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Conduct a case study interview like a pro (with sample questions)

Interviewing a customer for a case study can feel a little scary. Not because you don’t believe in your product. Not because you don’t think the customer is happy.

But because there’s something a little vulnerable about it. You’re putting yourself out there. You’re asking someone to reflect on their experience, and you’re hoping it all comes out well. That’s enough to make even experienced marketers or founders hesitate.

Before you even send the calendar invite, doubts can creep in.

Totally normal. In fact, this is where most people get stuck. They put off the interview because they don’t want to feel unprepared or uncomfortable. They tell themselves they’ll do it “next week.”

You can run a great case study interview, even if you’re not a pro interviewer. Even if you’ve never done one before. This article will show you exactly how. But first, let’s talk about what success actually looks like.

What you’ll learn (and why it’ll help)

This guide is here to help you run a smooth, confident, and productive customer interview. It’s not about sticking to scripts or fancy journalism tricks. It’s about showing up prepared, asking the right kinds of questions, and getting the richest possible story out of the time you have.

Here’s how we’re going to break it down:

  1. How to pick the right customer
  2. What to do before the call
  3. How to create (and use) a flexible interview guide

What a great interview feels like

Picture this: You hop on a Zoom call. Your customer is cheerful and engaged. Right away, they start sharing stories and examples, giving you a deep look into how they use your product in the course of doing business. For instance, their team used to spend five hours on a process that your product now completes in 20 minutes.

You’re not dragging answers out of them. They’re talking freely. They mention pain points, why they chose your product in the sea of other options available, how they use your product, and how it's helping them accelerate revenue, save time, or save money, or all three.

At one point, they say something like: “Honestly, we wouldn’t have been able to hit our goals last quarter without it.”

That’s gold. You know exactly what questions to ask, so the case study writes itself, and you exit the call with high-value quotes you can use across your sales and marketing funnel. That’s what we’re aiming for. Let’s get into how to make it happen.

Step 1: Choose the right customer

Not all happy customers are great interview candidates. Here’s what to look for:

They’re happy and getting real value

This one’s obvious. You want someone who’s not just satisfied but excited about what your product helped them do. Look for people who gave you positive feedback recently or use your product a lot. Your customer success team, satisfaction surveys, and customers who have left you positive reviews can all be good sources of happy customers who are likely open to a case study.

They represent your ideal future customers

Case studies are powerful tools to drive top-of-funnel traffic, leads, and bottom-of-funnel conversions. For your next case study, choose a customer whose job title, company size, use case, or industry matches the kind of buyer you want more of. Their story should feel relatable to the next person reading it.

There’s already trust

If you or your team already has a warm relationship with them, great. That makes it easier to ask for the interview and ensures a more relaxed, honest conversation. This is a nice-to-have rather than a must-have. You'd be surprised how many of you customers will say 'yes' to a case study, if you target the right client and you know how to ask.

A founder once told me he tried to interview a big-name client who barely used their product. The call was flat. No energy. No specifics. In the end, they didn’t even use the story. A month later, he interviewed a smaller, long-time customer who raved about their experience. That story? Became their highest-converting sales asset.

Step 2: Do your homework before the call

This is where most people cut corners. Don’t. Pre-call prep shows respect for your customer’s time. It helps you ask better, more relevant questions, and most importantly, it helps you guide the interview with confidence, no matter what direction it takes.

Here’s what you should do before each case study interview:

Learn about their business

Read their website. Look them up on LinkedIn. What do they do? Who do they serve? What’s their team size, and what’s the role of the person you’re interviewing?

Check your internal data

How long have they been a customer? What plans or features do they use most? Have they submitted positive feedback or referred others? Any product usage stats or milestones?

Set a rough goal for the interview

Is this story about time savings? Revenue impact? Scaling a process? Set an angle in your mind, so you know where to steer the conversation. You can always adjust.

Example:

If the customer has only been with you for two months but has high usage and early wins, your angle might be about fast onboarding or quick value. If they’ve been around for years and grown with you, it might be about long-term partnership or product evolution.

Step 3: Create an interview guide (not a script)

Notice we’re calling it a guide, not a script. Why? Because real conversations don’t follow scripts. If you treat the interview like a checklist, you’ll miss the magic.

Plus, you'll almost always have to adjust the questions or how you ask them to get the most out of your client. Every client and scenario is unique, and you never know what you'll encounter.

But if you have a strong guide—questions prepared, order mapped out—you’ll stay on track while staying flexible. You'll have help to make the most of every conversation, no matter what your client throws at you.

Let’s build that guide now.

A Simple Interview Framework: Challenge → Solution → Result

Every great case study tells a story. And like any good story, it has three acts: 1) The challenge; 2) The solution; and 3) The result.

For each of these sections, you’ll want 3–5 open-ended questions that help the customer talk freely. Here’s how to break that down.

Act 1: The Challenge

Your goal here is to set the stage. Help the reader understand what life was like before your product entered the picture.

Key themes to uncover:

  1. Priorities and goals
  2. Triggers that made them look for a solution
  3. Pain points and struggles
  4. Their initial requirements

When you're exploring the challenge phase, you're really trying to understand what mattered to the customer before they ever heard of your product. Explore these themes in the order suggested above. That order will make it much easier to weave a narrative after the interview.

We start with their everyday job. Then, something happens that gets in the way: either a problem or a new initiative. Because of this change, they start experiencing pain with their current tools and workflows. And finally, they decided they needed a fix.

1. Priorities and goals

Start by asking about their goals and priorities. What were they hoping to accomplish as a team or business? You might hear something like:

"Our job is to hire the best talent as fast as possible. We take care of everything from sourcing new talent to getting them onboarded once they join the company."

That tells you what success looked like to them. And sets a context that others like them (in this case, other hiring teams) can relate to.

Sample questions:

2. Trigger for change

Next, try to identify the trigger. Something always happens to move a company from "this is annoying" to "we need to fix this now."

"The company's new growth strategy called for expanding into new geographies." Or, it could be as simple as, "Our previous hiring software couldn't support international hiring and onboarding all on one platform."

One trick I almost always use is asking for example. If you asked for an example, your customer might even reply with: "We had three new international hires show up on the same day and nothing was ready for them. No laptops, no logins. It was embarrassing."

Triggers make the story real. They add urgency. We now have a problem that begging to be solved. Problems keep readers hooked on wanting to know what happens next. They want to see how this team or person achieved a solution, so they can learn from it in case they ever find themselves in the same situation. It's storytelling 101.

Sample questions:

3. Pain points and struggles

From there, dig into the pain. Essentially, you want to highlight all the inefficiencies and gaps of the previous solution, whether they were using spreadsheets, an alternative software, a homegrown solution, or doing nothing at all.

Try to understand what they couldn't accomplish or do well with their previous workflow or solution. This adds more color to the trigger covered above.

"Honestly, we had one guy leave in the first week because everything felt so disorganized. That was a wake-up call." When a new hire leaves in the first week, that's a costly mistake. Or, they may say, "It took days of manual work to finally get payroll, taxes, and benefits set up when we hired internationally.

Keep digging. Don't stop if they only mention 1 or 2 pain points. Ask follow-up questions like, "What else wasn't working with your previous approach to international hiring and onboarding?"

Sample questions:

4. Their initial requirements

Finally, wrap up the challenge section by asking what they were looking for in a solution. This sets up the rest of the story.

"We just needed something that would scale hiring internationally and help us stop dropping the ball."

This is the foundation of the case study. The clearer you get on the customer's context, the more meaningful the rest of the story becomes.

Sample questions:

A real example

If your customer says..

“We were trying to onboard 30 new hires in under a month, and our old system just couldn’t scale. It was taking days of work to get each new employee onboarded and we still had errors.”

You can follow up with...

"You mentioned onboarding took days and was error-prone. Why did it take days? What was your previous system missing that resulted in long onboarding times?"

That second question is what gives the story weight.

Act 2: The Solution

Now that you’ve established the “before,” it’s time to explore the turning point: how they found you, what made them choose you, and how your product or service helped them achieve their goals or overcome their hurdles.

Key themes to uncover:

  1. Decision criteria
  2. Why they chose your solution
  3. Which features or services mattered most

In the solution section, your goal is to get a clear picture of how the customer went from choosing your solution to putting your product into action.

1. Decision criteria

Start by exploring their evaluation process. What were they comparing? What did they want in a solution? This gives you insight into how buyers think and what stood out about your offer.

"We looked at three different platforms, but most were overbuilt for what we needed. Yours was the only one that felt lightweight and intuitive."

That’s a great window into buying criteria. You can get this kind of insight and dig further with the following sample questions.

Sample questions

2. Why they chose you

From there, dig into why they ultimately chose you. What tipped the scales? Here's where they'll replay your value props back to you. The only difference is that your customer/interviewee will use their own lens, which is quite powerful.

They'll say something like, "We needed a partner with global coverage, plug-and-play integrations with our tech stack, and infinitely customizable dashboards."

Sample questions

3. Which features or services mattered most

Next, zoom in on usage. Ask about specific features or workflows. First, get them to list all the features that made the biggest difference for them. You can always revisit this list later, but it's helpful to have a list for starters.

Now, you want to deep dive into each feature mentioned. You want to bring out the story behind why they mentioned that feature. Dig into how they used the feature to solve a problem, the experience before and after, and what the impact was on them individually, their team, and/or the business.

"We use your custom workflow feature all the time."

That’s a perfect place to pause and ask follow-up questions like, "What do you use custom workflows for?" and "why does solving the problem matter to you or the business?" and "What was the experience like before you could use our custom workflow tool?"

As you continue learning about the value of the feature, you'll eventually hear statements such as...

"We built out a custom workflow in less than an hour. Our old tool would have required a developer."

Follow up with one quick question about business impact: "What kind of time or cost savings did that mean for you? What could you do as a result?"

Although you won't write extensively about such business results in the Solutions section, these are the kinds of insights that set you up beautifully for the Results section. The story should start to transition naturally from what they did to what they got out of it.

Finally, ask about the ripple effects. What changed in their business, their team, or their day-to-day work?

"Honestly, once we got the dashboard live, our whole weekly ops meeting ran smoother. We spent less time arguing about numbers."

It doesn’t have to be massive. Even small wins add authenticity and relatability to the story.

Sample questions

Act 3: The Results

Now it’s time to bring it home. What changed? What was the impact? This is where you look for ROI. It can be numbers. It can be team morale. It can be strategic wins.

Key themes to uncover:

You’re not just collecting results, you’re collecting proof. This is the part of the interview that turns a nice story into something a buyer can point to and say, “That’s what I want.”

I’m going to share a few examples to help you get the most out of this final stage of the interview. Chances are, your customer has already hinted at the impact your product has had on their business in the Solution section above. This is the time to circle back to those clues. For every feature they mentioned, and how it solved a problem, ask a follow-up question: “How did that help improve the business?”

For example: "Before, we had four different tools duct-taped together. Now it’s all in one place. That alone saved us hours every week." That’s a result. But don’t stop there.

Ask: "Do you know roughly how many hours? What did that extra time allow your team to focus on?"

When possible, ask about quantifiable impact. Ask about metrics. Time saved. Revenue gained. Error rates reduced. Even rough estimates are helpful.

"We didn’t track it exactly, but I’d guess we’re saving 10–15 hours a week just on reporting."

That’s the kind of stat that sticks. Then go broader. What strategic moves did this enable? Did it help them grow? Take on more clients? Launch faster?

"We were finally able to launch in Europe because the team wasn’t bogged down by manual processes."

That’s huge and compelling. Don’t forget to ask about surprises. Sometimes the most impactful parts of a product are the ones no one saw coming. "We didn’t expect customer support to be so fast. That honestly made a big difference for our team’s confidence."

Sample questions

Real example

“We grew 2x last year, and I honestly don’t think we could have done that without [product]. It gave us the structure to scale.”

Follow-up opportunity

*"What did scaling look like for your team? What kind of changes did that allow you to make?"

Pro Tips to Make the Interview Even Better

Here are a few extra tips to take your interviews from good to great:

1. Always hit record (with permission)

This frees you up to be fully present. No frantic note-taking. Just active listening. Plus, you’ll capture quotes verbatim.

2. Put your customer at ease

Remind them there are no wrong answers. This isn’t a performance. It’s a conversation. Let them know they’ll have final say over what’s published.

3. Ask follow-up questions, especially for examples

If they say something interesting, dig deeper. Ask for context, emotion, or a real example. That’s where the best material comes from.

Final thoughts

When you follow these steps, everything gets easier. You avoid awkward pauses. You get better stories. You respect your customer’s time. And you end the call with everything you need to write a case study that actually resonates. And in the end, you won’t just get a great story. You’ll deepen your relationship with the customer, too.

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