5 Critical Sales Questions You’re Not Asking Your Leads (but Should)

Laura Morrison posted this in the Sales Skills Category
Reading Time: 5 minutes

In the race to close a deal, sales professionals often deliver an unending list of product features. Doing so ignores the important step of asking the customer sales questions.

Who says the sales professional needs to ask more questions? The customer.

Here are five sales questions that you should start asking your leads so you can drive more sales.

A study published in the Harvard Business Review reveals that after interviewing 200 customers, researchers found that “from the customer’s point of view, the greatest need for improvement is in salespeople’s knowledge of the customer’s business and industry.” It’s not surprising that 71% of B2B customers are not engaged, according to data from Gallup.

Sales professionals can rise above the competition by asking five critical questions.

1 How Does the Decision-Making Process Work?

Selling is time-consuming. An increasingly complex buyer journey has elongated the sales cycle. Therefore, you need to know that you’re talking to someone in a position to make a decision.

Asking about the decision-making process clarifies who you should be speaking with. This question also reveals who the influencers are and how the chain of command is organized.

Understanding the circle of decision-makers is critical given that the number of people involved in a buying decision is increasing. In many cases, you will face five to seven decision makers. Each has personal leanings. Each has a unique understanding of the problem and perception of what constitutes a viable solution.

You need this list because it will take time to address each person. Every decision maker involved represents a mini sales cycle within the larger sales cycle.

This point is illustrated in Richardson’s depiction of the new buyer’s journey.

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Few sales professionals ask this question because they fear offending the customer. They fear they may insult their contact if that person is outside the orbit of decision makers. This fear is understandable.

Therefore, the sales professional must ask the question in a respectful manner. For example, they could ask their contact “who in the company supports this solution?” Then, sales professionals can ask, “What is the next step in the decision process?” You can also ask your contact if they know how the CEO feels about the solution given that a person at that level will always have influence over the decision.  

2 How Does This Compare with Other Solutions You’re Considering?

Competition is always present. Even if there is no clear competitor, there is always the status quo looming over the sale.

Uncertainty keeps the status quo firmly rooted in place. In fact, the Global Economic Policy Uncertainty Index is at its second-highest point since measurement started more than 20 years ago. Businesses are uncertain about the future economy.

sales questions

Therefore, you must get a read of how the solution you’re providing stacks up against the competition, or the status quo. The solution must not only meet the customer’s needs, it must exceed the competitor’s capabilities.

This question is not an opportunity to diminish the competition. It is a way to understand where the customer is in the buying process and what kinds of solutions interest them. This information allows you to draw contrasts between your solution and the competitor’s solution in a tactful manner.

For example, you can ask how well the competitor’s solution handles an aspect of the business challenge that you know is better solved with your solution.

Consider different versions of this question, like, “How well does this address your needs?” Or you can ask, “How far are you in the buying process?” These are relationship questions that help you see where you’re positioned in the race. They reveal your strengths and weaknesses relative to others vying for the customer’s business.

3 How Does This Solution Fit into the Big Picture of the Business?

To understand the customer’s business, you need the ground-level view and the 30,000-foot view. Big-picture questions like this offer the 30,000-foot view.

The more you understand how the solution connects to the overall business, the better you will be able to position it. However, too many sales professionals avoid this question. Some feel it is too intrusive. Others believe it is a request for sensitive strategic information. In truth, the question serves the customer by ensuring that the solution is relevant.

Without having the details from the customer, you risk presenting the wrong solutions, destabilizing the sale and risking your credibility. Click To Tweet

For example, you might think that the customer needs one solution from your offering when, in fact, they need a different one. Knowing this information early is critical. Without this detail from the customer, you risk presenting the wrong solutions, which destabilizes the sale and risks your credibility in future opportunities.

Many buyers are rushed. They may answer the question in one brief sentence offering little detail. It is your job to respond to short answers with more questions. You can follow up with questions like, “What is your vision for the company?” You can ask, “How do you plan to grow the business?” The key is to understand what is driving the company.

If the customer needs a solution, it means they are interested in solving a challenge or increasing their existing capabilities. To know which is the case, you must ask about the big picture.  

4 What Would Your Ideal Situation Be?

The question reveals why the customer is pursuing a solution. Understanding the customer’s ultimate goal allows you to not only position the solution in their terms, it also offers opportunities to expand the scope of business.

This “need” question brings you closer to the customer’s thinking. It puts you in their world. This closeness is important because research covering 141 companies across ten industries found that “customer intimacy becomes a more vital performance driver” as solutions become more commodified.

This question is important because customers often discuss needs in terms of solutions. They state what they want and expect. However, they don’t often articulate what precipitated these wants. By asking the customer about their ideal situation, you get a wider view of their needs.

Moreover, this question signals your focus on the long term and devotion to a relationship that is more than transactional. A long-term approach is critical to success. Consider research from McKinsey indicating that companies with a long-term focus “outperform their shorter-term peers on a range of key economic and financial metrics.”

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Finally, this question helps customers overcome misperceptions of what they need. Richardson’s 2019 Selling Challenges Research Study found that “overcoming buyers’ misperceptions of what they need” was the second-biggest challenge to understanding customer needs.

Often, the customer’s idea of a solution comes before fully realizing the challenge. Asking about their ideal situation helps customers clarify their understanding of the hurdle and helps you shape their thinking.

5 May I Ask How You Arrived at That Expected Price?

You have entered negotiations once the customer asks you about pricing. Often, customers will enter this phase early and ask for pricing upfront before answering any sales questions.

You can't successfully negotiate without first understanding the customer’s needs and demonstrating your value. Click To Tweet

You cannot successfully negotiate without first understanding the customer’s needs and demonstrating your value. Therefore, explain to the customer that you can discuss pricing as soon as you get a few more details. If the customer presses for a “ballpark” figure, remind them that to provide a number, you need a bit more information.

Once you get to specific numbers you can expect resistance. Often, customers will remark that they expect a lower figure. Rather than take a defensive position, ask them how they arrived at that number.

Questions like this help convert demands to needs. Doing so is important because demands can only be satisfied in one way, which is to give in. A need, however, can be met in several ways. By asking how the customer arrived at an expected price, you’re exploring the underlying need.

Asking the comparison question ensures that the customer is making an apples-to-apples comparison. This approach politely reasserts the value of your solution and preserves the financial scope of the sale.


Successful selling hinges on not only asking questions but asking the right questions. The time in front on the customer is short and difficult to earn. You must make the most of this time by getting to the questions that matter.

These questions are a request to peer into the customer’s business. Therefore, be sure to reciprocate by offering transparency. Share information of your own. Doing so will encourage the customer to be more forthcoming in their answers. Additionally, it will build trust.

Research published in The Open Psychology Journal showed that “information alone was found to have a significant impact on the perceptions of ability and integrity.” Put this finding to good use.  

Remember, the answers to each of these five questions offer a path to closing the sale. The responses tell you what the customer needs and why they need it. With that information, you’re able to position the solution in a way that speaks to these stated needs and circumstances.

Consider these sales questions your “Big Five” in the sales cycle:

  1. How Does the Decision-Making Process Work?
  2. How Does This Solution Fit into the Big Picture of the Business?
  3. What Would Your Ideal Situation Be?
  4. How Does This Compare with Other Solutions You’re Considering?
  5. May I Ask How You Arrived at That Expected Price?


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