Brian Casel
Brian Casel

Questions to ask customers

by Brian Casel · Subscribe

I’ve become a bit obsessed with the practice of talking to customers.

Yes, it is a practice. The more conversations you have, the more fruitful they become.

Asking the right questions is essential.

BUT it doesn’t matter which questions you ask if you don’t know why you’re asking each one.

Having a handle on the underlying why behind each question ensures you get the most of out them. How will obtaining a particular answer help you? What can it help you do (or not do)? Which decisions will it help you make?

Below are my favorite questions I ask customers and leads—and their whys.

Don’t just copy/paste my list questions into your next interview or survey. Mix, match, and tweak until you feel like your customer conversations are fruitful and actionable as you need them to be.

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Tell me what your business does?

I’m looking to find out which industry they’re in (marketing, food, medical tech, etc.), and what type of business they run (service, software, e-commerce. etc.).

One set of industries & business types will likely answer the rest of the questions differently than another. Once you’ve had many conversations, you can identify these segments, and decide which one(s) to focus on.

What does your team look like? What’s your role?

I always want to know who I’m speaking to. A founder? A manager? A technician?

This also gives me a sense of their team size. That helps paint a picture of how my product might fit in their organization.

More importantly, it can tell me who and how many people are involved in the decision to buy or switch to a new product.

How did you come across (my product)?

This helps me know which marketing channels are working. Flat out asking them always gives better data than any spotty analytics tracking can. It’s better to hear it in their own words too.

“I heard your podcast episode with (name)” —tells me I should be targeting more pods like that.

“I searched google for these terms…” —Gives me more SEO-optimized content ideas.

“Someone mentioned it in a Facebook group called…” —Now I know where I should be engaging online.

What’s been happening lately that led you to search for a product like this?

This is key.

They must have experienced something recently that led them to decide to spend time on actively seeking out and evaluating product(s) like mine. Whatever that new development is, it must be meaningful enough for them to devote time to this effort.

I need to know what happened.

Sometimes it’s a clear event (“I just bought this business and I need to setup a new solution for…”).

Sometimes it’s not as clear (“I’ve been using XYZ tool for a while, but lately I think we’ve outgrown it and it’s showing in certain ways”).

This question in particular often requires a bit of proddding and follow ups, like “Hmm, why is that?”. There are golden nuggets hidden inside those follow ups.

How have you been handling that (issue or pain) up until now?

Your product is most likely not their first attempt at dealing with this problem or pain or aspiration.

They’re probably using another tool, or trying to handle it manually somehow.

Whatever that current solution is, you should consider to be your competitor—even if it’s a just spreadsheet.

This helps you inform your positioning. I see positioning as the effort to align your product so that customers can correctly categorize it in their mind while also differentiating in a few meaningful ways.

How are you using that current solution? What’s working well? How does it fall short? Why are you seeking an alternative?

I don’t think this gets asked enough but it’s super important.

You need to gain a clear understanding of how they’ve been using their current solution, and why they’re using it in that way.

This paints a picture (both in your mind and in theirs) of a world where they’re using your product in its place. Does that seem feasible? Does it improve on anything aspect in a meaningful way (to them)?

How much are you currently paying for that solution?

Skip the “is my product idea something you’d pay for?” question. You’ll rarely get an honest answer to that one.

Instead, ask how much they’re paying for their current solution. This gives you actual evidence of their willingness to pay, and the ballpark price point they’re comfortable with.

Oftentimes, customers are calculating in their minds how your product’s cost might replace what they’ve been paying.

If they’ve been using a free solution, it’s still possible that they’re looking to graduate to a better, paid solution. But you’ll want to separate the ‘free product to paid product’ people from the ‘switching from one paid product to another paid product’ people. They’re very different customers.

What is it about (my product) that’s most interesting to you?

It’s usually one key concept or feature that stuck out to them. You want to identify what that is and why that’s so important to them.

This helps you know what to lead with when explaining what your product does and how it’s different or better than the alternatives.

Hopefully, over many conversations, the same key feature or concept comes up again and again.

What would it take for you to switch to (my product)?

A common misconception is that once they’re sold on your product’s ability to solve their problem, the deal is done.

Not so fast. The next hurdle to overcome is their readiness to switch to your to product.

That’s often a lot harder—even when they know yours is the superior solution!

They have to get buy-in from their team. They have to do the work of migrating. They don’t want to disrupt their current work.

Ask them to describe to you how they envision making the switch happen. This helps you understand how likely that is. It might reveal ideas for how to make the transition easier for customers.

What do you think about the pricing for (my product)?

Don’t finish a call without asking them this question. Some will give more honest answers than others but it’s all helpful.

You want to get a feel for whether your price point is what they’d expect from this type of product or not.

But there are other aspects of your pricing besides the price point itself, which you’ll want to get your customer’s take on: How do they feel about per user pricing (if that’s your mode)? Is the trial length sufficient? Would they prefer annual or monthly billing?

What questions do you have about (my product)?

Throughout your conversation, you should be fielding your customer’s questions about your product.

The questions they ask you are often more valuable than their answers to your questions.

Look for patterns in which questions come up again and again. These point to must-have features that every customer wants.

Look for things that customers always ask to clarify. This tells you that your first go at explaining the product didn’t hit the mark.


Don’t build a product in a silo. Talk to customers early, often and ongoing.

If you make this a regular, weekly, practice, you’ll go from zero to paying customers a lot faster.