Mastering Discovery Questions: The Secret to Closing More Deals

In sales, uncovering a prospect’s true needs and challenges can be the key to closing a deal. Asking the right questions helps you dig into their motivations, identify pain points, and reveal any obstacles that your solution could solve. They can also help you tailor your walkthrough and product that fit their specific use case.

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Discovery Questions: Building a Strong Foundation

You want to ask good discovery questions in the beginning stages of a sale. These questions can help you identify if your product is a good fit for this customer type so you can qualify them. They can also help you understand their current process, what they’re doing now to solve this issue and why it is not working, and figure out what other solutions they’ve tried.

Some questions we like to ask are:

• Can you walk me through your current process, start to finish? Which part of this flow are you looking to improve?
• What are you doing now to address this issue? Are there specific tools or processes you put in place?
• Have you tried other solutions? What aspects worked well, and where did they fall short?
• When did this problem first arise? What roadblocks are you encountering?

*Bonus points, especially if you're selling to more senior executives or enterprise accounts: before asking each of these questions show an observation first to demonstrating value.

By doing this, you're prompting them to think through their business instead of just qualifying them. Makes it more about them and they're buying process instead of about you and your selling process.

example:

‍"We're hearing a lot of sales teams are struggling with response rates on email and LinkedIn, some are trying to scale more with AI and others lean towards more personalized outreach but customer acquisition seems to be a growing issue across the board.

Can you walk me through how your currently sourcing most of your customers?"

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Qualifying Customer-Product Fit

We also like to ask Product-customer Fit questions for SendKits. For example, for us, customers with long sales cycle with a lot of stakeholders are usually a good fit. Since we sell to sales people, we may ask:

• How long is the average sale cycle for your deals? What’s your average deal size?
• How many stakeholders are typically involved in each deal?
• What type of content are you sending your customers? (Decks, Case Studies, Videos, Proposals, etc.)

Ask probing questions to help you understand what type of customer this prospect is.

While we don't want discovery to feel like we're qualifying the whole time... it's still important to validate that there's a real fit here. Be honest if you think you can help and don't be afraid to offer alternatives if you think it's not a fit.

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Post-Demo Probing: Digging Deeper After Product Walkthroughs

The questions prospect raised during a demo can reveal critical needs, making it easier to highlight the most relevant features. Use this stage to address lingering questions and clarifying how your product fits into their goals.

Consider asking:

• Are there specific features or use cases this doesn’t solve for you? Can you share why these features matter?
• Do you have any hesitations to using this product? If we could wave a magic wand and give you the perfect product, what would that look like?
• During a trial period, what would success look like? What are the specific metrics or indicators you’re looking for?

The power of discovery and probing question lies not just in asking but also listening. Every response holds valuable information that can give you signal to address any frictions, and tailor sales to fit their use case that will ultimately help you close the deal.

Some say "Always Be Closing" but we say "Always Be Curious!"

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