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14 Favorite Interview Questions

What was the first way you made money?

Used by Pharma exec, Cindy Whitehead to assess entrepreneurial ambition and hustle for her sales reps. We think it reveals truths about a person’s drive, work ethic and creativity: Did they build a slime empire in grade school, or was their first job post-college thru a family friend?

I’m very curious about why a job with us strikes you as the logical next ‘chapter’ in the book of your life?

Used by restaurateur, Danny Meyer. Every candidate should be able to articulate why they want this job. 

Why did you choose the college major that you did? 

I like to ask this right out of the gate. I try to make it sound more casual, like “What did you go to school for?” It gives me a chance to get to know the candidate and their purest aspirations before they began their professional life. More often than not, they learned something about themselves and had to pivot, and I like hearing about how they navigated that. It’s a good segway, too, for the broader narrative of their job moves.

What’s the biggest misperception people have about you?

This question tells me how self-aware someone is, and if they’re willing to manage an innate behavior when the situation calls for it. For example, is a shy person able to step up when entertaining clients? Will a busy manager invite team members to ask questions?

Tony Hsieh of, uses this question often: “I think it’s a combination of how self-aware people are and how honest they are. I think if someone is self-aware, then they can always continue to grow. If they’re not self-aware, I think it’s harder for them to evolve or adapt beyond who they already are.” (How to Hire the Right Person, NY Times). 

Describe a recent goal you set for yourself and how you accomplished it?

I’m interested to know how candidates challenge themselves, if they’re willing to step outside their comfort zone, how disciplined they are in their approach, and if they’ll persist until completion.

This gives me clues about how curious someone is, their willingness to learn, step outside their comfort zone, how they plan and follow thru.

What qualities do you most admire in your current boss?

I’m interested to see if they can speak appreciatively about their current situation, even if less than perfect. This question also lets me back into their reasons for leaving without directly asking. Most people are prepared for this and it’s hard to get past a canned response. 

What proof do you have that you make your own luck?

I like to hire people that believe things happen for them and not to them. They believe they have control over their destinies rather than blaming others for their misfortunes. Zappos CEO Tony Hsieh likes to ask a similar question. 

Do you have a personal credo or words that you live by? What would you title a book about yourself?

I want to know what standards this person has for themselves and others.

Debbie Millman, who co-founded the Masters in Branding program at SVA and hosts the Design Matters podcast, has a permanent sticky note on her screen reminding her to “Avoid compulsively making things worse.” Which sounds like a lovely trait to have in a work colleague!

If I walked the halls at your office and asked what are you known for, what would your colleagues tell me?

This is different than key strengths — a vanilla question that begs a vanilla answer. It asks candidates to consider how they’re viewed through the eyes of co-workers; what kind of reputation they’ve made for themselves. And, is the attribute they mention important to your company culture?

Tell me about a new idea you suggested and implemented within the last six months. What was the goal and why was it important to you? 

I ask this when I’m looking for a concrete example of someone’s initiative. 

If you worked in a restaurant, what role would you want?

I like this one from ThoughtSpot CEO Ajeet Singh because it reveals what role people naturally gravitate to in groups. Are they an artist that wants to be left alone to create things, someone who enjoys interacting with customers, or someone who excels at operations? How they support their choice gives you insights into their perceived strengths and most comfortable work style. 

What would be on your greatest hits reel? What is the proudest accomplishment of your life?

What someone considers to be their greatest achievements can tell you a lot about their integrity. 

What did you need to master to achieve your last promotion?

Two reasons I ask this: 1) It gives me insight into their level, responsibilities, and degree of ownership, and 2) I’m listening to how they describe and distinguish where they are on career path. 

What would you change about yourself if you could?

The sneaky way to unearth weaknesses, as well as gauge cultural fit and self-awareness.

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