There’s a very fine line between asking appropriate sales questions and making the prospect feel as though they’re in the middle on an interrogation.

Think of it in this way, when meeting a new person for the first time, a certain amount of question from them is normal and even necessary in building a certain rapport, as long as their questions within the subjects that you feel comfortable talking about. If they ask questions about your favorite movie, sports or what do you do for a living are common questions that we feel happy to answer because the subject is interesting to us and we’re comfortable talking about it. However, what if they will start asking some peeking questions like what is your income, your bank account balances and such, we’re likely to end that conversation quickly and really question that person’s motives.

The same can happen in your sales calls when it comes time to dig in and ask questions. The first key to having a balance here is making sure that the questions that you’re asking revolve around a subject that the prospect is interested in and provides value to them.

So how do you do this?

Prepare Insights That Matter To Your Customer:

Not surprisingly, preparation is a fundamental part in building any productive conversation. This is the step in the sales process where we create insights for the prospect. One of the keys to successful selling is the ability to create conversations with your prospect that actually elevate urgency and motivate them to take action, preferably, of course, with your product in mind.

Providing relevant insights to a prospect about issues or challenges in their world is very engaging, and it draws the prospect into the conversation without feeling threatened. People are happy to discuss things that they’re interested in or that provide value to them. These insights provide a fantastic foundation for asking questions.

Remember The “What’s In It For Me?” Rule:

As humans, our brains are wired to want to understand if something is bringing value to us. This is described as the “what’s in it for me” or the WIFM tendency. The same role may apply to your prospects. When you’re asking questions, we need to make sure that they understand that this part of the process has value to them. For example, have you ever been asked to fill out an online survey? Chances are, we ignore most of these requests. Now if the survey is from someone reputable and offers some sort of gift at the end, we may be more likely to complete it.

In my experience, one of the best ways is through sharing insights with a prospect and then through questions, helping to validate the specific impact directly to the people that you’re addressing to. It now becomes very tangible and concrete to them.

Understanding The Client’s Pain and How You Can Help Him:

It’s imperative to paint a clear picture of a difficult world for your prospect by delivering relevant business insights and then using those very same insights to quantify the problem for them. These insights, when shared properly, earn you the right to ask questions because you have established the value of doing so in the prospect’s mind.

That will be the temptation here because by now you’ve started to realize just how much you can potentially help this prospect. Resist the urge!
Now is not the time to start selling. Have… patience. One of the key things that we want to get from the prospect is to understand what the downstream impact of their decisions or failure to make those decisions might have on their organization or simply put, what is his “pain”. This requires more preparation on your part. Get to know the industries that you sell in.

What is does client want?

Keeping It Conversational:

If your questions could be answered by a computer, are you asking the right questions? If you can Google half the answers to the questions of your needs analysis document, are you really gonna be in a position to create value for their organization?
While asking the right questions is critical, no less important is our tone. Think about the times when someone has asked you questions about yourself. Isn’t it true that some people seem to have the ability to pull all sorts of information out of you that you didn’t intend to ever share? Have you ever said, “I can’t believe I’m sharing this “with you right now.” Most of us have.
The reason for that is the person we were speaking with came across as genuinely interested in us and likely very trustworthy. If we add in an attitude of truly caring about helping our prospects succeed, we have the recipe for a great sales question step in our sales process.

The Recap:

The recap serves to reemphasize the points that you’ve covered, and it makes sure that they’re in agreement with the points.
So why do you do this? At some point, you’re going to come to the inevitable discussion of cost, or price. By reviewing the topics that you’ve uncovered, you sum up all the points that they themselves have agreed to, and you end up in a place where they realize that they must act for the betterment of their organization. When done properly, this recap stage has the positive effect of eliminating objections later on.

Want to grow your business? Let’s work together!


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Hi, my name is Alex Lyhovez. I am a marketing and business development professional, blogger, an online entrepreneur and an avid autodidact. I help ad-tech companies and startups in achieving their digital marketing strategy goals through extensive sales power and a lot of "outside of the box" thinking. Feel free to reach out and explore how we can work together.

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