What are some good ways to avoid asking dead-end questions? #Q&A

What are some good ways to avoid asking dead-end questions? #Q&A

By Scott Sambucci | May 13, 2020


How can I avoid getting a short, yes/no answers?


If you manage the sales process question, there is no such thing as “dead-end questions”, only dead-end conversations to the sales process because of lack of preparation.

To avoid dead-end questions (read: conversations):

  1. Maintain a 4:1 question ratio. For every four (4) questions you ask, deliberately offer an opportunity for the prospect to ask a question and make a statement. Think of your interaction as a conversation, not an interrogation. This will markedly increase your prospect’s interest, and further, their questions to you may often reveal more information to you than their answers to your questions. For example, suppose you are selling project management software for the enterprise:

Sales Question #1: “How many people in your organization are involved with the production of any of your products?”

Sales Question #2: “How is your team communicating project requirements to each other and deliverables along the way?”

Sales Question #3: “What is the typical timeline on your product development cycle? Is it a week, a month, several months, a year…?”

Sales Question #4: “Would you like to reduce that timeline? What cost savings would you attain by shortening your project timeline by 25%?”

At this point, pause and allow the customer to ask you a question or two. They’ll probably see where you’re going with your line of questioning above, and might ask:

Prospect Question: “What is the average cost savings that your XYZ software provides to its users?”

Woohoo! You’ve just discovered that the prospect cares about cost savings and you now can share information about case studies with other customers at the prospect’s request. This is far and way better than just puking examples on him without confirming that cost savings matter to the prospect in the first place. And most importantly, this stemmed from the prospect pushing intelligence to you instead of you pulling out of them through your questioning strategy.

  1. Consider what your customer hears in your questions. For example, if you really don’t know if your prospect is using any project management software, then Question A is better than Question B:

“Are you using any project management software right now?”

“Which project management software are you using?”

Why? Because the open-ended version (Question B) can be received as condescending to the prospect. When you ask question B, the prospect might think – “What a brat. I’ve been managing projects at my company for 15 years with more than 10 people per project involved. We use Excel spreadsheets and email and have bootstrapped the company to a $20mln run rate.” Consider the psychology of your questions, not just the information you hope to collect from them.

Question A allows you to follow up with “Which one?” or even better, Question C below.

If you’re not sure if the prospect is using any project management software, then the best way to ask this question at the onset of the sales conversation is:

“How do you manage your projects now? Are you using any specific project management software, or a combination of tools like email and shared spreadsheets?”

This indicates earnest interest on your end as the salesperson to understand the prospect’s situation and avoids the appearance that you are attempting to track the prospect directly into a feature/benefits conversation about your product. If you ask Question C from the start, you’ll be diving directly into the prospect’s workflow process.

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  1. Do your research.  If you need to ask a large number of yes/no questions or are looking for creative ways to manufacture open-ended questions from yes/no questions, that probably means that you haven’t done enough legwork ahead of the call/meeting. Additionally, the prospect will become bored very quickly because all of these types of questions (defined by “situational” questions in the SPIN Selling method) only benefit you, the salesperson. Meanwhile, the prospect might be sitting there wondering when you’re planning to get to the good stuff about your product and problems it solves.

For example, if my target prospect just spoke at a Project Management Software conference and their presentation discusses how they love using competitor’s ABC software, you shouldn’t be asking – “So…. what software are your using now? Do you like it?”

  1. Never assume. Say the prospect tells you they are using ABC software, which many of your current customers have converted from because of a particular weakness. Do NOT assume this customer has the same problem.

For example, suppose ABC software (your competitor) is only available as an install on a local system vs. your XYZ software which is web-based. The prospect tells you – “We’re using ABC software.” Do NOT assume this is a deficiency with this particular customer. Perhaps the users for this customer purposely do not have Internet access on the terminals where this software is used and is a condition the prospect prefers. Always qualify each condition.

If you wrongly assume that the local install condition is a negative for the customer, this will immediately lead to a dead-end to the conversation because 1) you look like a doofus for failing to collect enough information about the prospect’s situation and decision criteria, and 2) now you’ll be back-tracking and hunting for another reason to have the prospect check out your software, and the prospect knows it. You’ve ceded control of the conversation to the prospect out of arrogance.

**This Q&A article was originally posted on Quora. Check out Scott’s Quora page here.


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