How to ask insightful questions and why they are necessary for a bigger sale

Anybody can ask a question. But to to thrive in selling requires one to ask insightful questions. Insightful questions don’t merely yield knowledge- they shed revelation by eliciting a protracted response.

The importance of asking insightful questions in selling cannot be gainsaid. Insightful questions lead to a faster, bigger and better close. Faster because, once you have the correct prognosis (identified client’s problem), you give the correct diagnosis with the speed of a doctor writing a prescription. Bigger because through questions you unearth more. You discover that the reason why the trainee air hostess wants your bank account, is because the airline has told them that their salaries will only be paid through a bank and none of the 30 trainees have an account. Further insightful questions reveal that there are 150 trainees who will be joining quarterly. And just like that you move from one to 150 prospects. You also move, from one on one selling to doing presentations to every group as it arrives. And it’s better because the client feels you truly connected with him.

Read: Avoid high pressure selling: Use this 10:80:10 doctor’s prescription

Problem identification vs problem solving

Last week we spoke about identifying as opposed to just solving the client’s problem. With the latter you sell the drill he asked for but with the former you solve his real problem which is hanging pictures on the walls.

In the process of asking insightful questions you shed more and more light on the client’s challenge and inadvertently understand your product or service better. How? No amount of class product knowledge will get you to understand your product 100%. Classwork merely gives you a working (primary) knowledge. Experience in the field gives you secondary and tertiary understanding of your solution.

It’s how the hawker who was strictly selling slices of pineapples, realises that he can also sell a sliced whole one too. And this happened because an unusual client made that request. It is how you discover that shocks you sell of a Toyota RunX can perfectly fit, say, a Subaru Impreza.  And how? Because you engaged a client at the garage while awaiting the repairs on his Subaru to be done and asked him where he buys his shocks from, yet there is a ‘drought’ of the same in the market. Yes. Asking insightful questions quickly dispels darkness and spreads informative light.

Read more: Boost your sales with problem identification, not problem solving

How to ask insightful questions

But how does one ask insightful questions? First, the best questions are those one has prepared in advance. Admittedly, the practice monologue will rarely play out as the practical dialogue. Still, it gives you direction. Insightful questions are used for exploration (interviewing) and are thus, largely, open ended.

The open ended question should be easy for the client to respond to and vary in ‘mood’ depending on what needs to be achieved. “What problems have you been experiencing with the machine?” is more complicated to respond to than “Do you recall the last time this problem happened? (Oh, Yes) “Describe to me what you went through.” Insightful questions don’t merely bring out knowledge- they shed revelation by eliciting a protracted response.

Pain and pleasure

In addition, keep the questions ‘painful’ when bringing out the pain, and positive when getting to the solution. “How did the current system affect you the last time you struggled with it?” (We stayed at work three nights running because it kept on breaking down and we had to beat the KRA deadline). “How did that make you feel?” (Arrghh…) “And the staff? And on and on, until he relives the moment of pain. You will see it on his face. And then you shift gears to the pleasurable.

“How would you like it to be?” He will most likely reveal almost everything your solution can do and in essence practically sell himself the product. Insightful questions are also specific. For instance when asking for a referral, “Refer me to someone else who can enjoy our services” is a difficult question to answer compared to “Refer me to two people in your favourite WhatsApp group (or chama or department) who can benefit from this product?”

Asking your way into the sale through insightful questions (and actively listening to the responses) is more productive than answering your way into it.


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