Hiring · Interviews

What are your favorite interview questions to determine culture/personality fit?

Jessica Alter Entrepreneur & Advisor

February 20th, 2013

Hiring is literally one of the most important parts of my day to day. What I've realized is that it's not that difficult to figure out if someone is smart. It's much more difficult to figure out if they are curious and will go the extra mile on a regular basis. Wondering what your favorite interview questions are to draw this or other cultural fit type characteristics out. Just asking people straight out isn't a good way ;)

Matt Mireles

March 4th, 2013

I have a rule: Don't hire anyone until you've seen them drunk. 

This goes for co-founders and the first ~10 employees. Beyond that, it's difficult to scale this practice. The beauty, however, is that by getting sloshed with a potential hire, you get to understand the person's true motivation and character. It's easy to put on airs in an interview process, but after drink #3, that gets tough. 

Celu Ramasamy FX Artist/Developer at DreamWorks Animation

February 20th, 2013

may be asking about what kind of personal projects they have worked on and observing how much they light up about it? :)


June 16th, 2014

At one startup I worked at, the team and I were on the fence about whether or not we should give an offer to one of our infra candidates. Bright kid. CMU, 3 years at Facebook, but something didn't quite click. We eventually asked him to tell us about a project he did outside of Facebook or school.

We wanted to see what he was truly passionate about and if he loved coding enough to do it just for the sake of making cool things. His reply was "I can't think of anything off the top of my head."

It showed us a lot about them. If someone is truly passionate about something and has put a lot of time into it, they would definitely want to gush about it. It was a deal breaker for us.

Jimmy Jacobson Full Stack Developer and Cofounder at Wedgies.com

February 20th, 2013

We used a startup weekend to interview our last hire. A hackathon or other event is an amazing way to judge personality fit and work habits of a potential employee. Sent from my iJimmy http://twitter.com/jimmyjacobson

AJAY BAM Ceo and Co-founder at Vyrill Inc

February 20th, 2013

I always ask two questions - one open ended and one not.

1. Open ended question -  Tell me your story and how you ended up here? Personal stories can demonstrate passion in what they do/or have done. Stories also tell me on what they believe in, who they enjoyed working for and where they want to take their life. This translates to measuring culture fit..

2. I find that curious people are proactive in life and ask good questions during the interview. Thus, I ask them about what they would like to know about me and the company that is not listed on the site or on my linkedIn profile...

Robert Victor Founder and CTO at PebblePost

February 20th, 2013

I usually turn one of my business problems into a case interview style question. 
I often used this method in Product Management interviews and have adapted it to suit almost any level and role of employee. 

Anyone smart has a rehearsed answer to open ended personality questions or prepared "intelligent" questions about my business. It's best to shake things up.

Using a real business situation keeps people from feeling like they're being interviewed, putting them at ease and allows me to evaluate their ability and interest to work through a challenge.

Here's an example: Some people that visit our site go directly to the pricing page and leave. How do we make sure they read more of the home page content first or convert them to customers from pricing?

Juan Posada Technology executive, startup advisor and entrepreneur. Also a garage tinkerer and maker movement supporter.

February 21st, 2013

Two of my favorites are "what did you do to prepare for our conversation today" and "what haven't I asked you that you would like me to know".

Jessica Alter Entrepreneur & Advisor

June 16th, 2014

One of my favorites is "If I asked the person closest to you to describe you in one word, what would it be and why?" It really asks them to think of THE attribute they think is best about them and it's usually not canned so it's revealing.

Keegan Beljanski Community and Marketing Intern at FounderDating

June 19th, 2014

This topic was featured in today's FounderDating blog post, including some favorite answers from Dharmesh Shah and Micah Baldwin.


Vijay MD Founder Chefalytics, Co-owner Bite Catering Couture, Independent consultant (ex-McKinsey)

February 21st, 2013

Agree with Robert in that I love a case interview.  Anyone who can't structure a problem or gives me vague or superficial answers is already on their way out.

Usually I'll try to focus on something "crazy", so a generic and straightforward approach is unfeasible.  This then begins to test how they think when "edge" stuff happens.  If they can lay out what they'd do along a range of budget shrinking 75% through budget quadrupling (and related expectations in line or higher) then I have a sense that this person can work through uncertainty and change.