23 Penetrating Sales Questions You Need to Start Asking

Mar 28

A couple of weeks ago I wrote a post called, 11 Lame Questions You Need to Avoid. It generated several comments and one reader asked, “What questions should I be asking?”

What ARE the questions sales people should be asking to increase their sales and improve their results?

Certainly this depends on your industry and/or product(s). However, there are many questions that are generic in nature or that can be easily modified to your specific sales environment. Here are 23 high-value, tough, penetrating and powerful sales questions that will help you grow your sales.

Let’s start with high-level questions; these are important if you sell to senior executives.

The higher up in an organization you sell, the more important it is to ask these types of questions simply because executives are used to asking—and answering—tough questions.

  • What goals are you striving to achieve this quarter?
  • How do those targets compare to last year’s results?
  • What, if anything, is preventing you from achieving these goals?

However, do NOT start your conversation with questions like this because you have to earn the right to ask them, especially if you do not have an established relationship. It is much better to begin by demonstrating your expertise, industry knowledge, and understanding of your prospect’s business and/or company.

  • We’ve noticed several trends occurring in the industry lately. The two that stand out the most are… How are these affecting you and your business?
  • When I was doing some research, I noticed on your website that your company is… What progress are you making on that initiative?

These questions are effective because they show that you have done your homework and executives appreciate that. In fact, many of them would like their own sales team to take this approach before calling on a new prospect. Questions like this also demonstrate that you know what is happening in business as well as your customer’s industry.

Assuming you have captured your prospect’s attention you can move the sales process forward by asking other questions that focus on a problem they may be facing.

  • What are the 3 biggest mistakes being made by…?
  • What challenges or difficulties are you experiencing with…?
  • What two problems are giving you the most grief or taking up the most of your time?

Once you determine the key problems that your prospect is dealing with the next step is to determine the impact of the problem. You can do that by asking:

  • What impact is that having on your business?
  • What is this problem costing you in terms of (money, profit, market share, customer loyalty, time to market, etc.)?
  • What will happen if you don’t take action?
  • How will that affect your company? You personally?

It is critical to understand that business people do not make buying decisions based on your ability to spew out product specifications and information. Instead, they want to know what result they can expect. In other words, your prospect wants to know how your solution will affect their top line (sales) or bottom line (profits).

Will they make more money? Gain more market share? Improve brand recognition? Compete more effectively? Save money? Improve morale? Increase productivity? Reduce costs?

That means you need to be prepared to ask questions that focus on the future. When I talk to new prospects about sales training, I often ask what they want to see as an outcome or final result. This information then helps me position my solution and the positive financial impact training will have on their business. Consider these questions.

  • What is the ideal outcome you would like to see or experience?
  • How does this compare with your current results?
  • You mentioned that you want to improve employee morale with this initiative. Can you tell me what that looks like?
  • You have stated that increasing market awareness is one of your primary objectives. How will you know that you have succeeded?

You need to determine the priority of this decision, how the decision will be made, and what potential roadblocks may prevent you from moving forward. Here are few examples.

  • How does this project rank in priority compared to the others you are working on?
  • Walk me through the process you follow when you consider decisions of this nature?
  • Who else do you normally consult with on decisions like this?
  • What potential roadblocks might prevent you from moving ahead with this?
  • What concerns, if any, do you have about moving forward?

There are also questions that don’t fit into a specific category.

  • What are some of the qualities you look for in a vendor?
  • How will you measure success?

These may sound like difficult questions. And they can be. However, with practise you can develop the courage and confidence to ask these tough, penetrating questions. And in doing so, you will separate yourself from your competition and increase your sales.

Full disclosure: I can’t take credit for developing all of these questions. Here are some of the resources I referred to:

Paul Cherry, Performance Based Results
Jill Konrath, Selling to Big Companies
Scott Ginsberg, NameTagScott
Alan Weiss, Summit Consulting Group


21 Comments on 23 Penetrating Sales Questions You Need to Start Asking

  1. Hi Kelley: these are good questions. There are a couple that could be sharpened:

    Good: “When I was doing some research, I noticed on your website that your company is… What progress are you making on that initiative?”

    Better: “I learned on your website that your company has launched an initiative for . . . how does that fit into your overall strategy, and how have you innovated to make it happen?

    Good: “What will happen if you don’t take action?”

    Better: “How does your company determine which projects to fund and which projects not to fund?”

    A blog I wrote that might be of interest to your readers:

    “Strategic Questions Will Uncover Strategic Opportunities,”

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  10. I just found this. Seriously, I cannot believe there are no comments! Great article! This should be required reading in all sales trainings, regardless of the business or products.

    Lydia Sugarman
    President, Venntive

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