What to ask Customers to Validate their Pain Points?

Davide Turi
6 min readNov 22, 2017

Speaking with customers from a very early stage of a new product definition is an extremely powerful and informative tool to validate assumptions and get insights to define a Unique Value Proposition for a product for which there is a market need.
Even if it might sound quite straight forward — it’s just about having a chat after all — interviewing customers has its pitfalls, and the last thing we want from them is to spend precious time without getting to know the truth.
We have seen already a few tips on how to run successful customer interviews (read here).
It’s now time to understand how to conduct the actual interviews, which are the questions to avoid and which are the best ones to use.

Rob Fitzpatrick has written an great book full of practical tips on how to run Customer development interviews (get it here).
The whole point of Rob’s book is about how to identify early adopters, how to let them tell the truth about their pain points, and how to get a commitment when we finally get to show them our proposition.

Let’s focus on the pain points part here, and how to get the most from the time we (and customers) spend in our interviews.

There are two golden rules when investigating customer pain points:

  1. Never tell them about your new product idea. This is not about being secretive. The reason is that in general people tend to be polite, and anyone will say an idea is great if we are annoying enough about it. This will produce a big fat false positive. So when interviewing customers you should give them as little information as possible about the product or business idea, while at the same time you will still be still nudging the conversation in a useful direction. An example is to start the interview with a very broad picture of what you are trying to solve, at a very high level. e.g. “we are working on a service for people who love watching TV but are annoyed by the way current services work today“. It says nothing about what you have in mind, but at least it gives a little bit of context to the person participating to the interview.
  2. Always ask customers at least one question that has the potential to destroy your currently imagined business. This is a pain. Anyone is in love with their idea, and the last thing we want to know is that it’s not a good one. Entrepreneurship has a magic power, it triggers positive energies and it leaves people with an irresistible willingness to start doing things. That’s great, but all this positive energies can be very easily transformed into negative when they not channelled in the correct direction. And with negative I mean: having quit a day job, having spent most of our savings, having re-mortaged the house and ultimately having trouble explaining to our life partner, family and friends why we have done all of that and we haven’t been able to succeed. That’s awful. That’s because it’s much better to know if an idea is flawed (i.e. there is no market need for it) as soon as possible.

Now that we know the golden rules, what questions should we ask to customers?
When investigating customers pain points, we should aim at getting information about specific behaviours occurred in the past instead of generic opinions about the future.
A few example below to illustrate this:


  • Do you think it’s a good idea?
  • Would you buy this product?
  • How much would you pay for it?
  • Would you pay £x for a product that did this?

It should be quite clear already why those four questions are “bad”.
They assume we have presented our idea to the customer, and we trying to get their opinion on that. Unfortunately even if they said “I would definitely buy it!“, that won’t necessarily mean that they will do it. It’s because is an opinion about the future, not a behaviour occurred in the past. And it’s another big fat false positive.

These are the steps to effectively validate pain points:

  • Elaborate the problems you are willing to solve, one by one. While doing that, put them in context so that the customer can relate to them
  • Ask them how to show you how they currently solve each problem
  • Let them talk about what they love and hate
  • Ask which other tools/approach they are using
  • Ask how did they find out about the current solution
  • Ask whether there is budget for a different solution

These questions above are extremely powerful and informative. By asking them how they solve the problem today and what they love and hate, we will get to know pain and gain points for the jobs they are willing to do. It might be that customers don’t actually do these things or they don’t care at all about the problems you are willing to solve. That’s cool, you have learnt that they are not the right customer segment. The good news is that you haven’t spent much money till now. By asking them what tools or services they use today, we will learn how big is the problem. Because if they haven’t bothered exploring or finding a solution, it means the problem is not really a problem. By asking where did they hear about the current solutions they are using, we will get useful info on the marketing channels that we can use later, when the product is ready.

And finally, by asking about how much they spend for the solution, we will learn again how big is the problem, get insights about pricing and positioning, and finally understand if the target segment is attractive enough.


Here are a few good questions to ask during customer development interviews, and why.
Could you talk me through last time that happened? This should be the very first ammunition. It’s even better if the interview is conducted in context (so in the location where the problem occurs) so that customers can show us how they do it. By watching someone doing a task we will see clearly where the problems and inefficiencies are, not what customers think about that.
Why do you bother? This will help focus on understanding customers goals and motivations behind their actions and purchases
What are the implications of that? This will help understanding the size of the pain of a problem.
What else have you tried? If customers haven’t looked for ways of solving the problem already, there is a good chance that they won’t bother about what we are going to launch
How are you dealing with it now? This will allow to explore competition and how much customers are paying for them in order to have a price anchor
Is there anything else I should have asked? this is a must have, and should always come at the end of the problem list. People want to help us, we should just give them an excuse. The objective is to explore what we still don’t know we don’t know.

Final must have question: Who else should I talk to? Recruiting customers for interviews might be a pain, and might take time especially if we are targeting a market which is quite new for our background. Every interview should finish with this questions, as it will create a snowball effect and we will find extremely easier to recruit target customers to speak with. If they don’t do intro, take anything they have said with an extra grain of salt (see here a few tips on how to recruit customers to interview).

One last point about customer suggestions.
Certain customers just won’t resit from telling us how their dream service would work and suggest new features.
So let’s get this straight: it’s our job is to define how to solve customers’ problems.
As a rule of thumb, we should never accept feature requests or let customers dictate our roadmap.
However, feature requests are still a big opportunity to learn.
So in case someone tells us how they would see the service working, we should take a deep breadth, and use this opportunity to dig beneath the underlying need and understand why they requested it by asking:
— “Why do you want that?”
— “What would let you do?”
— “How are you coping with it today without that feature?”

Originally published on StudioZao.com on November 22, 2017.



Davide Turi

Innovation Programmes Director | Venture Builder | Exited Serial Entrepreneur