How to Identify Your Prospect’s Business Pain Points

(last updated August 22, 2022)

True business pain requires an immediate solution. The kind of business pain we’re talking about here keeps everyone wide awake at night. It is THE thing that affects the real bottom line of an entire organization, and it requires a solution for basic growth and functionality. 

There are often a series of pain points, depending on whom you’re speaking to within an organization.

So, asking the right questions of the right people at the right time is key to discovering their woes and helping a business with whatever it is that really hurts. 

Major business pain points and examples of what they can cause: 

• People Pain = employee dissatisfaction & retention 
• Positioning Pain = severe lack of leads 
• Productivity Pain = negative customer reviews 
• Process Pain = high customer churn 
• Financial Pain = all of the above

Prospects who say they’re experiencing these issues are definitely on the buyer’s journey, and they need assistance right away. 

The most common types of business pain points can be revealed by what your prospects say about their business. Listening carefully to their pain will help you know how or if you can help them. 

People Pain

People are a company’s greatest asset. Therefore, people problems like these affect the entire business: 

• "Morale is rock bottom."
• "Our best employees keep leaving for higher paying jobs."
• "Diversity affects innovation?" (Really?)
• "Our middle managers aren’t inspired." 

If your product or service helps organizations manage, incentivize, or delight their teams, here’s the place to relieve a lot of suffering with your offering.

Positioning Pain

Businesses work hard to understand what’s holding their marketing and positioning efforts back. Prospects who have positioning pain might say: 

• “No one knows who we are.” 
• “Our competitors are beating us.” 
• “The market is changing and leaving us behind.”
• “We’re so behind! We haven’t even considered digital marketing yet!”

Marketing is closely aligned with revenue, so providing solutions that fit their budget and their brand can really help solve positioning pain. 

Productivity Pain 

If there’s something keeping a company and its teams from working efficiently and effectively, they might say things like: 

• “We can’t keep up with market demand.”
• “Workers are just not working well together.”
• “Customers are unhappy with us.” 
• “My people are uninspired!”

If your business can solve productivity issues for other businesses, these words are your cue to show them what you can do to help.  

Process Pain

Operational problems that plague your prospects can be revealed when they say things like the following: 

• “We can’t find qualified candidates because our hiring process is overwhelming.”
• “Client attrition is high because our service department can’t keep up.” 
• “We have no idea how to qualify leads.” 
• “Employee workflow is disorganized, so their performance varies.” 

Repeatable processes = Repeatable success. Asking your prospect to imagine what a smoothly running company would feel like opens all kinds of doors here.

Financial Pain

Critical financial pain points require serious solutions. If you hear prospects saying things like this, they’re hurting: 

• “We can’t keep the lights on.
• “We’re selling, but we can’t make a profit.” 
• “We must not be making good financial decisions.” 
• “We’re paying a lot for equipment and tools. What should we cut?”

Helping a business reduce spending and manage its bottom line solves great suffering. 

7 Questions to Ask + Why to Ask Them

1. "What Keeps You from Growing as a Company?"

For: All prospects

The heart of the matter is growth. 

Every company is in the business of it, and when it’s not happening, there’s serious pain.

If your prospect hasn’t thought about this, asking this question and listening carefully to what they say can help you understand the company’s needs and show them your willingness to assist. 

Usually, a growth question can identify problems with revenue, client retention, employee dissatisfaction, production, or investment capital. These follow-up questions will open the conversation quickly:

• "Do you have a plan for addressing X problem?"
• "What’s your deadline to solve this issue?"
• "Will it be easy or hard to fix this?"
• "Who’s working to fix this right now?"

Drill down their answers to any of these, and you'll learn a lot about your prospect's pain and what you can do to help them.

2. "What Bothers Your Boss the Most?"

For: Individual contributors

You won't always be speaking to leadership, and asking questions of someone two or three levels below the C-suite executives can relieve the pain of the entire organization. 

How does that work, exactly? 

1. Budgets for B2B buying decisions are often made by team members at the middle management level.
2. A manager's pain rolls downhill, so understanding and relieving pain at the management level improves the lives of everyone in the organization. Lower-level management will often have good perspectives on specific blind spots that can help you understand how you can help. 

Pro Tip: This can be a good qualifying question. If they don’t know, they may be too junior to close a deal. 

3. "What Takes Up Most of Your Time at Work?"

For: Individual contributors and managers

This approach to business pain focuses specifically on your point of contact.

Buyers care most about value, and this question can dig up answers that give you an opportunity to show your prospect the concrete value that your product or service can add for them personally.

Follow this main question with more specific questions like these: 

• How will your teams be impacted when this issue is solved? 
• How many hours of work a day might this answer save? 
• How many meetings might this cut out of your work week?

.These questions will allow you to see exactly how you can add extra value to their organization with your offerings. 

4. "What Do You ALWAYS Discuss at Senior Management Meetings?"

For: Senior managers and leadership

Real business pain can’t be solved overnight because these are BIG problems that threaten the sustainability of the company overall.

Therefore, it’s definitely something that’s on every quarterly planning agenda. It’s something that they talk often and think about constantly. 

Asking this question will give you the business pain you're looking for to really help them turn it around.

5. "What is your biggest complaint?"

For: All prospects

This question can be extremely telling.

Incessant complaints are rooted in deep, painful soil that may go unspoken.

If you ask about it specifically, you might unearth the truth of the matter.

An experienced salesperson can shed light on a larger issue that you might very well be in a position to solve for them.  

6. "Are You Closing Deals with Clients? Why not?"

For: Individual contributors and managers

This question is designed to illuminate positioning, process, people, and/or productivity pain in the sales department where pain can really hurt.  

If you can make it clear that your product or service can help sales or marketing teams acquire more business, you win. 

7. "Why Are Your Customers Leaving?"

For: Individual contributors and managers

Losing customers is painful. Full stop. 

The question is painful to ask, but it’s helpful in the long run because it can give you the insight you need about what challenges they’re really facing so that you can offer a solution. 

3 Pro Tips for Addressing Business Pain

• Always use their language when talking about pain.
• Talk to the economic buyer as quickly as possible.
• Identify additional key stakeholders immediately.

Remember that inbound sales requires empathy. The more you ask, listen, and understand, the more you can really make a difference in an organization. 

When your purpose is to offer solutions to your prospect’s pain, closing more deals is just a given. 

We’re in the business of pain solutions for other businesses. Heck, we may as well change our name to Doctor Growth. Does your business need a check-up? We're happy to help. Make an appointment with our expert RevOps solutions team.