Best and Worst Questions for Salespeople to Ask

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:

Reading the HBR article kept me up at night!