How to Avoid 4 Common Sales Mistakes by Asking the Right Questions Blog Feature
Steve Bookbinder

By: Steve Bookbinder on June 1st, 2016

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How to Avoid 4 Common Sales Mistakes by Asking the Right Questions

Sales Tips | Sales Training | sales questions

Asking the wrong questions can get you the wrong response.

When you’re selling and trying to close the big sale, penetrate the account, upsell, or go wide and deep within an organization, you must be able to get below the surface in your sales conversations. By asking the right questions, you’ll be able to continue progressing the sale forward.


So how can you avoid making mistakes by asking the wrong questions? Replace your response in these 4 common scenarios:

Scenario #1

It’s a first appointment, where you’ve proactively prospected to get the sales meeting. The prospect begins by telling you, “ The reason I wanted to meet you is that we are currently looking to change vendors and I thought your solution might be what we are looking for.”

Typical sales response: “Great! Tell me more about what you’re looking for.”

The right question: “Before I go into our offering, can you tell me why you originally chose your current vendor and why their approach hasn’t worked for you? Did something change?”

Rationale: As you clarify the prospect’s original motivation for contracting an outside vendor, their buying role (then and now), as well as the new challenges and goals that your solution must address, you’ll get greater insight and naturally be led to ask deeper questions.

You may learn that the incumbent vendor is doing exactly what they always promised, but the customer’s needs changed along the way and now they are looking for new results. By asking your prospect to begin at an earlier point, you get to hear the entire history of who influenced and who made that previous, similar buying decision.

If you use the typical response, you deny yourself the opportunity to learn how to properly describe your offering. You’d now have to guess what would appeal to the prospect.

Scenario #2

You are presenting your solution to a prospect who says, “Wow! That looks interesting. We could use that here.”

Typical sales response: “Should I get you a proposal?”

The right question: “If you did bring in a service like this, when would you want the service to begin? Why then?”

Rationale: The fact that proposals generally precede the close does not mean that proposals cause the sale to close. Simply rushing a proposal too soon takes away all your moves.

Before you deliver a proposal, you can call and meet many times in order to ask questions and meet with various decisionmakers and stakeholders. But as soon as you deliver a proposal, there isn’t much left to do other than endlessly hound your contact by asking if they have any questions.

A proposal only closes when the client makes a decision to buy and they won’t make that decision unless and until they absolutely have to. If there is an underlying timetable then there is a reason to make a decision about your service, but if there’s no specified timeline in place, they won’t buy because there’s no date holding them accountable

Ask the right questions and you’ll be able to explore the prospect’s underlying timetable -- or lack of urgency.

Scenario #3

It’s a second meeting and you’re doing a full capabilities presentation. The prospect, who seems interested, mentions that they once saw a similar offering presented.

Typical sales response: “Really? Well, ours is really the best in the market. Let me tell you how our offering is better…”

The right question: “I’m just curious, but why didn’t you buy that service?”

Rationale: Knowing why your prospect didn’t purchase a similar service will reveal the true buying criteria they have in mind. And since you’re eventually going to suggest that they buy from you, the suggestion will sound less like unsolicited advice when you first ask, listen, and learn what they are really trying to accomplish.

Scenario #4

The prospect, at the end of a first meeting that seemed to go well, says, “Sounds good. Can you get me a proposal?”

Typical sales response: “Sure, when should I follow up with you?”

The right question: “If I come back with a proposal that shows you how well our solution fits -- and the budget was $X, how do you think you would react?”

Rationale: Why spend time and energy writing and sending a proposal if you don’t know what they’ll do when they see it? What will the solution have to be? What is the right budget? And when would a decision be rendered?

The prospect probably already knows. The only one who doesn’t know is you, so make sure you ask the right questions and find out.

Avoid being in any of these 4 common sales dilemmas by asking the right questions right away. You’ll more easily be able to discern whether something is worth pursuing and how you can quickly progress through the sales process.

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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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