Level Up Your Old-School Approach to Sales Questions

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It’s no secret that sales can feel overwhelming. This is especially true for introverts, new sales reps, or small business owners who wish they didn’t have to sell, but know they need to.

If you’ve read my blogs and books or have seen me speak, you know that I’ve long championed a structured, repeatable process for selling. When you have a reliable sales process to leverage again and again, you remove the guesswork, eliminate the pressure, and make sales feel natural, even if you’re among the many who find it uncomfortable.

You likely already know that sales questions are a critical part of a winning sales process. They help you understand the prospect’s needs, make conversations more engaging, and prevent you from sounding too pushy.

Most sales experts will tell you to ask open-ended questions, and will share a few that build rapport and keep the conversation moving. And while all this is helpful, it barely scratches the surface.

What people don’t consider is that sales questions aren’t just for understanding the prospect – they help the prospect understand themselves. The right question, asked at the right time, can completely change how a buyer sees their own problem, their priorities, and even their decision-making process, which all by itself can be game-changing in a sales conversation.

What’s more, the way you structure your questions affects much more than just whether you close a deal. It has repercussions for how you refine your niche, strengthen your messaging, and handle objections before they even come up.

So while most salespeople  – seasoned or brand new, entrepreneurs or sales team members, introverts or extroverts  – already ask questions, very few do it in a holistic, strategic way that impacts a whole lot more than just one sales conversation.

The Biggest Mistake I See with Sales Questions

Everyone knows to ask open-ended sales questions, but they won’t do you much good without a clear direction. Instead of leading the sale, I see too many people asking scattered, disconnected questions that don’t build momentum. This is partly due to not having a repeatable process, partly to nerves, and partly to not understanding the needs and pain points of the prospect.

I learned this lesson the hard way when I first started in door-to-door sales. I was nervous, inexperienced, and desperate to make a sale. So I did what I thought I was supposed to do: I asked a few basic questions, then launched straight into explaining the product. Predictably, prospects would nod politely and then say, “I’ll think about it.” Sound familiar?

Everything changed when I started following a structured questioning process. Instead of asking questions at random, I asked them in a sequence designed to guide the prospect toward the right decision. 

It’s worth noting that the concept of process goes far beyond just questions. For an insightful discussion of embracing systemization and iteration for ongoing improvement, check out my interview with 8-figure entrepreneur David Fastuca:

Ultimately, if your questions don’t build toward a clear outcome, you’re just having a chat, not making a sale. Without structure, you leave too much to chance.

So, how do you ask sales questions in a way that naturally leads the prospect to a confident “yes,” without feeling forced or scripted? 

How to Ask Open-Ended Questions for Maximum Sales Performance

Once I realized how much structure mattered, I made sure that each question had a specific purpose, and that it naturally led to the next.

Right away, prospects were no longer just giving me surface-level answers. They were actually convincing themselves why they needed what I was offering. Having the right questions to ask, in the right order,  made it easy for me to help prospects see the gaps in their current solution and recognize that my offer was the answer.

Here’s what worked:

1. Start by uncovering the real problem. I wouldn’t ask vague questions about their business. I’d go straight to, “What’s the biggest frustration you have with your current setup?” That got them thinking about what wasn’t working.

2. Dig into what they’ve already tried. Before I ever pitched my solution, I asked, “What have you done so far to fix this?” This helped them realize why previous solutions failed and positioned me as someone who actually understood their situation.

3. Lead them toward the solution. Instead of pushing my product, I’d ask, “If you could solve this today, what would that look like for you?” By this point, they had already mentally outlined what they wanted, which usually aligned with what I was about to offer.

Using a structured approach to ask the right questions helps prospects connect the dots for themselves. Instead of feeling like they’re being sold to, they’re coming to the decision on their own.

The Right Questions to Ask, in Action

One of the best examples of structured open-ended sales questions came during my work with a ghostwriter who was struggling to close any deals. He was having plenty of conversations, but none of them were turning into business. And while he was already asking some great questions, he was doing it in no particular order. Worst of all, he was then jumping to price before the prospect had fully bought into the value.

We changed his approach by eliminating many of his closed-ended questions and structuring the others more effectively. Instead of starting with logistics or pricing, he began with, “Why do you want to write this book?” That got prospects thinking beyond the mechanics and into the personal or professional impact they hoped to achieve.

Next, he asked, “What’s stopped you from finishing it so far?” This surfaced frustrations and made them reflect on why they hadn’t been able to do it on their own.

Then, when he finally asked, “What would it mean for you if this book were finished and out in the world?” the conversation shifted. The prospect was now envisioning themselves as an author with a completed book, something they’d struggled to accomplish for years.

At this point, price was no longer the barrier it once was. The structured sequence of questions had made the value clear before the proposal ever hit the table. Within six weeks of making this shift, he closed $80,000 in new business.

This is the power of knowing the exact questions you need to ask, and how to structure them to close the deal. You’re not interrogating the prospect or simply checking off a list of so-called best sales questions to ask customers. You’re guiding them toward their own realization that they need what you’re offering.

How Structured Sales Questions Improve Your Entire Business

An excellent side benefit of leveraging these structured types of questions is that they have profound ripple effects across much more than just your sales success. Every conversation becomes a source of insight, which means you can refine your niche, adjust your messaging, and improve your overall business strategy.

Here are just a few differences you’ll start noticing fairly quickly:

You stop chasing the wrong clients. Pay close attention to who responds best to your process, and you’ll recognize patterns. You’ll see exactly who is most likely to buy, what pain points they mention the most, and where your solution provides the most value.

You refine your messaging. When you hear prospects repeatedly frame their challenges a certain way, you can tweak your marketing and sales materials to speak their language. This makes everything more effective, including cold emails, networking, social posts, and website pages.

You uncover objections early. Structured questioning allows you to discover hesitations before they become deal-breakers. Instead of reacting to last-minute concerns, you address them naturally throughout the conversation, often before they even arise!

You evolve your offer over time. The more structured your questions, the more valuable feedback you get. You’ll notice gaps in your current offering, spot new opportunities, and continue adapting to what your market actually needs.

I saw this play out firsthand when working with a PR firm that struggled to land high-value clients, despite already receiving extensive sales training. They had great client results, but their messaging was all over the place. Once they started structuring their sales questions, they realized they were strongest in a niche they hadn’t even been targeting: faith-based organizations. As soon they adjusted their positioning and focused on the right clients, they saw an immediate uptick in both interest and conversions.

Questions Are Just One Part of Winning Sales Conversations

Having the right kind of probing questions in sales is key to connecting with buyers and making your product or service stand out. However, having great sales questions, asked in the right order, is only one piece of the overall sales process.

If you’d like an introduction to my 7-step sales process, which applies to sales professionals and business owners alike, download of the first chapter of my bestselling book, The Introvert’s Edge. In it, I outline the systemized sales methodology that has been transformative for my own sales results and those of thousands of clients and students.

When you’ve mastered a comprehensive system focused on transparent, authentic, and low-pressure selling, you can say goodbye to uncomfortable bulldog sales tactics and watch your sales results skyrocket!