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Ultimate Guide to Customer Interviews: Lessons From 5 years+ of Field Research
Read time: 4.5 minutes
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Hi Reader,
Customer interviews (aka compassionate conversations) are a powerful way to understand your audience’s problems and needs.
However, many people approach them incorrectly – asking leading questions, pushing for validation, or focusing on hypothetical future scenarios.
To gather actionable insights, you need to create meaningful, compassionate conversations where the goal is learning, not selling.
This guide will show you how to frame questions that uncover real customer pain points, dig into emotional triggers, and ensure you walk away with deeper insights that can drive your product development forward.
You’ll find these techniques useful throughout the customer development lifecycle. However, compassionate conversations are fundamental in the early stages of understanding a problem, where it’s best to get out in the field and talk directly with the people affected by the issue you are exploring.
We’ll cover:
- Why Most Customer Interviews Miss the Mark
- Preparation: Laying the Groundwork
- Structuring the Conversation: Building Trust and Openness
- How to Ask Better Questions
- Questioning The Job to Be Done Customer Journey
- How to Work Out If People Will Buy
- The Differences Between B2C and B2B Interviews
- How to Have Tough Conversations
- The RAISIN Framework for Compassionate Conversations
- Closing the Interview: Getting Referrals and Building Relationships
- The 7 Most Frequently Asked Questions (from beginner interviewers)
Today’s newsletter is all about how to ask the right questions to reveal what people truly need.
Over the years I’ve taken many insights from Rob Fitzpatrick, Nick Bowmast, Bob Moesta and the DUCTRI Model created by my co-author Dr. Christian Walsh and applied them to hundreds of interviews across many complex sectors. This is my distillation of that journey.
Let’s dive in!
Why Most Customer Interviews Miss the Mark
Common pitfalls that lead to shallow insights.
Many customer interviews fail because they focus on seeking validation rather than learning.
Often, interviewers ask leading questions that push the customer to give responses they think the interviewer wants to hear. This results in misleading data that doesn’t uncover customers’ actual challenges.
Instead of asking whether customers like your idea or would use a hypothetical feature, focus on past behaviours and real-world experiences. People are much better at explaining their actions than predicting what they would do.
Common Pitfalls to Avoid:
- Leading questions: Asking questions that guide the customer toward a particular answer. For example, “You like this feature, don’t you?”
- Hypothetical questions: Asking about future behaviour that people can’t accurately predict. For example, “Would you use this app in the future?”
- Seeking validation instead of truth: Looking for compliments or positive feedback instead of uncovering real pain points.
Example of Better Questioning: Instead of asking, “Would you pay for this feature?” – a leading and hypothetical question – ask, “Can you walk me through the last time you tried to solve this problem? What did you try, and what didn’t work?”
This focuses on actual behaviour and encourages customers to share frustrations and challenges that can provide deeper insights.
Remember, customers aren’t experts in knowing what they want, but they are experts in their life, experiences and context.
“To find ideas, find problems. To find problems, talk to people.” – Julie Zhou, former VP of Product Design at Facebook
Preparation: Laying the Groundwork
Success starts before the first conversation.
The success of a customer interview often depends on how well you prepare. With clear goals and the right target audience, you can gather relevant and deep data.
Key Steps for Preparation:
Define Your Goals: Be clear on what you want to learn from the interview. Are you identifying pain points, validating a solution, or exploring customer behaviours? Setting clear objectives will help you shape your questions.
Example: “Understand the top frustrations small business owners face with inventory management.”
Identify the Right Interviewees: Make sure you’re speaking to people who are representative of your target audience. If your problem area or idea is for small business owners, interview people who fit this profile – not larger enterprise executives.
Set Up Logistics: Choose the right tools for conducting the interview (e.g., Zoom for remote interviews andtranscription tools like Otter.ai for note-taking). Make sure the interviewee’s environment is comfortable.
Usually, it’s best to have the interview in the preferred place for the interviewee and that is their natural habitat (home or place of work) so that you can get a sense of the context.
Create a Flexible Interview Guide: Draft a small number of open-ended questions to help get you going, but be flexible and ready to explore interesting tangents.
Example: “Can you tell me about the last time you tried to solve [problem]?”
Structuring the Conversation: Building Trust and Openness
Creating an environment where customers feel comfortable sharing honestly.
How you begin the interview and build rapport with your interviewee is crucial. A structured yet open-ended approach can help create a space where they feel comfortable sharing candidly.
Starting the Interview:
Set the Tone: Explain why you’re conducting the interview and reassure them that you’re not there to sell or judge. This removes pressure and encourages honesty.
Example: “I’m here to learn more about how you handle [problem], and I value your insights. There are no right or wrong answers—just your experience.”
Warm-Up Questions: Ease into the conversation with simple, open-ended questions to get the customer talking about their role or daily activities.
Example: “Can you walk me through a typical day at work?”
Keeping the Conversation Flowing:
Use Laddering Techniques: Start with broad questions and narrow in on specific details using follow-up questions.
Example: “What tools do you use to manage [problem]? What frustrates you about those tools?”
Practice Active Listening: Give the customer time to express their thoughts fully. Use reflective listening to show engagement (e.g., “You mentioned this was frustrating—can you explain why?”).
Balance Talking and Silence: Take your time filling gaps in conversation. Pauses often lead to more thoughtful responses and deeper insights.
Use Mirroring: Occasionally mirror their words to ensure understanding. And, use subtle mirroring of body language to build rapport and trust.
How to Ask Better Questions
Focus on real experiences and dig deeper into emotions.
Effective interviews are about understanding the customer’s real-life challenges and motivations.
One of the most powerful ways to do this is by asking open-ended questions about past experiences.
This grounds the conversation, in reality, avoids speculation, and helps you uncover more meaningful insights.
It’s also essential to dig into the emotions behind these experiences. People make decisions based on how things make them feel.
By exploring the emotional context behind their challenges, you can better understand what drives their behaviour and choices.
Effective Questioning Techniques:
Ask About Past Experiences: The best way to understand what someone needs is to ask them about what they’ve already done.
- Instead of: “Would you use this feature?”
- Ask: “Can you tell me about the last time you faced this problem? How did you try to solve it?”
Use the “5 Whys” Technique: Ask “Why?” repeatedly to drill down into the deeper reasons behind their actions.
Example:
- “I don’t use this feature.”
- Why is that?
- “It’s too complicated.”
- Why do you think it is?
- “It requires too many steps.”
Probe for Specifics: Don’t stop at the surface. Follow up to get more details about specific incidents or actions.
Example: “What happened after that? How did you feel when you tried that solution, and what was the result?”
Avoid Hypotheticals: Asking what someone would do in a future scenario rarely provides useful data. Focus on what they’ve already done instead.
Instead of: “Would this solution help you?”
Ask: “What did you try the last time you faced this issue? Why didn’t it work for you?”
Explore Emotions: Decisions are often driven by feelings, so asking about emotional responses to challenges or frustrations is essential.
Example: “How did it feel when you couldn’t solve that problem? What was the most frustrating part of that experience?”
Questioning The Job to Be Done Customer Journey
Understand a buyers journey to learn about the triggers and critical moments about why people really buy and the jobs they are trying to get done.
“What people in business think they know about the customer and the market is likely to be more wrong than right… the customer rarely buys what the business sells” – Peter Drucker
1) First Thought (The Initial Awareness)
This stage is when customers first recognise a need or problem.
- “When did you start thinking something wasn’t working well or could be improved?”
- “What triggered you to start thinking about a change?”
- “What made you realise that your solution wasn’t cutting it?”
2) Passive Looking (Exploration Begins)
Customers are informally gathering information and considering options without commitment.
- “What did you do first once you realised a change might be needed?”
- “How did you start looking for solutions, and where did you turn for information?”
- “Who or what influenced you during this early exploration phase?”
3) Active Looking (Serious Consideration)
The customer begins to seek out new solutions and compare options actively.
- “At what point did you become serious about finding an alternative?”
- “What criteria did you use to compare different solutions?”
- “What were the main frustrations or challenges as you evaluated your options?”
4) Deciding (Commitment to a Choice)
This is the moment when the customer makes their decision.
- “What made you finally choose this product or solution?”
- “What hesitations did you have before deciding?”
- “Who was involved in helping you make the final decision?”
5) First Use (Post-purchase Reflection)
The customer begins using the product and reflecting on whether it meets their expectations.
- “What was your first experience like with the product? Did it meet your expectations?”
- “At what point did you feel like this solution was the right choice?”
- “What surprised you about using it, either positively or negatively?”
By aligning the questions with the JTBD timeline, we can better understand the customer’s journey at each critical stage, from initial awareness to post-purchase reflection, as they seek to make progress and fulfil their needs.
Here’s an example of how thinking through this lens might help you to innovate:
Snickers and Milky Way, though both candy bars, fulfil distinct purposes depending on what the consumer is looking for (job to get done).
- Snickers is geared toward satisfying hunger, with its mix of peanuts, nougat, caramel, and chocolate making it a more filling option. It’s often chosen by people who are looking for a snack that will help them feel full and provide a boost of energy to carry them through the day.
- Milky Way, by contrast, is lighter in composition, with only nougat and caramel wrapped in chocolate. It’s usually selected when someone desires a sweet indulgence rather than a snack that fills them up. It’s more about enjoying the sugary treat than addressing hunger.
In summary, Snickers caters to those seeking a substantial snack to curb hunger, while Milky Way appeals to those who simply want something sweet to enjoy.
Tip: This approach can be used on buyers of a competitors product so you uncover the forces and decision-making made along the journey and where your idea may better meet needs.
How to Work Out If People Will Buy
Once you have a potential solution in mind or perhaps you have an early-stage prototype then you want to gauge their usage or buying intent.
Be aware. Compliments are stalling tactics not intent to buy.
Here, you will need to ‘ask’ for a small commitment (time, reputation, money).
Time commitment – perhaps, an agreement to use the product for X hours over a period of time. Or, a commitment to another meeting.
Reputation commitment – perhaps introductions to other stakeholders. Or, testimonials, case studies etc.
Money commitment – perhaps a pre-purchase. Or, deposit, letter of intent etc.
The main concept here is that you are moving the conversation from exploring the problem to an exchange of value.
This approach separates the person from someone who wants to help to someone who wants what you’re offering. A big difference.
The Differences Between B2C and B2B Interviews
Essentially, there is little difference in my approach when I’m interviewing someone in a B2B setting compared to a B2C. People are usually willing to share what’s on their mind.
That said, B2B offers some unique challenges and opportunities:
- People are often busier and harder to get to (gatekeepers)
- If your interview doesn’t go well, it may be harder to find other interviewees (less ‘customer’s in the market)
- There’s often several layers to decision-makers and often decisions involve multiple personnel which could stifle your progress
- But, the buying signals are often stronger and clearer when dealing with B2B
Tips: Have many friendly, motivated conversations (Steve Blank calls these people ‘early evangelists’) before moving to intent conversations because when that happens their guard will be up to not give away budgets or current solutions etc. Keep it casual. But, beware of getting caught up in long processes and talk fests.
How to Have Tough Conversations
In my experience tough conversations tend to fall into two main areas – 1) sensitive topics and 2) hostile people.
1) Sensitive topics. I’ve had compassionate conversations in some of the most sensitive fields such as vulnerable young people in our care system and people suffering from chronic pain.
The one thing that holds true is if you present yourself professionally and build rapport through showing you are there to listen and learn through an empathetic manner you will gain trust and confidence because people in such situations have been wanting to share their experiences and pleased that you are there to help the situation.
Note: It is critical to never promise anything and that your role is to understand their perspective.
2) Hostile people. Sometimes people are just having a bad day and need to vent. In this instance, let them get things off their chest and in time bring them back to the starting questions you have.
If you the ‘venting’ continues and you are unable to get to more thoughtful conversations, you may have to draw a close early on the conversation.
In my experience, this situation is very rare. Most people genuinely want to help. And remember, it’s about them not about you.
The RAISIN Framework for Compassionate Conversations
Using the RAISIN framework to guide meaningful customer interviews
A successful customer interview isn’t just about asking the right questions – it’s about creating a compassionate and empathetic dialogue.
This allows the customer to feel comfortable sharing their true thoughts and feelings.
Compassionate conversations help you dig deeper into the human side of a problem, revealing insights that wouldn’t come out in a formal, rigid interview.
The RAISIN framework, from the DUCTRI Playbook, is designed to facilitate these conversations. It’s a simple yet powerful approach to ensure your interviews are centred on empathy, understanding, and openness.
RAISIN Framework:
Rapport: Establish trust from the start by explaining the purpose of the conversation and creating a relaxed environment. Ensure the customer knows you’re there to learn, not sell.
Example: “I’m curious about your experience and appreciate your time.”
Actively Listen: Focus completely on what the customer is saying. Don’t just wait for your turn to speak. Actively listen to their words and emotions, and use reflective listening to clarify and explore their answers.
Example: “You mentioned that you felt overwhelmed during that process. Can you tell me more about what made it so difficult?”
Impartial: Stay neutral and avoid influencing the conversation with your own biases or assumptions. Allow the customer to express themselves fully without steering them toward an answer.
Example: “How did you handle that issue?” instead of “Would our product have helped you?”
Shut Up: Resist the urge to fill every gap in the conversation. Silence is powerful—it gives the customer time to think and often leads to deeper, more thoughtful responses.
After asking a question, wait for a moment of silence before asking another one. This can prompt the customer to reveal more insights.
Invoke Emotions: Get to the issue’s core by asking how specific events made the customer feel. Emotional insights are key to understanding their motivations.
Example: “When that happened, how did it affect your work or your day-to-day life? How did it make you feel?”
Next Steps: Always end by thanking the customer for their time and asking if they can refer you to others with similar experiences. This creates a network of potential interviewees for further insights.
Example: “Is there anyone else you think I should speak to who’s dealing with these same issues?”
Tip: You are looking for revealing data rather than representative. Dive in to what is interesting.
Closing the Interview: Getting Referrals and Building Relationships
Wrap up the conversation with a plan for future engagement
When you close an interview, leaving the door open for future follow-ups and referrals is important.
These next steps help you continue learning from your customers as your product evolves.
Summarise and Show Gratitude: Recap the key points you discussed to ensure you’ve understood them correctly and express appreciation for their time.
Example: “Thanks again for sharing your experience with me. It was really insightful to learn about your challenges with [problem].”
Ask for Referrals: If the interviewee has been particularly helpful, ask if they know others who might be facing similar challenges.
Example: “Do you know anyone else who might be dealing with these same issues who would be open to chatting?”
Keep the Relationship Warm: Let them know you may want to follow up in the future to validate findings or share product updates. This keeps them engaged and opens the door for ongoing feedback.
Example: “Would it be okay if I reached out again to share some of the ideas we’re working on based on your feedback?”
The 7 Most Frequently Asked Questions
Wrap up the conversation with a plan for future engagement
What questions should I ask?
It’s common to feel uncertain about what to ask in a customer interview, especially if you’re new to the process.
The key is to start with broad, open-ended questions and then narrow in with follow-ups. Focus on real experiences and emotions, asking about past behaviors rather than hypothetical scenarios.
Example:
- Broad: “Can you walk me through how you manage [specific problem]?”
- Follow-up: “What was frustrating about that process?”
2. How many people should I interview?
The ideal number of interviews depends on the complexity of the problem you’re exploring.
Generally, you want to keep interviewing people until you reach a saturation point – this is when you stop hearing new information and the same themes, patterns, and insights start repeating across interviews.
- For smaller projects, saturation can happen after 5-10 interviews.
- For more complex problems or diverse customer segments, you may need 15-20 interviews.
Tip: If you’re consistently hearing the same responses and no new insights are emerging, you’ve likely reached the saturation point.
3. How do I handle customers who talk too much or go off-topic?
It’s great when customers are willing to talk, but sometimes they may go off-topic.
Politely guide the conversation back to the relevant subject without shutting them down. Acknowledge what they said and then refocus on your key question.
Example:
- “That’s really interesting. Can we go back to what you mentioned earlier about [problem]? I’d love to hear more about that.”
4. What should I do if a customer gives short, unhelpful answers?
When someone is giving short or uninformative answers, they may feel uncomfortable or unsure of what to say.
Try asking simpler, more open-ended questions, and ensure you’ve built enough rapport at the start to make them feel comfortable sharing more.
Example:
- Instead of: “Do you find this tool helpful?” (which might lead to a yes/no answer),
- Ask: “Can you tell me about the last time you used this tool? What was the experience like?”
5. How do I balance letting the customer talk and getting the information I need?
The balance between letting the customer speak and guiding the conversation comes with practice.
Allow them to share their thoughts freely, but don’t be afraid to gently steer the conversation back to the key topics. Use the RAISIN framework to keep the conversation structured but natural.
6. How do I get people to open up about their real problems?
The key to getting people to open up is to make them feel comfortable. Build rapport early, ask non-judgmental, open-ended questions, and don’t rush.
Use active listening to show that you’re genuinely interested in their experience, and ask about their emotions to encourage deeper responses.
Example:
- “What’s the most frustrating part about trying to solve this problem?”
7. What do I do if the customer brings up an issue I hadn’t planned for?
If a customer brings up an unexpected issue, take it as an opportunity to explore something new.
Ask follow-up questions to understand it better, even if it wasn’t part of your original plan. These moments often reveal valuable insights.
Example:
- “That’s interesting—I hadn’t thought about that. Can you tell me more about how that affects your process?”
⚡️ Call to Action
Conducting customer interviews is a skill that takes practice, but with the right preparation, questioning techniques, and compassionate conversations, you’ll be able to uncover the real problems your customers face.
Use this guide to ensure your interviews are meaningful, empathetic, and insightful.
The DUCTRI Playbook offers a practical new way to innovate with confidence and clarity. If you are in to human-centred design, or want to learn how to innovate and solve complex problems, this book is for you.
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Catch you next Wednesday,
Vaughan
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