How to Run a Productive Generative Research Interview

When it comes to understanding why customers make the choices they do, few people have made a greater impact than Bob Moesta. As the co-creator of the Jobs-to-be-Done (JTBD) framework, developed alongside Clayton Christensen, Moesta has dedicated his career to uncovering the hidden motivations behind customer actions.

In his book Demand-Side Sales 101, Bob outlines methods for asking the right questions, structuring interviews, and interpreting responses to reveal genuine customer needs. By applying this framework, you can run generative research interviews that yield deeper insights and help shape products that resonate with what customers truly want.

This framework is a summarised version of Demand-Side Sales. If you want more details on any part I would highly recommend reading the full book.

The Setup

You are going to want people to open up about their feelings because all decisions are emotional. This is not something that we typically do with strangers so it is critical that you start the interview on the right footing to put the person at ease and build rapport.

Begin by putting the interviewee at ease, explaining that there are no "right" or "wrong" answers and that the goal is simply to understand their perspective. Use the first names of any key people they mention, which builds rapport and signals that you are listening and care about their experience.

Another good practice is to ask the person to pretend we are shooting a documentary. You will be asking a lot of detailed questions about the environment, the people and what was happening before or after events so that you can build a complete scene. This will explain your probing questions later in the interview without making the person feel uncomfortable.

Framing the Problem

The key thing to remember in the interview is that it's about the person, their struggle, and their progress—not about our product.

In the five research interview question types, we outlined that you should avoid opinion based questions as the answers are unreliable. But the truth is that we need to start somewhere. Opinion questions, if phrased from a struggle perspective, can help us to figure out where to start our conversation.

Good opening questions are formed around the four forces, with a bonus one around time.

1. Push Questions:

   1. What are you struggling with?

   2. What’s not happening that you want to happen?

   3. Where’s your frustration?

2. Pull Questions:

   1. What are you hoping for?

   2. What’s going to be different once you’ve got something new in your life?

3. Anxiety Questions:

   1. What are you worried about?

   2. What’s your greatest concern about getting rid of the old product or service?

   3. What’s your greatest concern about putting something new into your life?

4. Habit Questions:

   1. Even though there are problems, what do you love the most about your current product or service?

   2. What are you willing to give up in order to get something better?

   3. What are you not willing to give up?

5. Time Wall Questions:

   1. When do you need to make this decision by?

   2. Why then?

As with all opinion based questions we need to be skeptical about the answers and validate everything that people are saying, which leads us to the next section.

Details, Details, Details

We need to shift from opinions to evidence based questions. Evidence based questions fall into three different categories:

1. Work Artifacts
   Tangible outputs and documentation that demonstrate how work is actually done
   "Can you show me your team's guidelines?"
   "I see you've created several custom templates - could you explain how these fit into your workflow?"

2. System Evidence
   Digital trails and automated logs that capture actual usage patterns without user interpretation
   "Can you show me your app usage statistics?"
   "Let's look at your browser history"

3. Environmental Context
   Observable setup and arrangements that reveal natural working patterns and preferences
   "What tools do you have open right now?"
   "I notice you have multiple tabs open - how do these relate to your current task?"

Details Jog Memory

Have you ever looked at a receipt or a ticket for an old concert and genuinely not remember buying the product or attending the event? It happens to us all. If someone is struggling to remember something ask for other details that were happening around that time. “Where were you”, “Who was with you”, or other events could help to jog their memory. Framing the interview like a documentary at the start can avoid this feeling like an interrogation.

Unpack Vague Language

“I bought it because I like it, it’s easy, it’s fast.”

These are all vague and relative words. We need to unpack what is driving the decision. Why did they like it? How is it easier? What does fast mean to them? 1 minute? 1 hour?

Summarise

You should periodically paraphrase what the person has said to ensure that you have understood what they are saying. This also give you an opportunity to dive deeper into an area where you still have uncertainty.

Energy Matters

How people say things is almost as important as what they say. If someone is really excited about something this is telling you that this has more importance. Equally if someone is bored and disinterested in a particular topic it can tell you that this is not a high priority factor in their struggle.

Contrast creates Value

People often don’t know why they behave the way they do. If you ask why they like an item they will likely give you an answer, but it is unlikely to be the right answer.

But by giving people alternative options they can quickly tell you why they preferred one option over another.

1. "Why go for the online option? Why not just visit a store and pick it up yourself?"

2. "Why do it yourself? Why not hire someone else to take care of it for you?"

3. “Why did you buy the brand name product? Why not choose the cheaper generic option?”

A useful trick you can use when providing alternatives is to provide one or more bad alternatives as people are often happy to explain why their choices are superior to bad options. Cunningham’s Law works in real life too.

Additional Interviewing Tips

Following the structure above can really help you to uncover new and interesting insights about the challenges that people are facing and how your product may be able to solve these challenges.

But sometimes interviews don’t always go according to plan and you can struggle to get real insights. Here are some tips to help you try to get the most out of an interview.

Interview in pairs

It can be easy to fall into opinion territory. Having a second person present will help to pull an interview back on track if it starts veering off.

In addition, we all have different skill sets and biases so we will pick up on different things. Having more than one person involved ensures that more insights are gathered from the same interview.

Finally, having more than one person allows you to play “Good Cop, Bad Cop”. If you feel you have pushed the person for details and it is not working, you can summarise a point and argue between each other on what it means. This allows the person to identify the area of confusion and clarify it.

Never make the person feel stupid

You may ask a question that the person doesn’t know the answer to. it could be about the detailed spec of a tech item but the person is not very technical. If a person feels stupid they will start to feel self-conscious and shut down, which is the opposite of what you need to uncover their true motivations.

The best way to respond is to play dumb yourself. “Who really knows all that tech stuff anyway”, “I do the same all the time as well”, “I find it really confusing as well”

Set up bad questions

You might need to ask personal questions that people might not feel comfortable answering. If this is the case, rather than putting the person in an awkward situation you can set up the question: “I’ve got a personal question, and if you don’t want to answer it you don’t have to, but…”

Conclusion

The JTBD interview framework provides a systematic approach to uncovering the deep motivations and struggles that drive customer decisions. By following this structure - from building initial rapport, to framing the problem, gathering concrete evidence, and using techniques like contrast and energy observation - you can move beyond surface-level feedback to reveal genuine insights that inform product development.

While the framework requires practice to master, even implementing a few key elements can dramatically improve the quality of your customer interviews:

• Start by putting interviewees at ease and building rapport

• Focus on concrete evidence over opinions

• Probe vague statements for specific details

• Pay attention to emotional energy when topics are discussed

• Use contrast to help people articulate their choices

Remember that the goal isn't just to validate your existing product assumptions, but to truly understand the progress your customers are trying to make in their lives. This deeper understanding of customer struggles and motivations is what enables you to build products that genuinely resonate with user needs.