Exceptional sales people ask questions; everyone else answers them.

If your working life involves you in any type of sales or selling activities then the effective use of questions is not only an essential skill it is also a critical success factor. Anyone who does not possess such skill is at a disadvantage to sales people from your competitors who do.

Seeing questioning as just a selling skill is a mistake as questions and questioning are invaluable tools that enable and facilitate effective communication in all walks of life. Common examples in business include; recruitment, coaching, appraisals, management and quality auditing, in fact; anywhere that there is a need to explore what another person knows or is thinking. Questions also have other valuable communication applications as I will explain a little later.

While the importance of questions, especially within the context of sales, has been explored by many, my recent experience with front line sales people, their managers and sales training professionals suggests that the real significance of questions in communication has by and large been lost. People may have read a book or attended a course where questioning is one of the topics but then it is simply added to the other tools in the box when it should be the primary communication tool when selling.

Much is said about different types of questions; the two main categories being closed and open. Simplistically, closed questions elicit a basic yes/no answer, whereas open questions require the other party to provide some detail. One common way of recognising open questions is that they all start with; who, what, where, when, why and how.

I keep six honest serving men
They taught me all I knew
There names are What, and Where and When;Kiplings 6 honest serving men
and Why and How and Who.

I send them over land and sea,
I send them east and west;
But after they have worked for me,
I give them all a rest.

I let them rest from nine till five,
For I am busy then,
As well as breakfast, lunch, and tea,
For they are hungry men.

from The Elephant’s Child; Just So Stories by Rudyard Kipling 1902.

Some commentators give the impression that closed questions are bad; they are not but they need to be used sparingly and in the right place within the overall communication. Also, there are a number of different types of closed question for example; the assumptive “would I be right to assume (or think) that …” and the alternative “would you prefer A or B?” The result is always the same you basically get a yes or no answer which is very useful in some circumstances.

So, it seems quite straight forward; closed = yes/no and open = an answer rich in useful information.
Easy tiger; not so simple.


The starting point is to treat questions and questioning as a standard part of the way you communicate. The moment you start thinking about questions and questioning as a technique or worse still a ‘trick’ you have lost the most powerful thing that good questioning can do for you; gain trust.

Questioning ‘techniques’ in sales often focus on trying to lead the prospect to a place where the seller wants them to be. In such a scenario, salespeople use questions to box the prospect into a place where they can present their proposition (demonstrate their product) and their perspective of the benefits and value they think they can deliver. It makes me cringe when I hear a questioning thread along the lines of “How beneficial would it be if you could … ?” The question is invariably structured to elicit a positive response “Well that would be really useful” and is then followed with something like “Well by using our … you can do that.

While the above simple example uses an open question such scenarios are destined to result in a closed outcome as the prospect will in most cases have been led to place they did not want to be. Might this be a common cause of people become unavailable when you call to follow up on a meeting or proposal that you sent after the meeting?

Rather than using questions to take the prospect to where the seller wants them to be, might it be more productive to help the prospect understand where they need to be and once the parties have a common and mutual understanding of where that is the seller can commence the process of presenting their solution to the agreed need?

So what makes for a really great question?

Some time back I sold my IT businesses to a US company and I stayed with them for 5 years reporting to the CEO in a range of roles all of which included me having sales and marketing responsibility for various bits of the world. From time to time I would get an unexpected call from the CEO who would start with a question “Hi Phil; what’s happening?” Now that really is a great question and in just two words it opens up the widest possible field of play. Of course, what you say when asked a question like this is whatever is uppermost in your mind which is also probably whatever is troubling you most so, with the purity and accuracy of a laser, the question got the boss to what really needed his attention.

Such direct questions work between people who know each other well, particularly when it’s the boss doing the asking but such directness is not appropriate in most cases between seller and prospect. Also, if you are speaking to a new prospect “what’s happening” is too general so you cannot predict what sort of response you might get. So, best not used early in the relationship but as it develops the approach might become relevant. In my experience customers often appreciate a relationship with a supplier where trust and mutual respect permits them to challenge each other.

There are ways to ask questions similar to “what’s happening” in the early stages of a sales prospecting cycle; but how might it help the conversation if you provided a context? This could be something like “I see from the trade press that recruitment is a real issue in your industry; how is that impacting on your business?” or “I saw on your website/annual report/newsletter that …, what impact is that having on your plan to open the new office?” Other sources of contextual material could be legislation or the economic environment.

Another contextual dimension involves giving due consideration to the background and interests of the person you are speaking to. The questions you would ask an FD, the chief engineer or the marketing director will be quite different. For example; the FD will be interested in RoI, the engineer will be more interested in specification and performance and the marketing director may want to know about the likely impact on say brand image; but each could also have their own perspective on the same topic, depending on how it impacts them.

When you have met the prospect or customer on a number of occasions you will have more knowledge about what is actually happening in the business so the context questions can move to “What is the current situation with your …?” or “Since we finished the project how have the … improved?” better still “I was thinking about [something in their business]; how useful would be to you to reduce that/speed it up, etc.?” The term is overused but this is an example of how a supplier can become a ‘trusted advisor’ to a customer; the scope is limited to relevant business matters but none the less the opportunity is there and that puts the seller in a strong position compared to new suppliers who try to muscle in.

Many sales people feel uncomfortable with the idea of advising the customer on their business or challenging them on something they have said they want to do. How can a sales person be an expert on a customers’ business? You are not an expert on their business; you are an expert on yours and how it can help businesses like your customer’s to achieve its goals. Recognising this distinction and working on this basis will help to shape your questions.

Similarly, when asking challenging questions the sales person is not challenging what the customer wants to achieve but how they are thinking of going about achieving it.

19 tips on using questions effectively

  • The first rule of asking questions; ask, shut up, listen, assimilate and only then respond – to what you have actually heard not with what you have pre-prepared.
  • Having asked, listen and wait for the answer. If the other person is taking their time responding don’t break the silence be patient and wait for the answer. If they pause while thinking or formulating their answer, don’t interrupt, be patient and wait for the complete answer. Silences can seem interminable with a few seconds feeling like an eternity – practise being patient and it will serve you well. Having listened and assured yourself that they have finished but you feel there could me more information to come ask a supplementary question such as “What else would be useful for you to have?
  • Remember questioning is not a technique or trick; it is a powerful communication tool.
  • Closed questions are just as useful as open ones when used correctly, e.g. to confirm understanding.
  • Questions can be used to progress any type of conversation and they are an antidote to the traditional selling technique of bombarding the prospect with features hoping they will submit. Questions enable the supplier to establish what the prospect needs not what the supplier wants to sell.
  • Ask questions to elicit answers that will matter to the prospect as well as to you. By doing this you are creating an interactive and progressive conversation not a one-way diatribe.
  • Use questions to explore all the possibilities not limit them.
  • Not all questions are born equal; while there may be a few killer questions that really make the other person think, most are quite basic with the simple purpose of progressing the conversation towards the preferred outcome.
  • While the primary purpose of questions is to; elicit information, check understanding, gain agreement, etc., there is an oft ignored benefit to the person asking; a well-crafted question speaks volumes about the person asking it. In a question such as “How valuable would it be to you if … happened?”, the subject matter alerts the person being asked to the fact that you understand their business issues and what might matter to them; asking the question tells them something about you.
  • Good questions make people think – ever found yourself half way through answering a question only to start to question what you are saying? People often have prepared positions on common subjects and a provocative or challenging question is a useful way to get the other person to question what they really think
  • Questions can be an effective way to steer a conversation; not to a false location but to where it really should be. Questions are also good for ‘shaping’ a need by refining the possibilities and therefore creating greater focus eventually leading to mutual agreement.
  • Don’t try to prod, prompt or interrogate; the purpose of questions is to create a conversation that flows naturally towards a logical conclusion.
  • Questions are a useful way of testing what someone has said “Would I be right that you want …?” This is a good use of a closed question and if the answer is “No” it will typically lead the person to expand and thus provide what is effectively an open answer to a closed question.
  • If you’re asked to repeat a question, consider asking it differently – might they be unclear about it rather than they didn’t hear it?
  • If people resist answering, consider re-asking later in the conversation rather than immediately after the first attempt. The approach should be one of patient, polite, persistence but always be aware of signs that the other person really may not want to answer on a particular point.
  • If you sense, or know from something already said by others, that an answer is incomplete ask a subsidiary question such as “What else would you like to see as part of the solution?
  • Asking similar questions of different people in the same organization will deepen your knowledge as you are not limited to the opinions of one person.
  • You may find yourself in the position that you know something but you need it confirmed by the decision maker who you are now meeting. So, a valid use of questions is to ask the decision maker about what you already know where the purpose is to ensure the information in the answer is ‘officially’ on the table.
  • Questioning should be planned and structured but not prescriptive:
    • If you are new to sales by all means write out some questions before a meeting but as soon as possible drop this habit as pre-prepared questions sound like a script.
    • A script interferes with the free flow of conversation as each question, after the opener, should be triggered by the previous response and you cannot know what this will be before the meeting has commenced.
    • Rather than questions your preparation should be to list down the topics you want to cover, the logical running order and above all the outcome you are aiming for. Just like planning a journey; you know the start point and the planned destination but not the beneficial diversions that may be encountered en-route?
    • Take notes, politely, then if something comes up outside the sequence or list of topics you were expecting you can choose to deal with it at the time or leave it until the end.

The effective use of questions helps both parties to think progressively moving them together to a common understanding. Getting people to think, not about their situation but about the possibilities, opens their minds which can lead to them accepting new and creative solutions. The role of the sales person should in part be about helping the prospect to visualise how, with the help of the supplier, to bridge the gap between where they are now, and where they need/want their business to be.