3 Revealing Questions That Could Win Your Next Deal

Today’s Skill: Digging Deeper

If you're a Founder and hear praise for your product but aren't converting prospects, you're not alone.

Often, it’s not the product at fault. It’s the questions you didn’t ask.

Discovery isn’t just about uncovering problems. In reality, the other vendors they’re looking at could be doing the same thing. It’s more about creating a comfortable environment where you can have real, transparent dialogue.

⇒ The goal is to get to the honest truth, not just be polite.

Quick story

I was in a competitive situation with several other vendors and had built a solid rapport with my main point of contact. I asked “Question #1” below and was told, “Well, right now you are 2nd behind another vendor.” When I asked if they could expand on it further, they shared that the other vendor had a feature they didn’t see with us but otherwise we were really close.

Here’s the reason why…

We were the first to present, which was a full 2 weeks before they saw that other vendor. They also had other demos in-between. Therefore, by the time they saw that other vendor, they were more acclimated to the questions they should ask. This exposed a potential new problem not even on their radar a couple of weeks prior.

By learning about this before it was too late, we were able to showcase that not only could we offer this feature, we did it in a way that helped the potential client solve their issue more effectively. We ended up earning the partnership.

Three Questions

Below are three questions I love to use in my sales conversations to gain more intel.

I’ve personally used all of these questions over the last several years. Some worked out to help me secure the partnership, and other times they didn’t. My use of them doesn’t guarantee I bring in the client. I use them because it allows me to understand where the project is at and what gaps exist that might have been unknown.

I talk about this often (read last week’s edition if you missed it). The more information you have, the better you can help the prospect make an informed decision. That might be the difference between earning the partnership or not.

Question 1️⃣ ⇒ Ranking Vendors

Why ask this?

It can reveal where you stand in their evaluation process and might uncover hidden objections you weren’t privy to. If you’re the “lead dog,” great, then find out what you need to do to earn the partnership. If you’re second or third, you can find out what’s missing and if you can close that gap before it's too late.

Remember, buyers don’t always know how to buy. They might be evaluating a ton of other options and things blend together. You don’t know until you can take a step back and see where things are at.

Bonus Tip:

As long as you’ve been open with them, they will be open with you. If that’s been the case and they hesitate or are vague, that’s a red flag. There might be details they aren’t telling you for a reason.

Question 2️⃣ ⇒ Decision-Making Criteria

Why ask this?

Without clear criteria, it’s hard to know what they prioritize and what they don’t. By understanding their process (or lack thereof), it gives you a direction to guide them down. If they have criteria, what is it? If they don’t, are you able to help them fixate on a few key pieces to use as the guideposts?

By surfacing their evaluation criteria, you can guide the conversation where it matters most.

Bonus Tip:

If you’re stuck, simply asking, "Would you mind sharing your top 2–3 must-haves for this project?" can help them expand the conversation.

Question 3️⃣ ⇒ Hidden Concerns

Why ask this?

I ask this later in the evaluation process when you’ve confirmed tight alignment because it invites honesty without confrontation. You're giving them permission to bring up what’s unsaid. You lose out on this opportunity if you always assume everything is great. Then, you wonder why that great conversation turned into crickets. People often hold back concerns to "be nice." Get comfortable surfacing this and having a peer-to-peer business conversation.

Bonus Tip:

This questioning is future-focused. You’re implying you are working together if there are no concerns. Typically, if there are any, they will most likely bring them up now. So, if they say “None, looks great!” there is no reason not to respond by saying, “That’s great, so are you ready to partner together on this project?”

Why Candid Questions Matter

As I’ve stated before, sales isn't about avoiding tension.

Tension is necessary to get the truth out.

Most deals become stalled or lost altogether because conversations stay surface-level. The prospect doesn’t feel compelled enough to act, or they hide objections until it’s too late.

You need to lean into healthy tension. It shows leadership. It shows confidence.

As the seller, you're the guide.

If you aren’t willing to ask the hard questions, someone else will and it might cost you the deal.

Your Action Steps

On your next call, commit to asking at least one of these questions.

You don’t have to memorize them word for word. Make it your own. The goal is to create space for honesty, not perform an interrogation.

And remember:

These three questions have nothing to do with some feature or widget. It is about the buying process and partnership. These types of questions need to be weaved into your conversations to keep track of those items as much as you do about alignment on how you can solve problems.

❓❓ Where do you get stuck the most in your sales conversations? Hit reply and let me know!

P.S. If you loved this, share it with another early-stage founder who could use a little extra help navigating their sales conversations.