1.  What is the toughest decision you’ve had to make in the past few months?

If you plan to fill in a managerial position, this is among the first crucial questions to ask. As the core of any company’s success are the people,  you need a manager who considers both the “business” aspects as well as human impact of any decision made. What replies too look for? A good candidate made a decision based on analysis and/or reasoning. An excellent candidate made a decision based on data and on interpersonal considerations. At the end of the day, all decisions may look smart on paper, but eventually affect and must be carried out by people.

2. Do you hold any opinions that most people disagree with?

While being a great reality-check question and quick insight into one’s life values and views, this question is essential for identifying risk takers and outside-the-box thinkers. Just the type of startup employees you should have in board if you aim high.

3. Are you willing to learn a new skill for the job?

The best employee for a startup is a versatile employee. Obviously, most candidates would try to woo you by telling “very willing”, however their true intentions can be easily verified. Browse through their resume and ask about their previous work experience. What skill set did they have when they just started working? If the candidate explains that they started out with one skill set and gradually built another one, that may be a sign of practical adaptability, rather than just the insistence of it.  At this point it’s good to ask about their hobbies/foreign languages.Do they speak Spanish? How and why did they decide to learn it?

4. What were you doing the last time you realized you had lost all track of time?

You want passionate and creative people on your team, right?  All exceptional candidates have experienced “being in the zone” at least once in their life (or on a rather permanent basis). The ability to commit passionately to a project is crucial for startups aiming big and during these moments of intense creativity and productivity – the best ideas are born. Try to understand what a candidate feels he was meant to do.  Lack of experience is less important if the candidate has drive and passion similar to your business ethos. You can teach the skills, but rarely you can inspire the true passion.