The Art of Asking Sensitive Questions

Information is king. Learning how much your colleagues make is an important piece of information that would be helpful for your next salary negotiation. Knowing how much your friends pay in rent can help you decide where to live. Why, then, is it so hard to ask? And more importantly—how do we get better at it?

The fear is that by asking sensitive questions we might make others uncomfortable and leave them with a bad impression of us.

Indeed, asking someone if they’re single, or a classmate about who they’re secretly in love with, might truly be uncomfortable. But surely that’s nothing compared to the uncomfortable conversation we’ll have when it turns out that we’re both trying to date the same person.

To avoid making others uncomfortable, people would rather miss an opportunity to learn something important, even if some of that worry is only in our head. Chances are, the person won’t be offended by the question at all. Colleagues might hesitate to tell you about their salaries, but they are also dying to learn about yours.

To get better at negotiations, interviews, and almost every other conversation that happens in life, we have to get better at collecting information. Asking good questions is where it all starts.

No such thing as a stupid question

In a conversation, people balance competing concerns. They want to gather information, and at the same time, they want to create a favorable impression. Impression management is an important social skill; you don’t want to look like someone who is always nosing around deeply personal secrets. And sometimes, you don’t want to look like you don’t know the answer.

“There are naive questions, tedious questions, ill-phrased questions, questions put after inadequate self-criticism. But every question is a cry to understand the world. There is no such thing as a dumb question.” —Carl Sagan, The Demon-Haunted World

The idea that people should feel comfortable asking dumb questions has strong support. Economically speaking, a community wins if its members have all the information they need to make good decisions. By allowing people to ask stupid questions, a community strengthens its ability to share knowledge.

On the other hand, etiquette experts have been warning against asking inappropriate questions for more than a century. Eliza Bisbee Duffey discourages asking virtually any type of question in her 1877 book, The Ladies’ and Gentlemen’s Etiquette because it’s impolite.

Whichever side of the argument people are on, before asking questions, they’re probably considering:

1. Is it ok to look dumb in this situation? This is an opportunity to embrace the beginner’s mindset. The naïve person’s advantage is that they don’t have to appear as if they know everything, and they can ask fundamental questions without being embarrassed by it.
2. Am I ready to admit if I am wrong? One problem with asking a question is that we might learn something we don’t like. The answer might very well be incompatible with some of our fundamental beliefs. People have to be curious enough to at least consider the different viewpoints of others.

Our questions convey information

Listeners will learn about us from our questions. If nothing else, our questions will tell a listener what we’re interested in.

Questions are not just useful for gathering information; they are a brilliant conversation tool.

1. Questions can be used to express interest in others. People like to talk about themselves, and they like when someone shows interest in them. Simply being curious about someone will build rapport and help you earn social credit.
2. Questions create opportunities to share information. You can direct the conversation by asking someone about a particular topic, and they might respond by asking a complementary question.

How to ask sensitive questions

The most important takeaway from this post is that you should keep asking questions. Rarely does anyone learn anything new from what they themselves say.

Questions can be a social minefield, but getting it right unlocks all the information in the world. Like anything else, it takes practice:

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1. Be a good chap. The conversation shouldn’t feel like an interrogation, but a discussion. Find a way to create an environment where it’s safe for everyone to share information and never use questions to make others look bad. Check in with the other person to make sure your questions are welcome.
2. Share information yourself. Nobody will put all their cards on the table while you keep yours close to the chest. If you want to learn about how much your neighbors pay for rent, offer what you pay first.
3. After asking the question — listen. Listen for the answer and “listen” for nonverbal clues. Does your question make the receiver uncomfortable? Is there something they don’t want to tell you? Are they telling the truth? Do you understand their answer?
4. If you don’t understand something, rephrase the question and ask again. We often come away from discussions without fully understanding some of the answers, kicking ourselves for not having clarified them there and then.

And sometimes, you don’t need to say anything; questions are often nonverbal. Good interviewers know when to keep silent for an (uncomfortably) long time, or just raise an eyebrow at the right moment.

Remember that asking a question is a powerful tool. It lets you access information you wouldn’t otherwise have, and your questions also reflect on you. Practice makes perfect, and as Voltaire wrote, “It is easier to judge the mind of a man by his questions rather than his answers.”