4 smart questions to ask before joining a startup

Part of our series on the future of Main Street

Startup founders need more than investors, education, and resources. They need employees. They need talent that will help their company grow. They need you.

Whether you're a marketing magician, a prolific accountant, or at the tip-top of your graduating class, there's a lot to consider before jumping into the startup life. Ask yourself these four questions. Assess the risk, then decide if you ought to say yes.

1. What will I actually be doing at this startup?

There's a lot of excitement and pressure in entrepreneurial settings to get in on the ground floor of a new company, says Scott Meadow, clinical professor of entrepreneurship at the Chicago Booth School of Business. But if you're well into a career path, be cautious. A fresh start might seem tempting, but startups are a meritocracy. Dashed CEO Phil Dumontet played double duty as his first bike-delivery guy in a business of one. Mark Zuckerberg was his own first developer. There's a flat structure in startups that isn't right for everyone. Be very clear on what you'll be doing — and ask yourself if you're okay with it.

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Many startups offer the opportunity to learn a lot, make mistakes, and be really involved in all aspects of a fledgling business. If you just graduated, joining a startup might be the right move. Just know that it's the first of a lot of moves. You almost certainly aren't going to become an instant millionaire or get promoted to CEO within a year. And remember, as the startup grows, you might not grow with it. For example, if the company is sold, the new owners might want to bring in their own staff. You'll probably have to build up your experience over time with multiple businesses and startups.

2. How will this startup make money?

Don't feel uncomfortable — it's fair to ask about the startup's cash flow status before you join.

The startup might be backed by venture capitalists, in which case you could ask about how much capital they have (or how much is left). Ask about other investors, too.

If the founders are footing the bill, it might be worth a little more soul searching. On his popular blog OnStartups.com, CTO and founder of HubSpot Dharmesh Shah says, "There is no real substitute for cash in the bank." He cautions that passion from investors is a positive thing, but it won't buy your groceries.

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Meadow also suggests asking about the competition. If there have been 12 startups in the same sector going strong (or failing), that's something to consider.

Get a sense of the economics of the business. What will it take to be profitable? Because at a certain point, your employer has to make money if you're going to keep making money.

3. How do I feel about this team?

Startup teams are often close-knit groups who burn the candle at both ends. Starting a business is hard work. A lot of hard work. Which means you'll be spending more than 40 hours per week with these people. A lot more.

(More on the future of Main Street: How mom-and-pop businesses can thrive in the 21st century)

A 2014 survey conducted by the Society of Human Resource Management found that 41 percent of employees felt their relationship with co-workers was important to their job satisfaction. Think about how important that is to you.

You don't have to be texting your work pals about the latest episode of Better Call Saul to have job satisfaction, but a strong working relationship will go a long way. Ask yourself, "Should the business be sold or go public, is there someone on your team that you can partner with [for the next venture]?" Meadow said. Institutional investors are more likely to back you if you've done it together before, Meadow said.

You don't have to be best friends with your potential startup team, but know beforehand if you see a productive working relationship.

4. How meaningful is this job?

While we'd all love to fulfill the adage, do what you love and you'll never work a day in your life, not all passion projects pay. Still, you should be able to do something you feel is fundamentally worthwhile.

"If those things are there and you feel you can contribute, then it's a good time to join," Meadow said. "If you guess wrong, you could waste five years of your life. It's imperative that you're relentless about your standards."


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