Joe OviedoWhen I’m preparing an interview and already have fifteen questions, I like to read them as if I were the guest. I usually find one I could answer without much thought: “How did you get started?” “What was your biggest challenge?” “What advice would you give someone starting out?” They aren’t bad questions. The problem is that I could ask almost anyone without changing a word.
Before filming, I want to find something I’d be curious to ask this person even without cameras. Sometimes it’s in an old interview. Sometimes two decisions don’t quite fit the way they usually tell their story.
The story they already know how to tell
Imagine interviewing someone who moved from custom projects to a fixed-scope service. They’ve told other interviewers they wanted to stop quoting from scratch, set limits on what was included, and found it easier to work with their team afterward. I could ask for that story again. They’d probably tell it well.
But while preparing, I find out they kept taking custom work for months. That interests me more than the benefits of defining a service. What did they need to see before turning down the next client who asked for something different? Setting boundaries is easy to recommend when you know how it worked out. I want the moment when they didn’t know yet and there was a project they could get paid for.
I’d ask, “Do you remember the first time a client asked for something you used to accept and you said no?” They may not remember the first time. They may remember a time they said yes. Either works if we can get back to what was at stake: what the client asked for, what they stood to lose, and what made them decide.
Plan a route without deciding where it ends
For that interview I’d bring three moments on a page: how they sold the work before, what happened when they tried a narrower offer, and what they still find hard to leave out. They don’t need equal time. If the second moment explains everything, I’d stay there rather than rush to question nine.
Suppose they correct me when I ask about turning down a client: “I wasn’t worried about the client. My business partner was the one who wasn’t convinced.” If I’m glued to my list, I might nod and move on to sales. But a different conversation just opened up. I thought the risk was losing customers; maybe the hard part was convincing someone who knew the business’s finances better than anyone. I’d want to hear her objection and whether it changed how the guest saw the decision.
Preparing well lets me move when that happens. I know why the scene mattered, so I can recognize a better one when it appears. With only a list of topics, I don’t always know whether an answer opened something up or took us off track.
What I’d share with the guest before filming
I’d explain what I want to explore. They don’t need to repeat their whole career. I’m interested in the months when both ways of selling existed side by side. If it helps, they can think of a case they remember well. I’d also ask whether anything should stay private. We can talk about a decision without naming a client, giving the exact price, or sharing details that aren’t ours to share.
I wouldn’t ask them to rehearse a conclusion. If I say the episode will prove setting limits always improves a business, the guest has to contradict me to say some projects were worth accepting. That exception may be the most useful thing for someone considering a similar change.
Before filming, I like to say in one sentence what I want to understand, not what I want the guest to say. Here it would be: “I want to understand how you decide to stop selling something people still buy.” If I have to change that sentence after listening, even better. I probably found something I couldn’t have written on my own before we sat down.
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