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There’s an expression in selling, a directive used frequently by sales managers and trainers, that I feel needs to be laid to rest.

“Ask more PROBING questions.”

Who came up with this term? Every time I hear it I get a visual of some distasteful medical procedure. One most of us would choose to avoid in our lifetime. Seriously… who wants to be probed? Being asked an interminable list of fact-finding questions… At best it’s boring for the client. At worst it’s irritating. Either way it stalls rather than advances the sales process.

Here’s my 2 cents on the subject of questioning. Stop probing! Ask fewer smarter questions that are valuable to both the client and the seller. Questions that provoke thought, pique interest and encourage engagement in a business dialogue.

This requires forward planning. And yes, that means mean sitting quietly at your desk (or wherever you do your most creative thinking) and planning your upcoming discovery call or meeting… and planning to make it valuable from the customer’s point of view… not just your own.

You can read any number of books on the subject of questioning skills but here are four elements overlooked by many sales pros… and critical to your sales success.

1. Intent. Know why you have a specific question on your list. If you can’t articulate why a specific question is valuable to both you and the client… then why are you asking it? And why would you expect your customer to answer it?

2. Context. Prepare, and ask, your questions in context of what you already know about this customer, their business or market. Your questions will not only have more credibility, they’ll sound more intelligent and contribute to your differentiation.

3. Sequence. Start with questions that open and engage the customer. For example, if I know a customer is expanding her sales team I’ll share that I know this (context) and ask: what’s fueling this growth? In addition to obtaining powerful information, this sincere interest in their situation starts to build the relationship. Questions that relate to decision making process, stakeholders, budgeting etc. should come later… unless, of course, you don’t want them answered.

4. Provoke thought. Buyers want a fresh perspective – especially from an expert. They’ll remember the sales pro who gets them thinking differently, and more clearly, about their own situation. “Based on what you’ve shared with me, coupled with what we’re seeing in your market, have you considered XYZ as an alternate course of action?” Thought provoking questions are not only differentiators. The answers will put you in a position where you are no longer competing head to head with your competition.

You can’t pre-plan every question. Nor do you want to. A lengthy script of fact finding questions will glue you to your sales agenda rather than free you to hear your client’s perspective. Plan the important ones, in context of what you know, and then “be present” in the conversation so that you’ll know when to take a deeper dive… with a mutually beneficial question rather than a probe.

If you have valuable tips on questioning strategy, or a question you need answered… I’d love to hear from you. Leave a comment and I will personally respond.