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10 Types of Questions Small Businesses Can Ask to Identify Pain Points

10 Types of Questions Small Businesses Can Ask to Identify Pain Points

Small businesses today must be relentlessly focused on customer success — so here at Salesforce, we’ve curated a list of the types of questions that best help us identify our customers’ pain points.

I dislike broad generalizations, but it seems fair to say that every small business was created to help customers in some way — to create efficiency, to satisfy a need, or simply to spark joy. So what happens when your customers are unhappy with your product or service? How do you understand their goals and drivers to uncover what they truly need?

It starts with asking the right questions. Small businesses today must be relentlessly focused on customer success — so here at Salesforce, we’ve curated a list of the types of questions that best help us identify our customers’ pain points. These questions can work for just about any function — for product managers thinking about features and design requirements, for sales teams to clear any preconceived notions as they work with potential customers, and for customer service as they get to the bottom of a pain point. Questions like these help us clear our assumptions and approach the subject from every angle; after all, only when we uncover the true pains can we determine the right way to fix them. We hope these questions are as helpful for you as they’ve been for us.

10 types of questions to identify pain points

1. Sequence questions

  • What to ask: “Walk me through a typical day in which X happened… How did it start? What did you do next? Then what happened?”
  • The benefit: These questions are objective and open-ended, which helps you discover the most significant pains. By learning how this customer actually operates, you can identify the disconnect between what’s happening and what they want to happen.

2. Specific examples

  • What to ask: “Can you tell me about the last time you did X?”
  • The benefit: People sometimes say they do one thing, but when challenged, they actually do something else entirely. This question brings focus to the last time they actually completed a particular action.

3. Exhaustive list

  • What to ask: Talk to me about all the times you did X.
  • The benefit: This request forces the customer to think about various situations relating to a particular action. The memory jog can make them realize a pain is more prevalent than previously thought.

4. Peer comparison

  • What to ask: How do you do with X against peers?
  • The benefit: This type of question sheds light on how these customers see themselves in comparison to others in the same situation. How do they handle adversity? What types of responses do they give?

5. Other viewpoint comparison

  • What to ask: What would your boss/subordinate think about that?
  • The benefit: This one sheds light on how this customer wants to be perceived, as well as how colleagues actually perceive them.

6. Naïve outsider perspective

  • What to ask: “I don’t know anything about X. Can you explain it to me?”
  • The benefit: This type of question highlights what’s most important to the customer since they tend to only highlight the important parts to someone learning about it for the first time.

7. Quantity

  • What to ask: “How many times do you do X a week?”
  • The benefit: This basic question is a simple way to quantify how important something is to your customer, though you’ll likely need to read into the content. Are they repeating a certain action because they want to or because they have to?

8. Changes over time

  • What to ask: “How are things different than they were a year ago?”
  • The benefit: This type of question uncovers the strategy and direction the customer is aiming for, as well as how much they’ve changed to date. This can help with positioning and alignment down the road.

9. Tasks and organizational structure

  • What to ask: “Can you draw me a diagram of your daily interactions in your org?”
  • The benefit: This question sheds light on the dependencies and complexities within the organization. Asking someone to draw out the structure forces them to think about things like interactions and reporting structures.

10. Suggestive opinion

  • What to ask: “Some people have very negative opinions about X, while others don’t. What are your feelings?”
  • The benefit: This is a simple way to test a hypothesis you have about their direction. However, be careful not to influence or anchor them towards a certain idea with this one.

We hope these questions help you better identify your customer’s pain points so you can work to solve them with your product or service. And hey, as you go, don’t forget to use those three simple words to help you discover and analyze: Tell. Me. More.

Salesforce Essentials helps you find more customers, win their business, and keep them happy so you can grow faster than ever. Learn more about our small business CRM solutions by following us on TwitterLinkedIn, and Instagram.


Jason Perocho

Jason Perocho is a Director of Product Marketing at Salesforce and a veteran of the U.S. Navy. He spends his time at Salesforce researching and evangelizing how businesses can use data to better engage customers or partners across all of their digital properties. In his spare time, he is an advocate and mentor for veterans wanting to start their careers in technology. Connect with him on LinkedIn.

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