatically from our own, or is sympathy as close we can get?

Actress, playwright and MacArthur Award winner Anna Deavere Smith has been exploring this ruthlessly for years.

You may recognize her from TV shows “Nurse Jackie,” “West Wing” or Shonda Rhimes’ new “For the People.” Or maybe you know her as “the most empathetic person in America,” a title bestowed upon her by the Huffington Post.

Her most recent original work is The Pipeline Project, which includes her one-woman, multi-voice theatre production, “Notes from the Field” (now a film on HBO) based on 250 interviews conducted in four regions of the country. In the show, Smith personifies 18 of those interviewees, including civil rights legend Rep. John Lewis and Kevin Moore, the Baltimorean who filmed Freddie Gray’s violent arrest.

“I’ve been chasing that other America,” she said — the parts unknown to her — “and it caused me to have a greater sense of belonging.”

I heard Smith speak during Leadership Philadelphia’s “Master Class on Empathy” on Tuesday afternoon during which alumni of Leadership’s Core program and Connectors and Keepers cohorts were challenged to meet and, indeed, empathize with unfamiliar co-attendees by listening to their stories of challenging times. Smith then asked several pairs to perform each other’s stories onstage. (Read an excellent recap of the full event by Philly.com columnist Ronnie Polaneczky here.)

The result: tales of structural racism, innocence, ignorance and everything in between.

“I am radically against passive observance,” Smith told us. Here are three lessons on leading with empathy from the artist.

1. Start by listening only.

Whether you identify with someone’s perspective straight away or not, you owe it to them to listen with an empathetic imagination.

Give them a chance to explain what their life has been like before assuming.

2. Follow the “changing move” when the speaker is responding to challenging or uncomfortable circumstances.

During a scene in Smith’s performance of Kevin Moore, she takes a pregnant pause and inhales before murmuring that she (as he) is “tired of being tired.” Why? An important thought takes more breath to say.

“Look for the moment when the person is most communicative to you” — without words, Smith said.

When having a difficult conversation with someone, note their body language and consider what each shift of leg position, posture, hand movement means.

3. Remember: You don’t have to agree with someone to try to understand them.

Take a lesson from character acting: Do not judge those whom you try to understand.

The person on the other end of an argument is still a person who has experienced strife just as you have — different strife, to be sure, but strife nonetheless. And it’s informed their worldview, just as yours has.

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This story includes additional reporting by Christopher Wink.