CareersThis Is How You Should Be Asking Questions

As you progress in your career, you’ll find that you spend more time asking other people for information. At one moment you might find yourself requesting the status of a project from a project manager; at another moment you might be asking your team what they think about launching a new product idea; the bottom line is that you’ll be asking questions wherever you go, and it’s important that you make the most out of...
Arjun GangakhedkarAugust 15, 2018

As you progress in your career, you’ll find that you spend more time asking other people for information. At one moment you might find yourself requesting the status of a project from a project manager; at another moment you might be asking your team what they think about launching a new product idea; the bottom line is that you’ll be asking questions wherever you go, and it’s important that you make the most out of each.

Doctors, lawyers, and journalists are experienced in making their conversations more productive by asking questions. Entrepreneurs, on the other hand, haven’t had the same exposure as medical and legal professionals. Not many entrepreneurs consider the profound impact of having questioning skills in their growth, leading to missed opportunities. Asking questions in any field not only stimulates an exchange of ideas but also establishes trust among workers in all walks of business and entrepreneurship – not to mention its instrumentality in uncovering crucial mistakes.

In his famous classic “How to Win Friends and Influence People,” Dale Carnegie explains the importance of being a good listener, provoking the excitement and passion in the other person by asking questions that they are happy to answer.

The next time you are in an interview, try it out! Try to ask questions that the interviewer will be excited to answer; you’ll leave a positive impression the interviewer will have of you when he/she sees a young candidate who’s interested in his/her work and what he/she takes the most pride in, all while building a connection to the interviewer and gaining more information about the position.

But why do most of us refrain from asking these kinds of questions? All of us love to talk about ourselves, impressing others with our accomplishments, experiences, and ideas. But in the midst of all of our “bragging,” we forget to ask questions to enliven the other person in the conversation. Maybe we just don’t care enough to ask!

Or maybe we’re too afraid to ask, in fear of being thought of as incompetent or unknowledgeable. Whatever it is, we just don’t ask enough questions leading us to be oblivious to the immense power of inquisitive conversation.

As important as they are, simply asking more questions isn’t enough when trying to build rapport and exchange information. You must also bear in mind how you ask, as tone and timing in questions are both extremely important. A good tip in figuring out how to ask a question in a particular conversation is to ask yourself, “Am I cooperatively or competitively speaking to the person I’m sharing the conversation with?” After you figure this out, use the following tips to make the most out of your discussion:

Holding a Competitive Discussion with Someone

Ask direct, binary (yes/no) questions that the other person will have a hard time evading, following up with more detailed questions to extract more information. Also, try to ask questions based on a negative premise or assumption. For example, asking baseline questions like “Lately, it’s been a little tough for your team to operate at the efficiency we need, right?” makes it more difficult for the other person to contend with your question, since it’s clear that your question is more of a concrete statement than just conjecture.

It’s important to ask the core, sensitive questions first, following up with some lighter questions to put the other person at ease. This will make the respondent more cooperative when answering your follow-up questions.

What do you do when you’re answering questions in a competitive discussion? The best tip to protect yourself from exposing too much information is to plan in advance what you are willing to reveal and what you are not. Keep in mind that having an idea of what you are willing to reveal doesn’t mean that you should openly share it – only expose this information when you’re being asked. Also, try to dodge questions as much as you can by answering what you wish you’d been asked. Of course, this does not mean evading a question from your investors about the financials of your company by telling them what your favorite jelly bean is, but you get the idea.

Try not to lose control of the conversation when you’re being interrogated. Subtly fight for control by asking the other person questions in response to what they are asking you. Lastly, think about building a bit of trust in the conversation by revealing a bit of negative information to the other person. This builds ideas of honesty and benevolence in the other person’s mind and gives you more control.

Holding a Cooperative Discussion with Someone

Ask open-ended questions to the other person to draw out both the positive and the negative thoughts of something in the other person’s mind. This is incredibly useful when a friend or colleague is shying away from revealing their true thoughts. Unlike competitive discussions, cooperative discussions are most productive when you start with easy questions to build rapport with the respondent, slowly building up to more sensitive questions and sides of the topic.

When answering questions in a cooperative setting, try not to ramble. We all love to talk about our own knowledge, experiences, or accomplishments, but spending too much time on a one-sided conversation can make it difficult for the other person to keep interest. Keep the conversation engaging by implementing humor and enthusiasm in your discussions. Lastly, you might even get some tough questions in a cooperative setting. The best way to respond in these situations is by countering with a rhetorical question or making a funny, lighthearted remark.

You might be wondering what kind of follow-up questions are the most powerful in competitive and cooperative conversations. There are certain questions for certain situations, and it is important to ask the right questions at the right time. There are generally four types of questions used in any conversation: introductory questions (e.g. “Hey, how are you doing?”), mirror questions (answering a question and responding with something similar; e.g. “Doing great! How are you?”), topic-changing questions (any question that shifts the direction of the conversation), and follow-up questions to gather more information. The latter of the four carry immense strength in any conversation, and mastering the art of follow-ups will uncover tremendous value in your discussions. Anyone who is faced with comforting follow-up questions will feel more attention and recognition.

Within the follow-up question category, there are two frames that you can use: open-ended questions and closed, binary questions. Open-ended questions ease any feelings of interrogation or aggressiveness in the discussion and are advantageous when it comes to uncovering new information or hidden ideas. However, it’s better to refrain from using open-ended questions in a competitive setting, as they give the respondent more room to avoid your question or to lie. As we discussed above, closed questions are best asked in a pessimistic, negative way; for example, a person is more inclined to tell the truth when asked questions like “Your division isn’t doing as well as it was last year, right?” rather than “Your division is doing pretty well this year, isn’t it?” Closed questions are a bit more The difference between the two is extremely significant.

Try it at home after reading this! Instead of asking your sibling, “What do you want for dinner?” experiment with closed questions like “Do you want pasta or pizza for dinner?” Chances are that they’ll choose one of your options; they might not have answered either if they were asked an open-ended question. Use this secret wisely!

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