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Pain Point Discovery: 5 Questions to Ask Your Prospects

A quick riddle for you.

I’m avoided by all, but finding me is vital to the success of a sales call. What am I? 

Spoiler alert - I’m the pain!

And by pain, we mean the problems faced by your target accounts and prospects. The thorn in their side.

9 times out of 10, you’re going to need to say something that resonates with a pain point your prospect is dealing with to capture their attention.

And it’s even more important to offer something that alleviates this pain. Otherwise, why would anyone bother spending their tight budget on your product?

So it’s crucial to know the right questions to ask to uncover pain points during a sales call. And in turn, the questions to ask after that to dig a little deeper.

So we asked those who know best, our very talented and experienced sales reps here at Cognism! Keep reading to find out what Ivana and Stephen told us about the questions they ask during pain point discovery.

Why is pain point discovery important?

There are several ways in which understanding your prospects’ pain can help you, for example:

  • Product positioning and messaging.
  • Justifying why they need a solution (hopefully, yours!).
  • Validating that your prospect is the right target.

It’s best to get this kind of information straight from the horse's mouth. If you assume you know their problems, this could steer your pitch in the wrong direction.

The types of questions you’ll need to ask will vary depending on what industry you're in or what kind of product you’re pitching.

But, it’s a good idea to remember to keep questions as open-ended as possible - avoid yes or no answers.

Remember, this is a fact-finding mission. So you want to get your prospect to open up and reveal what they’re struggling with.

With this in mind, what should you do?

You should ask them questions that allow them to go into detail. Then, ask follow-up questions to gather more information. Try to understand what result alleviating this pain will have for them.

Now, let’s get into the top 5 questions that are essential for pain point discovery 👇

1. Could you rate your current solution out of 10?

This is a very powerful question - especially if you're faced with objections that sound a little like:

“We’re very happy with our current process/solution/tool.”

Stephen says:

“Try replying with:”

“That’s great! What would you rate this solution out of 10?”

“Very rarely do people reply saying they’ve had a 10/10 experience with another solution, so then you have an opportunity to ask them what would make it better?”

“This is where you want to get to. Finding out what the pain of their current solution is. Because if your product can solve that problem, then there’s little reason why they wouldn’t wish to find out more.”

Another tip Stephen shared was to draw comparisons between their current solution and yours, highlighting the ways in which yours might work better.

This is a delicate dance, as you don’t want to slag off what they’re doing already - they’ve told you they’re happy with what they’re using just now and you don’t want to offend anyone.

However, drawing calculated comparisons between the two, especially in areas they’ve mentioned could work better, can help to build the argument for booking a meeting.

Stephen adds:

“You can even suggest doing a side-by-side comparison so they can visualise the differences.”

2. How long do you spend doing xyz without a tool?

Unlike the first question, which you would ask if someone says they already have an alternative solution, this one is good to ask if they don’t use a tool at all.

Maybe they say something along the lines of:

“We don’t have a tool for abc process because we don’t need to.”

Stephen suggests you could respond by saying:

“How long do you spend doing that process manually?”

Time is money in business. Not only might humans make mistakes, get distracted or dislike doing the manual process, it might take them longer - depending on what the process is.

“This way, when they reply with an answer, which is likely more time than a tool would take to do the same thing, you can focus on how much more efficient they could be with a tool.”

3. I often speak to x type person and they tell me y. Does that resonate with you?

Some people aren’t going to be super-open and expose all of their pains off the bat. Let’s not forget that SDRs are often perceived as untrustworthy, so you might have to take another approach.

One method Ivana suggests is saying:

“I typically speak to (insert job title here), and they’ve mentioned they’re experiencing xyz problems.”

“Does this sound familiar?”

By demonstrating you:

  • Have an understanding of their specific role and responsibilities.
  • Understand the pains they’re likely experiencing.
  • Have experience in helping other people in these roles.

You’ll likely put your prospects at ease and show them they are in safe hands to share more information with you.

And if not, they’re still likely to tell you if they’re experiencing the pains you’ve mentioned. This opens up the conversation for you to start sharing more about your solution.

Ivana adds:

“Even if they haven’t experienced or been aware of a particular pain you’ve mentioned, by telling them that’s what other people in that role have told you, you might spark an idea in their minds.”

“They might now be thinking:”

“Oh, I hadn’t thought about that, maybe I should be looking into this, maybe I’ve missed something in the market that I should pay attention to.”

4. Tell me what it’s like to do x or y work?

This might not sound like a question directed at finding pain, but you can ask general questions that give you a sense of how they feel about certain aspects of their work.

By asking them, ‘what’s it like doing tasks like a or b?’, or ‘what’s it like managing xyz process?’ you might find they give away something in their reply that indicates a pain point.

For example:

“Ehhh it’s alright. Things tick over but it requires a lot of maintenance.” 

Depending on the solution you're offering, this might be the exact information you need to land your pitch.

You could also follow this up with:

“If a year from now nothing has changed about the way you do this work, what would that mean to you?”

This helps to put the pain into perspective. Many of us are able to deal with a mild nuisance-type pain for a short while, but what if it was the same a year from now?

And of course, this is only intensified when the pain is bigger.

5. Why?

Don’t underestimate the power of the question: why?

If your prospect says something that you find interesting, and you want to dig into it a bit further, then just ask them things like:

  • Why do you feel that way?
  • Why is this your process?
  • Why did you make that decision?
  • Why did you mention that?

As long as you’ve managed to build up some rapport with your prospect, they should open up to tell you a bit more.

For example, they tell you ‘we have hefty growth goals for this year, but I’m not sure we’re going to hit them’. That would be a perfect time to ask why, as this could reveal really valuable information which could help you better serve your prospect.

Press play for more tips on dealing with pain points during a cold call from experts David Bentham and Morgan J Ingram. ⬇️


Active listening

Even when you’re not asking specific questions intended to uncover pain, by actively listening to everything your prospect tells you, you’ll likely discover various problem points.

Stephen says:

“One of the best tips I can give is to speak as little as possible.”

Your cold calling goal is to get your prospect talking, not for you to be talking at them. So ask the questions that get the ball rolling, but then sit back and absorb the information.

Ivana also suggests:

“If you hear them mention a pain point, then repeat it. For example:”

“I heard you mention that you’re finding xyz difficult, is that right? Do you think that could have a knock on impact on abc?”

This helps to:

  • Show you’re listening to what they’re saying.
  • Demonstrate you understand the impact of this pain point.
  • Shine a spotlight on this pain point.

Pain point discovery: You’re in control

We’ll let Ivana round this article out with some final words of advice:

“The SDR is in control of the conversation. You may not always feel that way, but you made the call, you’re setting the topics of conversation, you’re asking the questions, and you’re leading the conversation.”

“So just do your best to ask the right questions. If you uncover the pain, and show you can help to solve the pain, then you’re in a strong position.”

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