Increase Conversions by Understanding Customer Pain Points

What are our customers’ biggest challenges, and how do we solve them? 

Businesses working with other small and medium businesses (B2B) are focused on solving problems. Identifying them, then presenting the right solutions at the right time, and for the right price, is the role of sales and marketing teams. 

Salespeople need to ask the right questions to qualify leads. No matter how many leads you get into the pipeline, if they’re not qualified, there’s no way of knowing if they are viable.

Only sales-qualified leads (SQL) have the potential to turn into actual customers. In order to generate leads and identify viable SQLs, you’ll need a clear idea of customer pain points. 


Defining Customer Pain Points

3 Layers of Questions to Uncover Pain Points

How You Increase Conversion Rates by Understanding Pain Points

Defining Customer Pain Points

In business, pain points are problems that need solutions. 

When leads come to you inbound (inbound leads), this means a potential customer can see that your business can provide a potential solution to these pain points.

With outbound leads, those who respond have identified themselves — or you’ve identified — that they need a solution for pain points they are currently experiencing. 

Every company experiences a range of different pain points, such as: 

  • Financial. Revenue, profitability, or cost-based. Sometimes all at the same time. At other times, these are experienced separately and often need/require different solutions. 
  • Productivity. Are staff, systems, and processes ensuring a company operates as efficiently as possible?
  • Innovation. Are we innovating in the market? Creating new products and services that will keep us ahead of the competition? These questions often keep CEOs wondering, and therefore, asking team members for solutions. 
  • Support. Are we doing enough for our customers, is there more we can do? How do we keep our customers happy? 

A salesperson’s job is to uncover pain points, use the right range of qualifying questions, and tailor proposals to convert clients more quickly. Naturally, these should be pain points that align with the products and services you are selling. It sounds simple. But it isn’t. Otherwise, every salesperson would hit the target every month. 

Getting information from prospects is part of the challenge. Especially when not all sales happen face-to-face these days, with more companies working from home than ever before. Salespeople need to be able to build rapport and close deals remotely. 

Showing prospects you know how to solve these challenges is the other half of the challenge salespeople struggle with every week. 

The final stage is convincing prospects you are the right company to solve these pain points. Which is why qualifying questions are so important. Qualifying questions help salespeople uncover pain points, providing solutions that convert prospects into customers. 

3 Layers of Questions to Uncover Pain Points

Qualifying questions are an essential part of every sales process. How do you know what a client needs unless you uncover the solutions you can provide by asking a series of questions? 

Qualifying questions also assess whether a client is suitable, or not. For example, do they have a budget? Is there an aspect of urgency? Who’s going to decide on this? 

It’s useful to take a three-layered approach when it comes to identifying pain points and qualifying prospects. 

Layer 1: General Qualifying Questions

First-layer, or general qualifying questions are always useful for establishing a rapport, a relationship, and getting the ball rolling. Often, these should be asked in the first call or demo, known as the top of the sales cycle/funnel. 

Here are a few examples of questions you can use at this stage: 

  • How’s business (e.g. how is the company doing, what market share do you have)?
  • What are you looking to achieve with this project, or when buying in new product or service?
  • Who decides what happens / Who’s the decision-maker?
  • Do you have a budget for this, or could a budget be allocated to this?
  • Are you already using something similar (e.g. working with a competitor)?
  • What’s motivating you to attempt to solve this problem?

Please keep in mind before asking the questions: 

Do your homework. Never start a call unprepared. Have an idea of how a prospect is doing before speaking with them. That way, you can ask smarter, more tailored questions that show you’re paying them the attention they should expect. 

Layer 2: More Detailed Questions

Now you’ve reached a point in the conversation, or sales cycle, depending on how long it usually takes to convert prospects, where more information is needed. What you ask also depends on how much information is needed to create a proposal, or secure a conversion on a call/demo. 

All of this is influenced by the size of companies you usually work with, the budgets involved, and other crucial factors. Bigger clients spending more money take more time to convert. Smaller clients with lower budgets usually don’t take 3-6 or more months to convert. 

So make sure these questions are tailored to the needs of the sort of companies you normally work with. 

Here are a few examples of more detailed, second-layer questions: 

  • Why did you go with Vendor X for that project/in the past?
  • What services or features are you likely to need? 
  • What sort of timescale are you thinking about for implementing this?
  • What sort of ROI are you looking for?
  • Would training or support be useful once you are ready to go ahead?

Layer 3: Gain or Loss?

Both sales leads and sales teams need as much information as possible about one another. Give as much as you get. Ask questions, but also, be prepared to answer them. 

Have examples, case studies and testimonials ready. 

Use material that’s as closely aligned with the needs of a prospect as possible, so they can see you’ve provided solutions for similar companies facing comparable challenges. 

Be mindful of the fact that businesses are usually motivated to take action according to two simple motives: Fear of loss, or the motivation to gain more. 

Gaining more is usually centered around the need to increase revenue or profits hence why companies invest in sales, marketing, SaaS, and service-based providers. 

Reducing the fear of loss, or mitigating and reducing costs, is about making a company more stable and secure. Products and services that fall into this category include anything that makes operations more cost-effective. Alongside anything that genuinely reduces potential losses, such as secure software and systems, insurance, and related products. 

Digging deep into loss-based (fear) or hope-based (gain) questions can make a huge difference when identifying pain points. With these questions, you can also get closer to getting them to the decision stage in the buying cycle.

How they answer often proves a helpful indicator as to whether a prospect is serious.

Here are a few examples of loss-based (fear) or hope-based (gain) questions questions you can ask:

  • If we solved problem X for you, what impact would that have on revenue, sales, costs, or profits?
  • If you didn’t do Y in 3 months (e.g. buy/implement your product or service), how will that impact costs, profits, sales or operations for you?
  • What are the implications of not doing this, what impact will it have on the company? 
  • This is clearly very important for you: May I ask what this will mean if it’s resolved and you get the ROI you want?

Armed with all of this information, salespeople and business owners can tailor proposals that show you’ve understood a prospects pain points. Not only this but asking the right questions will show them that you are the right company to solve them. 

Now let’s take a closer look 5-ways you can use questions that uncover pain points to increase conversion rates. 

How You Increase Conversion Rates by Understanding Pain Points

Repeat back to confirm understanding on calls/demos

On a sales call, always make sure you are repeating back — paraphrasing — the answers to the questions you ask. Not only does it show you are paying attention. It’s also a way of practicing active listening. 

Active listening is essential when speaking to sales leads. Making it easier to identify pain points and come up with solutions more clearly.

Salespeople who fail at the understanding stage often fail to win them as clients. 

If you aren’t sure on what someone’s said, ask for clarification. There’s no such thing as a stupid question. Not when you are establishing a relationship with a new potential client. You never know what could be crucial for the next stage in the conversation. 

Make sure you’re clear on everything covered, take notes or record the call (tell them first), and then use this information to tailor a proposal showing them how you can solve the pain points discussed. 

Demonstrate solutions using case studies

Case studies, examples, and testimonials are essential for supporting conversations at every stage of the sales cycle. 

These examples are especially powerful when the prospect can see you’ve solved similar pain points for companies dealing with comparable challenges. It’s even more useful when you can demonstrate this, using product or service examples. 

For example: “We delivered X for company Y, it solved problem Z they were having.” If you can also provide examples of an ROI, or other kind of positive outcome, then even better. 

Have all of this sales enablement material prepared in advance. Usually, a marketing team, or external provider, such as a freelancer, marketing, content, sales enablement or sales solution company can create these. 

Highlight an ROI clients can expect 

Demonstrating a return on investment (ROI), or another positive outcome clients can expect is always useful. Depending on the nature of your business, sector, and the needs of the sector, this could be essential. 

So always have examples of these ready, whenever possible. 

Use these positive examples to add to the following: “We delivered X for company Y, it solved problem Z they were having, and it generated an ROI of XX%” 

Leverage a time/urgency factor

Speed is everything in sales. 

How long it takes to convert a prospect has a direct impact on revenues, profits, and cash flow. 

Salespeople and business owners naturally want sales to come in and convert quickly. Sales leads, however, operate on their timescales. There’s almost always a disconnect with the two, and it can be difficult at times to get the answer you want in a 

Even lower-ticket proposals (products, services) can take a while to convert, especially if prospects are busy, waiting on approval from several stakeholders, or getting distracted with more urgent matters. 

When it comes to leveraging time/urgency, and pushing sales leads forward, think back to these questions: 

  • If we solved problem X for you, what impact would that have on revenue, sales, costs, or profits?
  • If you didn’t do Y in 3 months (e.g. buy/implement your product or service), how will that impact costs, profits, sales or operations for you?
  • What are the implications of not doing this, what impact will it have on the company?

Depending on the answers to these questions, if there’s clearly an opportunity to encourage a quick conversion, then use this information wisely. 

Don’t give up, keep following up

Now we come to the post-proposal phase. Also known as the decision-making end of the sales cycle. Whether you’ve had one conversation or several, there always comes a point when a salesperson has asked every question possible. Provided a demonstration, and examples, and sent out a proposal. 

Success at this stage requires persistence. Salespeople who follow up have a much better chance of securing a win and closing a deal. 

Commit to following up more than once. Anywhere between 5 to 10 emails or calls to get an answer. Put reminders in your diary or CRM if you’ve not heard back from a sales lead after sending a proposal out. 


Identifying pain points is essential for success in sales. Only sales-qualified leads have the potential to turn into actual customers.

To identify viable sales-qualified leads, you need a clear idea of customer pain points. 

Start with asking the three layers of sales questions and once you’ve got all of the information from prospects, use these 5-steps to increase conversion rates: 

  1. Repeat back to confirm understanding on calls/demos
  2. Demonstrate solutions using case studies
  3. Highlight an ROI clients can expect 
  4. Leverage a time/urgency factor
  5. After sending out a proposal, keep following up