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Follow this guide to do a kickass interview and get the perfect material for a convincing case study.

How to do case study interviews that rock

Follow this guide to do a kickass interview and get the perfect material for a convincing case study.


Case studies are a great way to show the transformative abilities of your product or service. They’re effective because they use the power of storytelling—an age-old medium that we’re wired to enjoy.

But for the story to be compelling, your case study needs the classic narrative elements:

  1.  A hero on a quest to achieve a specific goal (think Tom Hanks’s character trying to find Private Ryan)
  2. Obstacles the hero must overcome to get it 
  3. A super-satisfying resolution at the end (think E.T finally going home). 

You don’t have to be an Oscar-winning screenwriter to use these story elements. But you do have to get the right material from your interviewees. Above all else, this involves listening like a veteran rock star during an epic jam session—but how do you ask the right questions?

Having created dozens of case studies for Philips, Microsoft and more, I’ve developed a proven process for getting great material. Follow this guide to do a kickass interview and take your case study from b-movie to blockbuster!

Get the right folks ‘in the studio’

Case Study Interview Session

Just like a great band, your interview needs the right lineup. Before you even start thinking about what questions to ask, make sure you’ve got the right people involved.

  • Writer 

Ideally, the person writing the case study should run the interview. A good writer who understands storytelling will know when they need to probe for more ‘material’ and when to move on.

  • Interviewees

Interview one or two key-decision makers who were responsible for bringing in the solution that the case study is talking about.  Sometimes you’ll get interviewees who know all the information but just aren’t good talkers, so two is a good number.

Depending on the goals of the case study, you may want to interview people who weren’t key decision-makers. For example, if the case study will show how the solution is making customer experiences better, you may want to speak with some customers in a separate interview. 

  • Account managers/Project managers 

Your lineup could also include a project or account manager from the writer’s team. They can make introductions and help keep the interview on track, and if they have been involved in deploying the solution, may be able to provide further context for the writer.

Get prepared

Remember, a case study interview isn’t just another conversation—it’s a focused effort to get valuable information in a limited time frame. So being prepared can make the difference between a face-melting guitar solo of an interview and an out-of-tune cringefest.

Man speaking in case study interview


Do your research

At the bare minimum, you should know:

  • The interviewee’s company. What do they do? Who do they serve?
  • Key features + benefits of the solution they used

If you have the time, you could also find out:

  • Why the interviewee’s company has been chosen for the case study – usually there’s something interesting about the story, or some sweet success metrics waiting. 
  • More advanced information about the solution 
  • Key industry jargon that may come up and what it means 


Resist the urge to script out shitloads of questions

In my own experiences of being interviewed by journalists as a musician, the worst interviewers have a long list of pre-prepared questions. They’re so focused on getting through their list that they miss opportunities to take the conversation to interesting places.

(I still haven’t got over that time the journalist didn’t ask me how I met Ron Jeremy.)

The same’s true when you’re interviewing customers. Having a few key questions in mind is ok, but focus too much on your pre-scripted questions and you’ll miss out on opportunities to ask even better ones.


During the case study interview

Case Study Interview Recording


Record your interview. This is not optional. Having to write the story from memory would suck, and it’s far easier to get a recording transcribed and work from there.

  • If you’re holding the interview in person, make sure your device works and will pick up the interviewee’s voices. 
  • If you’re interviewing online, use video conferencing platforms like Zoom that let you record.

Video conferencing platforms also give you an easy way to record phone interviews, as they supply a phone number so interviewees can dial in. I recommend using Zoom in combination with Otter.ai for easy transcribing.

Don’t write notes the whole time. If you’re too focused on scribbling notes during the call, you’ll probably miss something important. (Plus, you’re recording the call anyway.)

However, I still keep a pen and paper ready. If you get ideas for a follow-up question while the interviewee’s explaining something important, make a note of it and get straight back to listening. That way you won’t miss any key points and you can come back to your question later. Boom.

Make it easy to stay focused. If you’re going to uncover those juicy insights, it’s vital that you pay close attention to the cues your interviewees give you. So turn off your phone, hide any distractions, and make sure you’re focused.

Wrap things up professionally. When the interview’s over, thank the interviewee for their time and tell them what’s gonna happen next (your project manager may also handle this). If you need to follow up with anyone for further information, make sure you have their contact details.

What questions should I ask in a case study interview?

Ask open questions. Try to avoid too many ‘closed’ questions, i.e. ones that only prompt a yes/or no answer. Answers that are devoid of information are kryptonite for the case study writer.

So instead of asking ‘did you get good results from that?’ ask open questions like ‘what kind of results did you get from that?’ You’re far more likely to get solid material for your story that way. 

Look for a background, challenge, solution and impact. As I said earlier, good case studies are structured like a story. They have a beginning, a middle, an end, and involve a struggle that the ‘hero’ eventually resolves*.

So start at the beginning and make sure you have a solid understanding of the company’s challenge before you move on. This will help you ask the right questions and set the scene for a satisfying ending where everyone lives happily ever after!

*Note: the story’s hero should be the interviewee’s company, not the solution they used. In story terms, the solution is the hero’s sidekick or guide in the movie. The company is Luke Skywalker and the solution is Yoda.

Example background + challenge questions

  • How long has your company been offering [relevant product/service?]
  • What was happening in your company that led you to take interest in the solution?
  • Why was finding a solution to [X challenge] so important?
  • What impact was this problem having on your staff/customers/day-to-day business?
  • How were you handling [the task or problem] before you started using [the solution]?
  • Give me a specific example of a time your company struggled with [the challenge]

Example solution questions

  • How did you start working with [provider of the product/service]?
  • What other potential solutions did you look at?
  • Why did you choose the particular solution?
  • How did you deploy the solution to your team?
  • What was it like working with [the solution provider]?
  • What features of the solution solve [the challenge]?

Example impact questions:

  • What was the effect of the solution upon [the problem]?
  • How much time/money/stress has this saved you?
  • How did your staff respond to the solution? 
  • What surprised you about the solution?
  • What do customers think about the solution?
  • What are your future plans for the initiative?

Ask for metrics. Always ask for numbers that show the scale of the challenge or impact. If the story’s about how a company rolled out new project management software, ask how many projects the company was undertaking at once, and how many people were typically involved in them.

When it comes to impact, how much time or money did the solution save? If the solution means they no longer need to do a specific task, how long was that task taking them every week/month/year?

A few other questions I’ve experimented with.

  • “Describe what [the interviewee’s company] does and why it’s special, in your own words”.

Even though you should already know what the company does, this can be good to ask at the start. Every interviewee has a unique perspective on their company, so this question can unearth interesting background info. 

  • “Was there anything that you were hoping to be asked about that we didn’t get to?”

Usually the answer will be no, but occasionally the interviewee will reveal something interesting that you missed.

  • “If you were to write a tweet about [the project/product/company], what would you say?”

Ask this at the end of the call if you didn’t get a nice snappy summary to use as a stand-alone quote. Another way to ask this is “what would you say to someone else who was considering using [the solution/solution provider]”?


Key takeaways

Man Listening during a case study interview

So right now you’re probably thinking “holy crap Jon, that’s a lot to remember”. We’ve covered a lot of ground, but even if you only remember these key takeaways, you’ll have a good interview:

  • Look for a beginning, middle and end to the story (challenge, solution and impact)
  • Do your research
  • Don’t script out too many questions
  • Record the interview
  • Ask for metrics

The best single piece of advice I can give is this: above all else, be a good listener. When you genuinely pay attention and are invested in writing a great story, the conversation will flow and you’ll get some sweet material.

Now go and do an epic interview!

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