How to deeply understand your customers

When I was deciding on a crucial feature for the wittwise's MVP, I asked a potential user which of the two alternatives he would use. When he told me how strongly he preferred one, I thought "Yes! this is it!". We even went through how he would use it and how it would help him (as per the Mom Test). I spent a week building out that last feature to launch it before the new year.

Once I got it working, I immediately demoed it to him, thinking that I was about to score my first customer. How wrong I was. Even though we worked through the feature together, he wouldn't use it.

What happened?! I read the mom test, and tried to follow it. But that obviously wasn't enough. What was missing? Around this time, someone recommended I take a look at Demand-Side Sales 101, which can help you really understand WHY you are doing customer interviews in the first place.


Helping customers make progress

Why is this important?

Jason Fried (of basecamp) gave an eye-opening foreword that made me realize how we incorrectly approach this. He talks about the time he was a shoe salesperson in his earlier years.

I noticed that when people browsed shoes on a wall, they'd pick a few up and bounce them around in their hand to get a sense of the heft and feel. Shoes go on your feet, but people picked the shoe with their hands. If it didn't feel good in the hand, it never made it to their foot.

Turns out, people had different reasons for picking shoes. Different reasons than my reasons, and far different reasons than the brand's reasons. Hardly anyone cared about this foam vs that foam, or this kind of rubber vs that kind... I was selling wrong.... Great sales requires a complete devotion to being curious about other people. And it's surely not about your commission, it's about their progress.

Okay, you're convinced it might be important. How can I use this?

Customer's Timeline

There are just two questions to ask yourself. First, what is the customer's timeline?


If you're interviewing an existing customer, then the goal is to understand their timeline up to now. If you're interviewing a potential customer, in addition to understanding their timeline you also have to know where they are on it.

  1. First thought
    This stage is about creating space in the brain. It's the moment when the customer had the first struggling moments. When did the customer first have the thought that their situation was not ok?

  2. Passive looking
    After the customer realizes their situation is not great, they start to become aware of the possibilities. There's very little transition between the first and second step.

  3. Active looking
    At this point, the customer has actually put effort into looking for a solution. This might mean asking friends for advice, or doing a google search. They're forming an idea about the tradeoffs that exist between the different alternatives.

  4. Deciding
    Before any decision is made, a "time wall" has to show up that makes the customer realize, 'this is the day I buy it.' It could be an artificial time wall like a black friday sale. Or maybe the struggling moments have gotten to the point where the customer absolute can't deal with them anymore.

  5. First use
    When the customer first uses the product or service, it has to meet their expectations and deliver satisfaction and value. Some questions to ask about this: What did you expect the product/service to do? Did it meet those expectations? What did you find needed improvement?

  6. Ongoing use
    Just because the customer has signed on, doesn't mean you can relax. If there are any new struggling moments, even "little" struggles, it can repeat the whole process again. But this time, the customer will be looking for an alternative to your offering. Are there unmet expectations? Are there any "little" struggling moments?

Let's go through an example to make this more concrete.

Example interview about a Peloton purchase

This comes from a great interview where Bob Moesta (one of the pioneers of the jobs-to-be-done framework) interviews Amrita about her recent Peloton purchase:

  • Bob: We want to try to understand the language of what causes people to say today's the day I'm going to buy a piece of exercise equipment. You happened to buy a Peloton. We just want to hear your story, we don't have a long list of questions. Each question is going to come from the previous answer. And ultimately, we want to hear your story what happened and how did you pick a Peloton as something to buy. Think of it as shooting a documentary of how this piece of equipment ended up in your house, and how's it doing?
    • Note: This setup is useful for framing your questions if the customer finds them too specific.
  • Bob: Tell us a bit about your background, what you live and what you do, and a bit about your exercise background.
  • (Amrita tells about her background, and how she's been struggling to find time to exercise, been struggling for close to 4 years)
  • Bob: How long is a long time?
  • (Amrita has been trying this on and off for about 4 years. She has a gym in the buildling she lives in.)
    • Note: The first thought was 4 years ago and she's been passively looking since then.
  • Bob: When's the last time you used the gym in your building?
  • (Amrita used it a few months ago. It's usually empty, so it's great.)
    • Note: This is an example of a previous solution
  • ...
  • Bob: What does being healthy mean to you? Could you give an example?
  • (Amrita works with people who are younger than her, and when they do a physical activity together, she feels conscious of her age. She just wants to be able to keep up. Wear clothes that I feel good in).
    • Note: This is the progress that she wants to make.
  • Bob: Has something happened recently that made you take a step back and made you realize that you're not headed in the right direction?
  • (Amrita says that it's been on her mind for the last few years. All of a sudden she woke up one day and thought, where did this belly come from).
  • ....
  • Bob: You looked at a Peloton, did you look at anything else? There's several different alternatives right?
  • (Amrita said she didn't look at anything else. She recalled seeing a lot of people on their peloton and talk about how much they loved it. There was a specific post she saw from her friend who was similar in circumstances to her. The post on instagram said, 'I love being able to get a 20 min workout in between my meetings.' As soon as she saw that, she wanted to buy one.)
    • Note: The instagram post was the trigger for the decision.

Alright, now that we have a better understanding of a customer's timeline, is that it?

4 Forces of Progress

This next part is where you get a deep understanding of your customer. There are 4 main forces that determine whether the customer will stick to their same behaviour or change to a new behaviour.


Push of the situation:

  • In the Peloton example above, what really pushed Amrita to get the Peloton were a few reasons: the gyms were closed, she didn't get an adequate workout using a TRX band, and she didn't feel safe walking outside since there were reports of a molester walking around in their neighbourhood.

Pull of the new solution:

  • After reading her friend's instagram post 'I love getting a 20 minute workout between workouts,' she felt pulled towards the Peloton. The convenience and the trendiness of the solution were enticing.

Habit of present:

  • Amrita didn't have any exercising habits at that time.

Anxiety of the new solution:

  • Although she didn't really like stationary bikes, she considered the Peloton to be a bit different than them. Also, since she was rather technically savvy, she didn't feel anxiety about how to use it.

In order for someone to change to a new behaviour, the push of the situation and the pull of the new solution have to be greater than the habit of present and anxiety of the new solution.

Now we have a good understanding of our customer.

2 Questions to frame the customer interview

To sum up, when we interview a customer, we want to know two things:

  1. Where is the customer on the timeline and what does that timeline look like?

  2. What are the forces of progress that are determining how the customer is making progress? (push, pull, anxiety, habit)

With these two questions framing the interview, we'll be better able to understand our customers!

To get started, here are some tools to help you collect data: