12 Questions That Take Discovery To The Next Level

Today’s Skill: Discovery Questions

Most founders lose deals not because their solution isn’t good enough, but because they never slow down to truly understand the core problem and desires of their buyers. They jump to pitching, pricing, or over-explaining and end up missing the bullseye by a wide margin.

What’s the litmus test that you’re going too fast in discovery?

• 11 minutes into the call you are talking about your product/service.

• Your response to “this is my problem” is “here is my solution” (it should be, “tell me more”)

• You jump from question to question without a follow-up to learn more.

• You think their problem/need is exactly what they tell you it is.

These are signs you’re pressing your luck too quick.

Instead, Let’s slow the train down a bit and get thorough with your questions so you can build more value when you start talking about how you can help.

Discovery Questions

Here are 12 critical discovery questions you can keep in your back pocket to get to the root of any client problem and build more rapport early in your relationship.

1. What triggered you to start exploring solutions now?

This pairs urgency with some context. Often, timing matters more than budget. Imagine If you had a big leak in your ceiling or your alternator on your car crapped out. You’d be more likely to find a fix sooner than later.

→ I want to know why you are doing this now and not 3 months ago.

2. What would success look like in 6–12 months if you solved this?

This forces an outcome-based discussion. It let’s you into their world on what their ideal state might look like. It allows you to align with that, or coach on how that might be unrealistic.

→ Future-state helps you set the compass in the right direction to get them there.

3. Have you tried to solve this before? What worked, what didn’t?

I love this question. It shows patterns and let’s you hear past frustrations. It let’s you know if this has been a continual issue that they’ve duct-taped their way through or if they’ve used other vendors that didn’t work out.

→ Understand their past so you can compare before and after more easily.

4. Who else needs to be involved in this decision?

Are you dealing with the absolute decision maker or is this the “proxy” playing defense to protect someone that controls the final decisions. Understanding all of the players in the game make it easier to maneuver the pieces around the board.

→ Don’t assume this is a single player game.

5. What’s at risk if this problem isn’t solved?

Urgency is important. Tying it to something they care about is monumental. The stakes are higher when it’s going to cost them revenue, increase costs, put them at risk, etc.

→ If the pain isn’t clear, the deal won’t move.

6. How will you measure success if we work together?

It doesn’t get any clearer than this. How will they judge if you’ve done what they’ve asked of you. It puts them in a future-state to think about working with you but it also allows them to articulate the scoreboard we are looking at

→ When you know how they measure success you can use data and past experiences to talk through how you are going to make sure they get there.

7. What’s your timeline for seeing results?

This aligns expectations. “When are you looking to get started?” is a good question but “seeing results” gets to solving the root of their problem. Starting and getting results could be vastly different amounts of time depending on the product / service you sell.

→ When you know this, you can work backwards to coach them on when they would need to start to hit that mark.

8. What other priorities could compete with this?

You know those clients that are excited early and then drop off? It’s not that they don’t need what you offer, it’s that they might not need it now. They may have other things in play that you don’t know about. So, ask how this stacks up against all the other stuff on their plate.

→ Another way to ask this could be, “How would you rank solving this on your priorities list?”

9. What budget range have you considered (or had approved)?

Instead of waiting until several calls to talk about money, you should be surfacing it early. Providing “ballpark” pricing is helpful but this question is a way you can put it back on them. You know they know this costs money. Let’s hear it from them on what they are thinking initially.

→ This discussion early brings trust and openness to what can be a guarded conversation.

10. What other solutions are you considering, or have you already looked at?

Literally almost nobody asks this. They are scared that it brings up the potential someone will look elsewhere. You don’t have to worry, they are exploring options. It may not be another vendor, it could be a DIY thing or not doing it at all. They more you know the more you can educate and inform them on the different paths.

→ Remember, you want to be a guide for them not just another street vendor they walk by.

11. What is driving this priority from leadership?

If you’re selling into larger organizations you want to know if this is a pet project of some department head or some top-down mandate from the C-suite.

→ It also gives a hint into how much your prospect is plugged-in internally.

12. What concerns do you have about solving this?

A couple of weeks ago I shared the expert-level question to ask later in the sales process. This is a spin on that to ask early in order to surface potential objections. They might have concerns the project will take too long or the budget isn’t there or a myriad of others things.

→ This surfaces fears and feelings that ultimately drive(or derail) decisions.

Why This Matters

When you ask these questions:

• Clients feel heard (not pitched at).

• You pick up their exact language to use later in demos and proposals.

• You position yourself as a partner, not a vendor.

• You actually get to the root of the issues.

Many deals are lost early in discovery because the questions are boring and basic. Start getting more specific, draw out emotions and make it a little uncomfortable.

That tension you create could be the difference between being remembered or just being another vendor they checked off their list.

Your Action Item

On your next call, commit to asking at least 3 of these questions before you talk about you.

The truth is, good discovery isn’t about asking more questions, it’s about asking the right ones at the right time.

And remember, you can drill down deeper with their answer before you skip to another unrelated question!