List of sales discovery questions

Running list of different types of questions to help uncover more in your deals.

Discovery is the single most important thing you need to constantly work on in sales.

It helps you understand your prospect’s world.

The typical buying process looks like this:

I have a problem > do you understand my problem > do I trust you can solve my problem > how do I get started.

A lot of founders just jump straight to demos when they first get started with sales. They assume buyers only want to see the tech.

But it’s really hard to buy software. There’s tons of options. And as a buyer, you want to make sure you make the right decision.

So the folks that win the most deals are great at discovery. They go deep into the prospect’s situation, understand their pains, and how it impacts their business.

And they keep track of different pieces of information using a framework like FOUNDER, so they can classify how they understand the prospects world, and where they need to dig deeper.

Here’s a list of discovery questions you can modify and ask during your sales calls. I’ve organized them by different parts of the FOUNDER framework.

ANNOUNCEMENT:

1. I’m starting the waitlist for summer group coaching. Looking at either July or August start. Groups of 4-6 founders, meeting twice a month. Full access to the upskilling community as well. USD $500/mth - let me know if you want to be added to the waitlist.

2. I have capacity for two 1:1 coaching clients. You get full dedicated time and support, deal reviews, I’ll watch some of your call recordings for feedback. We implement the FOUNDER Operating System together. Two options depending how fast you want to move - twice a month at USD $1,500 USD or 4x a month for USD $3k. If you’re a TinySeed company, ask me for special pricing.

Table of Contents

The FOUNDER Discovery Framework

Here’s a quick reminder of the FOUNDER framework before we jump into discovery questions:

  • Facts - basic information about people, tech, processes. Example what tools do they use.

  • Objectives & Pain - what problems do they have in their workflows/processes, and where do they want to get to. This creates a gap in their business. This gap is what you can solve.

  • Uncovering Impact - what’s the quantifiable impact this gap is having on the business. Are they losing revenue? Are costs high? Are they at risk of falling out of compliance? What’s the business impact.

  • Negative Consequence - this is the cost of inaction. What happens if they don’t solve the problem? What toll will the business impact have? Will the need to do layoffs? Will they miss an important product launch? Will they lose customers? Will they get fined?

  • Driving Events - this is a compelling or critical event that’s leading them to a change now. Example “if we don’t solve this in the next 6 months I’ll need to layoff 10% of my staff.” The negative consequence is now tied to a timeframe. This combination creates urgency in a deal.

  • Reaching a Decision - how will they make this purchase? Who’s involved? What steps will they take? Where’s the budget? This is everything related to getting from “you can solve my problem” to “signed contract.”

Pain Funnel

The pain funnel was popularized by Sandler decades ago, but it’s still a useful tool for probing. The point of the pain funnel is once you’ve uncovered a pain, you use the pain funnel questions to help you further develop that pain and the impact it’s having on the business.

  • Tell me more about that (FO)

  • Can you be more specific? Can you give me an example? (FO)

  • How long has that been a problem for you? (FO)

  • What have you tried to do about it? (FO)

  • How much do you think that’s cost the business? (UN)

  • How do you feel about that? (U)

  • Where do you want to be? (O)

  • What’s stopping you from getting there? (FO)

  • What happens if you don’t solve this in the next 6 months? (NDE)

  • What’s driving you to make a change now? (NDE)

Facts

  • Walk me through how you're doing [[worfklow]] today.

  • What are you currently using to [[jtbd]]?

  • Help me understand how you do [[process]] now.

  • That’s interesting, tell me more.

  • Can you give me an example?

  • Foot in the door technique: You’re using [[tool]] right? And you’re actively looking for [[outcome]]? What’s your process for [[generating that outcome]]?

Objectives and Pain

  • Typically, when we speak with customers, they are struggling with [[problem 1]], they’re frustrated with [[problem 2]], or they worried about [[problem 3]]. Do any of these sound familiar to you?

  • Where is this process breaking down for you?

  • What’s not working about [[process]]?

  • In an ideal world, where would you like to be?

  • What's preventing you from getting there?

  • What have you done in the past to try to solve this problem?

  • Did it work?

  • What else?

  •  Anything else?

  •  What do you think is the real challenge there for you?

Uncovering Impact

  • How much has this cost the business?

  • What KPI suffers if you don’t solve this?

  • What metric is impacted by this problem?

  • How long has this been a challenge for you?

Negative Consequences

  • What happens if this doesn't get solved in the next 6 months?

  • What happens when [[pain]]?

  • How does [[negative outcome]] impact other departments?

Driving Events

  • What's happening in the business today that kicked off this evaluation?

  • What’s driving you to make a change now?

  • What happens when you miss your date?

Reaching a Decision

  • What criteria will you be using to make a decision?

  • What’s their order of importance?

  • How will you make this decision?

  • Who’s involved in the decision process?

  • What’s their role in the decision process?

  • What’s important to them?

  • Who makes the decision?

  • Who signs?

  • Who does it impact?

  • How does the budget sign off process work?

  • Who’s involved?

  • What are the typical timelines to get budget approved?

  • Is there a hard and fast date you need this live?

  • When does your contract end?

  • When’s the date of your event?

To get even more discovery questions including what to ask during your demo (along with a discovery masterclass), you can access the full resource in the SalesMVP Lab Upskilling Community. Start your 7-day free trial.

Let me know how these questions work for you. Best thing to do is modify a few to make them more tailored to your industry.

For more practical early-stage sales tips, connect with me on LinkedIn.

If you’re looking for more hands-on help implementing your first sales process, reach out for coaching packages.

Join the only upskilling community for founder-led sales. Start your 7-day free trial.

P.S. Starting the waitlist for summer group coaching cohorts. Reply if you’re interested.