Questions that I have found useful

When it comes to understanding users, it's all about the questions.

"If you do not know how to ask the right question, you discover nothing."

W. Edwards Deming

It’s all about the questions. There are questions you ask of yourself, and questions that you ask of others. Over the last few years of helping to build products, I have come to recognize that both are essential to building things people want. Internal (the questions you ask yourself) are an introspective conversation for another day. External questions will be the focus of this essay.

External Questions

Questions are like a magnifying glass that bring answers into focus. But that in and of itself leads to a question, where do you want to focus?

Research questions help you know where to aim, they make you think about what it is you want to learn. The simple question of "What do you want to learn?" is amazingly powerful. You may find that this question makes you ask questions that are not practical or too vague. For example, "I want to learn what customers want" is directionally correct but far too vague.

A simple way to get more specific about your research questions is to think about the future. Two useful tools here are "starting at the end" and pre-morterms.

Starting at the end asks you to think about the outcomes that you want. Continuing with our example, the outcome we want is to "Make a product that people want" while vague, this is still useful as a longterm goal. To get more specific, we then have to ask the question "what has to be true, to achieve this long term goal?". Back to our example, to make a product people want, it must be true that the product is, for example, useful, solves a problem for the user and is easy for the prospective users to find.

A pre-mortem asks you to invert your long term goal. Back to our example, what has to be true for people not to want our product? well, it might be too hard to use, hard to understand its value, it might be aimed at the wrong audience or maybe the product was hard to communicate.

Now we can think about our research questions more clearly because we know where we want to go, we have a hypothesis about what will get us there, and what will hold us back. All we have to do now is translate our hypotheses into clear questions.

What gets us to our long term goal?

solves a problem for the user → What problems do people have, that our product might solve?

useful → Is our product useful to people, why or why not?

easy for the prospective users to find → Where is the attention of our customers, how do they find and adopt new products?

What holds us back from our long term goal?

hard to understand its value → Do people understand the value of our products?

product was hard to communicate → What is that people perceive as valuable?

It might be aimed at the wrong audience → Is our product targeted at the right audience?

The above questions are your base, they are the true north of your research. It will serve as the signal in the noise of all the quantitative data you will gather.

Picking People

The next thing we have to do is pick people. Our question here is "who do we want to learn from?".

Again with our example:

Since we have the outcome in mind of "Building a product people want" we might want to talk to prospective customers and current customers.

and since we have research questions that focus on problems and perceptions, we might want to talk to current, prospective and past customers. More specifically, customers who have been both successful and unsuccessful with our product.

The Questions

Below is a non-exhaustive list of questions that I have found most useful thus far. I hope to continue to update them as I learn more.

The most important thing about the questions I have listed is their structure. Each set of questions relates to a method (what type of research) and a purpose (what kind of outcome).

Purpose: Understanding the greater context of a customers life situation

Method: 1on1 Discovery Interviews


  • Who - Understanding the social forces

    • Who influences you the most in your search for x?

    • Who do you look up to when thinking about x?

    • Who do you talk to when deciding about x?

    • Who frustrates you in the context of x?

    • Who do you care most about in the context of x? Who do you have to consider within the context of x?

  • What - Understanding the internal forces

    • What frustrates you most about your day doing x?

    • What can't you do that you wish you could?

    • What do you have to do, that you wish you could stop?

    • What excites you most about your day doing x?

    • What is the most important aspect of your day (or process) doing x?

    • What else have you used to solve this problem?

  • When - Understanding the external forces

    • When did you realize that x was a problem?

    • When did you realize that x was a solution?

    • When do you get stuck or blocked?

    • When do you feel motivated to move forward?

    • When is it most clear?

    • When are you most anxious about x?

    • When do you start to use x?

    • When did you realize that this was the right solution?

    • When do you feel the most pleasure or joy using or doing x?

  • Where - Understanding the environmental forces

    • Where would you look to find x?

    • Where do you get updates about x?

    • Where do you trust when looking for x?

  • Why - Understanding the hidden forces

    • Why do you find x more useful than y?

    • Why? (a great follow up question)

    • Why not? (Another great follow up question)

Purpose: Understanding how easy to learn and effective your experience or flow is

Method: 1on1 Usability interviews


  • How - Understanding ease and effort

    • How would you go about doing x?

    • How hard is it to do x on a scale of 1 - 10?

    • How would you find x information about y?

  • What - Understanding understanding

    • What questions does this bring to mind?

    • What are the questions that you are asking yourself here?

  • Where - Understanding discoverability

    • Where would you look for x?

    • Where would you find x information about y?

  • Wish - Understanding desirability

    • If you had one wish to add something, what would it be?

    • If you had one wish to remove something, what would it be?

    • If you had one wish to make something harder, what would it be?

    • If you had one wish to make something easier, what would it be?

Purpose: Discovering the underlying causes of user behavior, the hurdles they wish to overcome and the goals they want to achieve.

Method: Jobs To Be Done interviews


The timeline - Understanding the chain of key events

  • Point of purchase, use or decision

    • Tell me about the moment that you bought or started using x...

    • What was that day like? What happened that day? Who were you with?

    • What were all the details of the moment that you decided to follow through?

  • First thought

    • When did it first enter your mind that x would be the solution?

    • What was happening around the time that you first thought x could be a solution?

  • Key events and moments to point of purchase - Understanding all that helped and hindered in a user’s journey.

    • Forces

      • Key events

        • What were the things that happened that made you start thinking about or considering the solution more seriously?

        • When did it become clear that you had no other choice?

        • When did you feel that it had to be "now"?

      • Reasons to stay

        • Anxieties

          • What held you back from moving forward emotionally?

          • Was there any knowledge or information that was missing?

        • Objections and external blockers

          • What were you unable to do that held you back?

          • Was there anyone who was stopping you or holding you back?

          • Did you need the permission or approval of someone else?

        • Habits

          • Is there something that you were switching from, that you knew you would have to give up?

          • Did the new solution change and existing workflow or routine?

          • Was it disruptive to your routine in anyway?

      • Reasons to switch

        • Catalysts and current struggles

          • When did you realize that you needed to look for a solution?

          • What happened that made you think that there was a better way of doing x?

          • When choosing x solution, what were the biggest things you felt that you needed overcome?

          • How would you finish this statement:

            The highest priority problem right now is...

            The biggest waste of time right now is...

            The biggest waste of money right now is...

        • Desired outcomes

          • What did you think would change as result of solution to x to y problem?

          • Describe the new you after you have found the ideal solution...

          • What can you now do, that you could not do before as a result of the new solution or process?

          • When do you know that the solution you chose has worked?

      • Supply

        • What else did you consider?

        • What else did you try before?

        • How did you did you analyze the comparisons?

      • Constraints

        • What are the tradeoffs that you had to make when considering and choosing x solution?

        • Do you still have to consider those tradeoffs or did you overcome them?

Purpose: Gathering large sample sizes of data that can help you understand where to focus your attention.

Method: Surveys


Validating Jobs To Be Done:

  • Catalysts and struggles

    • I knew it was time choose solution x when_______.

    • The top 3 things that made me consider solution x were_______.

    • I knew it was time to start looking for a solution when_________.

    • The biggest problem x helped me overcome was_________.

  • Goals and desired outcomes

    • Before the new solution, I was not able to do _____ but now, with it, I can do_____

    • I stopped doing or using because the new solution helped me

    • I knew I could stop looking for a solution when______

    • The main benefit that I get product x is ______

  • Anxieties and barriers

    • The top 3 blockers for we were_____, when deciding on the new solution.

    • When I was considering the new solution, _______ made me feel that I could move forward.

    • The person or set of people that hold me back from pursuing or using product x were__________, because_________.

Understanding Language and terminology:

  • How would you describe x feature or y product to a friend?

  • The top 3 most confusing terms are______.

Existing product feedback:

  • The the top 3 hardest things about product x are _______.

  • I want to do_______but it is not clear how.

  • I wish x product could_______.

  • I wish x product was more like______.

  • The most annoying thing about the product is________.

  • If could ask an expert on product x, my top three questions for them would be_______.

  • The most time consuming thing about product x is_______.

  • When using product x _____ is complicated, when it could be simple.

  • The other products or services that I use with product x are_________.

  • The most confusing thing about the product is__________.

Target users:

  • What type of people do you think would most benefit most from product x_______.

  • If you could no longer use product x, would you be (a) very disappointed, (b)somewhat disappointed or (c) not disappointed

There are certainly many more questions that can and should be added here, but this is a start.

Thanks for reading. Leave any feedback in the comments.