Why Design?

“For anyone who doesn't know you, could you introduce yourself?”

A classic opening to allow the guest to frame their own identity and accomplishments.

“What was the spark that put you on this path?”

Used early in the conversation to uncover the guest's personal origin story and motivation.

“Where does the name [company] come from?”

A simple question that often reveals the core philosophy or a memorable story behind the brand.

“Does the [company] of today look like the picture you had back then?”

Asks guests to reflect on the evolution of their vision versus the reality of their business.

“Take me back to a moment of implosion where a company died because founders couldn't hold it together.”

A provocative prompt to elicit a specific, illustrative story about failure and its lessons.

“What did you see in each other that made you want to be business partners?”

Probes the interpersonal dynamics and foundational trust between co-founders.

“You describe yourself as a [specific term]. What does that mean?”

A follow-up technique that uses the guest's own words to dig deeper into their professional identity.

“Can you give a summary of what you do and who it's for?”

Asks for a concise 'elevator pitch' to clarify the company's mission and target market.

“Take me back to when [major project] first started. What was the pushback?”

Focuses on the challenging early days of an initiative to understand how the guest overcame adversity.

“What separates founders who can hire well from those who get it wrong?”

Leverages the host's expertise in recruitment to get actionable advice on team building.

“If you had to teach me one thing about [topic] in 60 seconds, what would it be?”

A framing device used to get a concise, core piece of wisdom from an expert.

“What did [experience A] teach you that [experience B] didn't?”

Prompts a comparison to draw out nuanced lessons from different career stages or cultures.

“How is the industry doing right now, based on your conversations?”

A timely question that taps into the guest's network to get a sense of the current business climate.