How to Sell More Effectively by Asking the Right Questions Blog Feature
Steve Bookbinder

By: Steve Bookbinder on March 4th, 2014

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How to Sell More Effectively by Asking the Right Questions

Sales Tips | Sales Training | account manager | sales questions | how to

Selling right means asking the right questions.

This is the single most important sales tip I’ve taken away from the digital world. It’s not just about asking, it’s about learning to listen and interpret the answers.


By working with thousands of account managers/directors who’ve struggled to get the renewal and/or upgrade contract signed, I’ve been able to come up with a magic formula: making sure that as soon as you touch the account, by either getting the contract signed or inheriting the existing account, you start asking, “What are you trying to accomplish?” and “How will you measure success?” These are the standard needs assessment questions for media sellers, however they apply to sellers of all industries regardless of whether they’re a hunter (account executive) or a farmer (account manager).

These questions help to clarify the client’s objectives, and perhaps not as obviously, they improve the sales conversation itself.

The discussions following these basic questions help the seller to close the sale, then deliver the right service, and finally, encourage that client to buy again. The client will feel comfortable in knowing that they’ve been understood and that knowledge sets the right tone for the sales relationship. It also helps the seller with other accounts. By learning from their clients, salespeople can turn their knowledge into stories which can be shared with other prospects to inspire confidence in their expertise.

Failure to ask these questions and interpret their answers properly results in the dreaded: selling wrong. Even if a deal is closed, it can still be sold wrong.

How is that possible?

Most sellers base their proposals, contracts, and service level agreements on what they learn, and fail to learn, during the sales process. When customers end the relationship or fail to renew, the seller can be tempted to blame everyone except themselves. Unfortunately oftentimes the blame is theirs alone. If they didn’t ask those big questions, and maybe only probed to find the basic needs, the client’s reluctance to renew may be the seller’s fault. Only by asking the right questions and later interpreting and even negotiating the benchmarks, can a salesperson understand the client thoroughly enough to deliver the right services. This also ties into the seller’s deep knowledge of their company, so they can ensure they’ve leveraged its strengths and avoided its weaknesses.

Borrowing the two questions: “What are you trying to accomplish?” and “How will you measure success?” from digital sales, and then learning to interpret their answers will help you sell right. It’ll improve your sales conversations and solidify client relationships.

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About Steve Bookbinder

Steve Bookbinder is the CEO and sales expert at DMTraining. He has delivered more than 5,000 workshops and speeches to clients all over the world and has trained, coached, and managed more than 50,000 salespeople and managers. Steve continuously refreshes his training content to reflect his latest first-hand observations of salespeople across industries and regions. Through him, participants in his workshops and coaching sessions learn the best practices of today’s most successful sellers and managers across industries. Steve understands that sales is a competitive game. To outperform competitors and our own personal best results, we need to out-prospect, out-qualify, out-present and out-negotiate everyone else, not merely know how to sell. Through his specialty programs in Pipeline Management, Personal Marketing, Great First Meetings, 2nd-level Questioning, Sales Negotiating, and Sales Coaching, Steve trains sales teams to master the skills they need to overcome the challenges they face in today’s world… and keep improving results year over year.

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