Sales and Sales Management Blog

December 17, 2008

Top 12 Sales Articles of the Year: Sales Techniques for the New Year: Asking Your Customers Tough Questions, by Paul Cherry

Top 10 Sales Articles has just released the 12 nominations for Sales Article of the Year.  From the tens of thousands of articles written over the last year by household names, Top 10 Sales Articles selected the 10 best articles published each week-over 500 great articles.  Then each week a panel of sales experts and trainers selected the best article of the week, and then at the end of the month, the article of the month.  The 12 monthly winners are now competing for Article of the Year.

I’m please that 6 of my articles have been nominated since July, 4 of which won Article of the Week honors, and one, “Why Decision Makers Hate Cold Calls,” won Article of the Month and is now in the competition for Article of the Year.

Over the next days I will be running each of the 12 nominated articles.  Read each and then go over to Top 10 Sales Articles and vote for the one you think is the Article of the Year (mine, of course).

Better yet, go over to Top 10 Sales Articles and read all 12 right now.

The first article comes from The Sideroad:

Sales Techniques for the New Year: Asking Your Customers Tough Questions
By Paul Cherry

A new year is on the horizon, and the pressure is on! How are you going to achieve your higher revenue goals? How will you get your clients to spend more money? Most importantly, how will you and your company make up for the accounts you lost? “By making our clients happy and keeping them happy,” you say. Sure, but where will you start?

Maybe you think the way to keep your customers happy is by avoiding ruffling their feathers with tough, uncomfortable questions. Think again! Your clients can’t solve their problems if they don’t acknowledge them. Or maybe they’ve had too many fires to put out this year. As a result, they’ve had little if any time to constructively think through their challenges and what steps need to be taken to achieve next year’s goals. And that’s where you come in, by helping them to see the bigger picture.

You can use the business version of “tough love,” in the form of probing questions that’ll help your clients recognize problems. And you’ll create some urgency so they’re more likely to take action. Best of all, because you dare to ask the questions that are critical to their success in the coming year, you’ve positioned yourself as part of the solution.

You know these tough questions are important, but maybe you’ve been holding back from asking them because they can:

  • Be imposing.
  • Be intrusive.
  • Be uncomfortable.
  • Take away your selling time.

You may even be a little afraid to hear your clients’ answers. What if she says she hasn’t exactly been elated with your work on her behalf, and she’s already shopping around among your competitors? Don’t let this possibility intimidate you! If those issues or anything else are a thorn in your customer’s side, you need to hear it from her and remove that thorn before it tears a gaping wound — perhaps a fatal one — into your business relationship. Instead of fearing negative answers, embrace them as tools that can help you give your client the intensive care her business requires–and put money in your pocket instead of your rival’s.



Asking probing questions can be the BUILDING blocks to providing your clients with the best solutions to their problems, because these questions will help you to:

  • Build rapport with your clients.
  • Understand your customers’ needs.
  • Illuminate your customers’ hidden needs and wants.
  • Look for information from your clients.
  • Direct the conversation.
  • Increase your customer’s comfort zone.
  • Name your customers’ fears to help conquer them.
  • Galvanize customers’ emotions so they’ll take action, with your help.

Honey attracts more flies than vinegar, so start off your questioning by capitalizing on what’s going right with your clients, then ease into problem areas. When you and your client begin this discussion, it’s important to concentrate on “you” — that is, your client — before going into what “we” — you and your client — can do as a team. The key is to make sure your client realizes she has ownership in this process, while validating your own role in your client’s success. Note that the following questions get more complex as you go along.

  • “What are your goals for next year compared with this year?”
  • “In what ways are you going to capitalize on this year’s success to ensure even greater success next year?”
  • “With a new year around the corner, what do you think you’ll do more of/less of/just plain differently?”
  • “In what ways can we ensure/change/do more of…to ensure your continuing success?”
  • “What is it that you value most about doing business with us (me)?”
  • “What do you feel we are (I am) doing right to sustain our business relationship?”
  • “In what ways are we (am I) helping you to achieve your goals?”
  • “In what ways can we (I) improve?”
  • “What changes do we (I) need to make to ensure greater success?”
  • “If you could change one thing about our relationship, what would it be?”
  • “What goals would you like to see us (me) accomplish with you in the next 12 months?”
  • “How can we (I) make your job easier?”
  • “Would you be willing to serve as a reference for my product or company? If so, can you elaborate on what you would say about us? If not, why not?”
  • “What will it take on our (my) part to win that portion of the business you are currently giving to our competition?”

Be sensitive to your customer’s concerns and issues; keep your antennae up for the potential speed bumps and barriers ahead. The time to address those small potential issues is now, before they magnify into overwhelming problems.



Your prospective customer has one of these four concerns on her mind:

  • “How are you going to minimize my fears?”
  • “How are you going to enhance my standing in my organization?”
  • “How are you going to save me money? Or make me money?”
  • “How are you going to make my life easier?”

Asking these tough questions will get your customers to start divulging critical info that they never shared before, because you probably never asked. You can only position yourself and your product as better solutions to your customer’s problems when you understand her true needs and desires. Digging into the dirt with tough but crucial questions is the best way to unearth the answers that will help you help your client solve her problems, and lead to a happy and profitable new year for all concerned.



  1. Hi Paul,

    Congratulation on being one of the monthly winners and now in the hunt for article of the year. I wish you well, you are a talented author.

    A correction, the article by Paul Cherry you have included in your blog should actually be credited to The Sideroad website. I appreciate you promoting but credit should go where credit is due.


    Comment by Clayton Shold — December 17, 2008 @ 4:25 pm | Reply

  2. Clayton, my friend, you are absolutely correct. Although I was obviously brain dead when I wrote ‘salesopedia’ instead of ‘the sideroad,’ at least I did get the link to the original article correct.

    The good news is Salesopedia has several articles from the list coming up.

    Thanks for pointing out the error.


    Comment by Paul McCord — December 17, 2008 @ 5:51 pm | Reply

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