MARCH TO IPO (Part of a series): What interview questions do you ask?

Today this question came from an entrepreneur in India who is on a hot streak with a rapidly growing startup:

"I'm a regular reader of your blog and your insights has helped me tremendously. Here is one more thing I want to ask you:

1. How do I go about interviewing candidates for positions like VP/CXO for Mktg, finance, sales etc.?
2. What questions will help me assess them right?
We have a recruiter firm to shortlist profiles, but they aren't involved in the actual interview process. I involve my key employees and investors for assessing them and then compare notes to get a 360 degree feedback to get better perspective.
Still, I believe there is scope to improve the process. Your feedback will help me make a better team."

Okay, here is how I'll respond to his email: Put yourself in this situation. Since yesterday's blog, you have decided to focus on getting the best people you can find. You may be pre-seed or as in this case, you are suddenly hot and need that missing core team of aces to help you convert from small to world-class. And you have run out of able friends and colleagues for candidates. Next come the strangers (resumes emailed by other strangers, the harried recruiters). What do you ask the candidates to be more likely you are getting the people you want. the ones now represented by their resumes and references?

Here is what I suggest:

1. Use the Search feature on my blog to look up "interview". You will find several suggestions. One popular set of interview tips is from a classic posted on 2006 October 24.
2. Trust your intuition more than resumes and references. You are the expert on the chemistry in your company. You understand how people will fit your company's working culture. You know what kind of person you need for your special business.
3. Ask sensitive and personal questions. You are going to become very intimate with your employees over the next half decade. Get to know their inner secrets before you hire them. "What makes you mad?" "What kind of person irritates you?" and then "Why?" Listen well and you'll learn a lot about the person. This is especially important to do with Asian startups.
4. Ask about their coping with failures. Your startup is a child that will get into trouble. Expect a few scrapped knees. But you want vice presidents who can keep the child from getting into serious trouble. Hire people that know how to keep the child from heading off to play on a dangerous highway.
5. Discuss issues rather than grill a person. Open sharing of ideas about how to solve real problems gives both you and the candidate a chance to be real people discussing important business issues. The goal is not to see who is stronger. Rather, you want to observe how the person thinks. This is relaxing to the candidate and more likely to open up the strong skills of the person for you to observe. And the candidate is more likely to admit shortcomings.
6. Ask "What do you think you can do to help me succeed?" That is an open ended question that is less threatening and offers the chance for the person to be creative during the interview. You will often be surprised at what you hear. I have. And I often get some great ideas as a bonus.
7. Ask yourself "When I am traveling, is this a person whom I can trust to be wise running the business while I am away?" The CEO does not run the business. There is too much for that person to do (constant communicating with investors, raising fresh capital, and endless interviewing and hiring all take 40% of the CEOs time away from managing the startup). The VPs have to be able to operate with very little guidance day to day. Look for such people. They are gems. Keep thinking about how this person would work with you out of touch and that person and others like that in the office. Then you can pick wisely.
8. Be prepared to answer your own question. Able candidates will expect you to respond to any question you ask them. Don't be surprised when the ask you to. Be ready. It's fun to do.

BOTTOM LINE: Get your interview questions ready. Practice them on a friend. Get so good that you can ask your favorite key questions anywhere, anytime, of any candidate. I've seen people interviewed on elevators in hotels, while waiting for an airplane and during soccer matches. Your quick questions lead to discovery of outstanding people who were later hired. As CEO, you'll be interviewing the rest of your life. Become a  master, a black belt, of interviewing. Then you'll add the most powerful element to building your unfair advantage: Great people. I wish you The Best!