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Ten Surprisingly Effective Discovery Questions (and why they work)

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Many sellers I work with struggle with what questions to ask in discovery.

Before you ask anything, you must know what you’re looking for. I covered this last week in 3 Things Every Seller Should Find in Discovery. This will vary wildly depending on your industry and the vertical you sell into.

But across a range of industries, I’ve identified 10 surprisingly effective discovery questions. These draw from the Gap Selling methodology – but you don’t have to be a Gap Selling expert to use them. See below.

First, a word of caution: any question that is lobbed out of left field – no matter how good – will sabotage your discovery. Be sure that any question you ask is contextual and responsive to what the buyer just told you.

Ten Surprisingly Effective Discovery Questions:

1. What prompted you to reach out to us? Why it works: this is the most effective way to start discovery with an inbound lead. It leaves the door open for them to share their problem, and avoids product-led discussion right off the bat.

2. Can you tell me more about that situation? Why it works: the story and context of why a buyer is speaking to you matters so much more than the solution they’re seeking.

3. Can you define what you mean by longer (or shorter/more/less, etc.)? Why it works: value is relative and changes from person to person. You must understand exactly what they mean. Don’t accept vague statement. Define everything.

4. What was [this business metric] last year, and the year before? Why it works: it’s critical to identify trends in a buyer’s business. Not just the snapshot of today, but what’s happening over time. That’s how you can identify blind spots and danger zones so you can help them.

5. Now that you’ve shared [current business metric], what do you want it to be? Why it works: Business plans are built around targets. Targets inform everything from projected growth to business cases made to investors. If they’re falling short of their targets, and if your solution can help them catch up, the delta between the current state and future state is the value you provide. You must know what this Gap is.

6. What happens within your organization as a result of [the way they’re doing things today]? Why it works: their current process/tool/software is NOT the reason for them to change (even if they’re telling you it is!) It’s the downstream effects (aka business problems and impacts) that will be the motivation for them to change. Zoom out! Don’t hyper-focus on how they’re doing things. Expand to what happens because of it.

7. Can you walk me through your process today? Why it works: once you’ve gotten a solid answer to number 6, now it’s ok to dive into the exact details of their current process. This is your diagnostic MRI to identify what’s causing their problems.

8. What criteria (requirements) do you have for whatever solution you choose? Why it works: their answer will give you insight into their priorities and thought process. It will also give you a chance to offer additional criteria they haven’t thought of. Plus you can challenge any of their requirements that don’t align with what’s causing their problem in the first place. Note: this question should be asked later in the discovery process, once you understand their problem better.

9. Why address this now instead of, say, a year from now? Why it works: this can help uncover other motivating factors they may not have shared up til now.

10. Finally, this question is FOR YOURSELF, NOT YOUR BUYER: What’s the next yes? (What does the buyer need to agree to, as a micro-commitment, to keep the deal moving forward?) Why it works: winning the deal isn’t just about one big YES at the end (like the yes to a marriage proposal). 

Getting to the big YES relies on many small next yeses from the buyer, such as:

  • agreeing with you on the size of the problem

  • agreeing to meet with you in a next discovery

  • agreeing to invite another stakeholder to the next meeting

  • agreeing on the Cost of Inaction (what happens if they don’t change)

Putting it into action

Spend time anticipating your buyer’s problems, and thinking about how to apply these questions to their world. Thinking about these questions in advance will also help you avoid those awkward moments in discovery when you don’t know what to ask.

But above all, the most important thing you can do in discovery is listen and respond with curiosity.

To do this, be present with your buyer. Forget about your product. Just focus on their problem and how you can help. Apply these 10 questions with that goal in mind.

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"Ten Surprisingly Effective Discovery Questions (and why they work)"



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