What’s the key to the elite case study interview? Painstaking preparation.
It’s certainly fun to interview people doing interesting things and write up their experiences in your nonfiction book. Case studies about individuals who gained influence or clever marketing programs hold plenty of interest.
But when it’s time to write about the CEOs of multi-billion-dollar companies, you’re going to need a different strategy.
I’m about to undertake a team writing project that will include many of these kinds of interviews. And we do have a conduit to these folks and the necessary credibility to get on their radar screens. But this caliber of case study interviews demands a whole other level of preparation.
Characteristics of the elite case study interview
Here are some of the challenges you’ll face when pursuing interviews like these:
- Your desired interview subject is surrounded by layers of PR and administrative folks who are tasked with protecting their time. So you need a powerful case for why you belong on their schedule.
- There is likely already a lot of coverage of their decisions and actions in public news media. Their handlers will tell you that’s sufficient for your needs, so there’s no need to make time for you.
- If you do manage to get on their schedule, you are only going to get one chance. So you need to make sure every moment of that interview is dedicated to getting exactly what you need for your book.
If you’re a great interviewer, you may have gotten by on instinct. That’s not going to cut it for this interview. The price of failure is not just missing out on key details that belong in your book, but a potentially valuable relationship damaged or destroyed.
Preparation is the key
Here’s the key insight: Your interview is not about facts. There are plenty of facts about your interview subject available already. Your interview is about emotions, happenings that were previously hidden from view, and the subject’s thinking process.
That means you need to go into the interview already knowing what events you’re going to write about. Questions like “What did you do next to close that acquisition?” won’t do you much good. Instead, you want questions like “How did you analyze the right approach to the acquisition?” and “Were you ever sure you were going to fail? How did you feel about that, and what did you do about it?”
Those are the kind of questions that will get you the money quotes and descriptions that will make the case study come alive.
To get there, though, you need to do extensive research on the events you’re describing. In fact, you should be able to write a version of the case study now, even before you talk to your interview subject. Insofar as public sources tell the story, you must have that story down cold.
Tools like ChatGPT and Perplexity are essential here. Use them to dig up what happened. Don’t take their word for what they find; review the sources they retrieve and create your own narrative of the events. You must assemble a narrative from the timeline, numbers, and actions already available in the public sphere.
I’ve been doing this to generate what I call a “briefing book” on the people and events we’re pursuing. My collaborators and I can then take that briefing book and use it generate a series of interview questions that will shake loose interesting insights about the interview subject’s reaction to the events.
But it goes further than that. Now when you plan your approach to the subject, you’re not doing a generic interview request. Instead, you can create an intelligent and customized pitch that demonstrates that you’ve done the research on what happened and explains exactly what you’re looking for.
Your interview subject wants to look like a hero. If you show that you’ve understood their actions and what made them successful, you’re a lot further along to convincing them and their handlers that the case study will benefit them as much as it will you.
Assembling a briefing book on every interview subject is a huge boatload of extra work. But without it, you’re going nowhere. These elite subjects are demanding, and rightfully so. You need to show that you’ve done your homework and that your project is worthy of their time.
And that will pay off when your book is published and it’s full of the stories, quotes, and hidden events that aren’t available anywhere else.