Here are some of the best questions for a Prospect survey about pain points, plus actionable tips for creating them. If you want to build a conversational survey like this in seconds, Specific can help you do it—fast and effectively.
Best open-ended questions for a prospect survey about pain points
Open-ended questions are where we get those deep, honest insights—things multiple-choice options miss entirely. These are ideal when we want prospects to freely describe their struggles in their own words, which helps us understand not just what the pain points are, but why they matter. Remember, open-ended questions can have higher nonresponse rates—Pew Research Center found that some open-ended items reach over 50% nonresponse, and on average, these questions see an 18% nonresponse rate [1]. The key is to limit the number and keep them easy to answer. Here are 10 proven open-ended options worth including:
What’s the biggest challenge you’re facing right now in your [industry/profession]?
How do these challenges impact your day-to-day work?
Can you describe a recent situation where this problem caused a setback?
What have you tried in the past to solve this issue?
What would resolving this pain point mean for you or your team?
Which parts of your current process feel especially frustrating or inefficient?
Have you found any partial solutions? If yes, why don’t they fully address your needs?
How do you currently prioritize or weigh different pain points?
What’s one thing you wish existed to help with these challenges?
Is there anything else about your pain points that we haven’t covered?
Pro tip: Put these questions later in your survey, as starting with an open-ended item can drop completion rates—surveys that start with closed-ended questions have an 83% completion rate, significantly higher than those that start open-ended [3]. For more practical advice, check out how to create prospect surveys about pain points.
Best single-select multiple-choice questions for a prospect survey about pain points
Multiple-choice questions are great for quantifying the weight of specific issues—and they’re easier for people to answer quickly. If you want prospects to pick an answer fast, or if you need structured, easy-to-analyze data, these are your tools. Surveys with predominantly closed-ended questions have much higher completion rates and tend to avoid the “survey fatigue” that comes with too many essay-style prompts [1][2]. Here are 3 multiple-choice questions we’ve seen work well for understanding pain points:
Question: Which of these is your primary pain point right now?
Lack of time/resources
Outdated technology/tools
Process inefficiency
Communication gaps
Other
Question: How frequently does this pain point disrupt your workflow?
Daily
Weekly
Monthly
Rarely
Question: Which area do you feel needs the most immediate improvement?
Project management
Client communication
Training/resources
Reporting/analytics
When to follow up with "why?" We use a “why” follow-up when someone chooses an option and we need to get at their real motivation—for example, if a prospect selects “Process inefficiency,” ask, “Why is this the biggest issue for you right now?” That simple extra step can uncover root causes and deeper insights.
When and why to add the “Other” choice? Always include “Other” if your list might miss less-common pain points. Prospects who use this option can then provide more context, and a smart AI-powered follow-up uncovers what matters most—sometimes surfacing new trends or vocabulary you hadn’t considered.
NPS question in prospect pain point surveys
NPS (Net Promoter Score) measures customer loyalty, but it’s also an effective pulse-check on how strongly your solution might address a prospect’s pain. Use the NPS format to ask: "On a scale of 0-10, how likely are you to recommend our solution to others dealing with similar pain points?" This format makes it easy to segment your potential customers into promoters, passives, and detractors, guiding you in tailoring communication and offers. Explore a ready-to-use NPS survey for prospects about pain points with Specific to see this in action.
The power of follow-up questions
Follow-up questions take ordinary surveys and make them excellent. Instead of leaving cryptic answers unexplored, follow-ups let you dig deeper—like a live conversation would. With AI-powered follow-up questions in Specific, your survey conducts real-time, context-aware interviews as if you had a sharp researcher chatting one-on-one. This means richer, more detailed feedback with less effort. Automated follow-ups can also save you serious time, replacing hours of back-and-forth emails with instant insights while making the interaction feel genuinely conversational.
Prospect: "The main problem is onboarding new staff."
AI follow-up: "Can you describe what makes onboarding especially challenging for your team?"
How many followups to ask? In general, 2-3 targeted follow-up questions per main topic are plenty. Enable the “skip to next” setting when you’ve gathered enough detail—Specific offers an easy toggle for this in the survey setup. You get depth without overwhelming your prospects or risking survey drop-off.
This makes it a conversational survey: Each answer triggers the next, just like real dialogue—bridging the gap between a static form and dynamic conversation. These are surveys people actually enjoy completing.
AI analysis of open-ended responses: Worried about messy text responses piling up? Don’t be. With AI survey response analysis, you can instantly query, summarize, and explore every bit of feedback—turning unstructured data into actionable insight in seconds.
Because automated follow-ups are still a new concept, I genuinely recommend generating a conversational survey today and experiencing the difference first-hand.
How to prompt ChatGPT (or other GPTs) to generate great survey questions about pain points
If you want to use AI yourself to create survey questions, prompts matter. Start simple:
Try this first to jumpstart ideas:
Suggest 10 open-ended questions for Prospect survey about Pain Points.
But AI always works best with context. Try adding details about your audience, goals, and any particular areas you want to explore:
We target B2B SaaS prospects in HR tech. Our goal is to uncover common pain points in hiring workflows and understand solution gaps. Give me 10 open-ended questions for a conversational survey.
Next, let the AI self-organize its results for you:
Look at the questions and categorize them. Output categories with the questions under them.
After you review, zero in on the themes that matter most to you. Then use:
Generate 10 follow-up questions for the categories “onboarding pain” and “reporting challenges.”
This approach keeps your prompts focused and leverages AI’s full power for survey generation. For those who want to skip the learning curve, the AI survey generator for pain points in Specific already does all this—no prompt engineering needed.
What is a conversational survey?
A conversational survey is exactly what it sounds like—an interactive, chat-style questionnaire that feels like messaging with a friend. The big difference? Instead of cold, static forms, prospects have a real-time exchange where every answer drives the next smart follow-up. This keeps respondents engaged and surfaces deeper insights than a traditional poll. Conversational surveys are intelligent, flexible, and can adapt on the fly—choosing which questions to ask (and how to ask them) based on what the respondent just said.
Why does it matter? Surveys built with an AI survey maker like Specific are not only easier to deploy, they have a substantial impact on response rates. AI-powered surveys can increase response rates by up to 40%—and that means more, better data for you [2]. Here’s a simple side-by-side:
Manual Survey | AI-Generated Survey |
|---|---|
Static, rigid form | Dynamic, chat-style conversation |
No follow-ups (unless planned in advance) | Smart, real-time follow-ups adapt to answers |
Time-consuming to create and edit | Fast, prompt-based survey building |
Hard to analyze open text | Built-in AI analysis for all responses |
Low engagement, often abandoned | Mobile-friendly, fun to complete, higher completion rates |
Why use AI for prospect surveys? Quite frankly, the right AI tools let you create better surveys, with deeper insights, in a fraction of the time. Plus, when you need to qualify, segment, or understand real prospect pain points, the AI ensures no detail gets missed. For a step-by-step walkthrough, see our full guide on how to create a survey for pain points research.
With Specific, you get best-in-class user experience, an intuitive creation process, and a conversational survey format that makes every feedback collection smooth and genuinely engaging for both sides.
See this pain points survey example now
Turn slow feedback into fast, actionable insight with conversational surveys that surface your prospects’ real pain points and remove guesswork. See how easily you can qualify leads, learn what matters most, and let Specific’s AI handle follow-ups and analysis—so you focus on what counts.