3 Unique Job Interview Questions You Must Be Ready to Answer

interviewI became an entrepreneur because I wanted to have an impact in this world: to build something bigger than myself. But to do that, I need a great team to help me make better decisions and see through those blind spots. 

The key to building a great team?


This lesson came from my days as a product manager at Google, where I discovered that a great team is based on a meritocracy of ideas backed up by data. Here’s what I learned:

  • Organizations make better decisions when they are based on data, not the HiPPO (Highest Paid Person’s Opinion).
  • In order to make the best decisions, the person who is closest to that decision and who has the data to back it up should come to a conclusion.
  • We need more than just ‘smart’ people; we need people with high EQ as well as high IQ.
  • We need people with passion.
  • We need people who aren’t afraid to take risks and invest their hearts in making the biggest impact possible.
  • We need people who want true ownership over what they work on and are eager to be held accountable for their successes and failures.

These are hard skills to measure, so I’ve worked over the last four years to refine my ability to assess them. I will be the first to admit that I have borrowed my best questions from other entrepreneurs. And to them, I give my thanks.

The following are the three questions I ask every candidate (and you must be ready to answer):

1. On a Scale of 1-10, How Lucky Are You?

Warren Buffett likes to say he won the ovarian lottery. If he had been born into another era, he might have been some animal’s lunch.

We need candidates who are self-aware enough to understand that hard work isn’t enough to guarantee success — we need individuals who are grateful for where they’ve landed in life. Our success is a function of putting you, with all your skills and luck, at the right place at the right time.

2. What’s an Opinion You Hold That Most People Disagree With?

We need risk-takers who are self-assured and confident in their abilities, so when I ask this question, I’m looking to see if you are creative and innovative and can debate to the norm. If you consistently agree with everyone else, we end up with an average outcome.

As humans, we naturally strive for harmony. But I look for people who can challenge themselves enough to step out of this comfort zone. In that same vein, I also like to ask, “Tell me about a time that you disagreed with your CEO. How did you reconcile the issue?”

Bottom line: I look for people who can tactfully disagree, without being disagreeable.

3. If You Had 10 Years to Live, What Would You Do?

I’ll keep this part brief, as I don’t want to “give away” the answer to this question. But it’s one that I’ve A/B tested over and over.

The answer to this third and final question is important to me because I want to make sure we hiring people who are passionate about our brand and our vision for the future. I want to avoid people who are on the “deferred life plan,” who want to work at Optimizely just to have a job or for the money – and pursue what they really want to do down the line.

At the end of the day, I’m looking for humble, down-to-earth and genuinely passionate people. And these three questions get me there.

How would you answer?


For this post, YouTern thanks our friends at Startup Collective!


startup collective


About the Author: Dan Siroker is the co-founder & CEO of Optimizely. The original inspiration for Optimizely came from his experience as the Director of Analytics on the Obama 2008 campaign. Optimizely is the product he wishes he had back then to make A/B testing much easier. Follow Dan on Twitter!




Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.



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