How to Handle a Difficult Interviewee (With Scripts!)

BY Holly Yoos
January 14, 2021

Without a good interview, your case study will suffer.

You can probably still write it. But it won’t have the coherent story and sparkling details that make good case studies so irresistible.

So how do you run a great case study interview with a difficult interviewee?

“Difficult” not because they’re a bad person or purposefully uncommunicative. (Although this CAN happen. Some interviewees are combative and gruff, and you need a thick skin.)

But sometimes, difficult interviewees are simply people who feel shy, go off course easily or just don’t offer up the information you need.

Thankfully, the interviewers here at Case Study Buddy have lots of experience with difficult interviewees.

We touched base with some of them recently to learn their strategies for navigating some of the most difficult—and most common—interviewee types.

Not only did they share their best tips, but they also gave us some example scripts that you can put to work the next time you feel stuck on a call.

1.   The tight-lipped interviewee

Sometimes it’s a struggle to get information out of your interviewee.

For whatever reason, they keep their answers brief—and you struggle to pull even basic details from them—nevermind juicy quotes and a compelling storyline.

What should you do when your interviewee isn’t sharing much information? Our case study interviewers recommend the following:

Help them feel comfortable

Some tight-lipped interviewees just need time to get comfortable, so do what you can to help them settle in.

Remember: as nervous as you might be running the case study interview, your subject is ALSO nervous about saying the right thing, the right way.

Get the ball rolling and take the pressure off by introducing yourself, recapping the purpose of the interview and previewing how long it will take. Talking about expectations for the call helps everyone feel at ease.

Then, lead with a couple of softball questions to give the interviewee time to warm up.


“I would love to set the scene. Could you share who your customer is and who it is that you serve?” 

“Could you start by telling me more about Customer X and the role that you play?”

Avoid jumping into sensitive questions or topics too quickly. Topics about their pain points or challenges might feel imposing to open up about too early in a call. Similarly, questions about results and ROI can feel downright invasive if you haven’t built up rapport yet.

Take it slow and ease in!

Keep your questions broad and open ended

Some interviewees need a bit of space to think and formulate their responses.

If you spray them with too many questions too quickly, they struggle to expand on their answers—so ask questions that are broad and open ended.


“How has the new ecommerce experience impacted your offline channels?”

“Can you walk me through what was happening in your company when you guys decided to make the switch?”

There’s a time to get specific and really dig into a concept or idea—but it’s better to go for the more granular responses and ideas once they’ve already given you their broader perspective.

Ask the same question a few different ways

Sometimes, people need a mulligan—especially when they’re just getting warmed up.

Don’t feel bad about asking what’s essentially the same question through a slightly different lense or angle.

Ask follow up questions

Even when you keep your questions broad, you may still elicit only short responses.

In that case, use follow up questions to pull out the rest of the story.


“You mentioned that you were spending hours on support issues when onboarding. What was going on?”

“Can you tell me more about the impact of that data breach?”

Reassure them that their responses are helpful

Sometimes case study interviewees worry that they’re not giving you the information you need, so they hesitate to expand on their answers.

Providing reassurance throughout the interview that you find their responses helpful can alleviate that concern and encourage them to go further in their descriptions.


“I love how you put that….”

“That’s a great qualitative description….”

You can combine these reassurances with follow-up questions when you need a little bit more info. This is a subtle way of making your subject feel great about what they’ve already shared, and showing them you’re interested in learning even more.

Express genuine interest

It can also help to express genuine interest in the project or details your subject is sharing with you.

This isn’t something you should need to manufacture. After all, the project wouldn’t be the subject of a case study if something impressive hadn’t happened!

Communicate to the interviewee that the steps they took, and results they achieved, are worthy of exploring and sharing.


“You rolled out the application in just three months? Wow!”

“I’m amazed at how quickly you guys were able to turn that around.”

“So you didn’t get any negative feedback from the team? That must have been a huge win.”

Interest can also take the form of a follow up question. When your questions sound like they come from a place of genuinely wanting to know more of the story (instead of ruthlessly barraging someone with a set of predefined questions), it makes the conversation much more natural and easier to contribute to.

Don’t rush to fill the silence

In your excitement to get to the heart of the story (or nervousness at the level of information you’re getting back early on), it’s tempting to plow through every awkward silence.

But sometimes, interviewees use that silence to organize their thoughts. If you rush to fill the void, you may stomp on what they were about to say and lose something valuable.

A momentary awkwardness might prompt an interviewee to reveal a hidden narrative nugget.

As a practice, try committing to silence: after asking your question, refuse to allow yourself to interject until the client has had time to speak. If you need to, count to 10 during silent pauses—you might be surprised to find that gaps that felt like ages are really only a few seconds long!
(Just make sure you listen in carefully when the subject starts sharing again!)

Give them one last opportunity to share

Before concluding the interview, give tight-lipped interviewees one last opportunity to expand on their answers or introduce something new.


“Before we finish up, is there anything else about this project that we haven’t talked about?”

“Is there anything you think would be useful or helpful to others making a decision like yours that we haven’t covered yet?”

“Thanks for putting up with all my questions. Is there anything else I haven’t asked you about that you think would be important for me to know about your experience?”

Sometimes, they’ve been waiting patiently to get to the aspect of the project they REALLY want to discuss.

2.   The “dry” interviewee

While some interviewees are forthcoming, they may stick to “just the facts” of a story with no extra details or anecdotes to add flavour and spice.

Fortunately, our professional case study interviewers have some tips here as well.

Ask for specific examples and stories

This may seem self-evident, but it’s easy to forget that you can ask for anecdotes directly.

Other times, asking a story-based question can get things ‘unstuck.’


“Within the scope of this project, are there any anecdotes that we can highlight?”

“Can you tell me about a time when….”

“Is there a specific example you can think of when things went awry when you didn’t have control of your data?”

Follow the emotion

A good way to get dry interviewees to share stories is to tap into their emotions.

If an interviewee experiences excitement, for example, that’s a good place to dig for more information—and it’s often a gateway to an interesting anecdote.


“What did that mean for you?”

“It sounds like that was important. Can you tell me a little more about…”

“Why did reducing that risk matter to you?”

Circle back to previous answers

When you’re finding that your interview is lacking colourful detail, it’s completely acceptable to circle back to previous answers, even if it’s much later in the interview.


“There’s a lot to unpack in what you told me at the start, so let me ask….”

“Something you said a minute ago has come back to me….”

3.   The off-topic interviewee

Sometimes interviewees are uninterested in discussing the topics you need to hit on for your case study. They go off course in directions that may be interesting… but aren’t particularly relevant to the story.

In these cases, give these interview tactics a try:

Keep gently pulling them back

Interrupting a one-way conversation without sounding rude is tricky. But generally, you need to wait for a short break in the conversation and then interject.

Before you pose your next question, emphasize that you’re determined to respect the time they’ve allotted you.


“I wish we could explore that more, but I still have a few more questions…”

“I know you have a hard stop at 11:00, so let me just ask….”

Ask for more time

You can also ask the interviewee for more time if you can see you’re going to run short.

They may or may not give it to you, but regardless it will often help to get them back on track and keep them there.

If an interviewee doesn’t have more time that day, ask if you can follow up via email to get responses to a few specific questions. Sometimes, people who ramble verbally do better with specific, written questions.

Take control of the interview from the start

Often, having an interviewee go way off topic can be avoided by taking control of the interview from the very start.

You need to set the agenda:

  • Let the interviewee know what you’ll be covering during the interview and how much time you have to do it.
  • Communicate which insights and aspects of the story you’re MOST hoping to cover during your limited time together, and why those are so important.

This will set expectations and help keep everyone on track.

Taking control of the interview at the outset can also help put nervous interviewees at ease. They relax knowing that you’re steering the ship, not them.

4.   The contrarian interviewee

In some cases, the interviewee’s perspective on a project may differ from what you expect.

You’ve been given a brief about the project, but the interviewee contradicts what you’ve been told.

It’s important to recognize that this is less of a “difficult” interviewee problem and more of a “client and customer aren’t on the same page” problem. Don’t beat yourself up if the interviewee contradicts or doesn’t give you the information you need.

Instead, recognize that there’s a disconnect between the two parties, and use the interview to get the interviewee’s version of the project. Continue to get the interviewee to confirm, clarify or contradict the information you have in the brief.


“I have in my notes that your team transitioned over to the new system seamlessly in just six weeks … does that sound correct?

“How would you quantify the results you achieved because of this implementation?”

Hopefully, you’re recording the interview so you can later check back with the person who briefed you—and hopefully get everyone back on the same page.

Similarly, don’t force a story that simply isn’t there.

If the subject is telling you that what you expected simply did not occur, or is not the right angle, trying to force the issue will only frustrate the both of you (and result in a shallow story that’s likely to get rejected during the revisions phase.)

Instead, ask polite, probing questions about the new storyline that’s unfolding. Part of being a great interviewer is knowing when to go off-script.

Tough Interviewees Can Make for Great Case Studies

Just because an interviewee is “difficult” doesn’t mean you won’t get an excellent case study out of the interview.

Often, you just have to make them feel comfortable, ask the right questions and follow their emotions.

When you do, you’ll uncover important details, colourful quotes and compelling anecdotes that will make your case study a page turner.

Want us to handle those tough interviews for you?

Contact us to start the conversation.

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