Best and Worst Questions for Salespeople to Ask

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The theme of my recent posts has centered around links sent by readers, asking me to weigh in with a counterpoint to the conclusions drawn in the articles. Today, I address yet another Harvard Business Review Blog article (how many misguided HBR Blog articles are there?), this one about the Single Worst Question a salesperson can ask.

The authors contend that “What keeps you up at night?” is the single worst question a sales rep can ask. I can think of much worse. The “what keeps you up?” question is inappropriate when asked:

  • at the wrong time
  • to the wrong person
  • in the wrong context
  • with the wrong lead-in or follow up
  • by a transactional salesperson
  • by a junior salesperson

Suppose a salesperson, trained to sell consultatively, meets with a senior decision maker. The issues are communicated so that the salesperson understands them, but doesn’t yet know the compelling reason for the decision maker to change/take action/buy. The salesperson should say, “I understand that issues A, B, C and D need to be addressed”, and then ask, “What impact are these four issues having on you personally?” If the salesperson learns that there is no personal impact, it is inappropriate to venture into the “darkness”. However, if the prospect talks about stress, pressure, time, money, staff, job security, promotion, etc., it should be, “darkness here we come!” Then, it is not only appropriate, but perfect to ask, “And of those, which one keeps you awake at night?” Followed by, “Why?” and “Tell me more about that” and “How would you feel if…”

It’s not the worst question. Oh no. The question is more like an automatic assault weapon. Very dangerous in untrained hands, but used for the right reason, at the right time, by the right person, with the right prospect, it uncovers the compelling reason(s) to buy!

So what is the worst question a salesperson can ask? There are two:

  1. “Do you have a budget?”
  2. “When do you expect to make a decision?”
  • 58% of salespeople don’t ask enough questions – whether or not they’re the right ones
  • 53% aren’t comfortable talking about money and can’t discuss the subject when the answer to question #1 is “no” or “not enough”
  • 86% are too trusting and believe the answers they get to questions 1 and 2
  • 40% never identify the amount of money a prospect is able and willing to spend
  • 68% aren’t with the person/decision maker who can actually answer the questions

Data aside, both questions trap salespeople in holes from which they cannot escape. Instead, and only in the right context at the right time, salespeople must ask:

  1. Are you able to spend $________ in order to solve this $ ______ problem (or take advantage of this $______ opportunity) the right way, the first time, right now?”
  2. How soon would you like to have this problem solved?

Obviously, your salespeople must have gone wide enough and deep enough to know the problem or opportunity (compelling reasons to buy), and the cost (of the problem) or size (of the opportunity) in order to ask the first question. Are they consistently effective doing that?

Asking how soon a prospect would like to have their problem solved shortens the sales process, whereas asking when a decision will be made extends it. When a salesperson hears, “yesterday” as an answer to question #2, they should ask, “How do you short circuit the decision making process in order to get started right away?”

Reading the HBR article kept me up at night!

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