Top 10 Questions To Ask People in Interviews

I’m really happy to see a number of young men and women who I have been working with over the past two years since moving to Boston starting their companies, making money, and growing their teams. It’s really, really cool to see young people discover their first couple of AH-HAH moments, catapulting them into making their hobbies legit businesses. I love it. And with graduation right around the corner for many of them, they have begun focusing their attention on taking their products and building teams around them. Many of them have been asking: “What questions should I be asking people in interviews?”

Great question. And to answer that, I have put together a combination of questions that I like to ask, and questions that I think are really interesting that I picked up from a recent recruiting event put on by Scott Savitz and a number of other entrepreneurs in town. Just remember that of all serious things within a company: managing your board, building your user base, closing deals, etc, there is one that trumps all, and that is BUILDING YOUR TEAM. Interviewing is one of the first steps in the process, and it will end up affecting your life and everyone else’s lives in the company more than anything else.

So, let’s rifle through them with a twelve gauged shot gun, shall we? Right!

1. Tell me about you, from as early as you’d like to go. Where did you grow up? Where did you go to school? (Simply to learn about the person, make them feel comfortable, and make you feel comfortable.)
2. Why did you apply for this job? (This is really telling with regards to motivation and why the person is on your doorstep. Where they pushed to you? Or drawn to you like a magnet?)
3. Why this company? (Ask this. I’ve found most people don’t. I think it’s important to see if the person buys into your vision here. Can they even relate the purpose of the company back to you?)
4. What do you like about work? (Do they like the people they work with most? Do they like the actual work? Do they like the competitiveness? Do they like things structured? Loose? What else can you learn?)
5. What do you like to do for fun? (Simply to learn about the person.)
6. How did you do in high school? (I’ve never asked this, but I was recommended to try it because it might show me how people view their prior selves.)
7. Tell me about something you are proud of. (My favorite question to ask people.)
8. Do you like to win? (Very telling from someone’s response how competitive they are.)
9. Do you like to hit deadlines? (See how quickly they respond with the word “yes.” Find out why they like hitting deadlines. Is it because you want them to, or because they do?)
10. What is your current compensation and what are you expecting? (The easiest way to find out if you are going to be able to afford someone is to ask.)