Standard interview questions are generally boring and don’t always reveal very much about the person you’re interviewing. When you’re talking to a candidate, you want to ask great questions--they’re more likely to engage and you’re more likely to learn important information.
So, we asked entrepreneurs in the community for the best questions that they thought were not only interesting and creative but also revealing. It’s hard to give canned answers to questions like these:
1. What business would you love to start?
Working at a startup requires entrepreneurial energy, so asking candidates about their own projects and ideas is a good way to see how enthusiastic they are about entrepreneurship.
Dharmesh Shah, Cofounder/CTO @Hubspot
2. Put them in a hackathon. What happens?
So this is not really a question, but it’s a great way to judge a candidate’s work habits and skills, as well as how they work with your team.
Jimmy Jacobson, Cofounder @Wedgies
3. What’s your proudest moment and why?
Find out where their head is and what they’re most passionate about.
Sammy Shreibati, Cofounder/CTO @SaveUp
4. Explain how the Internet works.
Having a candidate explain something like the Internet (something that nobody really thinks about), will give you insight into their on-the-spot thought process.
Borrowed from Akamai.
5. If I asked the closest person to you to describe you in one word, what would it be and why?
Forcing someone to think of just one word reveals what they think their best attribute is and shows you what they can contribute to the team.
Micah Baldwin, Cofounder @graphicly and VP of Product @Blurb
6. Ask about their life experiences.
For example, in Israel, questions revolve around a candidate’s military experience with the IDF in order to gauge how someone works on a team.
Eyal Gura, Cofounder @Zebra Medical Vision
7. What’s the worst sales experience you’ve ever had?
Shows a candidate’s ability to articulate a narrative and show intellectual honesty.
Pete Kazanjy, Cofounder @TalentBin
8. Describe one of the best/worst professional situations you’ve ever had. What made it great?
A lot of people don’t like open ended questions because they let the candidate deliver pre-scripted answers. But for me it’s all about the follow-up and drill down.
Frank Barbieri, Senior Vice President of Corporate Development @YuMeVideo, Cofounder @transpera
9. Look at what kind of phone they have. Why did you choose that phone over another one? (e.g. android vs. iOS)
Get a sense of how someone looks at products, as well as what they like and dislike about certain products.
Derek Dukes, Project Manager @Twitter and Cofounder @jetpac
10. What side projects or personal projects are you working on (doesn’t have to be for commercial purposes, but can be just for fun)?
This will give you a sense of how curious they are and how likely they are to take initiative - solve a problem they have or see. All extremely important in the startup environment.
Jessica Alter, Cofounder/CEO @FounderDating