How to Ask the Right Question in the Right Way

How to Ask the Right Question in the Right Way
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Longest serving CEO in Silicon Valley and author of Tough Things First
4 min read
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There is an old adage that says one should seek to understand before seeking to be understood. I say, we have two ears and only one mouth for a reason -- because we need to listen twice as much as we speak.

Communication is the most important skill a human can develop -- and this is doubly true for leaders. But listening isn’t haphazard. You are likely interested in listening for specific information. This means that in order to communicate well, you need to ask the right question and ask it at the right time. The wrong question is almost guaranteed to generate the wrong answer. The right question asked at the wrong time -- in the wrong context, while there are pressing distractions, asked of the wrong person -- is equally useless.

Related: 8 Costly Mistakes to Avoid When Interviewing a Job Candidate

Here are the steps I employ when I am ready to listen and need specific information.

1. Avoid asking rhetorical questions.

A rhetorical question is a figure of speech in the form of a question. They are typically asked in order to make a point rather than to elicit an answer. Such questions are not really questions but are designed to force someone into a specific response. This gets you nowhere.

2. Ask friendly, clarifying questions.

A good question lets you better understand the situation, and this requires not putting people on the defensive. Demeaning a person rarely produces honest feedback.

3. Don’t set traps.

Don’t put the listener on the spot. There is an old joke where a constituent asked his senator if he had quit beating his wife. The question was designed to force a denial of one type or another not to provide meaningful information. Articulate your questions without erecting a box around them.

4. Ask open-ended questions.

Few questions can be correctly answered with yes / no, A / B, forward / backward. Binary replies are often invalid. It is better to ask an open-ended question -- one without artificial bounds -- and to give the respondent time to answer with the appropriate level of detail and nuance. Open-ended questions also allow the listener greater comfort with the communication, since they are not forced to make incomplete choices.

Related: The No. 1 Communication Problem for Managers

5. Be grateful.

Thank the person for their response. After all, you will likely want their insights again.

6. Avoid stress.

Answers provided during tense situations are often poor ones. If the situation is tense but not an emergency, then waiting a short time improves the odds of a quality answer, since the respondent will have time and focus to contemplate.

7. Avoid being too direct.

Even if you are trying to get a specific answer, being too direct and too specific can lead to rigid answers. Instead of, “Should we create product A or B?” ask, “What product is the market asking for, and how do our options meet that demand?”

8. Silence is golden.

Be a willing listener. Even when the other person is not talking, communication is still active. Take a breather between questions to give you and the other person time to decompress. This makes your communications less like an interrogation, even if it is a fact-finding mission.

Most of all, ask questions as you would like to be asked them. Take that brief second to think about how you would answer the question you are about to ask, and if you feel uncomfortable, then you need to rephrase it.

Related: Startup CEOs Reveal the 1 Question They Ask Every Job Candidate

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