Asking Uncomfortable Questions

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There are many uncomfortable questions that we need to ask as consultative salespeople. The greatest value of these questions is to:

Help you qualify your audience and opportunity. I.e. is this an immediate opportunity, future opportunity or not a good fit?

Demonstrate a consultative approach

Understand how to win their business

These questions include (but are not exclusive to):

  • Timing?
  • Reason for the timing?
  • Budget?
  • Decision Making Criteria?
  • Decision Making Process?
  • Hurdles standing in their way?
  • Who the competition is?
  • Impact of doing nothing?

Why are these Questions Uncomfortable to Ask?

There are a variety of reasons. . From our perspective most of them have to do with the sales reps’ belief that the customer may see these topics as:

  1. Sensitive information
  2. Invasive – too pushy
  3. Providing you with an unfair advantage vs. the competition
  4. Giving you information that will help you, not them

How to handle these Questions?

Here are a few recommendations as to how to handle these tough questions:
Example: So we can be on the same page right away, I really want to understand what is most important to you when dealing with a partner company like us?    

Example: So that we can align each other’s expectations, what is timeline for this project and what could derail that timing?

Don’t avoid them:

They say that “the best defense is a good offense”. Rather than avoid them… initiate them. If you approach them head-on, in a sincere & frank manner, your customer will follow.

1. Trust/Relationship: While you should ask uncomfortable questions as soon as possible in order to help you qualify the opportunity, the stronger and more trusting your relationship is, the better the questions will be received. So think about the right timing. It’s a balancing act. – see Sales Rep’s Only Role: Creating Trust module.

2. Open Questioning: Ask your questions in an open manner – see Questioning Skills module.
3. WIFM – What’s In It For Me (them)? Communicate to them what benefit they will gain by answering an uncomfortable question. The precursor to any question should be the explanation of the why you are asking that question (see the 2 example questions above).

4. Use the “Permission Approach” to prepare them for these questions – see Permission Approach module.

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