How to Conduct Customer Discovery Interviews (The Right Way)

"Talk to your customers" is the single most common piece of advice given to budding entrepreneurs and intrapreneurs. Before you build anything, the advice goes, you should talk to a few customers and see what they think of your idea. 

This is dangerous advice when used incorrectly. 

If you talk to your customers in the wrong way as you explore a business idea, you are going to generate all sorts of misleading data. You will think you have a perfectly market-ready idea and subsequently invest months of time and thousands of dollars. You will quit your day job and start imagining yourself on the cover of Forbes. And then you will launch, and no one will buy what you’re selling. 

All because your early customer interviews weren’t done properly.  

To avoid this kind of disaster, when you talk to customers in the initial stages of your startup, you need to conduct customer discovery interviews. These interviews have specific formats and guidelines to ensure the data you receive is actionable and accurate. 

When you’re done reading this essay, you’ll know the questions you should avoid like the plague, as well as the exact questions that actually generate viable insights. You’ll also learn how to dive deep into the details of your customer’s life and troubleshoot common discovery interview problems. 

‍The 3 Questions to NEVER Ask in Customer Interviews

As Brian Rhea says, "the things that make you a great entrepreneur will make you really terrible at conducting customer interviews."

Your optimism and passion for your idea are two necessary ingredients to starting a valuable company. They are also the two things most likely to get you false data in your customer interviews. The essence of the problem is that most entrepreneurs pitch, instead of interview. 

Here are 3 questions new entrepreneurs and intrapreneurs typically ask in early stage interviews that ought to be avoided at all costs:

“What do you think of [my idea]?”

Never, ever, ever ask directly for feedback on your idea in a customer discovery interview.

Few people are cold-hearted enough to give honest negative feedback to an entrepreneur as they explain their idea. They can see your enthusiasm, they can feel your excitement. They don't want to be the one to ruin your dreams. Not to mention, as Rob Fitzpatrick writes in "The Mom Test", "anyone will say your idea is great if you're annoying enough about it."

Even if their feedback to this question is genuinely positive, it's still not helpful data. In early stage customer interviews, you are not interested in your interview subject's opinions. Their opinions may be biased, eccentric, or outright lies. You cannot build a successful business based on their opinions. 

“Would you use [my idea]?”

This is the hippopotamus of customer interview questions. Looks gentle enough, but it is surprisingly lethal.

This question is so dangerous because it will lead you to believe - falsely - that you have potential customers lined up for your idea. Here’s the brutal truth: in a conversation, any idea can sound useful. They might interpret all sorts of pieces of functionality that you’re not eventually going to include. They might not be thinking realistically enough about the costs of switching to your solution. Or they might just want to be nice to you. 

Many great entrepreneurs have been led astray by early conversations where interview subjects said "yeah, I'd use that!" only to be shocked when those very same interview subjects stopped picking up their calls. It's just too easy to hear "Yeah, I might use that" as "$$$" in your own head. To avoid this trap and the false ego-rush it provides, just don't ask this question at all. The answers cannot be trusted. 

“Would you ever....”

To quote Rob Fitzpatrick again, "The measure of usefulness of an early customer conversation is whether it gives us concrete facts about our customers’ lives."

Asking questions that begin with "would you..." or "if..." are surefire ways to get into the world of the hypothetical. This is, by definition, abstract and not concrete. Your interview subjects could imagine doing any number of things. But they actually do a limited number of things. To build a successful business, you need to know what they actually do, not what they might theoretically do. in the future.

The 3 Types of Good Questions to Ask in Customer Interviews

If you're not able to ask for feedback or about hypothetical situations, what are you supposed to ask about?

The key is to treat your customer discovery conversations the way a doctor treats their first conversation with a patient. A doctor doesn't ask their patients what they think of different medical options. A doctor doesn’t ask for feedback on some imagined medicine that the patient hasn’t tried yet. That's because the patient doesn't know what the solution to their problem should be. They only know their own problem. 

The job of the doctor is to get the patient to talk about their problem in a way that makes it easier to identify the optimal solution. Similarly, your job is to get your customers to tell you their problems with specific, detailed stories about their lives. 

With the doctor’s mindset, there are three areas you need to ask about: 

Exploration Area #1: Is this a problem?

The majority of startups die because they did not solve a real problem. Maybe the problem wasn’t well understood by the founders, or maybe the problem didn’t actually exist. But if you’re not solving a real problem, you have a near zero chance of success. 

Every one of your early customer interviews should be laser-focused on validating that the problem you want to solve is as real as you think it is.

The secret to great customer interviews is to ask for stories from the subject's life at times when you think they might be experiencing the problem you want to solve. Asking for concrete stories - as opposed to hypotheticals - will reveal dimensions of the problem that you may never have thought to ask about. 

If you ask for concrete stories and the subject has none, it’s a red flag that the problem you’re trying to solve doesn’t exist for that particular customer type. If on the other hand, you ask for stories and the subject says “"that happened to me last week!", you've likely hit on a real problem.

Examples questions to ask:

• "What are the biggest problems you've experienced when faced with [situation]?"
• "When was the last time you faced [problem]?"
• "What happened the last time you were in [situation where you think the problem occurs]?"
• "Tell me about a time when you faced [problem]"
  

Exploration Area #2: Is this a problem worth solving?

Some problems exist, but just aren’t significant enough to be the foundation of your business.

We all face daily annoyances in our lives that, on balance, we wish didn't occur. But are we willing to pay to get rid of all of these problems? Absolutely not. 

Once you've confirmed your subject faces a problem, you then need to confirm that it’s a problem worth solving. Customers will only pay you to solve important problems - solving minor problems is a surefire way to end up with a business that fails to get traction. 

If your interview subject can’t assign a value to their problem, either in terms of time, money, or reputation, it’s likely not a problem they’d pay you to solve. Similarly, if they’ve never tried to solve the problem before, they probably will not pay you to solve it for them later. 

But if they can identify how much the problem “costs” them, if they have tried to solve it in the past with mixed results, or if they are actively looking for solutions to the problem, you’re well on your way to starting a successful business. 

Example questions to ask:

• "How much does [problem] cost you?"
• "How much time does [problem] take for you to solve?"
• "What are the non-financial implications of [problem]?"
• "How big is the budget you have allocated to [problem]?"
• "Have you tried to solve [problem] before? If not, why?"
• "Have you ever searched for solutions to [problem]?"
• "Have you paid for any services to solve [problem]?"
• "What tools/techniques do you use to solve [problem]?"
  

Exploration Area #3: What don't I know?

At the end of each interview, you need to leave space to uncover the “unknown unknowns”. These are the facts, situations, and pain points that you don’t know you don’t know about. For obvious reasons, it's very difficult to craft questions to ask about things you don't even know you should be asking about.

Consequently, you should end every customer interview with a few open-ended and exploratory questions. These questions give the floor to your interview subject to bring up anything else that you didn't touch on, but that might still lead to valuable insights.

Example questions to ask:

• "Is there anything else I should have asked about [problem] that I didn't?"
• "If you had a magic wand, what would be your first wish with regard to [problem]?"
• "Who else should I talk with?"

Asking Follow Up Questions

Asking the questions listed above will help ensure you get stories. But to ensure you actually get detailed stories, you'll need to ask plenty of follow ups. These follow up questions are the lifeblood of a successful interview.

The magic words to use are "Can you tell me more about that?" Those 7 words are like a silver bullet that will get your interview subject to provide you actionable detail, without biasing them too much in any direction. Use this phase liberally in your interviews.

Remember that we want to get details about real life scenarios. If you find your interview subject repeatedly talking hypothetically ("I would do X" or "I might try Y"), the best follow up is to make them get specific again. For example, asking "What did you do the last time X occured?" is a safe way to bring them back into the world of the concrete.

Troubleshooting Your Interviews

Well run customer discovery interviews are the difference between starting a business with confidence and starting a business with hubris. But even experienced researchers occasionally run into difficulties and find themselves wasting time and energy. 

Having founded two businesses myself and advised dozens more, I’ve found myself frustrated by the customer discovery process more than once. Below you’ll find 5 things I’ve said to myself when interviews aren’t going well. To spare you my pain, I’ve also included solutions to each of the underlying causes that produce these problematic situations. 

"I'm Totally Lost!"

• Situation: You've had 10 conversations, but your data is all over the place. There's no clear patterns emerging and you feel overwhelmed.
• Underlying Cause: Your segment is too vague and you're getting responses from too many different types of potential customers. The inconsistency in your interview subject selection is resulting in inconsistency in your interview notes. 
• Solution: Identify a more specific type of user to get feedback from. If you're working on a savings app targeted at millennials, don't interview any 15 young people you can find. Instead, narrow down. Are you targeting millennials with jobs paying more than $100k? Millennials who travel frequently? Millennials who invest in crypto? The more specific you can be, the more likely you are to find actionable patterns across your interviews.

"I Can't Find Anyone Willing to Be Interviewed"

• Situation: You're struggling to find people to talk to. Maybe your customers are too unique or too wealthy for them to set aside a significant amount of time to be interviewed. This is particularly common in B2B focused startups.
• Underlying Cause: You're thinking that all interviews must be formal, white glove affairs.
• Treatment: Make your approach more casual. Plan for only 5-10 minute interviews, and try to get these interviews on the spot. Critically, you don't ask for permission for casual interviews. All you need to do is to weave your questions into a normal conversation. That means casually asking questions in a bar, in a meeting room, in a cab, in a cafeteria, etc. Any time you get a potential customer talking about their problems, you are conducting a discovery interview, whether they know it or not. 

"My Idea is Perfect!"

• Situation: You feel great because everyone you've talked to says they like your idea. You really had the perfect idea all along!
• Underlying Cause: You're fishing for compliments, which anyone will give you if you ask enough times.
• Solution: Stop asking for feedback on your idea. It won’t feel as good in the moment, but asking about your interview subject's experiences is far more likely to lead you to success. Remember: doctors don't ask people what medicine they think they should take. Doctors ask about problems and make decisions about the solution themselves.

"This is a Waste of Time"

• Situation: You are feeling frustrated that you're not getting any value out of conducting interviews. You're just hearing things you already know.
• Underlying Cause: There are a few underlying causes here, ranging from your mindset to your questions to your analysis. First, you might not be "open-minded" enough in your interviews. Second, you might be asking leading questions. Third, you might not be taking verbatim notes and are only capturing observations that support your assumptions.
• Solution: Three potential underlying causes call for three potential solutions. First, make sure you're "open-minded" in the true sense of the phrase. As a former colleague of mine, Alexis Baum, liked to say, being "open-minded" is really about having a willingness to have your mind changed. You should proactively be using your interviews as an opportunity to learn, not just confirm. Second, make sure you're asking broad exploratory questions about the interview subject's experiences. This will give you a chance to be surprised. Third, take verbatim notes (or record your meetings, with consent) to ensure you are capturing what is actually said, rather than what you think is said.

"I'm Spending Too Much Time Interviewing"

• Situation: You've scheduled 20 interviews for the next two weeks and feel stressed out by the avalanche of notes you’re about to capture. Your calendar is already busy and you feel like you just don't have time for customer interviews.
• Underlying Cause: You're mistaking the numerical requirements of quantitative research (e.g. surveys, data analysis), with the numerical requirements  of qualitative research (e.g. interviews, diary studies, etc).
• Solution: Counter-intuitively, less is more in interviewing. Jakob Nielson, a user research pioneer, did a comprehensive analysis of 83 of his own product studies and found that 85% of problems were observed after just five studies. A solid target is 5 interviews per user segment. This will ensure you don't spend all your time interviewing and have time to focus on actually developing your idea as well. 

Putting This Into Practice

Boiling everything down, there are two key takeaways for you when it comes to customer discovery interviews:

1. Before the interview, prepare a short list of questions about the customer’s problems and experiences. Do not pitch your idea and ask for feedback.
2. During the interview, make sure to follow up repeatedly to get into the specific details of their experiences. 

Of course, in the real world interviews are never as straightforward as they appear on paper. That’s why it's particularly useful to conduct these customer discovery interviews in pairs. Bring along a team member, a co-founder, or a friend and two amazing things will happen. 

First, you can focus fully on asking questions as your partner takes the notes. This will ensure you remain present in the moment and respond naturally as the conversation develops. 

Second, you'll be able to ask your partner for feedback on your interviewing style, ensuring that you’ll get better as an interviewer over time. 

When you're looking to evaluate a business idea, customer interviews done properly are an essential part of a successful entrepreneur’s toolkit. Now it’s your turn: go conduct 5 customer discovery interviews and set your business up for success. If you have any questions, shoot me an email at kashdhanda [at] gmail [dot] com and I’ll be happy to give you personalized advice. 

Thanks to Eeshan Sridhar, Brij Dhanda, Chris Elkin, and Sanah Dhanda for giving feedback on this essay. A special thank you to my former colleagues at LUMA, particularly Gavin Pryke and Amelie de Spot, for helping me shape my thoughts on interviewing generally.