Let’s be honest—B2B sales is a battleground. Especially in tech. It’s like you’re standing in the middle of an arena, surrounded by decision-makers who have all heard the same pitch a thousand times, each of them with their fears, hopes, and defenses. They’re not just buying a product; they’re gambling on their credibility, their future, and their company’s stability. So, how do you make them bet on you?
You ask the effective sales questions—not just any questions, but the questions that cut through the noise, the questions that show them you understand them better than they understand themselves. You become not just another seller, but a trusted advisor. That’s what this guide is about. I’m about to drop 25 questions that will shift your prospects from lukewarm to ready-to-buy, plus 8 mistakes that can cost you the deal when it matters.
The Power of Preparation: Starting Strong
Imagine walking into a meeting and feeling like you’re entering someone’s world for the first time, with no map, no compass. You’re just hoping the pieces fall together. But a well-prepared salesperson doesn’t just show up; they arrive armed—research, insights, strategy. Preparation isn’t an action; it’s a mindset. Think of it as sharpening your blade before stepping into the fray.
B2B sales aren’t just about charm; they’re about context. Knowing the latest company news, their challenges, and their industry trends isn’t just preparation—it’s respect. It says, “I cared enough to understand you before I even said hello.” This aligns with what’s called the “Challenger Sale,” where knowledge is your best weapon. Learn more about The Challenger Sale here.
Ask yourself—do you want to be a supplier or a consultant? Because only one gets invited to the decision-making table.
Qualifying the Right Leads: Saving Your Time
Time is precious—yours, theirs, everyone’s. Spending weeks chasing a lead that was never qualified in the first place is a crime against your calendar. The BANT framework—Budget, Authority, Need, Timeline—is like a sieve for sorting gold from sand. Before you even think about getting creative with your pitch, figure out if there’s a fit. The last thing you want is a deal that’s doomed from day one because the prospect never had the authority to say “yes” in the first place.
Sample Qualifying Questions
- What does an ideal solution look like for you?
- Who else needs to be involved in this decision?
- What budget has been established for this?
- What would a successful partnership look like to you?
- What business changes do you expect by working with us?
- Do you have a timeline for making this decision?
- When do you ideally want to have a solution in place?
These questions don’t just qualify; they reveal the landscape. They tell you who’s on the field, who’s watching from the sidelines, and whether there’s even a game to play.
Best Supporting Data
A report by HubSpot reveals that 61% of B2B marketers consider generating high-quality leads as their biggest challenge. The BANT framework helps prioritize quality leads over quantity, making sales efforts more effective. Read more here. Before you even think about getting creative with your pitch, figure out if there’s a fit. The last thing you want is a deal that’s doomed from day one because the prospect never had the authority to say “yes” in the first place.
Building Rapport: Trust is the Currency
Rapport isn’t built on flashy intros or fancy buzzwords. It’s like planting a seed—it needs patience and authenticity. You don’t want to be just another “call to action” in their inbox; you want to be the human behind the sale. Ask the questions that invite them to share and build customer engagement:
Sample Rapport-Building Questions
- Would it be helpful if I shared a case study of a similar business that faced this issue?
- How did you get involved in this industry?
- What motivated you to take this call today?
- What’s the one thing you wish this could solve?
- Can you walk me through how you’re currently doing it today?
- What will make this deal worth your while?
They’re not just talking business; they’re giving you a glimpse into their story. People respond to stories. Identifying buyer personas helps tailor these questions to each unique prospect.
Best Supporting Data
A Salesforce report shows that 79% of business buyers say it’s absolutely critical or very important to interact with a salesperson they trust. Establishing trust is foundational in B2B sales, and building rapport is key (read more here).
Discovery: Getting to the Core
Every ‘no’ hides a ‘maybe,’ and every ‘maybe’ has the potential to become a ‘yes’—if you dig deep enough. Discovery questions are like pulling at threads until you uncover what matters. The problem they think they have is rarely the actual problem. Use questions from the SPIN Selling approach to unearth what’s below the surface and enhance your sales funnel.
Sample Discovery Questions
- Would you be interested in a free audit of your current setup to identify potential bottlenecks?
- What made you realize your current setup was a problem?
- What motivated you to consider a change today?
- What could you be doing that you wouldn’t able to do today if this problem didn’t exist?
- If you didn’t solve it, could you live with it?
- What happens if you don’t do X?
- Could you walk me through your decision-making process?
- Are there any internal milestones we should be aware of that would impact our timeline?
Think of it like visiting a doctor—you don’t just say your back hurts and get a prescription. A good doctor asks about your routine, your habits, and your symptoms. They paint a picture of the entire scenario. It’s the same in sales—you’re diagnosing before you prescribe. You’re positioning yourself as the bridge between their current pain and their desired solution.
Best Supporting Data
According to Gartner, 77% of B2B buyers report that their latest purchase was very complex or difficult, which emphasizes the importance of thorough discovery to truly understand a prospect’s needs. This allows salespeople to help simplify the buying process. Check the data here.
Leveraging Pain Points: The Path to Urgency
Highlight Hormozi’s concept of using scarcity and urgency tactics to amplify the importance of acting on the pain points, enhancing the urgency. Leveraging these tactics can make the cost of inaction feel much greater and push prospects toward making a decision. Learn more about demand generation and pain points here.
Here’s the reality—people make changes not just because they want to, but because they have to. Pain creates urgency. No one moves unless the pain of staying still becomes greater than the pain of moving forward. It’s human nature. Leveraging sales techniques to highlight these pain points can significantly increase lead conversion.
Sample Questions to Leverage Pain Points
- What would your business look like in 12 months if nothing changed?
- What happens if you don’t address this issue?
- When does this need to be up and running?
- Walk me backward on how we get there.
- What’s the internal process so I can understand how to get you to success?
These aren’t questions—they’re spotlights on the reasons they called you in the first place. You’re helping them build a case against inaction.
Best Supporting Data
Research by Forrester found that 60% of B2B buyers want to speak to a sales representative only after researching and shortlisting their options. Identifying and amplifying pain points can create urgency and move potential clients toward making a decision sooner.
Handling Objections: Address, Don’t Dismiss
Incorporate urgency and scarcity tactics to handle objections effectively. For example, mention how creating a limited-time offer can alleviate cost concerns by adding a sense of urgency. Highlighting a time-sensitive discount can push prospects to see the immediate value and act quickly.
Objections are part of the process—they’re the prospect testing you, probing for reassurance. Don’t see an objection as resistance; see it as curiosity. Empathy is the antidote to doubt. Understanding sales objections and addressing them properly is key to effective customer engagement.
Common Objections and Suggested Questions
I don’t have time for this right now.
“What are your top priorities if you don’t have time for this now?”
I have a contract with a competitor.
“How is your experience with your current provider?”
I’m worried about the cost.
“What concerns do you have about the investment required?”
This shows you’re listening and that you understand this is a commitment for them. You’re inviting dialogue, not an argument.
Best Supporting Data
Dun&Breadstreet research indicates that 77% of B2B buyers state their latest purchase was very complex or difficult. Handling objections effectively with empathy can greatly simplify the decision process for the buyer.
Closing: The Art of Moving Forward
Consider adding a closing technique inspired by Hormozi’s strategies that involve showcasing missed opportunities if they delay decision-making. This could include emphasizing the potential consequences of waiting, such as losing out on early benefits or missing limited-time incentives, which can motivate prospects to take action sooner.
After all the questions, objections, and conversations—there comes a moment when you ask for commitment. But the best closers aren’t aggressive. They’re guides. You’re walking the prospect to the next stage, not pushing them over the edge. Your closing questions should help ease the decision-making process, reinforcing the value of your sales pitch.
Sample Closing Questions
- If there aren’t any other questions, what implementation timeline do you have in mind?
- Is there anything preventing us from moving forward by [specific date]?
- What would you like the next steps to look like?
- On a scale of 1 to 10, how confident are you in moving forward with us?
- What would need to happen for you to feel completely ready to get started?
These questions nudge the prospect to take action without feeling forced. You’re not just closing a sale; you’re opening a new chapter for their business with you as a partner.
Best Supporting Data
A study by Lead Response Management shows that 35-50% of sales go to the vendor that responds first. Closing effectively and on time is crucial to securing the deal before competitors do.
Follow-Up Questions: Staying Engaged After the Call
The deal isn’t done once the call ends and on top, lead gen and sales are rather omnichannel these days. Following up is crucial for keeping the conversation alive and nurturing the lead through your sales funnel. Bear in mind a salesperson must follow up an average of five to eight times to successfully close a deal…
Follow-up questions should remind the prospect of your value and show them that you’re serious about helping them solve their problem.
Sample Follow-Up Questions
- After our conversation, do you have any additional thoughts or questions?
- Can I provide more details on any part of our discussion?
- How does your team feel about our potential partnership?
- Is there anyone else I should be speaking to regarding this?
- What can I do to help you move forward?
8 Mistakes to Avoid: Don’t Sabotage Your Sale
Mistakes are costly, especially when the stakes are high. Let’s keep it real—you can do everything else right, but a few wrong moves can still cost you the deal.
Common Mistakes to Avoid
- Not doing homework on the leads: Makes you look unprepared.
- Dominating the conversation: Sales is about listening, not lecturing.
- Pitching too soon: Listen to their challenges before diving into your solution.
- Not actively listening: Shows lack of respect and interest.
- Rushing responses: Give the prospect time to think.
- Generic questions: Tailor your approach to their unique situation.
- Making assumptions: Let them tell you their needs.
- Accepting vague responses: Dig deeper for clarity.
Conclusion: Sales is a Conversation, Not a Performance
The best salespeople I know don’t just sell—they connect, they consult, they guide. They ask the questions no one else is asking. They dig deeper, and they’re relentless in finding ways to genuinely help.
Take these questions, use them as your compass, and remember—every sale is a conversation. And the right conversation? It can change everything.
