Sales Skills

by Jeremy Cassell and Tom Bird

Essential questioning skills

According to a study by the Sales Career Training Institute, salespeople typically spend too much time pitching and not enough time asking the right questions to discover the prospect’s/buyer’s real concerns and issues, as well as the hot buttons they need to press to get someone to buy.

So, what are the benefits of asking the right questions?

Judge others by their questions rather than by their answers.

  • By asking the right questions you will demonstrate that you are interested, rather than being focused on making a sale. This will increase the likelihood that the prospect/buyer will open up and that rapport will start to build.
  • You will identify what really matters and what the core issues are that you can help to address them.
  • It gives you an element of control.
  • It creates momentum, which is one of the core goals of every sales conversation.
  • Questions encourage emotional involvement.

Seven core principles

Here are seven core principles that will guide you to ask the right questions.

1. Start with an attitude of curiosity

The important thing is not to stop questioning. Curiosity has its own reason for existing.

Albert Einstein

Any salesperson used to a consultative approach will use questions naturally. Asking intelligent questions comes from an attitude of curiosity, and curiosity is infectious. You will soon find the person you are influencing becomes curious about his/ her own situation!

2. Have a clear outcome for your questions

Ask yourself: what am I trying to achieve by asking questions? This avoids asking unnecessary or random questions.

3. Let the conversation flow naturally

Good questioning techniques do not mean that you become an interrogator. Avoid the clipboard approach.

4. Use both open and closed questions

Open questions start with who, why, what, how, where and when.

Closed questions elicit a yes/no answer.

There is no evidence that we have ever seen that open questions are more successful in making a sale. However, it is likely that you will start with open questions to elicit information and there will be more open questions in a typical sales conversation. Use closed questions for clarification and agreement.

5. Make your questions understandable

I have heard many a sales question that is frankly unintelligible. Sometimes people use multiple questions, or ask a question and then answer it themselves, or ask a question that has no real link to what is being discussed. Make sales questions straightforward to understand – often the simple questions are the most powerful:

  • What do you want?
  • What are your key priorities?
  • What is really going to make the difference?
  • What is working for you?

6. Ask questions that help you pinpoint the dominant buying motivations

Buying motivations and specific needs are not always the same. Buying motivations are about desires and feelings – they are more emotional and intangible. You can find out what motivates your buyer – what he wants — by asking simple questions, such as: ‘What kind of similar products or services have you bought in the past?’

The knowledge you gain will tell you what benefits to emphasise.

7. Avoid offending your buyers!

Some questions can offend a prospect and cause them to reject you and your ideas. Avoid leading or ‘setup’ questions, such as, ‘You do want your children to have a fair chance, don’t you?’

What is the prospect going to say? ‘No! It’s a tough world – let them sink or swim!’

Nosey, gossipy or overly-personal questions can be a real turnoff. Stick to business!

Avoid appearing threatening: instead of asking, ‘How much do you want to spend?’, why not phrase it, ‘How much had you planned to invest?’

Where to focus your questions

Research suggests that you will make the most impact if you focus your questioning around the nine areas outlined below.

1. Needs and wants

This is absolutely central to the role of the salesperson (for more, click here).

2. Ask the buyer for selection criteria

Take the initiative and find out with whom your contact is dealing right now and who else he/she might be considering. This will elicit the buyer’s criteria and values and will help you align your service/product with what the organisation wants.

The more you can align the values of the buyer with what you can provide in terms of service and delivery, the more you are likely to build a long-term relationship. A former colleague was even more upfront: he just used to ask ‘What can I do to win your business?’

Here are some questions you might consider:


Think about your own context. What other questions are there that would work well for you?

  • What’s important in your commercial relationships with suppliers?
  • How do you choose your current suppliers?
  • How do you decide with whom to do business?
  • What do you really value in a salesperson?

3. Options

If they are still at the options stage, you can influence their decision making. Here are some questions you might consider:

  • What sort of options are you looking for?
  • Who are we up against?
  • Who else will you be speaking with in regard to this decision?
  • What have you been considering?

4. Your service/product

You need to gauge the reaction to your service/product to find out if they are likely to buy and what more information they need to make a decision:

  • What are your expectations/requirements for this product/service?
  • Have you seen anything else on the market that you especially do not like?
  • What further information do you need right now?
  • If you do decide to go ahead, what sort of consequences will this have?

5. People

Often a buying decision for an organisation will have implications for many people. Consider asking

  • Who will be involved if we progress to the next stage?
  • How will people’s roles change if you decide to take this product/service?
  • Who will be involved in the roll out?
  • What obstacles might be in the way of moving this forward?

6. Decision making

Find out what the decision-making process is and who is involved. This will allow you to focus your energy. Consider asking

  • What can you tell me about your decision-making process?
  • Who is the key decision maker within the business?
  • How can we help support you internally?
  • How much support does this have at the executive level?

7. Budget

There may or may not be a budget for your offering. It is really helpful to know what amount has been budgeted and with what timescale. When qualifying, assess where a prospect is in their buying cycle. They need to be injected into the sales process at the right point. Ignore the customer buying cycle and you’re likely to fail, so ask questions such as

  • How do you handle budget considerations?
  • What price range you are considering?
  • Who is paying for this?
  • How will the funding for the project be justified?

8. Momentum/qualifying

Salespeople sometimes spend too long talking to prospects when there is little hope of the prospect buying and thus no momentum. Ask qualifying questions to establish whether this is an opportunity is worth pursuing:

  • What do you see as the next action steps?
  • What is your timeline for implementing/ purchasing this type of service/product?
  • What constraints do you have in this area?
  • What further information do we need to discuss before we move this forward?

9. Extending the relationship

Of course, questions do not stop when the prospect becomes a customer. If they are delighted by you and your service then ask questions which will allow you to extend the relationship or cross sell. Or ask them to give you a referral – people will happily do this if they like the product/service and like you! Ask for referrals at the height of the gratitude curve – when they think you are great and have offered an outstanding service.

  • What else are you looking to address in the business right now or in the future?
  • What other opportunities are there within the business?
  • Would it be helpful for you to know what else we offer?
  • Who else do you know in business who might like what we have to offer?

So, take your time before each sales meeting you have in the future and ask yourself which questions are most appropriate and notice that questions are the answer to developing a better understanding of the people you want to influence.