Most people don’t ask enough questions. If you are a sales professional it’s your job to continuously improve your questions. How do you do that? Let’s start with applying the Pareto principle. What 20% of your questions create 80% of your insights? What makes these questions stand out? The goal of this article is to help you find the answers to these questions.

Imagine you face a particular problem to solve. You have only 60 minutes to solve it. How would you spend these 60 minutes? In particular, how much time would you spend choosing the proper question to ask versus looking for an answer?

If it’s the first time you ask yourself this question, you might be interested to know Einstein’s view on it (see picture below).

Why do you think Einstein suggests spending most of the time, in fact, more than 90% of the time, thinking about the proper question to ask? What does Einstein mean when he says “determining the proper question to ask”? How do you determine the proper question? What are the exact steps to follow?

Of course it’s a good starting point to know what other smart people are asking for a reference or starting point. However, if you follow Einstein’s intuition, it’s not nearly enough to repeat the questions other people are asking. Applying Einstein’s thinking to sales, you need to determine by yourself the proper question to ask. But, aren’t you already asking great questions? How much space is there for you to improve on the quality of your sales questions?

Here are some questions Hubspot recommends asking your customers:

What are your short-term goals? Long-term goals?
What does this purchase mean to you? What does it mean to your company?
What is your boss hoping to accomplish in the next year?

These questions and other recommended questions are definitely a good starting point, However they will not get you very far if you don’t improve on them with time. Why? Because insights will not come from answers to general questions. You need to ask open questions but make them specific enough to gather valuable information.

How to make use of this article?

Parts of this article might sound too theoretical for you. If you are focused on getting immediate value out of this article, I invite you to first read through all 25 questions below. Notice which question catches your attention most. Then instead of reading this article from the top to the bottom, please feel free to jump straight away to the right point.

How often do you come up with original questions?
What percentage of your messages contain no question? Why don’t you ask a question?
Which topic should you choose as a starting point for your question?
How often do you ask questions because of an extrinsic motivation?
How often do you find and explain your intrinsic motivation before asking the question
How sure are you that you know the right answer to your question?
How much are your questions focused on yourself versus your recipient?
How often do you state a possible behavior, opinion or belief of your recipient as unquestionable truth? How can you challenge and expose your assumptions that sneak into your question?
What percentage of your questions do you google before asking?
How many possible answers and emotional reactions do you consider?
How often do you minimize the commitment of your recipient to make it easier to comply with your request?
How often do you state a clear reward for the recipient to answer your question?
How often do you state various options to choose from?
How many alternative forms of the given question do you consider?
How often do you transform a closed-ended into an open-ended question?
How often do you increase the assertiveness of your language when making requests? When does it make sense to ask direct or “sales aggressive” questions?
When do you better ask indirect questions?
How do you narrow down the context for the question to make it easier to answer?
How often do you ask a broader or more ambitious version of your question?
How do you decide in which sequence to ask your questions?
How often do you pose the question to the wrong person?
How often do your questions incorporate perspectives from different stakeholders?
How often do you request feedback from a third party on the content or form of your questions?
How often do you harvest new insights from answers to your questions?
How often do your customers complain versus thank you for your question?

Introducing 25 methods to improve your sales questions

1. How often do you come up with original questions?

We, humans, have a tendency to repeat ourselves. MIT research conducted by Alex Pentland revealed that 90 percent of the time people follow established routines so that their behavior can be predicted with just a few mathematical equations (source). Of course the same is true for the questions you ask. Can you estimate how often you repeat the same sales questions? For example, what percentage of your emails contain a question that you ask over and over again? How satisfied are you, from 0 to 10, with the results of your questions?

Imagine you meet a new person for the first time. What are the first three questions you ask?

If you never thought about this question before, chances are high you are asking “standard” questions. One of your questions might be: “Where are you from?”

Now pause for a second. Can you find another way to express your intention behind this question? If nothing comes to your mind, allow me to help you with some ideas:

Where do you feel belonging?
Where have you spent the most time of your life?
Which group of people do you identify most with?

From my experience if you ask one of the 3 questions above, you will make the other person think. Chances are high that there is no predefined answer. And when you make other people think you establish a deeper connection with them.

Do you see how asking original questions generates a different result? I encourage you to find your unique balance between repeating old questions and trying new original ones.

2. What percentage of your messages contain no question? Why don’t you ask a question?

This is an actual LinkedIn message from a stranger I got some time ago. You will notice that this message ends with a statement and not a question. What happens if your message doesn’t contain a question? Why would you expect an answer? If you expect an answer, you assume that your recipient will come up with a question by himself. You also assume that the question your recipient will come up with will motivate him to answer your message. Why? To answer, I want to share with you the definition of an “answer”.

Merriam-Webster dictionary defines an answer as “something spoken or written in reply to a question” (source).

What does this definition mean practically? If your recipient has no time or energy to come up with meaningful questions at the point of reading, you will receive no answer.

If you want to get an answer, there is only one case where it makes sense not to ask a question. When? When you believe that the question your recipient will come up with will be better than your question. However, this will rarely be the case if you take a good amount of time to choose a question. Bottom line? Don’t be lazy and invest time to choose and include a question into each message where you want to get a response. Take luck into your own hands. If you want practical examples on how to do this, please explore another article I wrote on How to make your LinkedIn messages 3x times more effective using the RRR technique.

3. Which topic should you choose as a starting point for your question?

I would like you to think of a specific problem. For example, imagine you want to buy a new phone. You’re not sure which brand to choose. If you want to solve this problem, what would be the first question you would ask yourself? It might be something like “What is the best brand for a mobile phone?”.

Now I would like you to think of related topics or problems. What other questions can you come up with? Instead of focusing your question around the device or brand, you could explore questions around the target audience or technical aspects of the device. For example:

Who are the most satisfied customers from the given brand?
What are your actual needs?
How do I find out which phone fits my needs the best?

4. How often do you ask questions because of an extrinsic motivation?

You can have two different types of motivation to ask a question – intrinsic and extrinsic. What is the difference?

Intrinsic motivation is as engaging in an activity for its own sake.
Extrinsic motivation refers to doing something not because you enjoy it, but because you want to earn a reward or avoid punishment.

For example, If you want to learn something you have an intrinsic motivation. If you want to make more money it’s an extrinsic motivation (source).

Imagine you ask the same question twice. The only thing that you change the second time is that you explain your intrinsic motivation before asking the question. People are more likely to reply to questions if they are intrinsically motivated. Share your intrinsic motivation before you ask the question.

5. How often do you share your intrinsic motivation before asking the question?

Some questions might be perceived as too direct, private or irrelevant. If this happens you might struggle to get an honest answer. Here is an example of a question that might be perceived as too personal: “Why are you selling your company?”

To earn trust and make people comfortable answering your questions, it makes sense to reconsider your motivations. I’m not talking here about lying to yourself or others. I am talking here about actually finding an intrinsic motivation.

Consider using the following 3 intrinsic motivations:

You want to learn from the other person.
You want to help the other person to learn something.
(Ideal) You’re open to both options 1 and 2 at the same time.

Here is an example of how you can signal that you have an intrinsic motivation: “I’m not sure if I am right and therefore want to clarify…”. In this sentence you communicate indirectly that you are aware of your knowledge limitations. One can read between the lines that you want to learn. And when you want to learn it’s an intrinsic motivation.

I don’t know if you can always substitute an extrinsic motivation with an intrinsic one. What I know is that often it’s possible. And it’s a good practice to try.

6. How sure are you that you know the right answer to your question?

Watch out for confirmation bias when asking questions! What is confirmation bias? Confirmation bias is “the tendency to search for, interpret, favor, and recall information in a way that confirms or strengthens one’s prior personal beliefs or hypotheses (source).

Knowing is much more comfortable than not knowing. That is why you have the tendency to convince yourself to be absolutely certain about some “truths”. This is not a good condition to be in when asking questions.

If you doubt, you will be curious and if you are curious you will search for better answers. As Carl Sagan said: “somewhere, something incredible is waiting to be known.” Increasing your levels of doubt means often accelerating your speed of learning.

7. How much are your questions focused on yourself versus your recipient?

Every person is primarily interested in reaching their own goals and satisfying their own needs. If you want to increase the number of positive answers, talk less about YOU, YOUR company or YOUR offer. Avoid falling into the trap of asking questions that serve only your own ego. Instead think deeper about your recipient’s problems, needs, and goals. For more information check out my article on 3 steps to improve sales pitch by eliminating your ego.

8. How often do you state a possible behavior, opinion or belief of your recipient as unquestionable truth? How can you challenge and expose your assumptions that sneak into your question?

Remember the last time you asked a question and got a negative reaction? The person might have gotten upset or confused. It was surely unpleasant for you to get such a reaction. How do you explain strong negative emotions like these? I would like to share with you two common reasons for negative reactions:

Firstly, the person might not have understood your question. Secondly, the person might have disagreed with some of your assumptions that sneaked into your question. Do you want some examples of questions with assumptions?

Why are you in a bad mood?
- How sure are you that your recipient would agree that he or she is in a bad mood?
How do you explain your bad attitude towards her?
- How sure are you that your recipient would agree that he or she has a bad attitude?
What kind of punishment do you want to choose?
- How sure are you that the person wants to choose any kind of punishment and not do something else instead?

Indicate – or even better eliminate – your assumptions when asking questions.

9. What percentage of your questions do you google before asking?

Using google search is cheap and fast. How do you know if your question can be better answered by Google? If you are interested in general facts about the world – Google is definitely a great source of information. On the other hand, if you are interested in personal experiences, subjective opinions, recommendations or private information – asking a person is a good way to go.

People like to be appreciated. How does your recipient feel when they get a question that would be better answered by Google? Exactly! Not appreciated. Avoid asking questions that could be answered by Google.

10. How many possible answers and emotional reactions do you consider?

If the answer increases the perceived distance between you and your goal, you feel dissatisfied. You don’t like feeling unhappy. That’s why you avoid thinking about these ‘negative’ answers before asking the question. As a consequence ‘negative’ answers come often unexpectedly. ‘Negative’ answers catch you by surprise. Why does it matter?

Because if you don’t think about something, you have a blind spot. Because of this blind spot, you are not phrasing your questions in the best way possible. Let me explain by giving you an example.

Imagine you are selling lead generation services. You talk to John. John is the founder of a small software company. Your goal is to find out if you can help them increase their sales. If you ask “What is your biggest sales struggle?”, you would assume that the founder wants to grow sales. You also assume that he is aware of his particular sales challenge.

If your assumptions are not true, John might feel annoyed when answering or not answer at all. How do you avoid such ‘negative’ reactions? Paraphrase your question to eliminate your assumptions.

“If you focus on growth, what is your biggest sales challenge? If growth is not your priority, what exactly needs to happen for you to focus on increasing sales?”

It’s a good practice for you to list all the answers you don’t want to get before asking the question. Some answers you will not like sound to you like accusations. Christopher Voss in his book “Never split the difference” recommends listing all negative answers. Chris calls this process an accusation audit. He recommends conducting an accusation audit before any type of conflict situation. When you ask a question with a chance for a ‘negative’ response, it’s a potential conflict situation. List all ‘negative’ answers before asking a question to make sure that you ask the question in the best way possible.

11. How often do you minimize the commitment of your recipient to make it easier to comply with your request?

Why did so many American Prisoners collaborate with the Chinese during the Korean War in 1950? According to American investigators, nearly every captured American soldier collaborated with their captors during their imprisonment. How can this possibly be? Chinese understood one of the most powerful driving forces behind human psychology: the need to appear consistent. Let me quote Robert B. Cialdini passage from his book “Influence: The Psychology of Persuasion”:

“An examination of the Chinese prison camp program shows that its personnel relied heavily on commitment and consistency pressures to gain the desired compliance from prisoners. Of course, the first problem facing the Chinese was how to get any collaboration at all from the Americans. These were men who were trained to provide nothing but name, rank, and serial number. Short of physical brutalization, how could the captors hope to get such men to give military information, turn-in fellow prisoners, or publicly denounce their country? The Chinese answer was elementary: start small and build.

For instance, prisoners were frequently asked to make statements so mildly anti-American or Pro communist as to seem inconsequential (‘The United States is not perfect.’ ‘In a communist country, unemployment is not a problem.’). But once these minor requests were complied with, the men found themselves pushed to submit to related yet more substantive requests. A man who has just agreed with his Chinese interrogator that the United States is not perfect might then be asked to indicate some of the ways in which he thought this was the case. Once he had so explained himself, he might be asked to make a list of these “problems with America” and to sign his name to it. Later he might be asked to read his list in a discussion group with other prisoners. “After all, it’s what you really believe, isn’t it?” Still, later he might be asked to write an essay expanding on his list and discussing these problems in greater detail.

The Chinese might then use his name and his essay in an anti-American radio broadcast beamed not only to the entire camp but to other p.o.w. camps in North Korea, as well as to American Forces in South Korea. Suddenly he would find himself a “collaborator” having given aid to the enemy. Aware that he had written the essay without any strong threats or coercion, many times a man would change his image of himself to be consistent with the deed and with the new ‘collaborator’ label, often resulting in even more extensive acts of collaboration.”

When you make a request, ask for as little as possible. I will give you an example to illustrate how to apply this principle in sales. Often the first request you make is to ask for an initial meeting. How do you minimize the commitment of your recipient when you ask for a meeting? Simply minimize the time commitment you are asking for. “I would like to have a 15min meeting with you, to understand better…”

12. How often do you state a clear reward for the recipient to answer your question?

Good questions serve your needs. Great questions serve the needs of your recipient. Ingenious questions serve the needs of everybody involved. I call them win-win questions.

Your recipient might struggle to understand how answering your question will serve his needs. Showcase his reward before asking the question. Explain in detail how he will benefit from answering your question.

You might end your emails with something like “Are you open to discussing?”. Now, pause for a second. Why would your recipient like to discuss? The following 3 questions might help you find an answer:

What needs of your recipient does the question serve?
What’s the probability for your recipient to get the reward?
What else will your recipient gain when answering your question?

Let’s try to answer these 3 questions and transform “Are you open to discussing?” into something more meaningful:

“I want to propose an agenda for our 15min introduction call. My goal is to discover and help you clarify your needs around your company growth. There are two potential outcomes out of our first meeting:

We find out that we could be a good match to help you. We can then proceed to present a solution to your needs in the next meeting.
We find out that we are not a good match to help you. You will gain knowledge of what makes your needs unique. This will help you to better direct your efforts towards your goals.

Would it suit you speaking on Tuesday or Thursday after 15:00 CEST time?”

In this example, I’m making use of the RRR technique (Relevance, Reward, Request). For more information please feel free to explore my article How to make your LinkedIn messages 3x times more effective using the RRR technique.

13. How often do you state various options to choose from?

Avoid asking overwhelming or complicated questions. Why? Your recipient will have difficulty answering them. Let’s take a complicated question as an example and try to simplify it by offering some possible options to answer it.

Some of the sales people I hired for my marketing agency initially asked potential clients the following question: “What is your biggest sales challenge?”. In my experience, this is a very difficult question to answer. There are multiple reasons why you might struggle with sales. It is highly likely a combination of these. So, I coached my new salespeople to improve the question by indicating possible options:

“In your opinion, which of these 7 challenges applies most to your company?

1. So far you won customers through events or referrals and therefore struggle with cold outreach.

2. There are multiple decision-makers and you struggle to find best-fit prospects.

3. You operate in a highly competitive “red ocean” and it’s hard for you to communicate your unique selling proposition.

4. You lack the experience to effectively scale new business development while improving the quality of your sales process.

5. Prospects often misunderstand your value proposition and you struggle converting leads to meetings.

6. You’re selling a complex product and not entirely clear about the best business development strategy to pursue.

7. You have put everything in place but don’t have the time to execute it.”

Make it easy to answer your questions by indicating possible options to choose from.

14. How many alternative forms of the given question do you consider?

I propose for you to distinguish the content and the form of a question. What is the difference? Think of the content of the question as a candy. The form of the question is its packaging. There are different ways to present the same candy. Change a few words and the perception of your question changes as well. Here three examples:

In retail instead of asking, “Is there something I can help you with?” to which the usual response would be “No, just looking,” you could ask, “What would you be excited to find today?”
At a networking event, instead of saying, “What is your job?” you might ask, “What is the best thing your customer has ever said about you?”
At the grocery store, instead of asking “Did you find everything you searched for?” you could ask “What could you not check off your list today?”

Consider the impact of alternative forms when asking a question.

15. How often do you transform a closed-ended into an open-ended question?

There is a big psychological difference between closed-ended and open-ended questions. Be very careful when using closed-ended questions. When you ask closed-ended questions, your recipient might feel limited in their freedom of choice. However closed-ended questions might serve you well in the following situations:

To clarify if you have understood your recipient well.
To help your recipient narrow down on the available choices (make a decision).

Every journalist, psychotherapist and of course salesman loves open-ended questions. Why? Because open-ended questions help you reach the following goals:

Information gathering (learn)
Behavioral influence (help learning)

Imagine you are the manager of the local Starbucks. Which of the following 3 ice-breaker questions would you prefer your team to use? Which do you think will have the biggest positive impact on your revenue?

Do you want something to drink? (closed-ended)
Do you feel like having a drink? (closed-ended)
What kind of drink do you usually have at this time of the day? (open-ended)

If your objective is to gather information or to influence a behavior, transform the closed-ended into open-ended questions.

16. How often do you increase the assertiveness of your language when making requests? When does it make sense to ask direct or “sales aggressive” questions?

According to Robert Cialdini, author of Influence: The Psychology of Persuasion, in sales, it’s often a challenge to understand what would be the right level of assertiveness.

Amateur sellers often use a passive tone of voice out of fear. What kind of fear? Fear of offending and consequently losing the customer. Amateur sellers often use a polite, considerate and passive tone of voice when making requests:

Sorry, may you please tell me who I could potentially talk to, please?
Are you able to share your requirements with me, please?
I’m not sure if you could share how you assess the potential and risk of such an investment opportunity, please?

On the other side, you don’t want to be overconfident and use an aggressive approach:

If you’re not able to decide, who can?
I don’t care if you buy it or not because we have plenty of customers waiting to get it.
This is your last chance to buy it – do you want it or not?

The assertive approach is neither passive nor aggressive. Instead, an assertive approach creates a discussion that helps you and the customer to better understand what’s going on. That way you can move the decision-making process further:

Who is responsible for sales in your organization?
What are your specific requirements?
How do you assess the potential and risk of an investment opportunity?

Perceive your recipient as equal. Equals don’t use polite or passive voice with each other. Equals are direct and assertive.

17. When do you better ask indirect questions?

Imagine you ask a relevant stakeholder who has little or no decision power: “Can you make a decision to buy our solution?”. Your recipient might perceive your question as intrusive, impolite or inconsiderate. Why? Because nobody likes to feel irrelevant or unimportant.

If you feel you could hurt the feelings of your recipient, use an indirect question. For example: “Tell me more about your responsibilities. Where does your job usually start and end?”

18. How do you narrow down the context for the question to make it easier to answer?

Tim Ferriss recommends in his book Tribe of Mentors not to ask broad questions someone would not be able to answer quickly. Why? Because people have little time to answer your questions. And you want to maximize your insights from their answers.

“How did you become successful?” invites to tell the whole life story and can’t be answered shortly. Instead, you might want to use a question Tim Ferriss is asking many of his podcast guests: “What new belief, behavior, or habit adopted within the last 5 years, has most positively impacted your life?”

Consider how likely your recipient is to answer your question in a short form. If you expect a long answer, narrow down the context of your question.

19. How often do you ask a broader or more ambitious version of your question?

Be aware of times when your question narrows down your recipient’s options:

Where can I buy milk?
Do you like swimming in the morning?
Is she your neighbor?

To maximize your learning and impact, widen the ways in which the question could be answered. To illustrate you how you can apply this principle let’s widen your recipient’s options for the 3 questions above:

How do you find the best healthy local food?
What stands out in your morning routine?
What makes your relationship with your neighbor special?

20. How do you decide in which sequence to ask your questions?

How do you know when it’s the best time to ask a given question? What should be the ideal sequence in your questions? How do you avoid the mistake of asking a question too early or too late?

When you start a new conversation, it’s the best practice to focus on warming up the person. In the beginning, it’s good to start with a light and comforting topic. People like to talk about the recent future, opinions, and accomplishments. But what is the best way to proceed after you broke the ice?

You can borrow some principles from Carsten Hornstrup and Karl Tomm’s Interventive interviewing model. Carsten and Karl suggest their framework for use in therapeutic conversations. However, you can directly apply it in sales as well. Carsten and Karl suggest to categorize questions into four different types:

1. Situation clarifying – these questions help you clarify the sequence of events over time. Use them to understand better your recipient’s situation and focus.

What is your main challenge?
How did we arrive to have this challenge?

2. Other perspective – these questions help you change how your recipient views their situation. Use them to help your recipient see past events in a new perspective.

How would your colleagues describe this situation?
What is your co-founder’s view?

3. Generating opportunities – these questions help you influence your recipient. It helps your recipient to consider better the advantages of your ideas. Use them to create a space for new future perspectives.

What is the outcome that you would prefer?
What are some even better outcomes than you have imagined so far?

4 Actions clarifying questions help you correct your recipient’s decisions. Seeing the client as the expert and change agent in their own life.

How could you move towards those outcomes?
What steps are you considering to take right now?

To make good use of the interventive interviewing model, categorize your questions into the four categories. To make sure that you ask the question at the right time, move from one category to the next as illustrated in the picture above.

21. How often do you pose the question to the wrong person?

If you deal with big organizations you often deal with multiple stakeholders with different levels of decision power and experience. If you direct your question to the wrong person, the answer will be distorted or just wrong. It makes no sense to present your solution if the decision-maker is not in the meeting.

What do you do when a non-decision-maker asks you to present your solution? It is your responsibility to challenge your recipient before investing your time into the presentation. You can challenge by asking the following question: “Imagine I present to you our solution and you like it. How would you advise me to proceed then towards making a deal?”

Chances are high that a non-decision-maker will not see a clear path towards a deal. In this case, it’s your duty to request him to bring the decision-maker into the next meeting when you will present your solution.

22. How often do your questions incorporate perspectives from different stakeholders?

Humans rely heavily on social proof when making decisions. Your job as a salesperson is to facilitate this process. Here are some suggestions on how to obtain relevant information to understand how social proof can be better created:

Who do you consider an expert on this topic within or outside your company?
What are the opinions of your colleagues on this topic? What are your thoughts on their views?
How do you decide who to trust and who not to trust? How do you test for expertise?

23. How often do you request feedback from a third party on the content or form of your questions?

Do you believe that your opinions, beliefs, and actions are mostly better than those of others? Most of us do believe so, at least subconsciously. This phenomenon is called confirmation bias. Confirmation bias means interpreting information in such a way that confirms what you already believe.

It could be especially dangerous for you to fall victim to confirmation bias when making important decisions. Why? Because you make the most disastrous mistakes when you are 100% sure. A healthy dose of doubt can prevent you from making a dangerous mistake. How do you avoid falling into the trap of confirmation bias?

Share your questions with others and ask for feedback. Ask yourself “Who is the best accessible expert to get feedback on a given topic?

24. How often do you harvest new insights from answers to your questions?

Imagine you ask a question and you are bored by the answer you get. Why are you bored? Maybe it’s because the answer you got is irrelevant to you. And maybe you are getting irrelevant information because you asked the wrong question.

Next time you are bored instead of ignoring this feeling ask yourself: “How can I change my question to produce new relevant insights?”

25. How often do your customers complain versus thank you for your question?

Make sure that your recipient gets value from the question you ask. How do you do that? Listen closely to the tone of voice and the content of your recipient’s answer.

What do you do if your recipient complains about the question you ask? What if your recipient thinks your question is too hard or too easy? To avoid getting negative feedback, you can ask yourself the following 3 questions:

What learning can your recipient gain from answering my question?
How could I maximize the learning potential of my recipient?
What question would produce new insights for both me and the recipient?

Great questions provide value for both you and your recipient. How do you avoid guessing if your question is valuable or not? You ask!

I would like to use this opportunity and ask you for your feedback as well. What is the most valuable question you have taken from reading this article? Why?

Final word

We all have blind spots. Blind spots are an obstacle between you and your growth. Why? You grow when you overcome problems. To solve a problem you need to ask the “proper” question. Otherwise, you are shooting in the darkness.

Think right now about your biggest problem. What question describes best your problem? How can you improve the quality of your question?

About the author

Vyacheslav Ladischenski holds a master’s degree in computer science and is the founder of a sales consulting agency TechSalesBox. Over the last 2 years, Vyacheslav helped 41 small B2B technology businesses to generate over 14K marketing qualified leads and €21M in sales. Vyacheslav helps sales teams to accelerate their learning process and grow faster.

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