When he came on as a software architect at Zappos, one of Christopher Weiss’s first tasks was to start moving the Perl code base to a service-oriented architecture built on Java. When the first piece went live, he discovered he’d configured it with only two database connections -- a massive error for a website that takes hundreds of hits per second. The site crashed. Luckily, the team was able to flip it back and the outage lasted only about five minutes. It was embarrassing, though, especially for someone new to the company. “Now I tell all new developers when they come on, just half-joking, that you’re not a real developer at Zappos until you’ve lost the company a million dollars,” says Weiss, who’s now the company’s principal engineer. In IT, the possibility of failure is a fact of life. “Taking risks is virtually required to be highly successful in the tech world,” observes Ben Hicks, a partner in the Software Technology Search division of the Boston recruitment firm WinterWyman. “Think of tech as the high-growth, high-risk stock you have in your portfolio. The risk and growth go hand-in-hand, and often the most risky stocks are the stocks that make people rich.”

Tolerance for Risk

Many companies say they want their failures to come fast and cheap. How can you know whether your employer will really tolerate risk-taking, though? “You’ll know from the company’s culture and the day-to-day work,” says Everet Taylor, technical recruiter at Rackspace Hosting. “Fanatical” customer support is one of the Rackspace’s core values, so doing whatever it takes to solve a client’s problems – even if that involves some mistakes along the way – is viewed more kindly than not going the extra mile. Indeed, many companies ask job candidates, “What’s the biggest mistake you ever made and how did you handle it?” Here are some of the things they’re looking to find out.

• That You Have Ideas: Good ideas are essential, but that involves coming up with a host of not-so-good ideas, according to Richard St. John, author of The 8 Traits Successful People Have in Common. He based the book on 500 interviews with the likes of Bill Gates, Google’s Larry Page and Sergey Brin, and others.“They always say it’s quality over quantity. But I’ve found in my research that it’s usually quantity that leads to the quality,” he says. “To succeed a lot, you have to fail a lot. Most people think, ‘I can’t come up with the wrong idea,’ so they don’t come up with any ideas.”

• That You Can Assess Risk: Zappos’ online shoe-selling was at first considered an out-there idea. But there was some data to suggest it would work. It illustrates how the smart plan is to take calculated risks, Weiss says. “Taking risk for its own sake is stupid. Taking risks when the predicted value is higher than the risk of failure – that’s what we’re looking at.”“Even companies that say they’re willing to accept risk, how much failure they’re willing to accept from you to a certain extent is qualified on the amount of success you’ve delivered in the past,” he says. “So early on, you start by taking these smaller risks that prove that you’re the sort of person whose calculated risks are based intelligently. You don’t want the first risk you take in your career to be a career-ending one.”

• That You Proceed With a Plan: Have data to back up why you think the risk you take is intelligent, Weiss advises. “It shows that (A) you’ve thought through what the risks are, and (B) it’s not that you’re trying to prevent every potential failure. It’s that you have a plan and can communicate what you’ll do if things go south on you.”

• That You Persist: Everyone’s heard Edison’s quote that genius is 1 percent inspiration and 99 percent perspiration. Perseverance is a key trait among successful people, St. John found.

• That You Can Problem-Solve: “We want to see that they can identify what they did in that situation that caused them to fail,” says Taylor. “That they’re self-aware, that they’re humble enough to own that mistake and learn from it and have a game plan for going forward.”

• That You Learn: When they’re asked what they’d do differently in the wake of a failure, too many candidates simply respond that they don’t know and “I wouldn’t get into that situation again.” That, says Taylor, means “they didn’t learn anything.”St. John points out that people tend to not do post-mortems on success, but pore over and obsess about failures – and that’s where real learning occurs.

Weiss warns, though, that in IT, there’s the danger of over-learning from failures – and failure becomes like scar tissue. “What we do is say, ‘Well, I’m never going to do that again,’” he says. “So you build a rule set. Sometimes the rule set is in your head and sometimes the rule set is actually formalized into a set of procedures. Sometimes as companies grow larger, they build up this set of rules from their mistakes. ‘Before you do a deploy, you always do this’ to make sure this never happens again – and these rules are written in blood." “The problem,” he continues, “is that you build up such a gigantic rule book that you become paralyzed by your own scar tissue. Even in learning from mistakes, we have to not over-learn to such a point that you’re so busy not making a mistake that some new company comes along that’s not encumbered with all that and eats your lunch in the marketplace.”