6 Questions to Stop Asking Prospects — And What to Ask Instead

As salespeople, we have a difficult tightrope to walk. To win deals, we need to uncover sensitive information about our prospects‘ deepest goals, most pressing challenges, budgets, and decision-making authority. But research shows that buyers rank "Lack of trust in the salesperson" as a top reason they don‘t make a purchase (LinkedIn State of Sales Report, 2021).

Herein lies the dilemma. In most cases, probing into virtual strangers‘ business and asking them to open up their wallets would seem insensitive and presumptuous. But for us, it‘s our job.

The key to building trust and uncovering the full truth is Emotional Intelligence – being hyper-aware of how your questions are being perceived and adjusting your approach accordingly. By making small tweaks to the way you frame sensitive topics, you can have a huge impact on your prospect relationships and deal outcomes.

In this post, I‘ll share the most common qualifying questions that can make prospects shut down – and reveal the emotionally intelligent alternative to ask instead.

Building Trust Before Asking Sensitive Questions

Did you know it takes just 7 seconds for people to make a first impression? In those critical moments, our brains are hardwired to make split-second judgements of whether a person is trustworthy and likeable (Willis & Todorov study, 2006).

That‘s why diving into probing questions in the first minutes of a sales conversation can be disastrous. The prospect‘s guard will immediately go up and their answers will likely be filtered, vague or outright false.

The most successful salespeople, in contrast, are masters at building rapport before broaching sensitive subjects. They make their prospect feel emotionally comfortable through active listening, empathy, and finding common ground. Only then do they feel it‘s appropriate to probe deeper.

To uncover the full truth, ease into sensitive topics with casual, open-ended questions. For example, rather than asking "Do you have budget for this project?", try "As you evaluate solutions, what‘s the general investment range you have in mind?"

See the difference? The first asks for a yes/no answer, implying budget is either there or not. The second invites an open dialogue and shows you want to understand their situation, not strong-arm them into a price range.

Get Honest Responses With Casual Questions

How you phrase a question can completely change the response you get. Research shows that even subtle differences in wording can produce significant differences in how people answer (Journal of Consumer Psychology, 2016).

Here are some examples of aggressive sales questions that often lead to short, surface-level answers:

• "What results are you seeing from your current vendor?"
• "How much are you looking to spend?"
• "Who‘s the final decision maker?"

Now, here are those same topics reframed in a more casual, conversational way:

• "I saw on LinkedIn you‘ve been working with [Vendor] for a while now. How‘s that relationship going?"
• "To make sure I point you to the best options, can you give me a ballpark of what you typically invest in solutions like this?"
• "My recommendations usually resonate best when the head of [Department] is involved. What‘s the best way to get their input?"

The key is to position your questions in the context of being helpful and relevant to their needs, not serving your own agenda. Prospects can sniff out self-serving questions from a mile away. But when they sense authentic curiosity and a desire to understand their world, they‘ll open up with deeper insights.

Observe First, Then Ask "How‘s It Going?"

Want to fast-track trust with a new prospect? Do your homework and lead with observations about their business before you ask any questions. This shows you‘ve invested time to understand their world and goals.

Some ways to stay on top of key prospect news and events:

• Set up Google Alerts for the company name, key executives, product launches
• Follow their corporate blogs and social media accounts
• Check the executive team‘s Twitter and LinkedIn posts for updates
• Read their quarterly earnings reports and press releases
• Use a sales intelligence tool to track website changes, new hires, acquisitions

Armed with these insights, you can kick off your sales conversations with relevant remarks like:

• "I noticed you launched a new product line last quarter. How‘s the market reception so far?"
• "Congrats on opening your 4th new location this year! How‘s the expansion going?"
• "I saw you raised a new funding round. What are your big growth priorities for that investment?"

By starting with observations instead of interrogations, you demonstrate that you‘re knowledgeable about their business and there to talk about their needs. The casual "How‘s X going?" follow-up then invites them to share the full context – what‘s going well, what challenges they‘re facing, and where they could use help. No aggressive questions needed!

Show Prospects They‘re Not Alone In Challenges

Consider this – 79% of business buyers say it‘s absolutely critical or very important that sales reps demonstrate they understand their company‘s needs (Salesforce State of the Connected Customer, 2021). Yet in the same survey, only 39% say sales reps generally demonstrate that understanding.

The fastest way to show your prospect "I get you" is to highlight that you‘ve helped similar people in similar situations. When they realize their challenges aren‘t unique and you have a track record of solving them, they‘ll view you as a knowledgeable advisor, not just another vendor.

So instead of cliché questions like "What keeps you up at night?" or "What are your pain points?", try:

• "In talking with other [Job Titles] in [Industry], I‘m hearing a big focus on [Business Challenge] lately. Is that on your radar too?"
• "A lot of my customers are currently looking to improve [Key Metric] by [X%]. Is that a priority for your team as well?"
• "Many companies I work with are investing in [Technology/Initiative] this year. Are you also considering that?"

Using relevant industry benchmarks or aggregate customer data can be even more powerful:

• "Our State of [Industry] survey found that [X%] of companies are increasing budgets for [Category] next year. How does that compare to your plans?"
• "On average, our customers see a [X%] lift in [Key Metric] within [Time Period] of implementing [Solution]. Is that the level of improvement you‘re looking for?"

The key is to share insights prospects won‘t easily find elsewhere, backed by data. This demonstrates you have your finger on the pulse of their market and can offer unique value. It also "normalizes" the discussion around challenges or goals they might be shy to admit otherwise.

Uncover Past Attempts To Solve Issues

When a prospect reveals a challenge, our knee-jerk reaction is often to ask "Why?" Why haven‘t you solved this yet? Why hasn‘t your current approach worked?

Psychologically, "Why" questions can make the other person feel judged and get defensive (more on this effect called "Reactance" later). To uncover the real story behind their current situation without putting them on the spot, try:

• "Sounds like [Challenge] has been a frustrating issue. Has your team ever tried solving it before? I‘m curious what‘s been done so far."
• "Good question, have you looked into any solutions yet? What were the main reasons you didn‘t pull the trigger?"
• "Makes total sense. What‘s been the biggest blocker to fixing [Challenge] so far?"

The key is to position past inaction as completely normal and ask about it objectively, without a whiff of accusation. This gives prospects psychological safety to reveal hidden barriers like lack of time, knowledge gaps, or political headwinds without losing face.

Position Budget Questions Carefully

Of all things we need to uncover in discovery, budget is often the touchiest. Ask too bluntly and you risk offending the buyer or scaring them off with sticker shock.

To improve the odds of getting a solid budget range, keep these tips in mind:

1. Never lead with budget. Build enough value and understand their need first. Earn the right to ask.
2. Frame it around their goals and constraints. "To achieve [X] results, what level of investment do you typically make in solutions like this?"
3. Provide a wide range, not a single number. "Based on what you‘ve shared, a project like this typically falls in the $X-$Y range. How does that align with what you had in mind?"
4. Emphasize ROI over cost. "The price can seem hefty at first, but most of our customers see a full payback within X months and an ROI of Y% per year. Is that the type of return you‘re looking for?"

Ultimately, you want to position price as an investment, not an expense. By anchoring the discussion in business value and expected returns, you shift the focus from what they have to pay to what they stand to gain.

Focus On Timeline For Results, Not Just Purchase

Another critical but often overlooked detail to nail down is the prospect‘s timeline. And I don‘t just mean when they want to sign a contract or start implementation – the most important date is when they need to see measurable results from your solution.

Think about it this way – until your product or service actually delivers the promised impact, the prospect‘s job is at risk. They‘ve stuck their neck out to advocate for you and now their reputation (and budget) is on the line.

Clarifying this "need it done by" date is crucial for creating urgency and proving your value. To uncover it, ask:

• "Let‘s fast forward and imagine we implement the solution perfectly. At what point will you need to show [Key Stakeholder] measurable results to call this project a success?"
• "Putting the contract aside, when do you personally need to see [X] outcomes to feel great about this investment?"
• "I know locking in budget and a vendor is the first hurdle! Once that‘s done, when‘s the latest you can start showing progress on [Key Metric] to stay on track?"

By digging past the obvious milestones and surfacing the real-world expectations, you position yourself as the prospect‘s trusted partner in their success – not just another salesperson trying to rush a deal across the finish line.

Identify Decision Makers Indirectly

Even the warmest prospects can get cagey when asked "Are you the decision maker?" or "Who else is involved in this process?" They may feel you‘re questioning their authority or going behind their back.

The emotionally intelligent way to gather this intel is to make it a natural part of your sales process and give the prospect control over next steps:

• "Once I write up the proposal, I typically present it to [Prospect] and [Decision Maker]. Who else should I include in that meeting to make the best use of everyone‘s time?"
• "My most successful customers usually loop in [Decision Maker] around [X Stage]. Do you think it makes sense for the three of us to align on [Y Topic] in the next couple weeks?"
• "[Champion], thanks so much for your help narrowing down the best options! What‘s the best way for me to share this info with [Decision Maker] for final sign-off?"

See the difference? Instead of putting your champion on the defensive, you‘re empowering them to be the hero and highlighting how you can make them look good to their boss. It‘s a win-win approach that aligns everyone around the same goal and makes you a welcome partner vs. an outsider.

Bring It All Together: Your Action Plan

Mastering conversational, trust-building discovery isn‘t about magic-bullet questions. It‘s about consistently putting yourself in the buyer‘s shoes and ensuring every interaction leaves them feeling heard, understood and supported vs. interrogated and pressured.

As you prepare for your next discovery call, keep these key principles in mind:

1. Do your research first. Lead with observations about their world.
2. Prioritize building rapport before diving into sensitive topics.
3. Frame questions casually, in the spirit of being helpful vs. nosy.
4. Share relevant insights to show "You‘re not alone, I get you."
5. Be objective when discussing their past efforts or inaction.
6. Position budget as an investment in their goals, not a cost.
7. Clarify timeline for real-world results, not just signatures.
8. Give prospects a natural way to loop in decision makers.

To aid your own "before and after" self-coaching, here‘s a quick cheat sheet:

Instead of Asking	Try Asking
"What results are you getting?"	"How are things going with [X]?"
"What keeps you up at night?"	"[Challenge] is a big theme lately. You?"
"Why haven‘t you solved this yet?"	"Have you tried to solve this before?"
"What‘s your budget?"	"What do you normally invest in this?"
"When do you want to implement?"	"When do you need to see results?"
"Are you the decision maker?"	"Who should I include in the proposal?"

Bookmark this post to reference before your important discovery calls, and you‘ll be well on your way to building more trust, uncovering the full truth, and winning more deals!