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The Biggest Failure with Expert-level Content
When collaborating with experts to create content, marketers often fail to do one key thing.
Interviews can be a goldmine for crafting expert-level content.
But there’s one big thing I see marketers fail to do when conducting interviews…
Uncover how the expert acquired their expertise.
The first agency I ever owned was a video agency.
We often worked with prominent politicians, Fortune 500 CEOs, professional athletes, and subject matter experts to create short-form documentaries and social videos.
But I didn’t have a traditional media background. I wasn’t classically trained in journalism.
So, I had to learn how to conduct an interview and refine those skills.
After many blah interviews, I figured out one big thing: The most interesting part of a story is the journey.
When you collaborate with experts to create content for your organization, your readers or viewers don’t just want the framework.
They want the adventure leading up to the result.

Tristan Pelligrino & Justin Brown (Co-owners of Marketers in Demand)
Here are some powerful questions you can use to uncover the journey behind the framework:
What did you try? Understanding the experiments, trials, and errors gives context to how the interviewee became an expert.
Where did you fail? Failures often teach more than successes. They shape resilience and innovation.
What was a pivotal point in your journey? Identifying turning points reveals the moments of transformation and growth. An expert’s journey is not a simple linear path. So, ask about the ups and downs along the way.
What was your first major breakthrough? The initial success often sets the stage for future achievements.
LinkedIn is littered with frameworks, playbooks, and “tricks and tips” image sliders.
But the real magic lies in the stories of how these frameworks were built.
The trials, the setbacks, the “aha” moments.
Next time you interview an expert, dig deeper. Ask about the journey, not just the destination.
What are some of your favorite questions to use?
— Tristan Pelligrino
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— Tristan Pelligrino