Being a founder is an unbelievably challenging journey. The weight of a growing company rests on your shoulders--but it's made better by building a team of strong employees. The only catch? When things are moving fast, it's hard to find time to identify those quality candidates. Asking smart, focused questions helps you make good hiring decisions more quickly.

Having interviewed far more candidates than I can count, I love to ask questions that break convention (moving beyond the "tell me a little bit about yourself..."). One of my own tried-and-true favorites is, "What gets you out of bed in the morning?" It's a way for me to understand what motivates the candidate, and it can reveal people who are mission-driven--a key value in someone willing to take the leap to build a company.

Once I get past the more typical questions in the interview, I'm always on the hunt for smart new questions to ask. That's why I appreciate getting a 3 unique ones from some of the smartest entrepreneurs I know, thanks to conversations on my podcast, The Founders Project. They're too good not to share:

1. "On a scale of 1-10, how lucky are you?"

Jenny Fleiss, founder of both Rent the Runway and Jetblack, shared this one with me. The idea is to get to the heart of someone's optimism. Does this person generally have a positive outlook? When the going gets tough (and trust me, it will) is this someone who will lead by example and keep everyone moving forward?

We often think of luck and hard work at opposite ends of the spectrum. But this isn't meant to ask whether someone can achieve results--it's all a question of perspective. At the end of the day, I want to build and be a part of a team where positivity reigns. Candidates who respond with 8+ to this question are likely to check that box!

2. "Who do you go to for advice?"

This one comes from Brynn Putnam, founder and CEO of MIRROR. Given the emphasis we've all placed on mentorship in the workplace, it's increasingly common for candidates to have built up their own personal advisory committees, so to speak.

This question can help you understand two key things. First, how does the candidate make big decisions? Do they prefer to talk it through with numerous people or go with their gut? And second, what relationships do they value most? Perhaps she gets advice from a former coworker (showcasing her lasting workplace relationships), or an expert in her field (and she had the gumption to send a cold email to way back when and has now built meaningful dialogue with).

3. "If 'present you' were competing for a job against 'old you'--i.e. yourself, three years ago--what merits would you argue that 'present you' has?"

This scenario-driven question comes from Howie Liu, founder of Airtable. He always looks to hire people who are obsessed with learning constantly. Is this someone who looks for opportunities to grow his knowledge? Is he deliberate about his personal growth? An ideal answer would reveal that the candidate has invested time and energy in evolving their skills and knowledge over the past few years. For example, perhaps the candidate is a product manager who took coding classes to round out their technical skillset.

I love the question because it's all about self-awareness. It's a modern take on "What is your biggest weakness?" When I ask that, even though it can be cliché, I care far more about the self-awareness the answer unveils. We all have weaknesses, but managing them is made possible when you know they exist.

Have a favorite interview question? Share in the comments below!

Published on: Mar 29, 2019
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