18 effective sales discovery questions to ask on a first call

As a sales professional, you've likely put in hundreds of hours studying human behavior and learning how to build rapport with prospects. A sales discovery call is where you put all of that work to the test and pull out your top selling techniques. Having excellent sales discovery questions shows prospects that you’re prepared to empathize with their pain, actively listen, and ultimately inspire them to take the next step in the sales cycle if your product or service would help them.

But you only have a few minutes to get on your prospects’ level, find out exactly what bothers them, and show them how to partner with you for success. In this article, we'll show you how to pick the right questions and even leverage AI tools like ChatGPT for helpful brainstorming.

<a href="#what-is-discovery-call" class="anchor-link">What is a Discovery Call?</a>

<a href="#purpose-of-asking-questions" class="anchor-link">Purpose of Asking Sales Discovery Questions</a>

<a href="#sales-discovery-process-stages" class="anchor-link">Stages of the Sales Discovery Process</a>

<a href="#number-of-questions-to-ask" class="anchor-link">Number of Discovery Questions to Ask</a>

<a href="#researching-your-prospect" class="anchor-link">Researching Your Prospect</a>

<a href="#using-chatgpt-for-questions" class="anchor-link">Using ChatGPT for Discovery Questions</a>

<a href="#sales-discovery-question-examples" class="anchor-link">18 Sales Discovery Question Examples</a>

• <a href="#lead-with-questions" class="anchor-link">Lead with Questions</a>
• <a href="#understand-needs-communicate-value" class="anchor-link">Understand Needs and Communicate Value</a>
• <a href="#progress-the-deal-forward" class="anchor-link">Progress the Deal Forward</a>

<a href="#chatgpt-streak-ai-prompts" class="anchor-link">Prompts for ChatGPT and Streak AI</a>

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What is a discovery call?

A sales discovery call is the first call you have with a prospect after they've shown interest. It's a crucial point in the relationship that can make or break a sale. Typically, sales discovery calls are used in more complex selling environments, like consultative sales and enterprise sales. 

Here’s what we mean by that: You aren't going to do a whole discovery process if you're a retail worker at a consumer shoe store. However, if you sell high-end footwear at a boutique and make personal relationships with your clients, you may very well have an informal “discovery meeting” with new customers.

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What's the purpose of asking sales discovery questions?

You want two main things to happen as a result of asking discovery questions:

1. You want to qualify or disqualify a prospect.
2. If your prospect is a qualified customer, you want to move them to the next deal stage.

There's nothing wrong with a prospect being a bad fit, but you need to find this out quickly to not waste anyone's time.

And when you find that they're a good fit, you need to lock them into the next step of the sale, whether that's booking a demo, setting up an appointment, or maybe even making a purchase. A discovery call that ends without a concrete next step isn't complete.

What makes a good discovery question?

Good sales discovery questions cut through the noise. They get to the heart of each prospect's issue so you, as a salesperson, have a better idea of what they may need from your business. Engaging questions also keep the conversation flowing. Here are a few tips for crafting good discovery questions:

• Use open-ended questions — avoid asking questions with “yes” or “no” answers
• Repeat your prospect's thoughts and ask them to expand on them
• Set the tone from the start that the meeting has a purpose
• Find out where they're at in the buying journey (For example, figure out if they’re already comparing vendors or just starting to realize they have a solvable problem.)
• Ask how they evaluate success
• Have them explain why business as usual isn't working

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Know the stages of the sales discovery process

Different questions are more effective at different points of the discovery process. According to Gartner, there are three main stages of the discovery process:

1. Qualify leads: Verify your prospect's interest and fit for the deal.
2. Understand value points: Uncover what the prospect really wants.
3. Identify the buying process: Create the roadmap to finalize the deal.

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How many discovery questions should you ask?

Research from leading revenue intelligence platform Gong shows there's an optimal range of sales discovery questions to ask: 11 to 14. A dozen or so thoughtful questions should give you plenty of answers and information to inform your next steps without completely overwhelming your prospect.

Gong also notes that this “magic range of questions” can change depending on who you’re talking to. C-suite executives are on the receiving end of multiple discovery calls per week or even per day, so you want to get right to the point with just a handful of questions.

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Why researching your prospect is paramount

A sales discovery call should not feel like a cold call. Nothing will make your prospect shut down faster than feeling like you don't know anything about them or their business. Instead, conduct thorough research and let that be the foundation that helps you ask personal questions that mean something to the prospect.

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How to use ChatGPT to create the perfect sales discovery questions

Chat-based AI systems like ChatGPT can help you brainstorm discovery questions based on your situation and prospect. You can feed it non-sensitive information on your company and prospect, and then ask it for a list of sales discovery questions. Usually, ChatGPT breaks down the list by topic, which is helpful.

Below is an example of a basic prompt:

“My company provides brand protection services for other companies and removes counterfeit sellers from online marketplaces. I'm meeting with a representative from a shoe brand who is interested in protecting their brand online. The shoe brand has had issues with fakes and counterfeits online and would like to protect its intellectual property. Considering this, give me a list of discovery questions to use for the call.”

And here's a list of questions ChatGPT gave for the prompt:

• Current challenges: Can you describe the specific challenges or issues you've encountered with counterfeit products online? How have these issues affected your brand reputation and sales?
• Online presence: On which online marketplaces and e-commerce platforms does your brand primarily operate? Are there specific regions or countries where counterfeiting is more prevalent?
• Current brand protection measures: What brand protection measures do you currently have in place? Have you implemented any anti-counterfeiting technologies or solutions?
• Monitoring and detection: How do you currently monitor and detect counterfeit products and unauthorized sellers online? Are there any specific patterns or trends you have noticed in the counterfeiting of your products?
• Intellectual property documentation: Do you have all your intellectual property documentation in place, including trademarks, patents, and copyrights? Have you encountered any legal challenges in protecting your intellectual property?
• Enforcement efforts: Have you taken legal actions against counterfeit sellers in the past? How effective have these efforts been, and what challenges did you face?
• Desired outcomes: What specific outcomes or goals are you looking to achieve with brand protection services? Are there key performance indicators (KPIs) that you have in mind for measuring success?
• Budget and resources: Do you have a dedicated budget allocated for brand protection? What internal resources are available for collaborating on brand protection initiatives?
• Customization and integration: Are you seeking a customized solution tailored to your brand's unique requirements? How seamlessly do you want the brand protection services to integrate with your existing systems and processes?
• Education and training: Is there a need for educating your team members on identifying counterfeit products or suspicious activities? How important is ongoing training in maintaining brand protection measures?
• Reporting and analytics: What kind of reporting and analytics would be valuable for you in assessing the effectiveness of brand protection efforts? How frequently would you like to receive updates on the status of brand protection activities?
• Collaboration with marketplaces: Have you engaged with online marketplaces directly to address counterfeit listings? Are there specific marketplaces where you would like to strengthen collaboration?

This output has some decent questions to use, but not all of them make sense. You’ll get better output when you can provide more detail about yourself and your prospect. You can also ask ChatGPT to focus on a certain area, like questions about budget or questions tailored for a Chief Technology Officer (CTO).

You can refine the output by continuing the chat in the same window. For the example above, you could say “Now, choose the five most important questions from the list.” Or, you can simply type “again” to have ChatGPT redo the prompt.

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18 sales discovery question examples

Below are some popular sales discovery questions you can steal and use with your prospects. But remember, the best questions come from your knowledge of your prospect based on information they’ve already provided, so take these generic questions and tailor them accordingly.

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Questions to lead with

1. What led you to take this call today?

2. What's wrong with just continuing with the status quo?

3. Why not double down on your current process?

4. What challenges in this area would derail your business if they weren't solved by next year?

5. Are you able to transition to a new solution in the near term?

6. What’s driving you to prioritize this issue right now?

7. Are you familiar with the type of solution we provide? (This lets you know if you’re selling against competitors.)

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Questions to understand their needs and communicate your value

8. What’s the most pressing issue at your organization right now?

9. In working with other companies in this field, we know they deal with (issue). How are you handling this?

10. What effects are you seeing this problem have on your business?

11. Give me a picture of how things would look in a perfect world.

12. What needs to change now for your company to be a success five years down the road?

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Questions to progress the deal forward

13. If our solution works for you, how will things look in one year?

14. What's your decision-making process?

15. Who else is involved in choosing a vendor?

16. What can I do to make your decision easier?

17. Can I follow up with you on [DATE]? 

18. When can you and other decision-makers meet next week?

Keep in mind with all of these different types of questions that your job is to prompt your prospect to share helpful information — not to do all of the talking. Be sure your prospect has the mic for the bulk of your conversation by prodding them along with follow-up questions that make them elaborate, like:

• What makes you say that?
• Can you tell me more about that?
• What do you mean when you say [XYZ]?

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Use Streak AI to create discovery questions

Though ChatGPT can be helpful in creating discovery questions, you still have to go back and forth between different windows to generate ideas — and even then, you have to further customize them on your own. 

Why not save yourself some hassle and use Streak AI right inside Gmail instead? Streak is a simple CRM that lets you manage your pipeline from inside your email account. 

You can use AI functionality to set call agendas based on past interactions with each of your prospects, or based on your own prompts. Streak can look at all known conversations with a prospect to suggest an agenda for your next call. Or, you can prompt it to come up with sales discovery questions for a certain scenario right inside Gmail. This makes it way easier to stay organized with different lists of discovery questions that are tailored to each prospect.

‍Could you use an AI co-pilot to make selling easier? We’ve got you covered.