How to Ask the Right Questions During Customer Research

Ula Holovko
Nov 23, 2017 · 8 min read

No market research and analysts’ forecasts can give you as much insight and practical data as a well-thought-out customer interview. More and more startups acknowledge this fact and appeal to all sorts of user surveys. This, however, raises important problems — how to conduct an interview properly? What kind of questions to ask? Which questions are better for the interview and which you should leave for a survey?

We at KeepSolid team have gained some experience in this area over the years, got some inspiration from ProductMan club and now are ready to share couple of tips with you! 👇

Photo by Austin Chan on Unsplash

Ask the right questions to get the right answers

One may call it a hornbook rule, and rightly so, which by no means makes this requirement outdated.

How do you ask the right questions?

Well, in order to do this you must already, to some extent, know the answer. This may legitimately sound weird, but stick with us. Also, be ready for the surprises and have an open, but critical mind to what you are about to hear from your users.

Ok, let’s say, you are a marketing specialist or a product manager. Your are conducting a beta test of your product and need to gather user feedback. You may rely on your general knowledge and prepare lots of questions in different variations. Couple of them can sound like “Did you enjoy our app?” or “Please rate from 1 to 5 the following features of our product?”.

Stop right there as it won’t get you anywhere. We know that, because we actually asked the latter question for KeepSolid Sign (one of our products). And here is the what we got:

One of the questions in the survey for KeepSolid Sign

What insights, do you think, this questions reveals?

Actually, none. Moreover it misleads us, showing that everything is fine.

Such questions are only relevant if you need to determine the bottleneck in your product and dive deeper into the problem.

The better approach, of course, is to consult with your developers to know how your product works, and with sales managers to know its selling points. But you still need to develop your own perspective that will help you reach your goal, whatever it is.

Only in this case, you will be able to ask precise questions to learn very specific, relevant information. Sometimes it is all about which perspective to choose.

So, to start with, we deem appropriate to set apart three types of perspectives:

  1. Questions to analyze emotions. These can greatly benefit to an important goal — tell you about clients’ pains and how they try to fight it. Questions like:
  • “Why do you need to solve this problem?” Is it really so awful/irritating? Why?
  • “How did you try to solve it before?”

fit here well. Let the user speak.

This way, you will understand your customers better and, perhaps, will even come up with solutions and ideas that you’ve never thought of before.


Important notice: this type of questions is all about quality, not quantity. There’s no need to try building a statistical research at this stage.

Though every user’s pain is unique, likely, you will be able to figure out some clear patterns. That is why we highly recommend to arrange oral interviews for emotion questions. Then, you’ll be able to manually direct your conversation to the points that interest you.


Also, do yourself a favor and don’t suggest the answers while asking questions during the interview. Sometimes, we instinctively build questions the way to hear the answers we want.

And we did some mistakes like that in the past. 😞

For KeepSolid Sign we wanted to understand if native apps for Mac and Windows are indeed one of our competitive advantage as they allow to work with documents when there is low or no internet connection. Moreover, native apps work faster than the browser version.

So, we asked our users “How important is for you to have a native app for your Mac / Windows PC?”. Obviously, almost everybody we talked to said that it is very important and it is good that we have apps for these platforms, because our users did have a Mac or PC.

But, we actually wanted to learn if they are going to use KeepSolid Sign on Mac or PC and give these platforms a preference towards web version of the app because of the possibility to work with documents offline or on the go.

So, afterwards, we re-phrased the question and asked “How important is for your to work with your documents offline?”. That gave us better understanding and more specific answers.

Now, we stick to even more precise and easy-to-understand question like “Do you need to work with your documents offline? And on the plane? How often?”.

Again, double-check yourself, prepare for the interview, lead the conversation, but let the user speak first.


P.S. One of our favorite questions now is “What is the main benefit of this product for you?”. We start our interviews and surveys with it and though it is a broad question, it will grant you a meaningful data. Almost all our clients’ testimonials are based on the answers to this question.


2. Questions to analyze feature requests. These are more to the core of your product. Once again, the whys are more important than the whats. If you simply ask “What feature would you like to see in our app?”, you’re very likely to get a generic answer that you should have already learned from your marketing research at this point.

As an example, we were asking our users, both in-app and during interviews the following 3 questions:

Our feedback form for KeepSolid Sign

At that moment we thought that these questions were quite balanced and combined, but once we started to receive answers people replied the same stuff to question #2 and #3. Like, “no integration with OneDrive” (question 2) and “OneDrive integration is missing” (question 3) 😳.


Coming back to the feature perspective, if you ask something like “What kind of tasks do you need this feature for?” or “How do you manage your needs now, without this feature?”, you may stumble upon quite a priceless insight.

Additionally, apart from understanding the problem, you need to learn if this problem is really an unbearable pain now (remember, the questions to reveal emotions?) and if others also suffer from it. So, consider adding the following questions:

  • “Does the user need the feature now or you can add a bit later in the future?”
  • “How this feature can be embedded in the current workflow?” or “What is the scenario of usage?”
  • “Who else needs this feature (if your product is B2B)?” This is an interesting one, as your users can point you to those who also need your future solution (aka feature).

So, don’t ask about features — ask about problems & pains and create features that solve them. Oral interview is a sound option here.


3. Questions to analyze UI/UX. Well, here the best is to actually see how users interact with your app, instead of asking questions. But if you don’t have time for this or did not manage to arrange the process, then you can go all-in on statistical research, with quantitative and rating questions.

Such questions are most common for various beta tests, where you hand users a concrete product and need to gather an equally concrete feedback.
But even here, you have to be thoughtful and understand what you want to learn and why.

For instance, if you ask “Please rate our app design from 1 to 5”, you’ll probably get a lot of pleasant answers that, nonetheless, will not give you any valuable knowledge.

Instead, try to ask how difficult was for them to understand how to complete step X (i.e., send the first document for signing) or “What was your first impression about the app?”.


Sidenote regarding budgeting. Sometimes, it is a sound idea to survey users to understand how to monetize your products. This way you can learn how much are they ready to spend and for which features. But again, and we can’t stress this enough, be mindful of how you ask. Direct questions like “How much are you ready to pay for our product?” will give you overly optimistic values.

It’s better to enquire how much do users already spend on similar products or what is the budget for such kind of a solution, as it’s unlikely they’d be ready to spend more on yours (and they always compare you with someone or something).


So, the structure of your interview would be something like this:

  • Get to know the person — his/her position in the company, his /her tasks and challenges etc
  • Talk about his/her problems at work (if the product is B2B) or life (if it is B2C) — not about your product. Ask them about specific things that they experienced in the past and now — like how they were solving the problems before, how much they paid for that solution, what were the disadvantages of that solutions etc
  • Start asking specific questions regarding the features, functionality, design as described above to better understand the problems & pains.
  • After the interview send a follow-up with main points you discussed and say thank you.

You need to have at least 10–15 interviews with your users to start seeing patterns in their answers. But, of course, the more interviews the better.

And do listen more, than speak!


Bottom line

Obviously, every project is unique, so we didn’t want to try to come up with a list of universal go-to questions for everyone. Rather, we wanted to explain our point with the examples of the questions one may ask and shouldn’t ask in various situations.

We hope this small guide helps you build your next perfect interview or survey :) All in all, always keep in mind two things. First, you want to get specific answers, so design your interviews / surveys around those. Second, never forget the end goal of any product or feature — to help users relieve their pain. So, whatever questions you ask must help you bring your product to this ultimate point.

Have you ever conducted an interview or a survey with your users? How did it go? Share your story in the comments below. Cheers! 🎉

Follow us and our journey to create the best productivity and security solutions for business on Twitter, Facebook and our blog.

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Ula Holovko

Written by

Doing tricks and magic for KeepSolid Sign eSignature app (https://www.keepsolid.com/sign/). I am also a marketer, yoga lover 🙏 and a vegetarian 🥑.

The Startup

Medium's largest active publication, followed by +541K people. Follow to join our community.

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