5 Questions To Uncover The Buyers REAL PAIN POINTS

The other day I was in our salesman.org community trying to help a sales professional who sells a consulting product.

His issue was that when prospecting, his potential buyers would always say that the service he offers is a “nice to have” rather than a “necessity”.

So I started to engage with this individual in the community and it turns out he wasn’t doing a very good job of uncovering the real pain points that his buyers had.

He could get the point of uncovering the surface level pain (something is wrong), but he wasn’t asking the right questions to get to the bottom of what was really causing the issue (must solve problem).

I showed him the 5 pain point questions that I’m going to share with you in this video and is response in the community was epic. He said that these 5 pain finding questions had transformed his sales conversations.

So lets get into them.

When you engage with your buyers you’ll hear lots of potential pain points. When a buyer gives you their pain, it’s usually a “surface level pain” and not the real issue they need to solve.


When asked about their business pain points, buyers will only give you surface level pain points because they don’t have the expertise to really get to the bottom of the issues.

That’s good news for us sales people because if buyers had the knowledge, products or expertise to dive deeper into their pains they could solve them without your help.

So this leaves a gap between a buyer knowing they have a problem and not knowing how to fix it and that’s where we come in.

Before we get into pain questions there are four main categories that surface-level buyer pains fall into. Once you understand each of the categories, you’ll be able to quickly diagnose your buyer pain points on discovery calls with buyers.

Here are the four categories of surface level buyer pain and a few examples of how your buyers might describe them:

A: Financial pain

  • “Revenue is up, but profits are down”
  • “I don’t have enough visibility of the numbers to make sound financial decisions”
  • “We’re only profitable enough to keep the doors open”

B: People pain

  • “Our team’s morale is low”
  • “Our managers don’t drive innovation”
  • “Our best employees keep leaving to our competitors”

C: Productivity pain

  • “We keep missing our client deadlines”
  • “We have quality issues that are leading to higher refunds”
  • “We spend too much time in meetings”

D: Process pain

  • “Our hiring process is a mess“
  • “We have no system in place to monitor our sales pipeline”
  • “The customer service department is inundated and can’t keep up”

Do me a favour and leave a comment below sharing which category of pain your product solves. I’m interested to know what pain points you are experiencing and I can then focus some new content in that direction.

So now you know the categories of your buyers surface level pain points and you’ve heard some examples of how your buyers might share these pain points with you, lets look at some questions we can ask to dig deeper into the buyers pain.

We want to dig deeper into the buyers pain so that we can align the service we sell that solves the pain to the deepest pain we can.

When we align our service to a really deep pain, our service becomes a “must have” rather than “something to consider next quarter”.

Q #1: Main thing holding you back?

The first question that we can ask to dig deeper into the pain of our buyers is –

“What’s the main thing holding your company (or division) back from growing right now?”

Expect the response to this question to landing one of our four categories of –

  1. Financial pain
  2. People pain
  3. Productivity pain
  4. Processing pain

This question is the starting point to go a level deeper than the more generic categories of pain that we’ve already discussed.

Q #2: How do you plan to solve this?

The next question we should ask in follow-up is –

“How do you plan to solve this pain point?”

An uneducated buyer will tell you that they are unsure how to solve their pain point. This is an incredible opportunity for you to educate the buyer on how your service can solve the problem and relieve their pain.

A more educated buyer who is further through the sales process might have a few ideas on how they can solve the pain but clearly there is still something holding them back from taking action.

So the next step is to uncover what is holing them back.

Q #3: What is your deadline to solve this?

We uncover lots of information when we ask the buyer the next question –

“What is your deadline to solve this problem?”

If the buyer tells us that there is no deadline, then the problem is not very painful for the buyer and this individual is not very qualified to do business with you.

Alternatively, if the buyer does have a set deadline to solve this pain point by, you now have a very qualified buyer that is worth engaging further with.

Now we need to see if there is the budget and authority to solve the pain.

Q #4: What does your boss think?

This question is where we uncover the true level of pain the buyer is in. When you go through the previous steps and questions and then ask –

“What does your boss think about all this?”

You’ll find your buyer’s stress level will often go through the roof. Unless you are selling to the founders of the company, most of your buyers will care more about what their boss thinks of them, than their job performance.

So if you ask this question and your buyer says “my boss has been on my back about this for weeks now, I really need to get this sorted” you have uncovered that the buyer likely has budget and authority to solve the issue.

That leaves us with one final question to ask the buyer to go beyond the surface level pain they’ve been describing to you so far.

Q #5: What is stopping you?

The final question we now need to ask the potential buyer is –

“What is stopping you from solving this problem today?”

This is the most important question in this sequence of question.

So far we’ve been living in the future with questions like –

“What is your deadline?” and “What does your boss think?”

Now we need to pull the buyer back to the real world. This will intensify the buyers pain and they’re far more likely to take action on any suggestions you give them to solve it.

So that is the four categories of buyer pain and how to take the buyer on a journey to uncover the pain they’re in underneath the surface layer pains that they will share with you in the first instance.

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