The Generous Interpretation: A Tool for Understanding Others

Avoid Misinterpreting Others with These Two Questions

“I started spiraling immediately,” my friend Carrie (name changed) told me, as she described a comment from her father that sent her off.

Like many in our generation, Carrie is managing a busy career and full life while also trying to care for her aging parents. She was at their home one Saturday, delivering flowers and doing some light cleaning when her father made an abrupt statement.

“You should be better about money,” he told her.

It was a gut punch comment—the kind that felt designed to hurt while also being misguided. Not only had Carrie been exceptionally responsible in her finances and she’d recently taken a less demanding job to have more time for her parents.

“My mind went off on its own mission,” Carrie told me. She felt judged, as if her contributions were invisible.

Misinterpreting the moment

It’s so easy to read intentions into others’ comments—even people we know well—and get them entirely wrong. I saw this recently at work, when a retiring president told me about receiving letters of support from people he considered nemeses. He wondered: had he been misreading their attitudes all along?

This kind of misreading is common. As a leadership coach, I hear clients describe “nasty” emails from colleagues they consider enemies. They’ll read the messages aloud, infusing venom into the tone—but the words themselves are neutral.

A question you can ask yourself to diffuse

A friend once asked me a question that changed how I approached a tense work situation:

“What’s the most generous interpretation of this?”

I had been frustrated by a team member who seemed obstructive. Her question forced me to consider their perspective: what values or logic were they working from? Could their objections be valid?

It turned out they were. The question helped me extend more positive regard, reframe my approach, and work collaboratively with the team member to move our project forward.

My therapist offers a similar approach. After hearing my complaints, she’ll say:

“That’s one way to interpret this. What’s another meaning you could make?”

On my best days, I’m able to see that the world is not against me—most of the time, neither are your parents or colleagues.

Our minds often cast us as the main character in a drama, spinning stories that confirm hidden fears rather than reality. These questions let us explore alternative plotlines and extend positive regard.

Carrie could have used these questions as she processed her father’s comment. Fortunately, she paused and sought clarification instead of storming out.

“I want you to retire well,” her father explained. “And to do that, you should be good with money where you can.” I like to imagine he gestured to the fresh flowers on the table, the clean space, and the daughter who was caring for his needs.

BONUS QUESTION

Recently my teenage daughter got an invitation to attend a concert with a friend. She was interested in the artist and wanted to hang out with the friend—but the concert was on a school night, and she didn’t like the idea of getting back late and being sleepy the next day.

Helping her think through the decision, my husband asked a familiar question in our household: Which choice will make for a better story?*

That’s not a piece of advice (framed as a question) you could offer to every teenager, I know. But in our home, it’s a good reminder that life is meant to be lived.

So … here’s a question for your journal, dinner table, or lunch with a friend: What choices are you making that will lead to a good story? Where are you picking adventure over comfort? Purpose or play over a night at home?

Magdalene went to the concert, had a blast, and still made it to school on time the next day.

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*I think this question originated with an anecdote from Ira Glass, host of NPR’s This American Life, but I can’t find the citation.

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Photo by Kindel Media.