How Do You Ask The Tough Sales Questions?


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There always seems to be that moment in any sales process where you have to ask that one tough question. It can be awkward for most of us, but asking the tough ones let us know if we have a valid opportunity on our hands.

Generally, when my team is qualifying an opportunity we find the toughest questions to get a straight answer on usually surrounds our prospect’s budget and determining the decision making process.

Here are two questions that usually don’t work:

“Is there a line-item in your budget for this project? How much?”

When asked this question the average prospect is probably thinking- “there is no way in hell I would tell you that!”

Let’s face it, how many times has your prospect shared exactly how much of a budget they have set aside? It’s rarely a question we’ll get a straight answer on. While obtaining that line-item in their budget can be a stretch, how they allocate and approve budget is certainly something that can be fit into the flow of the sales conversation.

“Are you the decision maker?”

When asked this question the average prospect is probably thinking- “what, I am not good enough for you? Do you want to go over my head?”

There is a better way to ask this question. When it comes to making a decision on a project, it rarely seems that there is one person solely responsible for the evaluation and approval on the budget. Usually we’ll see the collective research being done by a team. Since we take the top down calling approach, more often than not, we’ll land with the evaluator/influencer in the process who is running point on the project.

So, are there ways to eliciting better responses from those lousy questions above?

Here are some suggestions on how to make it less awkward when qualifying your prospect

Feed their ego:

Everyone likes when you ask for their opinion. It makes them feel important. A way we’ve found to be useful in getting to the bottom of the decision making process is to ask- “It appears they’re relying heavily on you for your insight on this project. Outside of yourself, would there be others involved in helping to make the decision? “

You want to make the best use of their time:

Our prospect’s time is valuable. They need to know that we recognize that. When asking the tougher questions we remind them that the reason we’re asking these question in the first place is that we can be best prepared to present them with exactly what they want to see from us (demo/proposal etc.) No one loves a long sales process and they need to know that we ask these questions to move things along quickly.

Could you give me a general sense of how?:

Some questions aren’t received well when asked directly, but there are ways of asking the same question without it seeming as intrusive. Rather than asking about a specific dollar amount in budget, you could say something like “could you give me a sense of how you are allocating budget for this project?” At the very least it gets the conversation going in the right direction in order for you to uncover what you’re really looking for.

So how are you asking the tougher questions in your sales process?

Republished with author's permission from original post.

Craig Ferrara
Craig Ferrara is a Director of Client Operations at AG Salesworks. He joined the company in 2004 as a Business Development Manager, transitioned to Client Account Manager, and was promoted to his current position in 2007. Craig's daily responsibilities include inside sales team oversight, reporting, training, ongoing contact list development and refinement, and managing daily client engagement from a high level.


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