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What’s the Toughest Question to Ask a Potential Buyer?

Graphic Showing Two People QuestioningA few months ago, someone asked me a fascinating question via LinkedIn. The question, based on a post about my DISCOVER Questions® Get You Connected book, was "In your experience, what are the toughest questions to ask a prospective customer?"

For those who subscribe to an inbound sales approach, here’s what I find is the most difficult kind of question to ask a potential buyer.

The Hardest Question in Inbound Sales

Questions about our own performance and areas where we can improve are the hardest ones to ask.

What makes these questions difficult is that they require a certain kind of humility and patience. They’re questions that leave you feeling vulnerable. When we work with people remotely, it can be even more difficult to say anything that suggests potential weakness.

Tough questions -- ones I see sellers shy away from asking -- include:

  • "What caused you to decide to go with our competitor instead of us?"
  • "What is it that we need to do differently to earn your business?"

Asking and learning from questions like these helps to gain new customers and maintain existing ones. Setting aside ego and genuinely listening to the prospect's input isn't easy, but it can pay big dividends. The learning alone is a huge win when you ask this kind of question.

Among the 8 types of questions in the acronym that makes DISCOVER Questions®, these are the “I” questions, also referred to as "Issue Questions." In over 10,000 sales calls, fewer than 5% of sellers asked these questions. So another benefit is that you can differentiate yourself by being the seller who takes a personal risk and asks questions like these.  

Turn Your Weakness into a Strength

What we all forget at times is that admitting weakness is generally seen as a strength. It makes you appear human to the person on the other end of the phone -- knowing you are earnestly trying and genuinely looking for ways to improve. You can build trust, earn admiration and respect, and learn from your prospects and leads when you ask Issue questions.

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