Startups have an extraordinarily high failure rate. When interviewing with the CEO, your instinct may be to impress her with your extraordinary talents. But given the risk you’re taking by considering a job with a company that has an uncertain future, you might want to ask yourself whether you would invest in the company if you were an investor. To get an idea of whether the company, and the person you’re working for, is a good fit, ask about vision, culture and what gets the CEO out of bed in the morning.

Delve Deep Into Strategy

Strategy is fundamental to the growth and success of a startup. To get at the root of this issue, ask not just for a basic spiel on the company’s expected trajectory, but also how strategy will shift when unexpected issues arise. This is closely tied into the CEO’s definition of success: Does she want to run the company long-term, or want to be acquired? Since you’ll likely be offered stock options as part of your employment package, you might want to ask about the startup’s runway — how much cash it has in the bank and whether it will seek more funding soon.

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Assess the CEO’s Strengths

Since the direction and success — or failure — of the startup relies on the CEO’s vision, assess whether she can create a “unicorn” that will alter the industry status quo. George Anders says to ask her what she’s working on, the important skills of her top team members and the hardest choice she’s ever had to make. These show interest on the part of the job candidate, but also reveal a lot about whether the CEO is a good planner, respects those she works with and has self-awareness.

Learn About Company Culture

Culture is what makes the company different from the competition. You might want to compare the CEO’s answer with that of others who work at the startup. If they point out perks like free food and a games room, their culture might be ill-defined. Try to get at the root of what the CEO thinks makes the startup distinctive and worthy of the investment of your time and talents. If you want to develop and grow your skills, ask how the company culture will help you advance professionally and satisfy your need for a positive working environment.

Define the Problem and the Solution

Good CEOs don’t just describe their product; they define the problem it solves. Ask the CEO how it’s relieving a pain point for its customers. To show you know the history of the company, narrow in on a recent innovation and ask why the company chose to introduce it. This will also give you an idea of the company’s research and development process and responsiveness to its customers’ wants and needs.

Ask How Things Are Going

The answers to two questions — what keeps you up at night and how has your day been — give invaluable insight into the CEO’s fears about the company and its current state of affairs. Don’t expect her to be entirely candid, but nestled within those answers will be kernels of truth about the company’s present challenges and how the CEO is choosing to handle them. Your gut instinct can help you decide whether you want to work with her to overcome those challenges, or pass in favor of a different job opportunity.

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Box.net CEO: Aaron Levie by Robert Scoble is licensed under Attribution License

Isabelle Daigle
Isabelle Daigle

Isabelle Daigle runs all content marketing for Hello Focus. She's an avid writer and loves long Netflix binge sessions!