5 Types of Questions Every Salesperson Needs to Stop Asking Prospects ASAP

As a salesperson, you‘ve likely heard this advice over and over: to win more deals, talk less and ask more questions.

And it‘s true – great questions are one of the most valuable tools in any seller‘s arsenal. In fact, a study by Gong.io found that top performing reps ask questions 28% more often than their peers during sales calls.

But here‘s the thing – not all questions are created equal. Certain types of questions can actually hurt your credibility and decrease the likelihood of closing the deal.

Unfortunately, many of these deal-killing questions are extremely common. According to sales strategist John Barrows, over 80% of the calls he joins include at least one cringe-worthy question from the rep.

Yikes. Unless you want to lose credibility (and revenue), don‘t let these questions pass your lips. Here are the top 5 types to avoid at all costs, plus what to ask instead.

1. Rhetorical Questions

You know those questions that are really more of a statement than an actual inquiry? The ones where the "right" answer is painfully obvious to both you and the buyer? Yep, those are rhetorical questions – and they have no place in a sales conversation.

Examples include:

• "Wouldn‘t it be great if you could increase revenue without adding headcount?"
• "Shouldn‘t delivering amazing customer service be a top priority?"
• "Don‘t you want to be seen as an innovative leader in your industry?"

Why They Backfire:
Rhetorical questions make you seem less trustworthy because they‘re clearly designed to steer the prospect to your predetermined conclusion. It‘s condescending, inauthentic, and just plain annoying.

What to Ask Instead:
If you want to influence a prospect‘s thinking, ask genuine questions that prompt them to articulate their goals, challenges, and priorities – in their own words:

• "What are your current strategies for growing revenue and how are they working?"
• "How would you describe your team‘s approach to customer service today?"
• "What initiatives is your department taking to stay ahead of industry trends?"

2. Overused "Salesy" Questions

Buyers can smell a canned sales pitch from a mile away. If you‘re relying on generic, overused questions, prospects will assume you see them as just another lead to churn through your pipeline.

Classic examples:

• "What‘s keeping you up at night?"
• "If you could change one thing about your business, what would it be?"
• "What would it take to get your business today?"

Why They Backfire:
Not only do these questions make you sound like every other mediocre rep, they also fail to elicit any meaningful information from the buyer. You‘ll get surface-level, guarded responses at best.

What to Ask Instead:
Do your research beforehand so you can skip the generic questions and have a tailored, value-driven discussion:

• "I noticed your main competitor recently launched [product/feature]. How is your team planning to respond?"
• "In the research you shared, you mentioned struggling with [challenge]. Can you tell me more about how that‘s impacting your department goals?"
• "Last quarter you said improving [metric] was a top priority. How has that progressed and what are your plans for next steps?"

3. Guilt-Tripping Questions

Back in the days of hard sell tactics, some reps thought making prospects feel guilty or inadequate would motivate them to buy. In 2023, guilt-tripping will only motivate them to end the relationship ASAP.

Examples of what not to do:

• "Do you realize how far behind you are compared to others in your industry?"
• "Why did you miss our last meeting? I thought this was important to you."
• "Can you really afford to let this problem keep impacting your business?"

Why They Backfire:
Modern buyers expect to be treated as partners, not manipulated through shame or pressure. Attempting to guilt prospects destroys trust immediately.

What to Ask Instead:
Position yourself as an advocate, not an adversary. Ask questions that demonstrate empathy and a commitment to helping them succeed:

• "I know adopting new software can be challenging. How can I support your team through the transition?"
• "It seems like your priorities have shifted since we last spoke – is this still a good time to discuss this or should we reconnect at a later date?"
• "What‘s the business impact of this challenge? What improvements are you hoping to see by addressing it?"

4. Hypothetical "What Ifs"

Hypotheticals can be fun thought experiments, but in sales, they‘re often thinly veiled attempts to get the prospect to commit to something prematurely.

For instance:

• "If I gave you a 20% discount, would you sign the contract today?"
• "Let‘s say we threw in [feature]. Would that be enough to get your team on board?"

Why They Backfire:
These questions seem manipulative because the rep likely can‘t actually offer what they‘re dangling. It puts the prospect on the spot and erodes trust.

What to Ask Instead:
Be direct and transparent about what you can and cannot provide. Make clear proposals grounded in reality:

• "Based on our conversation, I think I can get approval for a 20% discount if you‘re able to sign by [date]. How does that align with your timeline?"
• "I‘ve spoken with our product team and we can include [feature] at [price]. I believe this addresses the concerns you shared – what other questions can I answer as you consider this?"

5. Questions You Should Already Know the Answers To

There‘s no faster way to lose credibility than by asking a prospect something you could have easily learned from their website, LinkedIn, or a quick Google search.

But shockingly, HubSpot found 82% of sales reps reported asking the question "What does your company do?" in early sales calls.

Other questions to banish from your repertoire:

• "How long have you been in business?"
• "Who are your competitors?"
• "What products/services do you currently use for [purpose]?"

Why They Backfire:
If you haven‘t invested a few minutes to learn basic facts about a prospect‘s company, why should they invest their valuable time to speak with you? Lack of research signals lack of real interest.

What to Ask Instead:
Do your homework before each meeting. Come prepared with educated, relevant questions that show you‘ve studied their situation:

• "I saw your company recently expanded into [new market] – how has that impacted your team‘s goals for this quarter?"
• "I noticed you used to use [competitor‘s product] but switched to [current product] last year. What prompted that change?"
• "Your LinkedIn post mentioned you‘re rolling out a new [program/initiative]. What challenges are you anticipating and how can I help you get ahead of those?"

Bonus: How to Master the Art of Asking Great Sales Questions

Now that you know what not to ask, here are a few tips to help you craft brilliant sales questions that create value for prospects and momentum for deals:

1. Always pre-call plan. Investing time to research and prepare targeted questions beforehand is what separates top reps from mediocre performers.

2. Aim for open-ended questions. You want to invite the prospect to share their perspective, not box them into yes/no answers. Questions that start with "What," "How," "Describe," etc. elicit much more insightful responses.

3. Listen more than you talk. The best sales questions are useless if you don‘t actively listen to the answers. Practice leaving thoughtful pauses and using follow up questions to dig deeper.

4. Balance rapport-building and deal questions. Your goal is to understand the prospect‘s world, both professionally and personally. Mix in questions about their role, background, and interests, not just the immediate deal at hand.

5. Tie questions back to value. Make sure each question lays groundwork for you to communicate how your product/service addresses the prospect‘s needs. The Sandler Selling System sums this up well: "When asking a question, only ask questions where the answers will help you better sell your product or service in the future."

Mastering sales questions takes practice, but it‘s well worth the effort. By focusing on quality over quantity, preparation over scripts, and listening over pitching, you‘ll build genuine relationships and close more deals.

Remember, great questions lead to great conversations – and ultimately, great conversions. Make each one count.