June 27, 2025
Tamanna Mishra
"What’s your biggest pain point?"
"What tools are you using today?"
"What are your goals for this quarter?"
Do your sales discovery questions still sound like they belong in 2015?
These questions aren’t wrong, but in a product-led world, they’re not exactly right either. They assume your buyer hasn’t already been in your product, poking around, figuring things out. They assume you’re starting from zero. But you’re not.
In a product-led motion, the buyer has already raised their hand. They’ve clicked, explored, invited teammates, maybe even activated a few features. They’ve even read at least 2-7 websites that cover your product or category.
And if you’re using the right tools, you already know all that.
The job of sales discovery today isn’t to collect surface-level information. It’s to connect the dots - to go deeper into the “why now,” the blockers, the business case, and the buying dynamics.
It’s about showing up to the conversation already halfway there.
With over 90% of B2B SaaS companies increasing investments in product led motions, it’s about time we upgraded discovery questions in sales.
In this blog, we’re sharing 26 product-led sales discovery questions designed for this new era.
Sales discovery questions that start where product usage ends.
Let’s get started.
Discovery questions in sales are the thoughtful, open-ended prompts that help sales reps understand a prospect’s needs, challenges, goals, and decision-making process. Think of them as conversation starters - but with a purpose. They’re how you uncover the story behind the deal.
In traditional B2B sales, discovery questions were largely about lead qualification.
"Do you have a budget?"
"Who’s the decision-maker?"
"What timeline are you working with?"
Useful? Sometimes. Limiting? Absolutely.
But then, things changed.
In modern, product-led sales, the discovery call isn’t your first touchpoint. It’s your first chance to add value. You’re not starting the journey. You’re continuing it. Your prospect may already be deep into a free trial, actively using your platform, or evangelizing it internally.
That’s why good sales discovery questions today are less about “Can you buy?” and more about “How can we help you win?”
They explore:
In a product-led environment, your buyer is often more informed than ever before. So, your sales discovery questions shouldn’t fish for basic info. They should aim for context, motivation, and momentum.
When done right, these questions don’t just help you close deals. They help you build trust, reduce friction, and create true buyer alignment.
Not all sales discovery questions are created equal. This is especially when your buyer has already been in the product, poked around features, and maybe even invited a few teammates.
In product-led sales, your discovery needs to meet the buyer where they are: informed, active, and curious.
Below, we’ve grouped 26 product-led sales discovery question examples into five buckets. These questions are designed to spark meaningful conversations and drive momentum. Use them as-is, or adapt them to your sales motion.
Your buyer’s already been clicking. Now, find out what’s clicking for them. These questions are all about validating product usage and surfacing insights you can build on.
Before your product entered the picture, there was a problem. Good sales discovery questions help uncover that pre-existing pain - and whether your solution truly addresses it.
Even in a product-led world, there's a buyer committee somewhere. These questions surface the key players, success metrics, and blockers so you can guide the deal, not chase it.
The trial clock is ticking. These discovery questions for sales help you assess urgency, guide next steps, and preempt objections. But without sounding pushy.
The best discovery calls aren’t checklists. They’re conversations. And sometimes, the second question is where the real insight lives. These follow-up prompts help you go deeper, validate what you’re hearing, and uncover the nuance behind a buyer’s response.
Here are 6 follow-up discovery questions every rep should have in their back pocket:
Think of these as conversational shovels. They help you dig past the surface and unearth the real reasons your buyer is talking to you.
Some questions have aged like fine milk. Here are a few that no longer serve modern product-led selling - and what to ask instead:
These swaps will make you sound less cringey and old-fashioned. And they help you respect your buyer’s time, intelligence, and product experience.
Because in product-led sales, they’re already halfway sold.
And that’s where Sybill changes the game.
Even the best sales discovery questions fall flat if they sound robotic or rehearsed. Today’s buyers can smell a script from a mile away. And nothing kills a product-led discovery call faster than questions that feel forced or out of context.
What’s also important is that you don’t over-do the questioning. Studies show that asking 11-14 discovery questions results in a 74% success rate, while asking 1-6 questions leads to a significantly lower 46% success rate.
So how do you ask the right questions without sounding like you're reading from a sales playbook?
If the buyer’s already been active in the product, there’s no excuse for generic questions. Instead of asking, “Have you explored [Feature X]?”, try: “I saw you’ve already tried out [Feature X]—what did you think?”
This shows you’ve done your homework and instantly builds trust.
If you’re asking discovery questions just to move on to your pitch, buyers will notice. Instead, treat discovery like a two-way conversation. Listen deeply. Mirror their language. Take notes.
Pro tip: With Sybill’s Magic Summaries, you don’t have to scribble furiously during the call. Everything - persona, pain points, objections, next steps - is captured for you, so you can focus on the conversation.
Surface-level answers are just the beginning. Don’t stop at “We’re exploring this for our team.” Go deeper. Try:
“Interesting - what does that look like in your day-to-day?”
“And how are you handling that today?”
This kind of follow-up probing often reveals the real blockers and motivations.
Scripted = skeptical buyer.
Conversational = collaborative buyer.
Your tone, pace, and curiosity all matter more than the exact words you use. And when the discovery feels like a co-working session - not an interrogation - you’re halfway to the close.
Sales discovery isn’t dead. But it does need a glow-up.
In a world where your buyer has already clicked, explored, and experienced your product, the old playbook of repetitive, script-based questions won’t cut it.
Today, sales discovery questions need to do more than just pulling answers out of your prospect. It’s about connecting the dots they’ve already given you - through product signals, behavioral cues, and past conversations.
That means asking fewer, better questions.
That means walking into the room already informed.
That means leading with insight.
And when you’re backed by a platform like Sybill, you:
Let Sybill do the heavy lifting so you can show up sharp, strategic, and ready to close.
Book a demo with Sybill and make your sales conversations truly human.
Product-led sales (PLS) is a go-to-market strategy where the product drives the buying journey. Unlike traditional sales-led models - where reps lead with demos and decks - PLS lets users experience value first-hand before speaking to sales. This flips the discovery process: instead of qualifying a cold lead, reps build on real usage signals. It’s not “Tell me about your pain,” but “Here’s what we see - does that align?”
Leading questions push the buyer toward a specific answer, often with bias. For example: “Wouldn’t this save you time?” In contrast, open-ended questions like “What’s your current process?” invite genuine insight.
In a product-led sales motion, leading questions often fall flat.
Buyers who’ve used your product want a collaborative conversation.
Open-ended discovery questions are better suited for product-led sales.
"What’s your biggest pain point?"
"What tools are you using today?"
"What are your goals for this quarter?"
Do your sales discovery questions still sound like they belong in 2015?
These questions aren’t wrong, but in a product-led world, they’re not exactly right either. They assume your buyer hasn’t already been in your product, poking around, figuring things out. They assume you’re starting from zero. But you’re not.
In a product-led motion, the buyer has already raised their hand. They’ve clicked, explored, invited teammates, maybe even activated a few features. They’ve even read at least 2-7 websites that cover your product or category.
And if you’re using the right tools, you already know all that.
The job of sales discovery today isn’t to collect surface-level information. It’s to connect the dots - to go deeper into the “why now,” the blockers, the business case, and the buying dynamics.
It’s about showing up to the conversation already halfway there.
With over 90% of B2B SaaS companies increasing investments in product led motions, it’s about time we upgraded discovery questions in sales.
In this blog, we’re sharing 26 product-led sales discovery questions designed for this new era.
Sales discovery questions that start where product usage ends.
Let’s get started.
Discovery questions in sales are the thoughtful, open-ended prompts that help sales reps understand a prospect’s needs, challenges, goals, and decision-making process. Think of them as conversation starters - but with a purpose. They’re how you uncover the story behind the deal.
In traditional B2B sales, discovery questions were largely about lead qualification.
"Do you have a budget?"
"Who’s the decision-maker?"
"What timeline are you working with?"
Useful? Sometimes. Limiting? Absolutely.
But then, things changed.
In modern, product-led sales, the discovery call isn’t your first touchpoint. It’s your first chance to add value. You’re not starting the journey. You’re continuing it. Your prospect may already be deep into a free trial, actively using your platform, or evangelizing it internally.
That’s why good sales discovery questions today are less about “Can you buy?” and more about “How can we help you win?”
They explore:
In a product-led environment, your buyer is often more informed than ever before. So, your sales discovery questions shouldn’t fish for basic info. They should aim for context, motivation, and momentum.
When done right, these questions don’t just help you close deals. They help you build trust, reduce friction, and create true buyer alignment.
Not all sales discovery questions are created equal. This is especially when your buyer has already been in the product, poked around features, and maybe even invited a few teammates.
In product-led sales, your discovery needs to meet the buyer where they are: informed, active, and curious.
Below, we’ve grouped 26 product-led sales discovery question examples into five buckets. These questions are designed to spark meaningful conversations and drive momentum. Use them as-is, or adapt them to your sales motion.
Your buyer’s already been clicking. Now, find out what’s clicking for them. These questions are all about validating product usage and surfacing insights you can build on.
Before your product entered the picture, there was a problem. Good sales discovery questions help uncover that pre-existing pain - and whether your solution truly addresses it.
Even in a product-led world, there's a buyer committee somewhere. These questions surface the key players, success metrics, and blockers so you can guide the deal, not chase it.
The trial clock is ticking. These discovery questions for sales help you assess urgency, guide next steps, and preempt objections. But without sounding pushy.
The best discovery calls aren’t checklists. They’re conversations. And sometimes, the second question is where the real insight lives. These follow-up prompts help you go deeper, validate what you’re hearing, and uncover the nuance behind a buyer’s response.
Here are 6 follow-up discovery questions every rep should have in their back pocket:
Think of these as conversational shovels. They help you dig past the surface and unearth the real reasons your buyer is talking to you.
Some questions have aged like fine milk. Here are a few that no longer serve modern product-led selling - and what to ask instead:
These swaps will make you sound less cringey and old-fashioned. And they help you respect your buyer’s time, intelligence, and product experience.
Because in product-led sales, they’re already halfway sold.
And that’s where Sybill changes the game.
Even the best sales discovery questions fall flat if they sound robotic or rehearsed. Today’s buyers can smell a script from a mile away. And nothing kills a product-led discovery call faster than questions that feel forced or out of context.
What’s also important is that you don’t over-do the questioning. Studies show that asking 11-14 discovery questions results in a 74% success rate, while asking 1-6 questions leads to a significantly lower 46% success rate.
So how do you ask the right questions without sounding like you're reading from a sales playbook?
If the buyer’s already been active in the product, there’s no excuse for generic questions. Instead of asking, “Have you explored [Feature X]?”, try: “I saw you’ve already tried out [Feature X]—what did you think?”
This shows you’ve done your homework and instantly builds trust.
If you’re asking discovery questions just to move on to your pitch, buyers will notice. Instead, treat discovery like a two-way conversation. Listen deeply. Mirror their language. Take notes.
Pro tip: With Sybill’s Magic Summaries, you don’t have to scribble furiously during the call. Everything - persona, pain points, objections, next steps - is captured for you, so you can focus on the conversation.
Surface-level answers are just the beginning. Don’t stop at “We’re exploring this for our team.” Go deeper. Try:
“Interesting - what does that look like in your day-to-day?”
“And how are you handling that today?”
This kind of follow-up probing often reveals the real blockers and motivations.
Scripted = skeptical buyer.
Conversational = collaborative buyer.
Your tone, pace, and curiosity all matter more than the exact words you use. And when the discovery feels like a co-working session - not an interrogation - you’re halfway to the close.
Sales discovery isn’t dead. But it does need a glow-up.
In a world where your buyer has already clicked, explored, and experienced your product, the old playbook of repetitive, script-based questions won’t cut it.
Today, sales discovery questions need to do more than just pulling answers out of your prospect. It’s about connecting the dots they’ve already given you - through product signals, behavioral cues, and past conversations.
That means asking fewer, better questions.
That means walking into the room already informed.
That means leading with insight.
And when you’re backed by a platform like Sybill, you:
Let Sybill do the heavy lifting so you can show up sharp, strategic, and ready to close.
Book a demo with Sybill and make your sales conversations truly human.
Product-led sales (PLS) is a go-to-market strategy where the product drives the buying journey. Unlike traditional sales-led models - where reps lead with demos and decks - PLS lets users experience value first-hand before speaking to sales. This flips the discovery process: instead of qualifying a cold lead, reps build on real usage signals. It’s not “Tell me about your pain,” but “Here’s what we see - does that align?”
Leading questions push the buyer toward a specific answer, often with bias. For example: “Wouldn’t this save you time?” In contrast, open-ended questions like “What’s your current process?” invite genuine insight.
In a product-led sales motion, leading questions often fall flat.
Buyers who’ve used your product want a collaborative conversation.
Open-ended discovery questions are better suited for product-led sales.
