THE BLOG
09/13/2013 01:24 pm ET Updated Nov 13, 2013

5 Questions You Should Ask in Every Selling Situation

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Over 500,000 startups are born each year in the United States alone.

Impressed by that number? Don't be -- because 50 percent of those startups fail within their first year. And, within the next four years, another 50 percent or more will fail. The environment for small business is hostile. If you're running a small business today, you know what I mean. Luckily, there are ways to master your environment and give your company a leg up. The number one rule is this: You absolutely must know how to sell your product or service. And you need to do it better than your competitors do.

The good news is that your competitors are out there right now enthusiastically pitching the features and benefits of their products to your prospects. They're making cheesy sales calls, inundating people with their boring information, using outdated closing techniques, and finally wasting their time following up on prospects that are unlikely to do business with them.

The bad news is that you're probably doing the same exact thing.

Having worked with thousands of small business owners and salespeople in a wide range of industries, I have a unique perspective on how companies are selling today. I can tell you that most companies are doing it all wrong. Rather than pitching their products or services, salespeople and business owners should be asking effective questions to understand their prospects' challenges and goals. By asking great questions, salespeople create great value in the eyes of their prospects.

Here are five questions you should ask in every selling situation:

1. "Tell me about your challenges with regards to..." Every great salesperson must first understand his prospects' particular sales challenges. If the salesperson sells marketing solutions, then he wants to understand his prospects' marketing challenges. If the salesperson sells kitchen cabinets, then he wants to understand his prospects' challenges with regards to their existing kitchen. This is an effective start to any selling conversation because it immediately shows that your goal is to focus exclusively on the prospect and not on yourself (which most salespeople do!).

2. "Give me an example of this challenge." Once you've learned about the key challenges, you want to get examples of those challenges. This question takes a challenge from theoretical to personal. Ultimately, the prospect will only be motivated to buy from you if the challenge is personal and truly frustrating. You will learn this by asking for an example. "Our marketing hasn't been working lately," isn't enough. I want you to learn that, "We just launched a $10,000 marketing campaign that hasn't produced any results."

3. "Ballpark how much this challenge costs you." If a challenge isn't costing the prospect anything then he will not feel motivated to fix it. Therefore, you want to understand exactly what the challenges are costing the prospect. If you sell to businesses, then you want specific dollar values such as, "Our ineffective marketing has cost us $500,000 in lost revenues this year." If you sell to consumers then you want to at least understand what the problem is costing the prospect in terms such as, "Our ugly kitchen has meant that I'm too embarrassed to have dinner parties anymore."

4. "What would it mean to you if you could solve this challenge?" Before you ever get into presenting your solution, you want to understand just how committed the prospect is to solving his challenges. Thus, by learning what it would mean to solve the challenge, the prospect starts to paint you a picture of exactly what the upside will look like. Understanding what it would mean to solve the problem allows the prospect to articulate the value that you bring to him.

5. "Big picture, what are you looking to accomplish?" Salespeople often have no clue as to why their prospects would even want to buy from them. This question is the ultimate paintbrush in the hand of your prospect. This is where you fully understand what the prospect wants to accomplish from a high level. In the case of the salesperson selling marketing solutions, this is where the prospect might share with him how he's looking to double his small business over the next two years, and sees effective marketing as a huge part of accomplishing that goal.

Just think: Most salespeople are pushing their products or services onto prospects, whereas you will simply be asking great questions to let the prospect sell himself.

By asking these five questions in every selling situation, you will begin to understand your prospects on a deep level that will help you dominate your competition.

What is one question that you like to ask your prospects? Please share below in the comments.

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