Seven Tips For Asking Sales Probing Questions

It has often been said (or at least I say it often:) that professional selling is a lot like be a detective or a journalist. What makes a good detective or journalist??  They ask questions. They ask lots of questions and they ask well planned, thought provoking questions. They also ask tough questions. Detectives of course need to ask their questions in order to re-create the crime and determine who the perpetrator is.  Journalists ask lots of questions to find the truth.

In sales, prospects typically know more about their needs and the challenges they face and the goals they’re trying to achieve (at least initially) then salespeople do. They also (initially) have a better idea of the types of solutions they might need to solve their challenges and achieve their goals than the salesperson.  In order for salespeople to uncover the needs and goals of their prospects, they must ask sales probing questions. In order to build rapport and understand what a prospect values and finds important the sales person must ask probing questions. But there is a right way and wrong way to ask sales probing questions. In fact, you could say there is an art to asking sales probing questions.  This is why knowing when and how to ask sales probing questions is a key component to mastering consultative selling.  

Below I share with you seven tips for asking sales probing questions.

Earn the Right to Ask Questions

In some sales scenarios it is mutually understood between the sales rep and customer that the sales rep is there to ask questions but in many other scenarios it is not. Before you start asking a prospect questions it is important that you first earn the right to ask questions.

What do I mean by “earn the right?” You must demonstrate that you know something about the prospect and his or her role in the company and that you know something relevant about their company and/or project they are working on.  Either referencing something that your know about your buyer's persona or sharing a piece of insight selling are great ways for earning the right to ask sales probing questions. 

Salespeople also need to offer something (nothing huge) of value to the prospect in order to get information in return.  Customers will not feel comfortable answering your questions and sharing information unless they feel they are getting or will receive something of equal value in return.  If getting answers to your questions feels like pulling teeth, it may be because they don’t believe you've earned the right to the information being requested. Either they don't see the value or they’re thinking “I don’t think Dan understands my business and therefore I don't think he could solve my problem(s) so why I should bother sharing this information and engaging in this conversation? There is nothing in it for me.”

Disarm by Asking for Permission

To build rapport and make your customer feel in control of the conversation and to put yourself in the best possible position for getting well thought-out answers to your sales probing questions, ask your customer for permission to ask questions. You might say, “Mr. customer I would like to learn a little more about your upcoming initiatives for next year, would it be O.K. if I asked you a few questions?”  Customers really appreciate it when sales people take the time to ask for permission. This also sets their expectations for what is happening next in the conversation which puts them at ease. They know you don't have a hidden agenda.

Don’t Ask for More than What You Have Earned

I hear many salespeople dive right into their sales probing questions immediately after introducing themselves (on a cold call) by asking “what are your top challenges?”  Or they might ask “what is keeping you up at night (which is a horrible question to ask in those words)?” “How big is your budget?” “In what ways are you not happy with your current vendor?”

It’s not that these questions are bad (although I would rephrase them), it's the timing of when these questions are being asked. You can’t expect a prospect to open up to you in the first couple of minutes of an introductory cold call and start sharing with you all of their pain points and how their current vendors are struggling. You have to work up towards that by structuring and sequencing your sales probing questions.  Start with easy questions and slowly build up to the more sensitive questions as you build rapport and demonstrate value.

Start Broad, Then Get Specific

Starting off with broad, open-ended questions is an easy and non-threatening way to start learning about your prospect and gathering intelligence. Open ended questions allow the prospect to respond however they want.  Based on how they reply you can and should ask follow up questions to further drill down and clarify for specific details.  For Example:

Sales Rep Question: “I understand you are building a new mobile application for online banking. Tell me about the role you and your team will play in that project.”

Customer: "We are doing the architecture and design."

Sales Rep Drill Down Question: “What are your specific goals for the project?” “What deliverables are you responsible for?”

Build Off Previous Responses

A good detective and a good journalist knows that asking good sales probing questions stems from building off of previous responses. This is where active listening (and not thinking about what you will say next) comes into play.

Customer: “Our goal is to have a completed design of the application by November 1^st and beta ready by January 1^st."

Sales Rep Question: “What is driving the November 1^st delivery date?”

Notice the drill-down questions for further detail by building off the previous responses? This is also why documenting in your CRM/ATS is so critically important. You can build off prior responses and discussions if you fail to document your conversations.

Speak The Language of Your Customer

If you are talking to the Director of Human Resources don’t talk technical or in financial terms. Instead talk in terms that are relevant to an HR executive such as cost of hire, or turnover rates. If you are calling on the Director of the PMO be prepared to talk about project management using the relative language such as critical path or IT governance. The point is, you need to understand the language of your buyer and speak their language when asking questions. When you do this you build credibility because you are now wrapping your expertise around the question. And when sales people do that, they are far more likely to get well thought-out responses which means they learn more about the prospect than the competitor.

Prefacing Your Questions

Prospects like to know where you are headed when you are asking questions. In short, they want to know what your goal is or if you have some sort of hidden agenda. To put prospects at ease with answering your questions you can preface them. Prefacing your question simply means that you explain the rationale (why you are asking the question) before you ask them. This lets the prospect know that you don’t have an ulterior motive which keeps them engaged in the conversation. For example, you might say "Mr. Customer, to ensure we are on the same page financially and that we don't waste each other's time with candidates who are too expensive, would it be O.K for me to ask you a few questions regarding your budget?"

What sales probing questions do you ask of your customers to learn about their needs, goals and challenges?  What do you find most challenging about asking sales probing questions? Lets start a conversation in the comments section below.