7 Mission-Critical Questions to Ask Buyers at Every Stage of the Sales Process

As a sales leader at HubSpot for over 10 years, I‘ve seen the sales profession undergo a massive transformation. Prospects today are better informed and more empowered than ever before. They expect sales reps to be visible experts who deeply understand their business and goals. Generic pitches and premature offers just don‘t cut it anymore.

To succeed in this new era of sales, reps must master the art of consultative selling. That means focusing first on asking questions and surfacing needs before ever mentioning their product. By becoming skilled at strategically questioning buyers, reps can determine if prospects are a good fit, tailor their approach, and ultimately, maximize revenue.

But it takes more than just asking "What keeps you up at night?" to get to the heart of a buyer‘s objectives and challenges. Reps need an arsenal of targeted, thought-provoking questions to ask at each distinct phase of the buyer‘s journey.

I like to think of it as "question-based selling." Just as software developers release new iterations of code, sales reps should continuously refine the questions they ask to uncover deeper insights. Here are seven crucial questions to ask prospects, broken out by buyer stage, that I‘ve pressure-tested over thousands of sales calls.

Awareness Stage

Question 1: What prompted you to explore solutions like ours? What challenges are you trying to solve?

In the early awareness stage, prospects are just beginning to understand their problem and research potential fixes. They‘re looking for vendors who can help articulate their issues and provide education on different solution approaches.

Avoid the temptation to leap into a generic pitch about your offerings. Your first objective is to get prospects talking about their situation and needs. Ask open-ended questions to draw out more details on the challenges that drove them to engage with your company in the first place.

For example, if a prospect downloaded an ebook on improving their sales close rates, you might say: "I noticed you grabbed our guide on sealing more deals. What challenges are you experiencing with sales productivity? What areas are you focused on improving?"

Actively listen and drill down into their responses. The more you allow prospects to elaborate on their problems and objectives, the more ammunition you‘ll have to personalize your messaging.

Question 2: How are those challenges impacting your organization? What happens if you do nothing?

It‘s not enough for prospects to acknowledge they have a problem. To be motivated to take action and invest in a solution, they need to viscerally feel the consequences and costs of inaction.

Guide the buyer to articulate how their current challenges are hindering their team, organization, and high-level business goals. Encourage them to project into the future and envision what will happen if those problems continue or escalate.

Say the VP of Sales shares that deals are getting stuck in the pipeline because reps struggle to communicate value. You could ask:

"What impact is that having on your team‘s ability to hit quota and drive revenue growth? If more deals keep stalling out, how will that affect your organization‘s expansion plans and budgets?"

Highlighting the urgency and scale of the problem sets the stage to discuss your solution‘s ROI later on. But for now, keep the focus on the prospect‘s world and resist offering your two cents.

Consideration Stage

Once prospects decide to evaluate solutions in earnest, sales reps need to simultaneously build trust, demonstrate the value of their offerings, and assess if the buyer is truly qualified.

Question 3: What criteria are you using to evaluate solutions? What does success look like?

It‘s crucial to understand the buyer‘s decision-making process and purchase criteria upfront, especially for complex B2B sales involving multiple stakeholders. The last thing you want is to invest months nurturing a deal only to be blindsided by a new decision-maker or requirement.

Ask questions to tease out how the prospect will assess vendors and what factors matter most to them. For example:

• Who else is involved in the decision? What are their top priorities and concerns?
• What specific capabilities are you looking for? Which are must-haves vs. nice-to-haves?
• What does your ideal solution allow you to do? What outcomes are you trying to achieve?
• How will you measure success and ROI? What metrics matter most?

Document the answers so you can map your offerings to their needs and customize your demo and proposal. This shows prospects you‘ve done your homework and are committed to helping them succeed, not just closing the sale.

Question 4: What‘s your timeline and budget for implementing a solution?

Countless hours are wasted chasing prospects who have a hypothetical need but lack the urgency, resources, or authority to purchase. That‘s where BANT comes in.

BANT stands for:

• Budget: What budget is allocated for this project? Is it approved?
• Authority: Are you the ultimate decision maker? Who else will be involved?
• Need: What specific problems are you trying to solve? Why now?
• Timeline: What‘s your timeline for implementing a solution?

Uncovering these essential details allows you to prioritize high-quality opportunities and disqualify poor-fit prospects before investing too much time.

But you can‘t just robotically check off each BANT box. Weave the questions organically into your conversation, ideally after you‘ve established rapport and trust.

I might say something like: "It sounds like improving your sales productivity is a major initiative. To make sure I can provide the most relevant guidance, can you share your timeline and budget for putting a solution in place? I want to ensure I‘m respecting your resources."

If you learn their budget is TBD or there‘s no real timeframe, you can adjust your nurturing approach accordingly.

Decision Stage

You‘re in the home stretch. The buyer has narrowed down their options to you and a competitor or two. How do you get them to commit? By reinforcing your value prop and squashing any lingering doubts.

Question 5: What remaining questions or concerns do you have? What‘s holding you back from moving forward?

Deals can easily derail in the eleventh hour if sales reps fail to surface final objections and resolve cold feet. Before you break out the contract, proactively probe into how the prospect is feeling about their impending decision.

Ask questions like:

• How confident are you that our solution will meet your needs and deliver ROI?
• What sticking points or hesitations do you or other stakeholders have?
• How can I make this decision easier for you and your organization?

This accomplishes two things. First, it demonstrates you care about the buyer‘s success, not just your commission check. Second, it gives you visibility into any barriers threatening the deal so you can navigate them proactively.

Maybe you learn the buyer is on board but their boss is waffling. Armed with that intel, you might offer to do an executive briefing call to walk through projected results and ROI. Or if the buyer expresses doubt about user adoption, you could introduce them to your Customer Success Manager to talk rollout strategy.

The key is asking the right questions to shine a light on deal-killing issues before it‘s too late. Then mobilize your team and resources to instill confidence and keep the deal on track.

Question 6: What will success look like 30, 60, 90 days post-implementation? How will you measure results?

According to HubSpot Research, 74% of buyers choose the rep that first provides value and insight. One powerful way to demonstrate value is painting a vivid picture of how your solution will measurably improve their business.

Get the buyer talking about their expectations and definition of success. What outcome are they trying to achieve in the next month, quarter, year? How will they evaluate if the solution was worth the investment?

Say you sell marketing automation software. You might ask:

• How many additional MQLs do you project to generate in the next 90 days using our software?
• What conversion rates are you aiming for at each funnel stage?
• How much revenue and ROI do you expect our solution to generate over the next 12 months?

Encourage the buyer to translate the abstract concept of "success" into hard metrics and KPIs. Then walk through exactly how your offerings will enable them to achieve those benchmarks. Where possible, cite past customer results and ROI stats.

Getting prospects to articulate their anticipated value and outcomes creates a stronger emotional connection to your solution. It allows them to envision their future business state with your product at the center.

Bringing It All Together

Asking prospects strategic, probing questions throughout the sales process is essential to understanding their needs, building trust, and accelerating revenue. But don‘t feel pressured to cram all 100+ discovery questions into your first call.

The best sellers weave in different questions across multiple touchpoints, tailoring them to the buyer‘s industry, role, and stage. They also know when to go off-script and let the conversation flow naturally.

Aim to ask more questions than you answer, especially early on. Gong data shows that top-performing reps ask 10+ targeted questions in the first meeting alone.

Above all, operate with genuine curiosity. Don‘t interrogate prospects or fire off questions in quick succession. Listen intently to their responses. Probe deeper to unearth new angles and details. Then use those insights to personalize your messaging, demo, and proposal.

When you lead with questions and make the buyer‘s needs your north star, you‘ll build deeper relationships, showcase your expertise, and ultimately win more deals. Master the art of strategic questioning and you‘ll reap the rewards for years to come.

Now I want to hear from you. What questions do you find most valuable to ask buyers at each stage of the sales process? Drop a comment below with the ones that have yielded the greatest insights for you and your team.