The five sales discovery questions to ask before you pitch anything
The five sales discovery questions to ask before you pitch anything
Sales conversations aren’t normal conversations. You’re talking to someone with the intention of selling your thing, and at the same time you’re trying to work out whether they’d actually benefit from it. As our co-founder Daniel Priestley puts it, “there’s a kind of strange negotiation taking place.”
That’s why they shouldn’t be improvised. “Sales conversations are a little bit performative,” Daniel says. “They should be scripted, they should be role-played.” Here are the five sales discovery questions he recommends asking before you present a solution, and how to get them answered before the call even starts.
The short version
- The mistake: recommending your solution before you understand the problem.
- The fix: five questions, asked in order, before you pitch anything.
- The upgrade: build those questions into an interactive assessment, so the answers arrive before the call.
- What Daniel hears back: “My sales conversations have gone from over an hour to under 30 minutes.”
What’s going on in your buyer’s head
Daniel describes every buyer the same way. They arrive with a current reality that’s less than perfect. They have a desired reality that would be much better, and a time frame in mind. The gap between the two creates tension.
Sitting in the middle are the obstacles and criteria that make it hard to get from one to the other. So when someone evaluates your offer, they’re asking one question: is this the path of least resistance between where I am and where I want to be? They’ve probably tried things that didn’t work, and they don’t want to make that mistake again.
Once you know that’s the mental model, your sales conversation should follow it. Each question moves the conversation one step forward and makes it obvious whether someone should buy, or not buy if they’re wrong for what you offer.
The five sales discovery questions
1. The current reality question
“Tell me a bit about your current situation, and tell me what’s not perfect about your current situation.”
This is the starting point. You’re not diagnosing yet – you’re letting them describe the problem in their own words. Those words are what you’ll reflect back later when you present.
2. The desired reality question
“Tell me about where you’d like to get to 90 days from now.”
Now you know the destination and the time frame. That tells you how big the gap is, how urgent it feels, and whether what you sell can realistically close it.
3. The obstacle and criteria question
“What have you already tried in the past that didn’t live up to expectations?” Or: “Do you have any key criteria that you’ve already established for how you want to get this result?”
This is where you find out what’s in the way, and what they’ve already ruled out. If your offer looks like the thing that disappointed them last time, you need to know that before you describe it.
4. The potential solution question
“Have you formed an opinion about what you think might work?”
People often arrive with a view. Some say, “I really want some software.” Others say, “I really want training for my team.” They might also share a price point or the budget they have available. Daniel calls this the potential solution question, and it’s the one most people skip.
5. The open “anything else” question
“Is there anything else you think I should know?”
It sounds simple, but it surfaces things you’d never think to ask about. “I’ve already read your book and I’m really looking forward to getting started.” Or, “A friend of mine has worked with you and recommended you really highly.” As Daniel says, “they tell you all sorts of information when you ask that question that is relevant to the sale.”
The biggest mistake: pitching too early
“The number one mistake that I see people making when they’re trying to make a sale is they recommend their solutions or their products and services way too early,” Daniel says.
Skip the five questions and “there’s a high chance you’ll kill the sale by saying something that’s completely irrelevant or saying something that is just in conflict with their mental model as to how they want to solve their problem.”
That’s the real cost. It’s not that your offer is wrong. It’s that you described it in a way that didn’t match how the buyer already thinks about the problem.
Why it works
“It’s not magic, it’s not voodoo,” Daniel says. “It’s just simply asking the questions and getting the answers that give you the mental model that’s going on in somebody’s head.”
When you know someone’s current reality, their goal, what they’ve tried, and what they think will work, your presentation stops being a pitch. It becomes a recommendation. That’s why Daniel hears from people whose sales calls have gone from over an hour to under 30 minutes.
It also cuts both ways. The same answers that make the right buyers say yes make it clear when someone isn’t a fit, and both of you find out sooner.
How to borrow the playbook
Start on your next call. Before you present anything, ask if you can go through a few questions first so you can explain what you do more usefully. Then work through all five, in order.
Script it and role-play it. Write the five questions down in your own words and practice them until they feel natural. Treat them as the bases every call has to touch.
Then move the questions into an assessment. Once the questions are working on calls, automate them. A lead comes in from social, an ad, or a piece of content, and instead of booking straight onto a call, they complete an interactive assessment first. Here’s how the five questions map across:
- Current reality: multiple-choice questions about their situation and what’s not working.
- Desired reality: where they want to be in 90 days.
- Obstacles and criteria: what they’ve tried before and what matters to them.
- Potential solution: the type of help they want, and their budget.
- Anything else: one open text question at the end.
Daniel recommends building these in whether your assessment has 15, 20, or 30 questions. “We’ve seen this formula used in hundreds of different quizzes and scorecards,” he says. It’s the same thinking behind qualifying better leads instead of chasing more of them, and you’ll find more on pre-qualifying leads before a sales call and using your assessment questions to pre-qualify elsewhere on the blog.
Read the answers before you join. Now you walk into every call already knowing their situation, their goal, what’s failed before, and what they think will work. For a real example of an assessment doing the qualifying, see how Niall turned one sales objection into £120k of new business.
Get the answers before you get on the call
We built our software to qualify leads, reveal readiness, and personalize the next step with interactive assessments. Put the five questions into yours, and your sales calls start where they used to end.
