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Why and How to Ask Questions When Selling

Sellers should understand why and how to ask questions.

How to Ask Questions

There’s more to it than inserting an occasional question in a sales conversation.

Instead, sellers should be strategic and deliberate with their questions in order to realize all the potential benefits of asking questions and to eliminate the perceived risks associated with asking questions.

Beliefs that Interfere with Learning How to Ask Questions

Part of the challenge for sellers is in overcoming two mutually exclusive perceptions about questions. Believing that asking questions is so simple and natural that there’s no need to learn how to ask questions is one barrier. On the opposite extreme is the cover for site 2015belief that asking questions buyers will respond positively to is so difficult it’s not worth the time and effort.

Neither belief is accurate. While it is true we can all form and ask questions with relative ease, there is also room for improvement in the way we structure and sequence our questions.

Why It's Beneficial to Learn How to Ask Questions in Selling

By being more thoughtful and strategic in crafting questions, sellers can create value for buyers and advance the sale.

Questioning with strategic intent demonstrates that the seller has a plan. The questions asked are all purposefully linked to the seller’s plan. This automatically eliminates a whole host of random questions that seem, to the buyer, like a fishing expedition.

Knowing where you want to go with your questions keeps you from meandering and enables you to recognize which answers move you closer to your objective. Knowing the purpose of your questions gives you clarity about when to drill down for more information and when to change direction.

When a seller knows it is time to close the sale, for example, her plan should be to tie up any loose ends and go for the close. With this goal in sight, the seller would ask very narrow questions. The intent is to keep the sale advancing forward, not to open up entirely new discussion topics.

If you'd like to learn more about how to ask questions that are truly effective in advancing the sale, be sure to read DISCOVER Questions® Get You Connected. It's based on 20+ years of field research with both buyers and sellers.

The CONNECT2Sell Blog has been discontinued as our focus has shifted to leadership at every level. Research with buyers demonstrates that buyers respond favorably when sellers show up as leaders. If you'd like to step into your full potential as a leader (and boost sales!), take a look at our free and affordable courses on