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What 15 Top Tech Entrepreneurs Say About Startup Hiring and Culture Fit Assessment

When a business chooses a new hire, that person is becoming a part of the team. Often hiring managers spend so much time focusing on finding the right fit for a specific job, they lose sight of the big picture. But for companies of all sizes, it’s crucial to always ensure a candidate is a good fit for the organization, as well as the current job opening.

Through utilizing cultural alignment strategies, startups can implement hiring processes similar to those used at some of the biggest, most successful companies in the world. Here are a few tips from top tech entrepreneurs to help small businesses make sure they hire the right candidate at the right stage of the company’s development.

Robert Scoble, CEO, Rackspace

Scoble is straightforward about his cultural alignment strategy. He believes in the advice recommended in Robert I. Sutton’s The No Asshole Rule, which helps entrepreneurs learn to filter out those who might be toxic to an organization.

Tony Hsieh, Zappos CEO

Culture is so important to Zappos, the company requires a second round of interviews solely dedicated to culture fit during the hiring process. Through performance reviews, Zappos also eliminates any employee who emerges as a poor culture fit at any stage of employment. His primary tactic is to look for and prioritize candidates that use "we" and "our" statement in regard to past work history versus "I" and "me" statements.

Dave Carvajal, Former Co-Founder, HotJobs

For startups, Carvajal says the answer is in determining its “cultural DNA.” By taking the time to first understand the personal DNA that makes up an organization, leaders can be more effective during the interview process.

Andy Jassy, Senior VP of Web Services,

In an interview with Gigaom, Jassy cited six major things he seeks in potential hires: intelligence, stick-to-itiveness, big vision/big energy, willingness to debate, people who listen, and startup DNA.

Mark Castleman, CEO, Vobi

Knowing oneself and making clear, unemotional decisions is the key to success in hiring, Castleman believes. True hiring talent comes from experience in both hiring and firing and, unfortunately, this means leaders must sometimes learn through trial and error.

Michael Hughes, VP of Community Development, CoFoundersLab

For startups, Hughes feels it’s more important to provide a simple problem and see how a candidate solves it, rather than going solely by a person’s past experience.

Greg Waldorf, Former CEO, eHarmony

Waldorf sees career progression as an important factor in finding a good candidate. Too many startups focus on finding someone who has an equivalent position, but he has found the best candidates are the ones who have achieved substantial upward mobility.

Jonathan Brill, Startup Specialist

Finding a good candidate is similar to finding the right spouse, Brill believes. He recommends spending as much time as possible with a potential candidate and, at the end of it, ask whether or not that person could run the place for a day while the boss is away.

Nathan Brown, Director of Information Technology,

Brown has six criteria he uses when seeking a new employee: don’t hire out of desperation, never ignore a red flag, personality fit matters, skill sets are sometimes less important, involve team leaders in the process, and interview all potential internal hires before an offer is made.

John Greathouse, Entrepreneur and Investor

Greathouse’s unique approach paints great hires as bank robbers in the early days, spending most days helping business owners “plan the heist.” As a business grows, business owners should look for ATM operators in order to find reliable employees who will provide stability.

Bryan Beal, Angel Investor

When hiring, entrepreneurs should rely heavily on their network initially. Beal believes referrals are essential, especially if they come from colleagues who are familiar with the hiring manager. Once your first key players are in-house then resource outside your network.

Tom Katis, Founder, Voxer

The hiring process will never be perfect, Katis says. For that reason, he believes it’s important that entrepreneurs be ready and willing to quickly remove someone who isn’t working out.

Rob McClinton, VP of Sales, Cyber2Media

McClinton has observed that most of his best hires have had three things in common: an entrepreneurial spirit; honest, straightforward answers to interview questions; and passed interviews with multiple people in his organization.

Erica Friedman, Information Ninja

Any hire of Friedman’s must be able to contribute real thoughts that move the conversation, business, and team forward. Idea people or negative thinkers have no place on a business’s team.

Chris Rickborn, COO, BoomTown

When he was COO at Unrabble, Rickborn described several things he looks for in a job candidate. Among his criteria was a startup mentality—anyone working for a startup should think like a startup, including an ongoing willingness to pitch in.

Over time, entrepreneurs learn to phrase interview questions properly to get the information they need. By following the advice of these 12 experienced professionals, however, some entrepreneurs may be able to more quickly learn to spot someone who isn’t the right fit.



Philip Foti

CEO Sonata Talent Technical Staffing