Note: Upon her indictment on federal money laundering charges and her arrest February 8, 2022, Inc. dismissed Heather Morgan as a contributing columnist. As is our practice, we do not unpublish editorial content, and rather have added this note for full transparency.

The most lucrative sales conversations are useless if you show up for them armed with the wrong questions.

Ineffective sales questions come in many forms. "Have you seen our latest set of features?" will immediately make your potential buyer feel like a hostage. A vague question will put them on the spot--especially if said question is so surface level they can't answer it right away. "What are you looking for in a cloud platform?" is a classic example of this.

I could go on. But rather than spend an entire post on what you shouldn't be asking, let's go over the kinds of questions customers will react to positively, whether you're holding an in-person meeting or sending a follow-up email.

Here are five questions that will ensure you probe deeper into your customers' needs and keep the conversation meaningful for both of you.

1. What?

I used to swear by asking, "Why?" Then, in 2017, I interviewed a former FBI hostage negotiator, who told me anything starting with "why" makes people feel like they're part of an interrogation. In other words, it raises their defenses, which is never helpful for gathering information.

Instead, he suggested asking "how" or "what" questions. Something like, "Why are you interested in our platform" would become, "What made you look into our platform." Starting a question this way tends to make it more specific, too, which can help you learn more about your potential customer's motives.

Same goes for the "Why now?" question. It's important to understand your prospective customer's reasons for agreeing to a meeting--especially if they haven't in the past. But instead of asking, "Why are you interested now?"--which has a ring of accusation to it--say something like, "How would our software platform help you out right now?"

2. Who makes the decisions?

So your potential buyer watched a demo and seems really interested in doing business. That's great, but do they actually have the power to push a deal through?

Especially in larger companies, where hierarchy reigns, your prospective customer is one person in a multi-level decision-making structure. It's important to understand who gets final say and if that person's actually present in the meeting. To do that, ask questions that probe into what the potential customer's decision-making structure looks like: "Who will use the product?"; "Who else is involved in this process?"; "What do we need to do to get a purchase approved?" Questions like these can give you an idea of how complex the buying process is. They also sound a whole lot more sophisticated than something like, "Who's your boss?"   

3. May I show you?

Don't barrel into the meeting announcing your product demo and expect to make a good impression. Your potential customers get asked to view demos all the time; they don't want to be assaulted with another one right away.

Instead, start out by asking, "What would a successful scenario for you look like?" Only when they've described this ideal outcome do you proceed towards demo territory. For example, you might ask a potential buyer how they see themselves using the software you sell. If they say something about faster performance, you can spotlight that aspect of your product when you finally do go through the demo.

4. What happens if you don't?

This question is all about uncovering your potential customer's alternatives. If they choose not to go with your product, does that mean they're not ready for it or that they're getting a better deal from a competitor? If it's the latter, what or who else are they considering?

Again, avoid the word "why" here, so the potential customer doesn't feel put on the spot. For example, if they say now's not the right time to invest in a CRM (customer relationship management) platform, ask something like, "Where will you store your sales data instead?" If they hint at another platform, it might be time to adjust the terms of your potential deal. And if they're hesitant to adopt any software, you may have to spend a few more months cultivating that relationship before entering into an actual sale.

5. Don't ask questions.

In sales, you will inevitably run into people who just hate questions. In their case, it doesn't matter if you ask "why," "how," or "who." They'll deflect all of them.

This is when you turn questions into simple observations: "It seems like you have a good reason to move your sales data into the cloud right now." When you simply state a fact, the recipient's brain will subconsciously try to verify the statement. That person will ask themselves, "Do we have a good reason to go cloud? Does anyone at our company object?" Suddenly, your prospective buyer will feel in control of the conversation and more inclined to share the kind of information you need to keep the relationship going.

While the observation tactic can be hugely effective if done right, it's best to use it as a last resort. The majority of your would-be customers approach sales meetings expecting to get asked about their goals and motives. Which means nine out of ten times, your energy is best spent on fine-tuning the kinds of questions that will put the other person at ease and spark a productive conversation.