The Expert-Level Question Most Founders Avoid Asking

Today’s Skill: Surfacing Concerns

Have you been blindsided by a prospect before?

You heard things like “This looks great” or “I’m definitely interested” and take that to mean your prospect wants to commit to a partnership.

When it doesn’t happen, you’re left going, “WTF?”

Most of the time, it’s because you got “happy ears”. You heard what you wanted to hear and stopped getting curious about all of the underlying unknown details.

And, I get it, you feel if you press the prospect on specifics it might come off as “salesy”.

However, the opposite is true.

When you are confident asking the tough questions it builds trust and respect from your potential clients because secretly they want you to uncover all the facts in order to give them the best solution to their problem, even if the conversation is uncomfortable.

My favorite: “What concerns do you have with the partnership?”

or asked another way, “Do you have any concerns before we move forward with a partnership.”

or another, “Are there any concerns you have with partnering on this project that we haven’t addressed?”

It can be phrased in various ways but it’s one of the most important (and underused) questions in sales.

If you want honest conversations, if you want clarity, if you want to move deals forward you have to be the one who invites those conversations.

Here’s why this questioning works and how to make it part of your process.

It Builds Trust

When you ask about concerns, you’re show that you’re open to hearing the truth, even if it’s difficult. In return, it’s a gesture to bring trust into the conversation.

That alone gives them the confidence to actually be honest. It creates mutual respect.

“Transparency” is an often over-used buzzword that sounds great on a values chart.

But most aren’t brave enough to invite it into their conversations.

I want you to embrace it.

Not “Do you have any questions?”

Not “How are you feeling about this?”

Be specific. Be direct.

Buyers notice. And it immediately shifts the dynamic.

(Yes, the first time you ask this you’re going to feel weird.) That’s a good thing!

You’re not trying to push them to a decision. You’re actually trying to make sure you have a complete understanding from all angles.

You Learn

You can’t solve what you don’t know.

Most people wait until the very end, when the deal’s gone dark, to realize something was off.

They had “happy ears” the whole time.

The buyer seemed interested.

They said the product looked great.

So you assumed everything was fine.

It wasn’t.

If you want to win more deals (and stop chasing the wrong ones), you need to learn how to surface concerns before they become deal-killers.

This line of questioning opens the dialogue.

And once the concerns are out in the open, you can address them head-on.

And, here’s the good news. Even if they don’t end up going with you, knowing the real concerns prospects have help you ask better questions or share more specific details on future deals. The earlier you get ahead of these, the less amount of concerns you hear on the back-end.

You Expedite the Process

Here’s what kills momentum: Inaction

The buyer keeps stalling.

They say they’ll follow up.

They ask for “more time to think.”

You keep sending emails and hoping something lands.

It’s frustrating, yes. But, it’s also avoidable.

Ask about concerns early, and you bring those doubts to the surface.

• You don’t need 5 more calls.

• You don’t need a new pitch deck.

You just need clarity.

Lay the concerns on the table and work through them one by one.

This single question can shave weeks (or months) off your sales cycle.

Nobody Else Is Doing It

This might be my favorite reason to start asking this question:

It instantly separates you from every other vendor.

Most people are afraid of objections.

You’re not.

You know that real conversations create real outcomes.

Let the other folks hype their product and avoid tough questions.

You’re here to have a grown-up business conversation. This is how you have an honest business conversation…

Rewrite it in your own voice but make it a part of your process as you’re firming up the partnership.

→ If they say none, great. Then follow-up with, “Are we ready to move forward with the partnership?”

→ If they bring up something, great. Now you can address it head on. Once you confirm it’s addressed to satisfaction, ask what other concerns they have. And, so on.

Either way, you now have clarity. You’ve opened the door for honest conversation. And you’re leading the sales process like a pro.

It’s the kind of dialogue that serious buyers want to have.

Final Thoughts

Creating tension is part of your job as a seller.

We’re not being confrontational, we’re adding some polite pressure. 😊

• You need to surface uncertainty so you can remove it.

• You need to challenge assumptions so they don’t derail the deal later.

This question is how you do that.

It’s simple, clear, and powerful.

And yes, it takes guts.

But trust me, wouldn’t you rather address concerns directly versus guessing why the deal stalled out?

Your Action Item

On your next “closing” call or when it’s at that point for a decision, ask what concerns they have. If you’re nervous, practice with a friend to get the awkwardness out.

It’s only awkward the first time. Once you own it, you won’t avoid it.

So, Ask it!

You’ll be surprised what comes up. Either way, at least you now know!