The customer is talking about a specific task, either complaining about it or expressing the wish to do it faster, better, or not at all.

This isn’t a question as much as an invitation to speak freely. It doesn’t make sense to ask questions that measure time, effort, cost, or value because you don’t yet know whether any of those attributes are interesting.

Another important feature of this question is that you’re asking about a tangible past action, not a potential future action. When people talk about things they may do in the future, they tend to be more aspirational, more positive, and less accurate.

When you don’t imply that you’re looking for a specific type of information, the customer will simply talk about what is most significant to her about that task. It may be related to who, what, why, when, or how; it may be a positive or negative emotion.

This question is an effective way to help a customer who is fixated on a specific solution or hampered by a real or perceived limitation.

This question forces customers to identify their biggest pain point. It’s often a way to learn more about a customer’s environment: would his magic wand help him do something faster or better, or eliminate obstacles or bureaucracy?

This question elicits specifics. It helps to prompt a customer to move beyond generalized descriptions of how he completes a task or deals with a situation.

Even when you have made it clear that you are interested in a customer’s specific experiences, she doesn’t always believe you: “Oh, I didn’t think you wanted me to mention individual websites or apps that I use—I figured you’d want a general answer that might apply to other people too.”

Specific websites, equipment, software programs, apps, or methods that the customer uses. If the customer is using tools to try and solve a problem, that’s a good sign. It shows that she recognizes the problem and is already committed to trying to solve it. (A customer who intends to try a solution to a problem but hasn’t gotten around to it yet is usually a red herring.)

Use this question if the customer thinks his problem is solved. He’s using a product that at least partially addresses his pain points. He may not be actively seeking a better solution.

The customer’s initial expectations around solving his problem. If the tool is a commercial product (as opposed to something like pencil and paper), it’s useful to look at that product’s marketing. Compare the value promised by the product’s marketing with the customer’s expectations.

Usually I find myself asking this question when the customer has expressed interest in a product or feature to help her solve a problem with a task or routine.

“How often” sounds appropriately conversational so it doesn’t put the person on the defensive. Since people tend to be bad at estimating the frequency of events, following it up with a specific window of time in the past (not too long a window; here I used a month) makes it easier for them to give you an accurate count. Using a “how many times” framing is also helpful if you are asking about behaviors that are less socially acceptable or that the customer is embarrassed about.^[77]

Obviously, you’re asking how often a situation occurs, which helps you figure out whether this is a significant enough problem to invest in solving.

You’re also implicitly asking about priority. It’s not uncommon for someone to describe a situation that happens all the time and then admit that it hasn’t happened in the past month. How does the customer then react? Does she laugh and admit that, “OK, maybe it’s not that big a deal after all,” or does she say defensively, “Well, it seems like it happens all the time.” The latter is a clue that this is a particularly severe problem or one that causes constant low-level stress. That’s a problem worth looking into!

You’ve identified a problem but you’re not sure if you can fix it profitably. This question is also helpful if you’re uncertain of the severity of the customer’s pain point because the customer is not showing much emotion. (Of course, in a public space such as a conference or sales meeting, people tend to exhibit more reserved emotional responses.)

How this customer thinks about time and money. Is he the one responsible for budgeting either of them? Is this customer the primary user of your product but not the person who makes a purchasing decision?

You’re looking for additional segments of customers to target, or you’re not sure if your initial target customer profile is accurate.

Who else you could be talking to. Another benefit to this question is that your customer may have a better sense than you of what he has in common with other customers. For example, if you were building a product for babies, you might assume that your target customers are parents. But parents know that they are not the only purchasers of baby things—buyers include grandparents, doting aunts, neighbors, and anyone invited to a baby shower. A more accurate target customer description may be people who buy presents for babies.

You can always ask this question—almost any task or routine includes preparation steps that we don’t always think about. This is also a useful ice-breaker question when you’re talking to a customer who doesn’t seem to have anything to complain about, such as an existing customer who has fallen into a routine. Nothing is explicitly broken, so she doesn’t think about what could be improved. Or perhaps you asked the “tell me about how you ____” question and you sense that the customer’s answer was too narrow in scope.

There may be existing preconditions required for the customer to use your product (I only use X when I’m on a business trip). If there are related activities or tasks that someone always does before using your product, that’s an opportunity to extend your feature set or partner with a complementary product or service.

Always ask this question at the end of every interview! Don’t wait until you have a formal beta testing program in place. It’s extremely useful to have a bank of email addresses of people who’ve already agreed to help you out in the future.

If you’re solving customer problems, people will say yes to this question. If you get a lot of “no” answers, view that as invalidating your hypothesis.

You’d like to learn more about customers’ subjective experience. Procedural questions sometimes get you a more detailed answer.

Depending on how you measure your product usage, you may get the factual answer to this question from your quantitative analytics. I’m often surprised, though, by how frequently a customer’s subjective recollection of what she does differs from our objective logging of the actions she takes.

You have a hypothesis about what customers value the most. You’d like to validate it to determine where to invest in improving your product.

People who build products tend to believe that customers will derive the most value from the most difficult or technologically advanced features. This is often not true! I’ve often heard customers explain that the most used and useful features relate to easy actions like sharing or exporting.

A customer has just asked for a specific feature or change to your product. Maybe you don’t think it’s aligned with your product vision or maybe you just aren’t sure you understand what the customer is asking for.

You may need to adjust the level of language formality, depending on your customers and your existing relationship. There’s a small risk of customers perceiving this question as glib or dismissive. I do recommend keeping it deliberately personal and vague, though—“make your life better” or “make your job easier.” If you ask about something more specific, like saving time or money, you’ll get a more constrained answer.

The problem that this customer is trying to solve!

As a last resort question in a customer development interview. If you are trying to validate that a problem affects other customers, it’s a stronger signal if someone mentions the problem unprompted. But sometimes you have a strong intuition: you just know this customer experiences a problem, even though she hasn’t mentioned it yet. When this happens, a nudge may help get her talking.

When you don’t have time for an extended interview. You can also use this question if you don’t have enough time for an extended interview, in which case it serves as a useful standalone conversation starter. (Note that it’s not a yes/no question but an invitation for the customer to start talking.)

When you see a pattern and want to challenge it. As patterns begin to emerge, you can use this question by stating the opposite of the pattern and claiming that mythical other people do it another way. See Chapter 6 for details.

For some reason, the mention of other customers seems to trigger people to give more thoughtful, honest responses than blind agreement or disagreement.

This may be because it is perceived as being granted permission to complain. Those of you who’ve been on the other end of an angry customer phone call may find this hard to believe, but most customers don’t actually feel comfortable complaining, which means that their problems go unresolved.