To Become a Better Ally, Keep Asking ‘Why’

Learn to look beyond the first question

Photo: Luis Alvarez/Getty Images

One of the best pieces of business advice I received when I was starting out as a consultant was to keep pulling on the thread.” In other words: Don’t fall for the first answer, or the second answer. To get to the root cause of a challenge, you need to keep asking “why” to cut through the excuses and red herrings. It’s only after asking a long series of questions that you’re able to get from “Why is this company’s stock price in the toilet?” all the way to, “Oh, this company’s growth is stalled because no one wants to work with the executive in charge of innovation, who is an arrogant jerk,” for one totally hypothetical example.

Breaking through each layer of “why” takes hard work. It often means pushing through long-held myths. It doesn’t happen in one conversation with one person. It takes looking at the numbers, listening to the stories, doing your own math, listening to more stories, and bringing in outside comparisons until a leading hypothesis emerges and the other hunches fall away.

I’ve realized that training ourselves to ask “why” can also help us become better allies to women and BIPOC leaders. It allows us to move beyond our unexamined biases to create a stronger bridge of understanding and empathy.

For example, say I have a professional meeting with someone who keeps me waiting and arrives very late. That someone is a woman of color.

I might be looking at my watch, feeling irritated (even though I myself am a woman of color). I might start by filling in the “why” of her action with a negative story before she even says anything, assuming that she doesn’t care about our meeting, or she doesn’t value my time, or she’s lazy and inconsiderate. In this context, as in every human interaction, asking “why” in the most open, tuned-in way is likely to elicit more insightful realizations. So instead of demanding (even with my “inside my head” voice), “Why were you late? Is it because you don’t value my time?” I ask about what happened before our meeting in a more open-ended way: “How’s your day going so far?”

She might be suspicious, or embarrassed, or want to dig into the meeting because of limited time. So often I don’t get to ask all my “whys” in the same meeting.

Maybe the next time I see her, I’ll ask if she has kids, and maybe the answer will turn out to be that she’s sometimes late because she is struggling under the burden of doing 80% of the childcare and laundry in her home and finding help for her diabetic son with little to no reliable support.

Or maybe I’ll ask about her workload on the team she’s on, and if she feels like she’s succeeding. Maybe it will turn out that she’s late because she didn’t want to walk out of a meeting with her boss, who keeps telling her she is on the cusp of a promotion while stealing her ideas and bad-mouthing her to his colleagues so that she can’t move elsewhere in the company.

Even better, I can try to figure this out without making her describe the pressures that are squeezing her empty. Instead, I can ask HR what our company is doing to retain and promote women. On my own, I can try to suss out if there is a broader pattern impacting my tardy colleague. Maybe I can ask my junior women colleagues how they are doing, and how they are struggling. Maybe I can read a book about the additional hours of work women are doing at home. (An excellent one is The Second Shift).

Landing on the most complete story is hard because structural sexism and racism are often buried in the details. Moreover, the loudest stories are most often the ones told specifically with the purpose of invalidating a group’s narrative and power.

That’s why one of the most effective acts of allyship is to dig. And keep digging.

I say this because I have noticed a pattern. The times I’ve been dismissed as “mousy” or “greedy” or “abrasive” by otherwise thoughtful people who truly care about not being jackasses and contributing to systemic injustice, it’s almost always because the person has stopped at the easiest first answer. The thing he saw when he walked into the room. The parallel he drew with the stereotype of Asian women in popular culture. His lack of familiarity with the lives of working women in general, and working Asian women who are daughters of immigrants in particular.

While digging deeper is a good idea in general to promote more meaningful human connection, it’s absolutely essential as a first step for successful allyship.

To be anti-racist, or anti-sexist, we must ask “why” — over and over (and over). We must get curious about the people around us, especially when they are women or BIPOC colleagues. And most especially when they are letting us down or pissing us off.

To be clear, this is not to say that someone’s gender or color of skin should be an excuse in and of itself. “She’s late because she’s a woman” is not good allyship.

What is good allyship is to train yourself to get more curious about the situation behind your colleague’s tardiness if she’s a woman. To be suspicious of your first answer and work instead to build greater understanding.

“Pulling on the thread” helps me to operationalize my desire to become a better ally. By zooming into the situation around me, then zooming out to educate myself about the history of misogyny, I can become a better ally to other women and a more curious witness to myself.

Entrepreneur + Essayist. CEO of sustainable gifting company: Speaker, writer: Addicted to making meaning.

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