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If you have ever been in the position of making a purchasing decision, salespeople have undoubtedly asked you horrible questions. Rest assured, that nobody asks an awful question intentionally. Millions of professionals have been given poor advice and coaching with either outdated, or poorly conceived strategies. Misguided questions generally have great intentions. However, such questions will trigger an adversarial response from a potential client. To that end, please be advised of the three worst questions salespeople ask clients. I’ve included effective alternatives to each one.

1. What Keeps You Up At Night?

Someone once suggested that business salespeople should ask their potential client, “What keeps you up at night?” On the surface it seems pretty innocuous. It might appear to make good sense if you are trying to uncover your potential client’s priorities. The risk is that your potential client might not have any context for how you might be able to help. You might offer information technology solutions. In response to your question, your client could respond with something you can’t address at all. For example, they could say “My neighbor’s kid keeps throwing parties late at night.”

Instead: You want to entice their interest by describing problems you solve with extraordinary results that might pique their interest. You then need to quickly disarm the notion that you are there to sell something and learn more about their situation. This is the Entice Disarm Discover formula we describe in detail in our book Same Side Selling. I also outline steps for the Entice Disarm Discover in the article The Best Elevator Pitch Has Three Elements.

2. Who Is The Decision Maker OR Have You Made A Decision Yet?

I understand and appreciate that you want to know who signs off on your sale. The problem with either of these questions, though, is that neither is likely to produce an honest answer. The most common response to the question about who is the decision maker, regardless of facts, is, “I am.” Understand that asking this question will most often make the person you ask feel defensive. Are you planning to go around their back? Are they not important to you?

Just about every business can recall overhearing a sales professional say something like, “Hey, just checking in to see if you’ve made a decision yet.” The bigger problem is that this question focuses on a decision associated with the customer buying something. Though your goal might be to sell something, your client doesn’t consider “making the purchase” their goal. –They see the finish line as them realizing results.

Instead: Ask questions about who will be involved in ensuring and measuring results of your solution. Also ask questions about who has the most to lose if the issue is not solved. Rest assured, those individuals are critical to the decision process. In taking this approach, you’ll have a common goal of results, not just a sale. The question might sound like “Just because you spend money with us doesn’t mean you saw results. How would we know if we were successful six months after delivery? What would we measure?”

3. What’s Your Budget?

There are variations on this question. Sometimes, salespeople ask how much the customer is spending with another vendor. For example, if you offer accounting services, you might ask your client “How much is the other vendor charging you for accounting services?” Unless you have the complete trust from your client, you are not likely to get an honest answer. Worse yet, you are falling into a trap of making everything about price.

Instead: In business decisions, customers want to maximize the difference between the cost of the solution, and the impact of their results. Think of it this way, if your customer feels you can solve a million dollar problem, then they might be willing to spend a boatload more money than if they think you can help them address a ten thousand dollar problem. Ask about the impact of not solving the issue, the measurable results they would anticipate seeing, and what else they have tried to accomplish reach their goal.


Each bad question has a great intention. However, the alternatives suggested are more likely to get the buyer and seller on the same side of the table compared to the original script. You’ll see a dramatic difference in customer response if you embrace these alternative methods. You are still allowed to laugh when you are on the receiving end of the original questions.

It’s Your Turn

Which horrible question should have made the list?