Most salespeople are well versed in the importance of asking questions. Questions help uncover opportunities. Questions help uncover objections. Asking questions helps to retain control of the and guide the discussion. Questions are not simply the power technique of top salespeople. Rudyard Kipling knew the importance of asking the right questions: “I keep six honest serving-men, (They taught me all I knew); Their names are What and Why and When and How and Where and Who.”

Philosophers have long pondered questions of great depth and importance. The meaning of life … man’s purpose … morality, etc. Isaac Newton asked why the apple falls from the tree. A wise man once asked, “If it’s to be, why not me?” Every sales manager has asked, “Why do some reps achieve quota and others not?” Every child has asked, “why?” approximately 12 billion times by age seven. (As a side note, I have a grandson who is six and he is apparently an overachiever in this area.) The difference between empowering questions and all the others is simple: empowering questions are designed around a worthy quest or goal. And for the purposes of this post, the worthy quest is the realization of revenue.

Each of the three empowering questions, the three questions that every salesperson, sales leader and business owner needs to ask during the sales development process, is incredibly short, easy to remember, tremendously powerful and unlike most things, 100 percent within control of anyone who truly seeks the real answers.

  1. Why?
  2. Why not?
  3. Why now?

Why? The trick is that when doing the asking, you must make sure you do NOT do the answering from your own personal perspective. Sales Rep A asks himself, “Why should the prospect buy from me?” And just as quickly as his mind has finished asking, he begins to answer, “They should buy from me because we _____________.” While this MAY not be entirely incorrect, it IS ENTIRELY wrong. To answer “Why they should buy from me?” requires putting oneself into the mind of the prospect. After all, the only opinion (all decisions are opinions) that matters is that of the prospect.

John tells his sales manager, “BigCo should buy from us because we are the only company that can deliver the (insert official company-provided regurgitation of the mythological unique value proposition) we bring to the market.” Newbie Sales Manager Neil responds, “Great! It will be good to see them come on board.” Hopefully Neil’s team has a huge excess of prospects because he’s going to need them.

Senior Sales Manager Sam responds, “Tell me a little more about the why. Is (insert value proposition here) important to them? How do you know?”

Why Not? After vetting the “why” question to the best of your ability from the perspective of the prospect, the next question that needs to be asked (again from the same perspective) is, “Why not?” What are all the possible reasons that they may not buy from you? Don’t automatically discount any of the 57 or 157 things you come up with. Consider each one, ranging from, “The incumbent supports their charity to the tune of $1 million a year” to the dreaded not a “no” but a “no decision.” The discomfort of change and risk aversion can be a mighty mountain to climb on the way to success.

By now, 85 percent of the average rep’s pipeline has already fallen apart because there is no compelling answer to “why” in the mind of the prospect but no shortage of “why nots.”

Why Now? Finally, the true determinant of whether the deal moves forward: the answer to the question of “Why now?” Why make a decision now? Why not wait? And yes, we know March is the end of the first quarter and you have a number to hit but that is NOT a reason for why now. Sure, it’s the rep’s “why now,” but unless there is a compelling reason to take action now, chances are it simply won’t happen and the deal will move into the “seriously aged” pipeline bucket.

If you are looking to the answer for a prospect to take action, whether it’s a purchase or a simple meeting request, ask yourself, “Why should they? Why might they not? And why should they now. These three simple questions will help you close more sales and move more opportunities forward.

Get out there and ask some questions! And don’t forget the best question of all: “Cash or check?”

Brad Roderick
Brad Roderick

is executive vice president of InkCycle Inc. He is an industry veteran with more than 25 years of sales and marketing experience. He is an active member of the imaging industry as an author, trainer and speaker. Contact him at broderick@inkcycle.com.