Paul Cherry

Article Summary:

Ask clients the right kind of probing questions to help their businesses blossom in the New Year.

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

This is an award winning article!

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.

This article was chosen as top sales article for the month of January 2008 at Top 10 Sales Articles.

Paul Cherry is President of Performance Based Results, an international sales and leadership training organization serving 1,200 organizations to date. His book, “QUESTIONS THAT SELL”, is available from AMACOM Books. Paul can be reached by phone at 302-478-4443 or email. For more information see

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