A recent conversation in a sales meeting revealed something that I hadn’t thought about for quite a while – the seemingly lost ‘Art’ of questioning, which of course is a skill that should always be accompanied by its close relative, listening.


It occurred to most of us in the room that in today’s busy work environment and especially in sales, we are in such a hurry to get to the finish line that we sometimes ignore the manner in which we try to get there.


We further concluded that when we fail to reach the final objective, which is invariably to close the deal’, a forensic examination of our failure often reveals a lamentable lack of information has been gathered. In other words, we didn’t ask enough of the right questions to establish a credible proposition, so we didn’t really know our customer well enough and more importantly what they were trying to achieve?


As we all concluded, the only way to find this out is to ask the right questions and really listen to the answers. Only then can we hope to realistically ‘match’ the wants, needs and expectations of our customer. So, what do we mean by questioning and listening skills and what can it do for us?


Without resorting to a pure interrogation style of interaction by simply firing off lots of questions and not listening to the answers, the subtle art of questioning is one of the most powerful tools in our armoury. Whether you are a business leader or salesperson trying to close the next deal mastering this art will help you to achieve success.


As in many instances, we can learn from our children about questioning skills, as anyone who has a child will testify to the fact that they can be relentless when they want something.

“Can I have an ice cream Mummy?”


“Why not?”

“Because you will spoil your dinner”

“Can I just have a small one then?”


Well, you get the picture, this can go on for some time!


The point being that until we arrive at our desired conclusion, we need to continue to ask questions in such a way that doesn’t make our subject feel uncomfortable but does tease out and reveal the information that we are seeking.


In order to this we would do well to remind ourselves of the different kinds of techniques at our disposal. For example, asking probing questions is great to gather information about someone or something. You may want to ask a prospect if they can tell you what great customer service means to them or an interviewee when they have experienced the best level of service themselves.


Asking ‘leading’ questions has to be treated with respect as this can sometimes come across as interrogation with you being thought to ‘put words’ into the mouth of your subject. In a Police interview leading questions are frowned upon; “You were there on the night of the 25th weren’t you?” would be construed as coercive. This would need to be changed to a more open question, such as, “Where were you on the night of the 25th?”.


Where leading questions can be useful in business is when you want to establish a need for something, so for example, once you have demonstrated the item, you might say, “Our new X7 is a far better machine that our old X6 isn’t it? The simple answer of “Yes it is” gives you the approval you require and you can move on.


Open questions allow us to place our subject into a position where they can talk freely. One of the best ways to open up a conversation with someone new in a sales meeting is to ask, “Did you always want to work in this industry?” I’ve asked that question many times along with “How did you end up working here?” and in most cases you can then sit back and listen for the next few minutes as many people are then happy to give you a precis of their last 20 years of working life, which can be fascinating. It’s a great way to build rapport and get to know someone quickly.


Other types of techniques include funnelling questions where you can start asking about a particular subject and then continue to narrow your questions down to establish a proposition. For example, again in much the same way as a child would ask “Are we going out at the weekend Mummy?”, then “Where are we going”? then “Can I ask Samantha to come too?” then the killer finish, “Great we can take our bikes with us!”.


In a similar fashion, linear questioning can keep a conversation going for some time and help you to build rapport and gather information. This is a technique based on asking questions which can seek to clarify information for you and are often based on the last answer you received. “Where did you go on Saturday night?” Answer, “For a meal”. “What kind of food did you eat?” etc.


In education many believe Socratic questioning to be extremely powerful as it allows you challenge assumptions and clarify information as it is received. It can be used to probe deeply into a subject and help you to gather masses of information about a person’s knowledge of a given subject. So, if an answer given to your question is “We need to have two bases and four lids”, you might say “Why is that important?” and so on.


Finally, we can use two techniques that are really useful in a business environment and the first is asking closed questions. That is to say, asking a question that simply requires a ‘yes or ‘no’ answer. “What is your birthday?” or “Do you like working at weekends?”. Great for simple confirmations and information gathering.


This can be used in conjunction with assumptive questions, which can be really useful in a sales situation. For example when you feel that you have enough information and you are ready to close the deal you can try closing with, “Thanks for meeting with me this morning, I’ll call our delivery team to ensure that we get these to you by the end of the month, so do you prefer a morning or afternoon delivery time?”. When they say, ‘afternoon is better’, it’s a done deal!


With all of these techniques it is really important to listen carefully to the answers you receive. The subject of ‘active listening’ is covered elsewhere in more detail, but a couple of ways that you can let someone know that you have been listening to them is to, not only, to ask them a question based on their last statement, but also to refer to something they said ten minutes earlier in the conversation. “When we were talking about colours earlier, you said that blue would work well for you and as it happens this model does come in blue”.


Improving your listening and questioning skills can benefit many areas of sales and management, helping you to gather information, build relationships, handle difficult customer or staff situations and help you to achieve your personal and business goals.


At Maguire Training, not only do we offer classroom-based courses and programmes, but we are also proud to offer a versatile and intuitive suite of over a hundred e-learning modules on our website, which covers a range of sales and customer service topics. Have a look at the on-line module ‘Questioning and listening Skills’, which would be a perfect complement to the new classroom-based sales course on the same subject.


If you need further information then you could always call us of course on 0333 5777 144 for a no obligation discussion about your training requirements. Alternatively, simply hit the ‘Contact Us’ on any page of our website at and we’ll get right back to you.


Either way it would be great to hear from you.

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