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This One Question Can Shorten Your Team’s Sales Cycles



Some of your team’s deals might seem to move at a snail’s pace, inching along as their buyers mull things over.


To you, it’s baffling. Your sales team has conducted discovery, and their buyers have said they need your product. So what’s missing? Why is the sales cycle so drawn out?


What’s missing is what I will refer to as the One Question: This One Question is what your team members should ask themselves (and you can ask them) repeatedly throughout the discovery process.


The one question is this: “Why does it matter to the buyer's business?”


A sample scenario (granted, an oversimplified one)

Your team sells an accounting software. Their ICPs are small businesses who do their own bookkeeping. Most of those ICPs are still using Excel spreadsheets.


You ask your team members when certain deals are expected to close.


“By the end of the month, for sure,” they reply. “The buyer loved our demo, and they’re only using Excel right now so our software is perfect for them.”


You: (Ask the One Question) “Why does it matter to their business that they’re using Excel for accounting right now?”


AE: “Because using Excel is a hassle.”


You: “Yes, but why is it a hassle?”


AE: “Because they have to input their own formulas, and sometimes they mess up those formulas.”


You: “And why does it matter to the business if they mess up those formulas?”


AE: “Because the business could be making accounting errors that become a tax liability or a miscalculation of profit and loss.”


You: “Aha! Now we’re getting somewhere. So how do you know this particular buyer should buy our software?"


AE: "Because they don't have an accounting program right now."


You: "No, that's not why they should buy. Missing a software program is just a technical problem. The technical problem only matters if it impacts their business. Do you know what business problems have manifested for this buyer?”


AE: “No, I don’t know.”


You: “Ok, this is a good reason to have another discovery meeting with them. What questions could you ask to uncover business problems?


AE: "I can ask them: Have they experienced accounting errors in the past? What was the size of the error? How much did it cost them? Have they considered how much they would be fined if they underreport earnings? Am I on the right track?"


You: "Yes, now you're on the right track."


A step toward Gap Selling

Your buyer won’t ever care about your product as much as you and your team do. What matters to your buyer is the business problems that occur as a result of not having your product.


In the example above, the hassle of Excel (or the nice features of your software) isn’t enough to compel the buyer to make a change. They’ll view it as a “nice to have” but will drag their feet because they aren’t connecting the value of the software to the bigger business problem.


When your buyer does see the true size of their business problem, the impacts of that problem, and the root cause (such as a bad accounting process), they’ll see a reason for taking action sooner than later. They’ll also see how much it could cost them if they stick with what they’re using now.


But that will only happen if your team asks questions to understand the buyer’s full business environment. If your team only stays focused on the direct use and "need" for the product itself, the more important context will be missed.


The discovery process is a lot to navigate, and the Gap Selling framework involves a lot more than just one question. But by returning to the One Question (“Why does it matter to the business?”) you’ll help your team shift their perspective to what matters most to their buyers.


That’s how you shorten the sales cycle.

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