The Five Toughest Sales Questions You Shouldn't Ask Your Prospects

Asking the right questions builds rapport, influences buyers, and seals deals like gangbusters. But asking the wrong questions is sinking your sales numbers like a 20-ton anchor.

In this video, we look at five stupid sales questions that are costing you sales and cutting your chances of closing off at the knees.

But part of the difficulty in both cases is not knowing the right questions to ask. Questions let you identify whether your prospect’s problem is one you can solve. They uncover hidden motivations that’ll help you craft a perfect pitch. And they aid in spotting who’s an ideal client and who is going to be a major pain in the ass.

But the problem is asking the wrong questions leads to sunk sales. Bad questions make you look like an idiot, a conman, or just a waste of your lead’s time.

And even if you have the most groundbreaking, world-shatteringly amazing product in the universe, a single crappy question in your process will leave you struggling to meet your goals every month.

But don’t worry, I’m going to help you avoid that completely by pointing out these five worst questions you can ask in sales.

Now, I’m also working on a follow-up video where I tackle the five most powerful sales questions successful reps ask buyers. So be sure to subscribe and keep an eye on this channel so you don’t miss it.

But for now, let’s get into the bad questions you should avoid asking prospects with every fiber of your being.

Here we go!

1: “Can I Give You My Pitch?”

Just hearing this one should make your neck hairs stand on end.

First off, don’t call it a pitch for god’s sake. Nobody actually wants to be pitched, especially when it comes to sales.

But beyond that, the very structure of this question is setting you up for a troublesome power dynamic. Can you see why?

You’re asking for permission here. Doing so pushes the psychology and dynamic of the conversation towards the lead having all the power. They are the ones granting you permission. They are the ones who are so generously donating you their time.

In reality, the best sales relationships stem from a place of equality. You are bringing real, tangible value to the table. And the buyer is exchanging that value for money.

So don’t ever, ever forget—you and the buyer are equals. So remember to act like it

2: “Can You Tell Me About What You Do?”

This one’s a bit tricky, partly because so many people ask this question, especially online.

And it’s easy to see why—it’s seen as a solid conversation starter. I mean, who doesn’t love talking about themselves?

The problem here is this question is a real value suck. You are getting all the benefit here. And though people do like talking about their business, their time is also precious. They likely don’t want to spend it on explaining their job.

On top of all that, asking the question also indicates one huge red flag—you didn’t do your research beforehand.

Instead, take a minute to look up their profession beforehand. And glean insights about their day-to-day from other value-based questions like the ones we’ll be talking about in our later video—don’t forget to subscribe for those by the way!

3: “But…?”

That’s it. One little word. But using that little word in sales conversations can lead to big consequences.

Simply put, this word is the start of an argument. And that’s tough. Because it’s a verbal slip so tiny that most reps don’t give saying it another thought.

But the word by its very nature is meant to draw contrast. It’s acknowledging your buyer’s previous point and saying, “Here’s why you’re wrong.”

In the heat of sales, emotions can run high. And when you’re talking money specifically, both reps and buyers are going to be quicker to react than in normal talks.

So rather than test the limits with this word, try to cut it from your vocabulary entirely. Instead, acknowledge their point and just move on to your point without drawing a contrast.

4: “So You’re Saying You Can’t Afford This?”

Even in the more logic-based world of B2B sales, emotions like pride can still factor into making deals.

And when you frame the question like this—where you’re attributing the low budget to the buyer themselves—it’s going to get them to go on the defensive.

And to an even larger point, insulting the company as a whole—even if it is just implied—is never a good way to do business.

Instead, try using subtler language when trying to determine if price is the biggest obstacle. Ask, “Is price your biggest sticking point here?” or “Do you currently have the budget for this?”

But remember, there’s always money to be found in large companies. Usually it just comes down to an issue of budget reallocation.

5: “When Should I Call You Back to Follow Up?”

This one again comes down to simple reframing. Putting the fate of the follow-up in the hands of the buyer is a mistake. People forget. They lose track of time. And their priorities shift over the course of days, even hours.

That’s why it’s so so so important to close on the next step yourself.

Frame the question so that you determine their level of buy-in while weeding out any objections.

A lot to do in one question, right?

Here, you should take a page from the Selling Made Simple Academy’s Closing Framework. Rather than saying, “When should I call you back to follow up?” instead try…

A: “Does It Make Sense to Jump on Another Call?”

The “Does it make sense to…” question intro is fantastic for solidifying commitment from the buyer. But the beauty of it is that if there is an objection, maybe they’re not sure if your product is right for them, then you can follow up with…

B: “What Do We Need to Do to Move This Forward?”

They’ll then tell you verbatim what’s holding them back from moving to the next step. And you can address those objections now rather than dealing with them later.

And that’s going to save you tons of time and hassle down the road.

Summary

There you go! Five downright terrible questions you should never ask in sales…

1. “Can I give you my pitch?”
2. “Can you tell me about what you do?”
3. “But…?”
4. “So you’re saying you can’t afford this?”
5. “when should I call you back to follow up?”

In this business, it’s all about knowing what to say and what not to say. And if you avoid these five questions like grim death, then you’ll be one—or five—steps closer to making more sales and boosting your numbers.