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8 sales-closing questions that win more deals

September 17, 2021
Jonathan Costet

Jonathan Costet

Selling Skills

Sales cliche:

Top sales pros could sell ice to eskimos.

Sales reality:

Today’s top sellers know their jobs aren’t about tricking buyers into a sale.

Your job isn’t to use closing techniques, it’s to lead.

Here are 8 sales closing questions that are 0% closing gimmicks and 100% effective.

But first, a quick scenario:

Here’s where things go wrong (and how to fix it)

The reason most deals don’t close is misalignment.

It’s true for in-person.

And it’s even worse for virtual sales.

Here’s what that sounds like:

You: “Are you ready to move forward with our sales proposal?”

Your buyer: “We’re not quite there yet.”

You: “I’m surprised, but I’ll be happy to discuss any part of our proposal with you…”

Your buyer: “I’ve gotta jet to another call, but let me reconnect when we’re ready on our end.”

Cue weeks (if not months) of follow-ups, side-steps, and back-and-forths.

Instead, regain control the moment misalignment rears its head.

This is where asking the right sales closing questions comes in. And they’re based on understanding three things:

  1. What changed
  2. Where they stand
  3. Which steps will get us to close

There are eight (magical?) sales closing questions that can get you the answers you need in all three categories.

P.S: Stuck at the beginning of your sales process? Wishing you could drive toward sales closing questions instead? Grab our 3 money-making sales call scripts to boost your cold call, discovery call, and demo call effectiveness. It’s all about selling value and these scripts show you how.

Question #1: Confirm Timing

what changed question

This is a “what changed” sales closing question.

You need to understand what has changed internally (something has), and whether your deal is still on track, just delayed, or worse.

If you don’t know that, you’ll be taking shots in the dark when you offer up potential solutions. 

It’s important to name your planned close date when you ask this sales closing question.

Why? Because you want to avoid moving that close date if possible.

Data shows that moving close dates is bad for deals. Plus, the further out a deal gets pushed, the less likely it is to close.

So moving that date is a last resort.

Question 2: Ask a close-ended question

uncover hidden obstacles

This is a “what changed” sales closing question.

This is a close-ended question you can use if things are messy and you can’t get a clear answer from your buyers when you ask the first question (or some version of it).

If they’re being coy or evasive, this is a Yes|No move that can push them a bit.

It works because although it’s closed-ended and you’re likely to get a monosyllabic answer, it leads to some pretty obvious and even unavoidable next questions that will help you out…

If they answer no, you can straight up ask them what the main barrier is to see whether it’s solvable.

And if they say yes, great! You’re back on track. Ask them to set the stage in terms of what’s needed to get there.

Question #3: Understand their decision-making process

decision maker question

This is a “where they stand” sales closing question.

Now that you know whether there’s any chance of moving forward, this sales closing question helps you validate your position through the lens of a DM.

If the DM is in the room, ask them this question directly.

If they aren’t, it’s a great way to gain insights from someone who may be a bit more candid about their DM’s position.

Use their answer to move toward concrete next steps. For example, if you know whether the timeline has changed, or which internal issues are cropping up, you can begin to make a plan.

Question #4: Uncover (hidden) obstacles

deal obstacles

This is a “where they stand” sales closing question.

How it works: Unlike the last sales closing question, this one allows you to identify one or multiple big hurdles your deal still needs to clear.

Think of it as the risk-mitigation that was missing when your buyer threw up a roadblock after the proposal.

Don’t let them catch you out again!

Use their answer to build a defensive strategy based on insider information.

The truth is that this question is another way of asking what’s standing in the way of the deal right now. It’s just framed a bit differently, and it allows you to validate what you think are the main hurdles to closing.

Do they see a path to closing like you do? Find out.

Question #5: The virtual close

virtual close

This is a “which steps will get us to close” sales closing question.

Your aim here is to walk the buyer through the whole process so there’s a sense of alignment around what can and should happen.

Discuss points like who is involved in the approval process, and how many steps are on the path ahead. Don’t forget: You’ll need to involve more than DMs who are well-versed in your proposal. You have to think about bringing in legal, IT/security, etc., as people who might be able to block the deal once it’s rolling again.

Once you align on a path forward and agree to who’s involved, you can start navigating your deal behind buyer lines with multi-threading and other stakeholder-focused tactics.

Looking for some sales proposal do’s & don’ts? Check out these examples.

Question #6: Mitigate deal risk

mitigate deal risk

This is a “which steps will get us to close” sales closing question.

How it works: This is more than what could prevent a sign date. It’s a bigger picture of any hurdles that could crop up now that you’ve discussed (and aligned on!) the path to closing.

Your goal with this sales closing question is understanding which of the remaining steps (if any) are critical based on the internal process you’ve outlined.

Now that they’ve had a chance to think about the larger process, it’s a good time to trigger them to think of any obstacles they haven’t mentioned before.

Because risk mitigation. Risk mitigation. Risk mitigation.

Question #7: Use a compelling event

compelling event question

This is a “what changed” sales closing question.

It’s okay to ask for a gut check from the buyer sitting in front of you. If they know something you don’t (and hopefully they won’t at this point in the process), you’ll read it all over their faces when they answer. Are they relaxed in their answers or short and clipped? 

We’ve mentioned before how important body language is to your sales process [see our post,”How video REALLY impacts remote sales in 2020 (According to data)“], and this is a case in point.

During this discussion, you can also introduce a compelling event to reignite urgency in the deal.

Important note! A compelling event is a timeline the buyer perceives as important (like launching a new initiative, meeting an internal deadline, obtaining results in a certain time frame, etc), such as a need to grow the team or quota by a certain date.

Remind them that your offer can help them do that!

Question #8: Validate your concerns

validate your concerns

This is a two-part “what changed” sales closing question.

Part one: You make a statement that your buyer can agree with or counter. Sure, it’s closed-ended, but if the buyer disagrees with it, you can be sure they’ll say so. 

The first half of this sales closing question is also a good way to qualify whether momentum is really dipping in a deal, or whether there were just a few hurdles that needed to be addressed.

Part two of this sales closing question: You cut to the heart of the matter. There’s nothing wrong with being direct at this point in your deal. Your connection with your buyer is well-established, given that you’re beyond the proposal stage, so there’s no harm in being clear. That’s something everyone can respect, as long as it’s done politely.

Send “Where Do I Sign” Proposals

With these eight sales closing questions in your back pocket, you’re perfectly equipped to regain control if there’s any post-proposal misalignment. Keep the buyer engaged and calmly take the lead in your conversations. If your buyer is hedging for any reason, seeing you handle the situation with calm and clarity will help turn things around.

Hoping your buyer won’t balk at the last minute?

Us too.

That’s why we created this Ultimate sales proposal template for you.

You’ll learn to build a solid business case, navigate finish-line push-back, and more.

It’s a nine-slide deck template that’s ready to take on the world.

Ready. Set. Sign.

proposal slide deck

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