Do you truly understand your customers’ biggest problem and whether your product is the solution they seek? In this article, top insights from a seasoned Operations Manager and a strategic Chief Marketing Officer reveal powerful validation questions that can transform your approach. Discover how asking about referral criteria can open doors and why identifying recovery obstacles is crucial. With twenty-one expert insights, this article offers a comprehensive guide to refining your product’s market fit.
- Ask for Referral Criteria
- Identify Tried Solutions
- Assess Product’s Daily Impact
- Uncover Main Roadblock
- Highlight Workflow Frustrations
- Quantify Time Wasted
- Explore Unmet Needs
- Pinpoint Daily Frustrations
- Understand Problem’s Business Impact
- Recall Problem Instances
- Detail Problem Process
- Identify Desired Changes
- Review Recent Shopping Experience
- Request One Change
- Identify Process Bottlenecks
- Discuss Energy Cost Challenges
- Identify Compromises Made
- Analyze Sales Drop Causes
- Identify Recovery Obstacles
- Manage Online Reputation Frustrations
- Uncover Specific Task Challenges
Ask for Referral Criteria
I like to ask, “What would make you recommend our agency to a friend?” This question helps customers consider what they value most and what could turn them into supporters. It has been helpful in finding out what people like about our services and where we can improve. Clients often share what they appreciate and suggest ways to make things better. This method gives us a good sense of satisfaction and ideas for improving our services, helping us know where to grow.
Shane McEvoy, MD, Flycast Media
Identify Tried Solutions
A powerful question for validation is: “What solutions have you already tried, and where did they fall short?” This question not only helps uncover their core pain points but also reveals why existing solutions aren’t hitting the mark, which is invaluable for aligning your product to fill that gap.
In my experience, one startup I worked with wanted to replace email with a “better inbox.” When we asked customers what they’d tried (email-sorting plugins, Slack channels, Trello boards, etc.), they consistently cited issues like “losing track of conversations,” “overwhelming notification noise,” and “poor integration with CRM tools.” These insights highlighted not only their frustrations but also specific functional gaps that our solution could address uniquely.
This question also lets you gauge how motivated the customer is if they’ve gone through several workarounds already, they’re likely eager for a tailored fix, which can drive higher engagement with your product.
Jayen Ashar, CTO, Scaleup Consulting
Assess Product’s Daily Impact
To find out if you’re addressing your customers’ most significant issues, ask them this pivotal validation question: “If this product vanished tomorrow, how would that affect your everyday life?” The responses will unearth the product’s actual importance, as well as whether you’re scratching an essential, unmet itch. This question aligns perfectly with the PMF (Product-Market Fit) Matrix. It’s almost a test for figuring out if you’re placing a bet on solving a real, urgent problem that necessitates a solution in order for a customer to get on with their life.
The PMF Matrix helps clarify whether the main thrust of your work should be the product or the audience. If customers tell you they would have a hard time getting by without your product, it is a good sign that you’re on the right track. If they tell you it would not make much difference one way or the other, then it’s iteration time. That could mean refining the product so that it’s a better fit to the problem. Or it could mean revisiting the target audience to make sure you’ve got that in the ballpark as well.
The PMF questions help identify gaps in either value or relevance. “Okay, guys, if we don’t have these solved, then you tell us why we should get out of bed in the morning and keep working on this.”
Blake Smith, Marketing Manager, ClockOn Australia
Uncover Main Roadblock
“What’s the biggest roadblock you face that keeps you from achieving [specific goal related to the product]?”
This question gets to the core of the customer’s frustration without fluff. When you give them a chance to lay out their main pain point, you’re not just learning about their struggles—you’re setting up the conversation to see if your solution directly addresses it.
For instance, if I were designing a new social-media-management tool, I’d ask, “What’s the biggest hurdle you face in managing and growing your social media presence?” Their answer would tell me whether my product can bridge that gap or if I’m missing the mark entirely.
Tom Molnar, Operations Manager, Fit Design
Highlight Workflow Frustrations
To effectively determine your customer’s biggest problem and ensure your product addresses it, ask: “What is the most frustrating part of your current workflow, and how does this product make it easier or more efficient for you?” By framing the question around their existing pain points and potential improvements, you gain insight into their priorities and perceptions of your product’s value. From my experience as a SaaS business owner, understanding this relationship can highlight how well your solution aligns with their needs.
This specific inquiry allows customers to express the tangible impact of your offering, letting you assess its relevance and effectiveness. As someone who has witnessed the evolution of customer-value optimization, I’ve found that direct, open-ended questions reveal the alignment between product capabilities and user expectations.
Valentin Radu, CEO & Founder, Blogger, Speaker, Podcaster, Omniconvert
Quantify Time Wasted
I’ve found asking, “What’s your biggest frustration when managing web projects, and how many hours per week does it waste?” really gets to the heart of things. When I asked this to agency owners, they opened up about spending 12-plus hours weekly just coordinating feedback between designers and clients, which helped validate our communication solution. I recommend following up with, “What would you do with those saved hours?” to gauge how meaningful the problem really is.
Dan Ponomarenko, CEO, Webvizio
Explore Unmet Needs
My recommended question for determining customers’ biggest challenges and product fit is: “What’s the one thing you wish you could accomplish but currently can’t with the tools you have?”
This question not only uncovers unmet needs but also highlights potential obstacles that our solution- or any innovative product- must address to be truly valuable. It gives customers space to express their most pressing frustrations or goals, offering clear insights into gaps within existing solutions.
When customers tell you what they wish they could achieve, they’re revealing their biggest pain points and unmet needs- key insights for building a product that truly matters.
Lucas Botzen, Founder, Rivermate
Pinpoint Daily Frustrations
To determine my customers’ biggest problem and ensure my product addresses it, I use the question: “What daily task in your business most frustrates your team, and why?” This query pushes customers to reflect on operational inefficiencies that consume time and resources, offering a straightforward pathway to identifying real issues.
Years ago, a client shared how juggling multiple vendors for various business services was their greatest pain point. Realizing this, we revamped our offerings into a comprehensive package, streamlining their processes. In one instance, a startup under my guidance saw their online revenue triple by reducing vendor complexity and focusing on core business tasks.
This approach not only aligns solutions with customer struggles but also emphasizes our unique ability to simplify and integrate services, turning inefficiencies into growth opportunities. It’s about changing client feedback into practical, structured solutions that bring tangible results.
Dylan Cleppe, Co-Founder & CEO, OneStop Northwest LLC
Understand Problem’s Business Impact
One of the best validation questions I use is: “What would it mean for your business if this problem remained unsolved?” This question helps me understand not only the depth of the problem but also its urgency. If clients can clearly articulate the negative impact, it’s often a strong indicator that they see our solution as necessary. This question shifts their perspective to the potential benefits of using my product, allowing me to see if my solution truly aligns with their needs.
As a chatbot founder and SEO specialist, I have found that clients are more open when they are allowed to discuss the potential consequences of an unresolved issue. By focusing on the impact, I can assess whether the problem we’re addressing is core to their business. This insight also enables us to tailor our approach to meet the specific demands of the industry. The feedback we get from this validation question directly impacts our messaging and development priorities.
This question also helps us gauge how to improve our product’s relevance and usability. If clients emphasize certain pain points, I know which features to prioritize and which areas need extra refinement. This level of focus keeps our product aligned with market needs, ensuring it remains both useful and wanted.
Azam Mohamed Nisamdeen, Founder, Convert Chat
Recall Problem Instances
To really understand if your product is hitting the mark and solving your customer’s biggest problem, ask this: “Can you describe the last time you encountered this problem, and what did you do about it?”
This question goes beyond simple “yes” or “no” answers and digs into the real-world experiences of your customers. It forces them to recall a specific instance of their problem, how they felt, and the steps they took to address it (or not!). Their response will give you valuable insights into the severity of the problem, its frequency, and the workarounds they’re currently using.
This approach helps you truly understand the context of their problem and whether your solution fits into their existing workflow. You’ll gain a clearer picture of their needs, expectations, and potential pain points. And that’s invaluable information for validating your product and ensuring it truly addresses your customer’s biggest problem.
JJ Maxwell, CEO, Double Finance
Detail Problem Process
From my experience, the essential validation question to understand customers’ biggest problems and the viability of a product solution is, “Can you walk me through your process when encountering X problem, and how would you ideally like to resolve it?” This open-ended question not only reveals the customer’s existing pain points, but it also provides insights about their desired solution, which can be compared against the product features.
In my role as Director of Finance, this type of questioning has helped us in tailoring our financial solutions, such as introducing automated-payment platforms or customized financial reports, to the specific needs of our clients. By understanding their daily struggles and ideal outcomes, we were able to deliver solutions, enhancing customer experience and driving our business growth.
David Chen, Director of Finance, Srlon
Identify Desired Changes
The question, “If you could wave a magic wand and change one thing about your current process or tool, what would it be?” is invaluable because it allows customers to focus on their most significant pain point without the restrictions of existing solutions. This open-ended approach helps us understand their true frustrations and priorities, often revealing underlying issues that might not surface with traditional, product-specific questions.
For instance, when we asked this question to early adopters of our platform, we initially expected feedback on performance speed or security features. Instead, many users highlighted the complexity of integrating our tool into their existing workflows as their primary challenge. This insight was eye-opening—it wasn’t that they didn’t want our solution, but that the friction of onboarding was a larger issue than we’d anticipated.
Based on this feedback, we shifted focus to simplify our integration process, making it more intuitive and adding resources to guide new users. This led to a substantial increase in adoption rates and user satisfaction, as we addressed the core barrier to our product’s effectiveness.
In short, this question not only reveals whether our product aligns with customers’ needs but also identifies key areas for improvement, helping us make targeted adjustments that enhance the product’s value and usability. It’s a simple yet effective way to dig deeper and gain actionable insights into what truly matters to our customers.
Marouen Zelleg, Co-Founder, Crestal
Review Recent Shopping Experience
The best validation questions, in my opinion, are those that address a customer pain point that your product or service can solve.
As we sell kids’ school products like lunch boxes and school bags, a great question we ask customers is something like:
“Can you walk me through your most recent back-to-school shopping experience? What was the most frustrating or challenging part of finding products that both excited your child and met your standards?”
This question is open-ended and asked about a recent experience. From here, we can help them in their decision-making process.
Chantal Kietzmann, Owner, Creative Kids Lab
Request One Change
Firstly, it is important to understand that sometimes customers will be hesitant to share their pain points or may not even be aware of their true pain points/problems.
Asking the right questions to validate a customer’s needs can make all the difference. One question I have found to be effective is: “If you could change one thing about your current solution, what would it be?”
This approach often invites the customers to share their thoughts and can help identify the biggest pain points directly, which helps gauge if our products/services align with their expectations or if adjustments are needed.
This question works well because it uncovers specific issues while keeping the conversation open and constructive.
For an SME, where resources are precious, this insight is invaluable. It guides us in refining our product to address real problems, ensuring that what we offer truly resonates with our clients.
It is also important to remember that just because you feel that your product/service solves their problem, they may not agree, and while it is important to give the customer as much information as possible, you also need to be okay with accepting that not every logical (at least from your standpoint) solution will turn into a sale.
Christopher Wells, General Manager, INCA TRADING & CONTRACTING
Identify Process Bottlenecks
One powerful question I often use to validate customer problems is, “What aspect of your process would, if improved, make your team achieve an extra milestone this quarter?” This question digs into operational bottlenecks and highlights areas ripe for improvement. For instance, at a multinational firm, I leveraged CRM data to pinpoint and re-engineer sales bottlenecks, resulting in a 28% reduction in sales cycles—far exceeding initial company targets.
In a project with a client focused on customer experience, I identified inaccuracies in their CRM data as a significant hindrance. By addressing this with 24.4% improved data accuracy through customer-feedback integration, the business improved both efficiency and client satisfaction. These examples show how asking the right, specific question can reveal strategic insights for elevating business operations and achieving growth.
Ryan T. Murphy, Sales Operations Manager, Upfront Operations
Discuss Energy Cost Challenges
A great validation question to determine if our product solves the customer’s biggest problem is: “What’s the most significant challenge you’re currently facing in reducing your energy costs, and how are you currently addressing it?”
This question does a few important things. First, it invites the customer to identify their pain point—high energy bills, reliance on non-renewable energy sources, or concerns about sustainability. By asking how they are currently addressing the issue, it helps us understand what solutions they’ve already tried, and more importantly, it highlights whether they’re actively seeking a better solution.
Once we have their response, we can directly align how our solar products can provide value—by significantly reducing energy costs, offering long-term sustainability, or giving them more control over their energy consumption. Suppose they express interest or frustration with their current solution. In that case, it becomes clear that they are looking for something more effective, which presents a perfect opportunity for us to showcase how our solar solutions can fill that gap.
In essence, this question validates the customer’s problem and gives us insight into how they view the value of our solution, which is crucial for adjusting our approach and offerings.
Phill Stevens, Founder & CEO, Avail Solar
Identify Compromises Made
One of the most telling validation questions I would suggest is, “What compromises or sacrifices have you made to deal with this problem up until now?”
It isn’t just about a pain point; it is also about the cost of not solving this and how much the customer has already spent addressing this problem. It prompts an exploration of what compromises they’ve made, whether it’s losing precious time with their family, scrimping in other areas of their life or business, or simply dealing with stress that affects their health.
By asking this, you’re not just proving that your product fixes something; you’re measuring the severity of the problem in their life. If a customer can reference the actual losses, then your solution may prove transformative because you take those losses off their shoulders. It tells you which aspects of your product you should highlight, such as time-saving, stress reduction, or life optimization. Plus, knowing these trade-offs will help you develop an offer that addresses their lives and lets them know they’re heard.
We’ve always approached our business with the question, “How is this going to make a client’s life better?” The product of that viewpoint is our FlexBeam—a portable red-light therapy device.
On the other side, if customers can’t specifically mention any sacrifices, perhaps the issue isn’t so critical, or your product’s focus needs to shift to a more immediate problem. But when they do spot trade-offs, that’s a strong indication that addressing this problem will have profound appeal to them and distinguish your product as a key enabler, not just an optional tool.
Even Fusdahl Hulleberg, Chief Marketing Officer, Recharge Health
Analyze Sales Drop Causes
When talking to Shopify store owners, I ask, “Walk me through your biggest sales drop in the last 6 months—what do you think caused it?” This question has been game-changing because it reveals both technical issues and broader business challenges while getting store owners emotionally invested in finding a solution.
Joshua Uebergang, Founder, Digital Darts
Identify Recovery Obstacles
An understanding of the client’s greatest concern is essential in personal injury law because each case represents a unique challenge and need. One question I find very effective in identifying such needs is: “What’s the biggest obstacle you face right now in recovering from this accident, and what would an ideal solution look like for you?” It facilitates the clients to pose their legal issues as well as personal and financial woes. It informs us whether the lion’s share of assistance they require is for medical expenses, sick leave at work, or purely emotional healing.
We listen closely to these answers to tailor our approach better for every client. If the client is more concerned about controlling immediate medical costs, we’ll focus on either early compensation or even working with healthcare providers to defer payments until the case is resolved. Emotionally or physically struggling to recover? That’s okay. I can connect them with local resources or support groups. This approach isn’t just about winning cases; it’s addressing every client’s needs.
Using client feedback and translating it into practice has reminded me that, at the end of it all, our work centers on trying to understand and advocate for those who entrust us with their recovery journey.
Justin Lovely, Personal Injury Lawyer & Owner, Lovely Law Firm Injury Lawyers
Manage Online Reputation Frustrations
One of the most insightful questions we use to understand our clients’ needs and confirm the value of our solution is: “What’s the most time-consuming or frustrating part of managing your online reputation, and how have you tried addressing it before?”
This question does two things. First, it helps clients articulate the specific pain points they’re facing, which allows us to see if our services are directly aligned with those needs. If they share challenges like time management, lack of control over online reviews, or ineffective past solutions, we gain a clear understanding of whether our offerings resonate.
Second, this question reveals the urgency of their needs. If clients have already tried other solutions, it signals that their problem is significant, and they’re actively seeking an effective answer. This kind of feedback not only validates our service but also provides insights into potential areas of improvement. Engaging clients in this way helps us tailor our approach, ensuring we meet their needs and continue offering valuable solutions.
Chris Hinman, CEO, TheBestReputation
Uncover Specific Task Challenges
A powerful validation question to uncover your customers’ biggest problem and assess if your product addresses it is:
“What’s the most frustrating challenge you face when [specific task or goal related to your product’s purpose], and how have you tried to solve it so far?”
This question works because it invites customers to open up about their pain points and the limitations of existing solutions. Their answers not only reveal the depth of their need but also help you gauge whether your product aligns with their expectations.
I’ve used this approach when validating a SaaS product, and it revealed that many customers were trying to patch together clunky workarounds because they couldn’t find an affordable, integrated solution. Their feedback helped us refine the product features and focus on the key frustrations they shared. It’s amazing how much clarity a well-framed question like this can bring to your strategy.
Runbo Li, Co-founder & CEO, Magic Hour
