Why Salespeople Should Ask The Same Question 5 Times In A Row

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Mike Renahan
Mike Renahan



One short, Liam. (You’ll understand soon.) 

The first thing that you’re taught as a sales rep -- it’s pretty much Sales 101 -- is to solve for the customer. After all, prospects won’t buy your product if it doesn’t do something for them, right?

You need to understand their pain point, and then explain how your product not only solves it, but actually makes that problem a strength going forward.

But how the heck do you figure out what their problem is in the first place?

LinkedIn doesn’t have a “I need a product to fix this for me” section. Odds are, no one can fit a pressing business need in 140 characters or less, either.

So what’s a salesperson to do? Ask questions, of course. Specifically, the same question, five times.

Let me explain.

The “Five Whys” theory was originally coined by Sakichi Toyoda, who instituted it at Toyota Motors.

Here’s how it worked: If a problem arose during mass production of a vehicle, everything had to be stopped, which cost Toyota a ton of money. So to avoid the same problems coming up again and again, Toyoda would ask his employees why something failed, five times.

Here’s what this looks like in practice:

Overarching problem: Why isn’t the car running?

Why #1 - The battery is dead.

Why #2 - The alternator is not functioning.

Why #3 - The alternator belt has broken.

Why #4 - The alternator belt was well beyond its useful service life and not replaced.

Why #5 - The vehicle was not maintained according to the recommended service schedule.

After five whys, the solution to the root problem emerged. The lesson? Get your car checked when it’s time to get it checked. 

Salespeople can also benefit from this strategy, by simply asking their prospects why five times.

Here’s an example. Let’s say you sell a customer relationship management service and you notice that a VP of Sales has visited your website a few times during the past few days -- specifically the CRM page. You want to act quickly to set up your first call and capitalize on their interest.

After some initial research, you learn the VP oversees a team of 10 people at a company of 100 people. They’ve already read about your CRM and visited the pricing page several times.

This is how some salespeople might approach this call.

Rep: "I saw you were on our CRM page a few times this past week. Why the interest?"

Prospect: "We’re just always looking at different products. Thought it might be cool to see what you offered."

Rep: "Great. Well, let me tell you about all these awesome things you can do with our CRM."

What a shame. The rep dove straight into the product without really understanding why the prospect was on the pricing page to begin with. In other words, the rep has not yet discovered the buyer’s need, and this will make it difficult to sell much of anything.

Here’s how to use the five whys to understand the prospect's real need and naturally cue up your value proposition.

Rep: "I saw you were on our CRM page a few times this past week. Why the interest?"

Prospect: "Oh, we’re just always looking at different products. Thought it might be cool to see what you offered."

Rep: "Why did you choose to come back to our CRM page a few times?"

Prospect: "We really liked the simple interface, and how the system recorded the last contact with a prospect for you."

Rep: "Why did that feature catch your eye?"

Prospect: "It’s just a little different than the method we use now. Thought it could benefit my team."

Rep: "Why would that help your team?"

Prospect: "Well, they’re always calling the same prospect over and over again because the spreadsheet we use now to track our prospects isn’t as up-to-date as it should be."

Rep: "Why isn’t it as up-to-date as it should be?"

Prospect: "Often times, we’ll just forget to update it as soon as a call ends. It’s really inconvenient. It’s actually resulting in lost leads."

We’ve now discovered the problem: An inefficient CRM is leading to a disorganized sales team, and lost leads. This is the pain point you want to address.

Five questions have revealed what you need to solve for this company. During the next few conversations with this VP, hit on the pain point (lost leads) and lay out your strategy for assuaging it. Explain how easy it is to track everything in your CRM and how your product will keep the VP’s sales reps happy and on track.

The Five Whys method is a simple tactic folks can use to get to the root of their prospect’s problem during their sales qualification process. By using this method, we can truly understand and solve the customer’s pain point, and, in turn, make it a strength of their business.

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