24 Discovery Questions That Lead to Six-Figure Contracts

Deals don't die because your price is too high.

They die because your discovery is too shallow.

I've been closing six and seven-figure deals for two decades, and the pattern is always the same: consultants who struggle with sales aren't uncovering pain points deep enough to justify their fees.

Your prospects don't wake up thinking, "I need a consultant today." They wake up with problems—some visible, some hidden—that drain millions from their business every year. 

Yet conversation after conversation, I hear most consultants, founders, and service providers never uncover those problems because they settle for scripted, surface-level questions that produce surface-level answers.

When you ask better questions, you close better deals. It's that simple. In this guide, I’ll walk you through a few discovery questions you can ask to understand your prospects better.

What is a discovery call?

A discovery call is the first call you have with a potential client when they show interest in your service. It's not an interrogation. It's a diagnosis.

Think of yourself as a doctor, not a salesperson. Your job isn't to push your solution—it's to understand the problem so deeply that your prospect sees you as the only logical choice to solve it.

The best discovery calls follow a simple formula:

• They build rapport without wasting time
• They uncover pain beneath the surface symptoms
• They quantify the cost of not solving the problem
• They create urgency around fixing it now, not later
• They position you as uniquely qualified to help

But the magic happens in the questions you ask—not just which questions, but how and when you ask them.

I don't ask discovery questions to fill a checklist. 

I ask to figure out: What's the cost of not solving this? 

That's the difference between a stalled deal and a closed one.

25 questions to ask in a discovery call

The questions below are organized to flow naturally through a discovery conversation. Think of them as tools in your toolkit—you won't use them in every call, but having them ready gives you options to dive deeper when you spot an opportunity.

Questions to learn more about them

1. "What does a typical day look like for you right now?"

This reveals their current workflow without directly asking about problems. Listen for inefficiencies, bottlenecks, and frustrations they've normalized. Their everyday routine contains clues about where your value truly lies.

2. "What's working really well for you at the moment?"

Counter-intuitive but powerful. By identifying what's working, you avoid fixing what isn't broken. Plus, it frames the conversation positively before diving into challenges. This builds trust by showing you're not just looking for problems.

3. "Who else is on your team or supports you?"

This maps the organization's structure and identifies key stakeholders in the decision process. It also reveals resource gaps you might fill. Listen for signs of overwhelm or understaffing.

4. "What goals are you focused on this quarter?"

Their near-term priorities show you where your solution needs to fit. You'll struggle to create urgency if you can't connect your offering to current objectives. This also reveals their planning horizon and strategic thinking.

Questions to understand the triggers

5. "What made you start looking for a solution now?"

The timing question reveals the event that moved this from "someday" to "today." There's always a trigger—find it, and you'll understand the true urgency behind their search.

6. "What's changed recently that pushed this to the top of your list?"

Similar to the previous question, but focused on external factors. Market shifts, competitor moves, or internal reorganizations often create windows of opportunity for your services.

7. "What's no longer working the way it used to?"

This question uncovers deteriorating systems or approaches. When something that used to work stops working, it creates pain and openness to new solutions. This question taps directly into that readiness for change.

8. "Was there a moment that made you realize you needed to fix this?"

The emotional trigger often differs from the logical one. This question uncovers the story behind the search—the frustration, embarrassment, or fear that catalyzed action. These emotional drivers influence decisions more than logic.

9. "If this hadn't come up, would you still be searching for help?"

This tests whether the need is genuine or merely exploratory. If they'd be fine without solving it, your sales process will be uphill. You've validated true need if they confirm they'd be searching regardless.

Questions to understand their pain points

10. "What's the biggest frustration you're dealing with right now?"

Direct but effective. This cuts through politeness to real pain. Where there's frustration, there's motivation to change. The strongest pain points create the strongest urgency.

11. "What happens if this problem doesn't get solved?"

This is where million-dollar deals are made or lost. They won't justify a serious investment if they can't articulate serious consequences. Push for specific outcomes—lost revenue, wasted time, missed opportunities.

12. "How is this challenge affecting your revenue/time/stress?"

Quantification turns vague problems into concrete business cases. A problem that costs $2M annually justifies a $200K solution. Help them do this math themselves during discovery.

13. "What have you already tried to fix this?"

Past attempts reveal both the problem's persistence and what approaches won't work. Failed efforts create openness to new solutions, especially when you can explain why your approach differs from what they've tried.

14. "How much time or money is this costing you right now?"

Financial impact creates a rational justification for your fees. Even "soft" costs like time and stress have dollar values in business. Guide them to quantify these costs themselves, and your price will seem reasonable by comparison.

Questions to qualify prospects

15. "What are you hoping a solution will do for you?"

Their success criteria tell you exactly what to address in your proposal. If their expectations don't align with your capabilities, it's better to know now than after you've invested time in a proposal.

16. "What does success look like in your eyes?"

Beyond features and benefits, this reveals their vision of transformation. Your value proposition lives in the gap between the current and the desired state. The bigger the gap, the more compelling your offer.

17. "Have you worked with someone like me before?"

Previous experience shapes expectations, positively or negatively. If they've had bad experiences, you'll need to differentiate yourself. If they've had none, you'll need to educate them on how the process works.

18. "What's your timeline for making this happen?"

Urgency drives decision speed. A prospect with a three-month timeline will move faster than one without a deadline. If they say "as soon as possible," dig deeper—that often masks a lack of true urgency.

19. "If we worked together, what would make you say this was worth it?"

Their definition of ROI tells you how to structure your offer and what metrics to highlight. This also plants the seed of future success, helping them imagine a positive outcome from working with you.

Questions to understand their budget

20. "How have you budgeted for solving this problem?"

More subtle than asking directly about numbers. They're not serious buyers if they haven't budgeted at all. If they have, it indicates organizational commitment to finding a solution.

21. "Have you invested in something like this before?"

Previous investments create psychological anchors for pricing. If they've spent $50K on similar services, your $75K proposal seems reasonable. If they've never spent more than $5K, you'll need to build more value before presenting your price.

22. "What's the cost of not fixing this problem?"

The flip side of ROI is the cost of inaction. When prospects calculate this themselves, they create their own justification for your fees. The higher this number, the less resistance you'll face on pricing.

23. "How do you typically decide about financial investments like this?"

This reveals their decision process and buying committee. Understanding whether it's a single decision-maker or a complex approval chain helps you navigate the sales cycle more effectively.

24. "If we found a solution that fit your goals, what kind of investment would you feel comfortable with?"

A gentle way to test budget boundaries without demanding a specific number. Their answer reveals both financial capacity and how they value solutions to this problem.

How to use these questions effectively

Discovery isn't about running through a checklist of questions. That’s where almost everyone goes wrong. 

In fact, you can largely skip 95% of these questions. I often have to remove questions when working with clients, not add more. 

Instead, it's about creating a conversation that reveals value.

The way you ask matters as much as what you ask. Each question should flow naturally from its previous answer, creating a diagnosis, not an interrogation.

A few principles to remember:

• Listen more than you talk. The prospect should be speaking 70% of the time. Your questions are just prompts to help them articulate what matters.
• Take notes visibly. This signals you value what they're saying and creates accountability—they know you'll remember what they told you.
• Dig deeper with follow-ups. Don't move on to the next question when you hear something interesting. Ask "Why is that important?" or "Can you tell me more about that?" The deeper layers are where the real value hides.
• Connect the dots they don't see. Your expertise lets you recognize patterns and implications they might miss. When you hear separate problems that share a root cause, point it out. This demonstrates your understanding.
• Don't pitch prematurely. The moment you start selling, discovery ends. Resist the urge to offer solutions until you fully understand the problem and its costs.

Turning discovery into deals

Great discovery transforms the entire sales process. When done right, your proposal becomes a mere formality—they're already sold on the value of solving their problem, and you've established yourself as the right person to solve it.

The questions above aren't just sales tactics. They're the foundation of truly transformative client relationships. They help you understand prospects deeply enough to create real value, not just close deals.

Your prospects don't wake up thinking about your services. They wake up with problems—some visible, some hidden—that drain value from their business every day. Your job in discovery is to bring those problems into focus, quantify their impact, and show how solving them creates returns that dwarf your fee.

Ask the right questions, and the deals will close themselves.