You are here
Home > Self Improvement > An A-Z of Techniques for Transformation – Q is for Questioning

An A-Z of Techniques for Transformation – Q is for Questioning

As humans, one of our principle survival tools is data processing. It is ultimately what keeps us alive, allowing us to process information from stimuli around us and make constant judgements on how to react and adapt, based on both the present situation and also on historical experiences. This brain functionality also gives us the gift of reason, the power to think, understand and form judgements logically. However, as with any data processing system, the information that comes out can only ever be as good as the information that goes in.

One area of life in which it is necessary to constantly process vast amounts of data and make constant decisions is entrepreneurship. Indeed, one could venture so far as to say that the ability to process data appropriately is one of the single biggest factors of whether or not you ultimately succeed as an entrepreneur.

So how does an entrepreneur ensure that they have the right information when it matters most? The answer lies in the art of questioning. Contrary to popular belief, there is no need for an entrepreneur to know the answer to everything. What makes a great entrepreneur stand out is having access to the people who will have the right answer, and knowing exactly when and how to ask the right questions. This concept of harnessing the power of others’ knowledge is detailed in Napoleon Hill’s ‘Think and Grow Rich,’ and was a huge factor in GE’s success under the leadership of Jack Welch.

How can I ask questions more effectively?

In order to get the information you need in the most direct way, it is essential to understand the different types of questioning and when they are most appropriate. Let’s take a closer look at some of the most commonly used techniques.

Open and closed questions

Closed questions generally elicit a yes/no answer. The question “Do you have the sales figures for yesterday?” is a closed question and would typically result in a simple yes or no. Such questions are important when you need a simple answer, however do not allow you to gain more information. If more information is required, an open question will need to be used – “Why are the sales figures for yesterday not available?”

Recognising the right time to use open and closed questions can allow you to get the exact information you need without becoming distracted by unnecessary detail.

Closed questions do not make for good conversation, but are highly effective for fact-finding, frame-setting, confirming and concluding. Open questions, on the other hand, are good for building conversation, getting a feel for the ‘bigger picture’ and exploring issues and opinions.

Leading questions  

Leading questions generally steer the respondent to your way of thinking. When used intentionally, they can be a very useful tool in your questioning arsenal. One word of warning is required here, however –

Care must be taken not to use leading questions simply to obtain the answers you’d prefer to hear.

On the other hand, if you are arguing for a particular outcome, they can help to achieve your objectives. A leading question might be “How late are the sales figures for yesterday going to be?” In this example, rather than asking a closed question as to whether they are late, you have instead already indicated this assumption in the question. It allows you to get much more directly to the crux of the matter by eliminating the opportunity for small talk and excuses to enter into the equation.

On the other hand, if you were negotiating a finance deal, you would be keen to get your preferred proposal agreed so might approach it with a question such as “So would you agree that the first option would be the most attractive to the stakeholders?” This is likely to get a much more favourable response than “So which do you think is the better option, A or B?”

Probing questions

Probing questions are typically used when it is necessary to drill down into a matter and shed light on more specific issues. If you’ve ever had to describe a situation to a police officer or an insurance representative it is likely you’ll have encountered such questions:

“What were you doing at the time of the incident?”

“I was eating dinner in the restaurant.”

“And where exactly were you sitting?”

“By the window, in the corner.”

“Did you have a clear view outside?”

“Yes, I could see everything.”

“How many people did you see?”

“Maybe five or six.”

“And what were they wearing?”

“Black hoodies.”

“Did any of the hoodies have distinctive markings?”

And so on. Such an approach to questioning is designed to help the respondent relive a situation, recount exactly what happened drill down into the finer details. It can be an important tool in business where things have gone wrong and there is a need to get a complete understanding in order to resolve the situation, prevent it from happening again or establish if further action is required. By its very nature, such questioning can be very much like an interrogation in nature and may create a feeling of doubt or distrust. It is therefore often uncomfortable for the respondent, so should be used with extreme caution.

Rhetorical questions

The most commonly used rhetorical question is almost certainly “How are you?” We ask it to almost everybody we encounter, and yet rarely have any genuine interest in the response, which is an automatic ‘Fine thanks, and you?” In reality, a rhetorical question is actually a phrase that is simply presented as a question – and this is where the danger lies. They are great for encouraging respondents to agree with your views and opinions but do not generate constructive criticism or genuine feedback – basically they encourage people to tell you what you want to hear. “Isn’t this business idea so amazing?” “Don’t you think that logo is so clever?” “Don’t you think that the pictures on the new web page really make it look incredible?”

The answers are likely to be flattering. But they probably won’t help to get objective input on your project – the likelihood is that your ego and enthusiasm will win, but this is dangerous when it comes to longer term business strategy.

Which is the right type of question to use?

Deciding which type of question to use depends on the situation. If you are looking to lead and influence people, then rhetorical or leading questions can be perfectly acceptable. However, if you are looking to harness the power of other people’s knowledge, then it is ultimately a learning scenario and you will need to use open and closed questions along with probing questions. However, be aware that you can only use so many probing questions – so take the time to carefully think where some probing questions may be best deployed and be sparing. No mentor wants to face a constant interrogation!

Related Articles

Check out the list below for previous articles in this series:


Bucket List


Daily Intention






Journal Writing







J.Allan Longshadow
J.Allan Longshadow MCMI , NUJ. Editor in cheif, Magazine Motivated by over a decade of experience in the fields of coaching and educational publishing, I strive to inform, inspire and empower individuals through compelling storytelling. I am driven by a mission to bring quality, credible journalism to the field of personal development and self-improvement, working with individuals of every background to create an inclusive media brand that offers both established and aspiring writers and reporters the opportunity to showcase their talent through the publication of engaging and insightful editorial.

Enjoying Magazine? Please spread the word!