Why one CEO and serial entrepreneur always asks job candidates, 'What's your favourite business?'

Cindy WhiteheadJP Yim / Getty ImagesCindy Whitehead.

A lot of CEOs have that one interview question they ask every job candidate before making a decision. And some are easier to answer than others.

When the New York Times’ Adam Bryant recently asked Cindy Whitehead, a serial entrepreneur who is currently the CEO of her new venture, The Pink Ceiling, “How do you hire?” she said there are two questions in particular she likes to ask.

She said she first asks candidates to tell her about themselves, and allows them to give her their “three-minute commercial” in which they share their story “soup to nuts.”

Next, she said, she wants to know what their favourite business is, and why.

She told Bryant she asks this to determine whether the candidate would be a good cultural fit for her company.

“It’s probably not a question they’re commonly asked, but those who will fit in with our culture will find it pretty quickly. And it will probably not be a formulaic answer. It will probably be about some mum-and-pop store that they grew up going to and why it was great.”

Whitehead has founded four companies, including Sprout Pharmaceuticals — the maker of the first “female Viagra” drug — which was acquired by Valeant for $1 billion in August 2015.

Read the full New York Times interview here.

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