“Everyone’s got a plan until they get punched in the mouth” — Mike Tyson. Speaking with customers is often a nice, plan-breaking punch in the mouth.

Customer Interviews:

8 min readFeb 25, 2015

So you’ve decided to take your startup seriously.

I used to hate dancing at weddings.

I’m tall, goofy, and an awful dancer. Triple threat. Dancing made me self-conscious, so I’d just make some excuse and stay at the table while everyone else had a blast on the dance floor. I don’t remember when or why, but at some point I realized no one cared how I danced. Everyone’s got their own shit. No one was taking bets in the car on the way to the wedding about how low I’d get to “Shout.” So now I dance awkwardly at weddings with everyone else and it’s the best.


I also used to hate speaking with customers while I was building a product. I would get this weird, pre-embarrassed feeling — what if people thought my idea was dumb? What if they didn’t need what I was building? What if they mentioned a competitor I hadn’t heard of? What if they didn’t like it? What if they laughed?

Your startup begins the first time you speak with your customers and not a second before. If you can’t build something magical, you’d like to figure that out as soon as possible. If you don’t know your perfect customers better than the competition does, you’re cooked.

You can’t have fun at a wedding if you’re sitting at your table and you can’t build a meaningful product if you don’t speak to your customers. So now I do both — early and often.

“The second counterintuitive point is that it’s not that important to know a lot about startups. The way to succeed in a startup is not to be an expert on startups, but to be an expert on your users and the problem you’re solving for them. Mark Zuckerberg didn’t succeed because he was an expert on startups. He succeeded despite being a complete noob at startups, because he understood his users really well.” — Paul Graham, Before the Startup

Dance like nobody’s watching and interview customers like you can’t get hurt

How to Run Early Customer Interviews

The Seven Interview Commandments

  1. You’re not pitching your startup. You’re Sherlock Holmes. You’re searching for clues. You’re building a story. You are not just describing your idea then asking people if they would use it. Ask questions that will help you deeply understand your customer and their interactions with the problem you’re solving. At this point, “Why,” “talk more about that,” and “how did you feel when” are your best friends.
  2. No Surveys, No Facebook, No Yes/No Questions. A great product takes a customer from point A to point B. These conversations are about learning every detail of that journey — for the right customers. Surveys, Facebook, and Yes/No questions get the wrong information from the wrong people. Feedback from customers who wouldn’t use your product is worse than no feedback at all.
  3. Don’t ask questions you know the answer to. Lawyers never ask questions they don’t know the answer to. Customer interviews are the opposite. Questions like “if I could make you $900 every time you went to sleep… would that interest you?” are a waste of everyones time. You sound like a used car salesman and are obviously omitting important information. Only ask questions with complete information that you don’t know the answer to.
  4. No leading questions. Don’t force people to tell the story you want them to tell. Never lead them one way or another. Manufacturing a story together that fits your product is more harmful than information that disputes your idea.
  5. No “would you do ABC if XYZ” questions. People have grand visions of things they’ll do and what they’ll become. Stick to things they’ve already done. It’s a much better indicator of how they’ll behave in the future.
  6. Remember the Operating Table. Picture your idea on an operating table. You are trying to save it. Information from your customers will help. Anything fake, manufactured, leading, assumed — those don’t help. It’s not you on the operating table — try (as hard as this is) to remove yourself completely and ask questions objectively to get helpful information only.
  7. Get customers to tell stories. Watch the first 19 minutes of this video. It’s a fantastic primer on the process and how you should phrase and ask questions to get customers rambling. Questions like “tell me about the last time you…” or “tell me about your worst experience with…” will normally trigger stories.

THE GOAL: What are we trying to learn?

We want to walk a mile in our customers’ shoes. To understand how they feel before, during, and after they encounter the problem we’re solving.

This will give you insight into the following:

  1. Are you building a pain killer or a vitamin? Do people need a solution to this problem, or is it a “nice to have”?
  2. How do customers solve this problem now? What’s the exact process? How do they feel during this process? What are the biggest pain points? Specific products, workarounds, “hacks,” etc.
  3. How much money/time does this problem cost people now? If you can, get a sense of how much they’d pay to have it solved properly.
  4. Who else has this problem? Establish a persona for the customer who needs your product the most.
  5. Are you on the right track? Validate your assumptions to this point.
  6. What is everyone missing? Where are the holes? What are customers missing? What are the products they use lacking?
  7. Are customers locked into some existing solution? What would it take to get them out of it?
  8. What would a product look like that made this experience 10x better than what currently exists?

How many customers is enough?

You want to know your chosen customer segment well enough to give your product a beard. We chose who we will build for, now we need to make sure we know them well enough that their behavior becomes predictable.

Generally, you’ve spoken with enough customers when answers to questions all start to sound the same.

  • For B2C (consumer products): Minimum 3–5 perfect customers (ideally, 5+). The goal is to be able to say “if this person doesn’t need the product I’m going to build, no one from this customer segment will.” That way there’s no doubt. You don’t want to say “well this person didn’t need it, but they weren’t really the right person to speak with.”
  • For B2B (products for businesses): Minimum 2 perfect companies. It’s easy to say “speak with 3–5,” but realistically it’s tougher to speak with companies. Focus tightly on who you speak with. Treat these interactions as the first step in the sales cycle. In your head, you’re going to sell to this company eventually.
  • For Marketplaces: Speak with both sides of the equation. Building an airbnb for boats? Speak with 3–5 people who would be renting the boats, and 3–5 boat owners.
  • Housekeeping: Don’t take notes, record if you can. More of a personal thing, but note taking is distracting to both sides. Furthermore, you shouldn’t need notes. The important things will be repeated by customers, and the really important things will be your instincts and reactions to what’s being said. You won’t forget either. Focus on what the customer is saying, how they’re saying it, and why.
If you need a recording device, I recommend the Talkboy. Or your phone. Both work.

How do I find these customers?

  • Start with who you know. If you’ve got the problem you’re solving, you likely know some people who do as well. Reach out to them first.
  • Meet your friends’ friends. At the end of each conversation, ask your friends who they’d recommend speaking with. This will get you out of your immediate network and hopefully move you towards some more honest feedback (friends are too nice).
  • Think about your problem. Where are people the moment they have the problem you’re solving? Get there.
  • Think about your customer. What do they do in their spare time? Who do they follow on Twitter? What Meetups do they go to? What coffee shops? Where can you reliably find them?

What types of questions should I ask?

The goal is empathy. You want to be able to put yourself directly in the shoes of your customer. Some questions that will get to the root of their experience with your problem are:

  • Walk me through the last time you encountered (problem)?
  • When (problem) happens, what do you do?
  • What’s the most important thing you do each day pertaining to (problem)?
  • If you had a magic wand, how would you solve (problem) / build (product that solves problem)?
  • How much time / money does (problem) cost?
  • Why doesn’t a solution to (problem) exist?
  • Have you tried to better solve (problem) in the past?
  • What is missing from your current solution?
  • Where is this industry headed in the next 5 years? 10?
  • How do you feel about (problem)? The existing solution?
  • What else should I know about (problem)?
Go into customer interviews like you’re Sherlock Holmes. You’re job is to uncover things no one else can.

Woah, woah, woah… Wait a second. I’m not telling people my idea. They’ll steal it!

This gets brought up constantly, so I’ll close this post with it *jumps on soapbox.*

Tell everyone you know that you’re working on a startup. Immediately. And not just because lots of people smarter than me say to.

Because the good you can gain from telling people your idea far outweighs the bad that can happen if they steal your it.

To steal your idea, they’d have to drop everything, catch up to where you are, build a product, launch, get users, etc. It’s extremely unlikely. It’s also impossible if you’re truly building something only you can build.

To help you, they’d just have to say “hey — my college roommate is a developer. You should meet her,” or “my cousin would be super helpful — I’ll introduce you.” That conversation will happen constantly. People want to help. And that help might be the difference between success and failure.

And if you still aren’t convinced, watch this 6-minute video about how TaskRabbit started because the founder told everyone her idea.

It takes a village to raise a child, and a city to launch a startup. Your city is your network. Use them.

Further Content:

Further Content:

18 Tips and Tricks on Conducting A Killer Customer Interview, LIFFFT (really good slideshare presentation)





We help founders with full-time jobs validate their startup before they quit. The posts are tactics we use. http://gettacklebox.com