B2B case study interviews: 7 life-changing questions

Ultimately, if you want a reader to really engage with your case study, they have to identify with your customer. And after seventeen years of writing this format, I’ve realised the questions you ask in your interview make all the difference.

I’ve also learned that the best responses often come from questions you won’t find in a case study best practice guide.

Sometimes, you need to step off the beaten path, and try something surprising.

Engagement through identification

It’s pretty clear why the humble case study is such a go-to staple of B2B content. You get to prove your product or service works for real people in the real world. Your customer gets to look clever. And your prospect gets to find out how another company just like them achieved the thing they want to do (which, let’s face it, is way more interesting than another list of features and benefits).

Everybody wins, right? Well… almost.

Because case studies promise so much, there’s a shedload out there, scuffling for attention. It’s difficult to stand out and make people actually want to engage. So it’s no surprise that a Propolis member asked the community to recommend features that make a case study stand out.

The result was a lively discussion, full of excellent advice. But in truth, there’s no magic trick that’ll transform engagement, and make people want to read. 

When prospects enjoy a case study, it’s because they get your customer’s view. They step into their shoes and walk through the story, hopefully recognising the challenge and pausing for a moment to gaze admiringly at the difference your solution has made.

Your job is to build the world around them as they go. Your raw materials are the insights from your customer. And your only source is the case study interview.

Ask what only they can answer

Before we get into the most important questions, let’s talk about what’s not important. 

Your time with your customer is probably limited. So why would you ask questions you could answer by looking at your sales records, talking to your salesperson, or Googling their company?

What they bought. When they bought it. Which specification they chose. When it went live. What their company does and how many sites and employees it has. All very important to include in your story – and all things you could find out elsewhere.

The most compelling part of any case study is the thing that only your customer knows. Their own, unique, perspective on the story. Because a company didn’t make the decision to buy your product or service; a human being did. So you need to ask questions that provoke a human response.

Questions like…

Q1: “What’s the most important thing you have to achieve in your job?”

Admittedly, it’s a bit of a bold, probing question straight out of the gate, so you might want to ask them a little about their role first, and then slide this into the conversation.

However you do it, your goal is to find out – in their own words – what their biggest priorities are, and why. With luck, you might find out whom they report to; how they’re held accountable and for what; their worries and ambitions. 

This achieves a few things. First, when you’re writing up the context and the challenge, you can add a little more personal perspective and build the hero of your story. You want your next customer to identify with the decision maker more than the company. (Companies don’t buy your stuff; people do.)

Also, you gain an insight into what your reader cares about. Your ideal prospect likely looks a lot like your best customer. Now you know a bit more about what’s important to them, and – crucially – the language they might use to talk about it. Every case study makes me a better writer for this reason.

Most importantly, it helps you ask…

Q2: “…And how does [product or service name] help you achieve that?”

More powerful than lists of features, benefits, and competitors; this gives you a reason. It puts your product’s strengths and capabilities right where they count the most – meeting the challenges, pains, frustrations, and opportunities of your customer’s daily work.

This is the heart of your story. They’ll have to tell you about the challenge they faced, and how this purchase decision specifically links to their work outcomes – the real-world difference they wanted. 

In broad strokes, you now know the message you have to share. You can spend the rest of the call filling in the details. (Hey, just because a case study goes context-challenge-solution-results, there’s no reason you have to ask the questions in that order.)

Q3: “Why did you choose [product or service name] in particular?”

OK, this is already a case study staple. But it’s not the question that’s unexpected here; it’s the answer.

You can absolutely still ask this if you want. It’s important to know what informed the choice. (And if they’re happy to talk about the other options they considered, that’s interesting too, but it’d be a bold move to include it in your copy).

However, be aware that an honest answer to this is rarely what a marketer wants: a neatly-packaged list of the features and benefits that informed a rational buying decision. In my experience, they’ll probably say they like and trust your salesperson, or that your brand intuitively feels like a good fit.

B2B buyers are an object study in System 1 and System 2 decision making. It’s an emotional, gut response that’s post-justified with sensible reasons.

That makes the resulting quotes tricky to use in your case study content – but they’re very useful to know.

(Actually, I once wrote a whole blog post about this very subject.)

Q4: “Tell me about the moment you knew something needed to change.”

The more specific you can get, the better your chances of coming up with a mental image that’s truly memorable – or one that your reader will recognise in their own daily work.

It’s all very well talking in general terms about wanting to improve productivity or reduce costs. But that’s not a compelling reason to make a decision right now, and it won’t help your reader to identify with your customer and their challenge.

Instead, search out the exact moment a switch flipped in your customer’s head. Maybe it was a terrifying backlog – or a physical pile of work, teetering over their desk. It could be a near-miss incident or a lost deal. Perhaps they had to work late and missed their child’s music performance. 

This is your story’s inciting incident. In the classic three-act story structure, it’s the challenge in the middle of act one. It’s when your hero (the customer) decided in earnest to make a change. And by asking about the occasion specifically, you bring up all those emotions – and boost your chances of getting a really personal, colourful quote.

Q5: “What can you say about how much faster/cheaper/more efficient it is?”

Everyone gets stuck on this one. Numbers are powerful. They’re unequivocal. They cut through and help your reader to build a business case. 

Problem is, your customer doesn’t have the numbers.  

In 17 years of case study interviews, I’ve asked quantifying questions literally hundreds of times. And in all that time, maybe a dozen interviewees have had neat metrics they’re confident to share. Sometimes, it’s seen as sensitive information. More often, they’re simply too busy to measure. 

They’re happy to say it’s better – but how much better? That’s anyone’s guess.

The trick here is to re-approach the question a different way. If you can’t get a direct performance figure, see if you can quantify the indirect effect. Has their team’s output increased? Are they winning more business? Has the terrifying backlog come down?

If you can tie things back to Q1 and Q4 – the thing they most need to do, and the problem they were facing – those are high-priority, big-picture items. Most managers will have a reasonable estimate of how things are going at the front of their mind, and to give your story a hook, an estimate is often all you’ll need.

“We used to close about eight cases a day – now it’s more like 12” quickly becomes “Since implementing PRODUCT, Marcie estimates the team’s productivity has increased by 50%.”

Q6: “What difference does that make to your business… and to you?”

In other words: “So what?”

Results are great – especially if you have some nice, juicy stats to share. But what do they really mean?

By the time you get to this part of the story, your reader should be really rooting for your customer. To finish the hero’s journey, you need to return to the start – the thing the company was trying to achieve in the first place. 

(You know the bit in a makeover/DIY show where they compare the “before and after” shots? That.)

This is an opportunity to tell the end of the story and demonstrate business impact – and to do it in the most powerful way possible: using your customer’s own words. 

In the best cases, you’ll be able to reflect their emotions in that conclusion, too. Even though it’s a B2B purchase, this has also affected their daily life. They might be more successful now, less worried, not so exhausted. Maybe they make it to all their child’s performances now. 

In short, what has changed, and how should your reader feel about it? 

Q7: “What is [company/salesperson] like to work with?”

Finally, this is a bonus question, with a very specific function. You’re prompting your customer to say things your company could never say about itself.

You’re friendly. Trustworthy. Professional. You go above and beyond for every client. You’re the smartest people and you give the best advice. Working with you is a daily joy. All those things can be absolutely true, and you still can’t say them without looking disingenuous or boastful. 

Besides, your competitors can say all the same things, whether they’re true or not.

It’s virtually impossible for effective marketing copy to claim anything positive about your character – you have to prove it. (Seriously, would you believe someone who told you they were honest – or would the statement itself make you doubt?)

You can’t say this stuff. But your customer can – because the fact they’re endorsing you is the proof. So, if you have time, it’s worth giving them space to talk about the softer bits of the relationship, and what you’re like as a vendor.

(Actually, one of the privileges of being a third-party copywriter is that customers often praise my client in ways they’d be far too embarrassed to do face-to-face. It’s always fun passing that feedback on.)

Think about the story – then prepare your questions

Most of these questions sit on the fringes of what’s considered normal in a B2B case study interview – but they’re completely understandable from the perspective of what a case study needs to do.

You need to make your customer the hero. You want your reader to identify with the buyer, so they feel motivated to copy them. You should reassure your audience that this decision has made a real-world difference to your customer’s business. 

And, most importantly, you need to do all these things using the most powerful asset in B2B copywriting: your customer’s own voice.

From there, it’s just a matter of asking the questions that give yourself the best chance. These ones should make your conversations more specific, honest, and direct – and hopefully, that’ll flow through to your finished content.

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