8 Essential Questions for Uncovering Customer Pain Points

Sales isn’t about quick transactions and telling customers how to solve their problems. 

Sure, you can go about it that way, but you won’t get very far. If you’re still clinging to a traditional sales playbook, your journey to success might feel like pushing a boulder uphill with a toothpick.

So, what’s the solution to modernizing your sales approach and disrupting the status quo?

Getting to customer pain points. Being a Buyer Facilitator is all about asking your clients the right questions so you can uncover their challenges, needs, and desires. You want to become a credible and trustworthy partner, all while building a lasting relationship that should benefit both sides for years to come. 

When it comes to effective selling, understanding your customer’s pain points is paramount. Forget quick fixes; the real power lies in being a Buyer Facilitator, which starts with asking the right questions.

 Eight essential questions will help you discover and address your customer’s pain points.

1. What Is Your Biggest Challenge?

Understanding your customer’s pain points begins with this fundamental question. 

It might seem obvious that asking about a challenge would naturally uncover pain, but you’d be surprised at how many salespeople omit this simple question from their discovery calls. So make sure you ask it.

When you ask, “What is your biggest challenge?” you open the door for your customer to express their primary concern and get the ball rolling on your conversation. 

This question encourages them to articulate the central issue causing frustration or difficulty. It will undoubtedly catalyze more in-depth discussion about their needs (and how you can address them).

Have you seen our new AI Pain Discovery tool to help you ask better questions?

2. How Long Has This Been a Problem?

Knowing how long your customer has dealt with their most significant challenges gives you much to work with.

Imagine a potential client responding, “Our biggest challenge is maintaining consistent lead generation.” You might follow up with, “Can you provide some context? How long has this been a problem?”

For instance, they might respond, “It’s been an issue for about two years. Our lead generation strategies used to work like a charm, but things started to decline slowly. We thought it might be a temporary hiccup, so we tried tweaking our approaches and haven’t recovered on our own.”

This type of response offers crucial insights. 

It tells us that the issue has persisted for a while, impacting their business continuously. Understanding this timeframe helps us appreciate the urgency of finding a solution and working together effectively.

3. What Have You Done to Fix It, and How Did That Work for You?

This question serves two crucial purposes

Firstly, it demonstrates your genuine interest in their experience and expertise. It shows that you respect their efforts and value their insights, which builds trust and rapport.

Secondly, perhaps more importantly, it offers a valuable window into their problem-solving history. By understanding what they’ve tried before and how successful those attempts were, you gain critical insights into the dynamics of their challenge and, if needed, can adjust your approach accordingly. 

Suppose they’ve previously attempted solutions that didn’t fully meet their expectations but are trying to solve the problem again (maybe with your help). In that case, it highlights their commitment to finding a resolution. This demonstrates their persistence in seeking a successful outcome. On the other hand, if they’ve explored multiple strategies with limited success, it signals the intricate nature of the problem. Knowing you’re dealing with a tougher situation may help you to tailor your approach more effectively.

This information equips you to offer more targeted and practical solutions in both cases. You can leverage their past experiences to proactively avoid repeating unsuccessful strategies and tailor your approach to address their unique needs. 

4. What Other Things Have You Tried?

Sometimes, clients or prospects hesitate to give you all the information you need the first time you ask. So, disrupt your prospecting strategy, and don’t be afraid to push back more.

This is an excellent question to ask in follow-up to #3 above. Exploring your client’s past efforts is just the beginning. The question, “What other things have you tried?” dives deeper into what they’ve considered trying or tested before.

Understanding what your customer is open-minded to when it comes to solving problems opens the door for you to implement innovative solutions and enables you to emphasize that you’re here to co-create the best-fit solution for their specific needs. Bottom line — ask this question to continue the journey of uncovering their path to resolution, step by step.

5. How Much Has the Problem Cost You So Far?

Money talks, and in sales, numbers matter. 

So, ask this question to get to the bottom of the tangible impact of their challenge. It goes beyond the surface and uncovers the financial losses, missed opportunities, or wasted resources.

This question serves as a reality check, helping you and your client comprehend the actual cost of inaction — but don’t be surprised if they’re not fully prepared to answer it. 

Being curious about the costs of not fixing their problems helps them register how severe (or not) the issue is, setting the stage for demonstrating the value of your solution. It’s a powerful tool for aligning their investment with the potential returns.

6. How Has That Affected YOU Personally?

This is the relationship part of the deal. Sales isn’t just about numbers; it’s about people. 

The question, “How has that affected YOU personally?” taps into the emotional and personal side of the challenge. It’s about connecting with your client on a human level and allowing them to offer insights into their feelings on the matter.

When you ask this question, you’re showing empathy and a genuine concern for their well-being and establishing a foundation of trust. You’re acknowledging that business challenges have personal implications, recognizing that focusing on strengthening the client-agent relationship makes it more likely that they’ll choose you as their solutions partner. That’s how you develop clients for life.

7. What Would Happen if You Didn’t Do Anything to Address the Problem?

Sometimes, doing nothing is the correct answer. Other times, making drastic changes is necessary. Your customer’s needs may fall somewhere in between.

Change often requires a push, a nudge towards action. This question wakes your clients up by making them paint a vivid picture of the consequences of inaction. If they haven’t gone through this exercise before, it’ll hit them hard  — and help your case. 

By asking this question, you’re helping your client envision a future with unresolved challenges, highlighting the risks and potential setbacks they face if they don’t take decisive action. This question is the spark that can ignite the motivation to seek a solution (ideally, your solution).

8. Are You Ready to Throw in the Towel?

Sometimes, your customers might feel at a crossroads in their journey. So, here’s the question for you to ask them: “Are you ready to throw in the towel?”

This isn’t about them giving up. This is about acknowledging a pivotal moment of decision and recognizing their determination to conquer the challenges that have plagued their business for too long.

Their response to this question is a statement of intent—a declaration of their commitment to transform challenges into opportunities. If they’re ready to throw in the towel, it’s a sign that they’re prepared to take the necessary steps toward a brighter, more successful future.

See how asking more questions in their sales process has helped our clients succeed.

The Role of Empathy in Uncovering Customer Pain

Empathy is a powerful tool, allowing you to connect with your customers on a deeper level and understand their pain. By showing genuine concern and asking thoughtful questions, you can uncover their needs and provide solutions that address their challenges.

Here’s a quick overview of why empathy matters throughout the sales process:

• It builds trust: By showing empathy, you establish a foundation of trust with your customers and show that you are genuinely invested in their success.
• It reveals hidden needs: Empathy allows you to uncover deeper pain points that your customers may not have initially shared, giving you a better understanding of their challenges and how to address them.
• It helps tailor your approach: Understanding your customer’s unique needs and situation allows you to provide a solution that meets their specific needs rather than a one-size-fits-all approach.
• It fosters loyalty: By consistently showing empathy throughout the sales process, you can build lasting relationships with your customers and create loyal clients who will continue to turn to you for solutions.

Always ask open-ended questions and actively listen to your customers to better understand their pain points and develop lasting relationships built on trust. 

Some empathetic conversation techniques include:

• Active listening: Pay attention to what your customers are saying and how they are saying it. Listen for underlying emotions and ask follow-up questions to gain a deeper understanding.
• Reflective listening: Repeat back what you have heard from your customer to ensure that you understand their perspective correctly and validate their feelings.
• Open-ended questions:  Ask open-ended questions that allow your customer to share their thoughts and feelings freely, rather than yes or no questions that limit conversation.
• Non-verbal cues: sometimes, what is left unsaid is as important as what is said.  Pay attention to your customer’s body language and tone of voice, which can also reveal their emotions and pain points.

Incorporating empathy into your conversation can build stronger customer relationships and uncover their real pain. The end result is a loyal customer who trusts and values your partnership.

The Power of Uncovering Pain

The key to unlocking meaningful solutions and building lasting partnerships lies in your ability to ask the right questions. These questions aren’t meant for small talk or filler but are purposeful gateways to understanding your customer’s pain points. When you understand their pain, you can offer solutions that truly make an impact — it’s that simple.