In addition, you'll want to incorporate behavioral lines of questioning that can help you better understand and analyze the candidate's personality traits. Woods suggests one of the most important traits for a CTO to possess is top-notch communication ability.
"The best ones know that a lot of the people they talk with are not technologists, so they need to be able to escape that world of technology and present a clear model to everyone else," he says.
Of course, each CEO has her or his own standards to meet. For Teree at Ticketfly, new hires should be genuinely interested in music, ticket sales, and the technological infrastructure that goes into the operation.
"You want people who really dig it," he says. "Just as you don't want an architect who loves modern homes rebuilding an old Victorian, people are going to be at the end of the day more productive if they like what they are building."
And, on the flip side, they should not be in it for just a good "next step" or resume-builder. "I'm always wary of people who are looking for titles," he says.
One target area to focus on in CTO interviews is the growing – and occasionally volatile – nature of their trade. Woods says CTOs are often capriciously dismissed for a variety of reasons, from a mismatch of expectations to an abandoned project. Ask for reasoning behind job transitions if the candidate has many, and specifically inquire as to what they could have done better in the position. 'For me it's a warning sign when people can't explain what they should have done better,' Woods says.
Checking a candidate's references is the most overlooked part of the hiring practice, but experts say it is absolutely essential, even at the executive level. Many employers also ask that applicants agree to credit-history checks and pre-employment drug screenings; those are optional, and often depend on vocation.
Of three references, have a phone conversation with at least two, and pay attention to the tone of a reference's recommendation, not just its content. Most people feel that it is not wise to hamper future employment for a past employee or coworker, so savvy references won't say anything negative. One tip: Leave a voicemail message that says, "I would appreciate a call back only if you feel this candidate is exceptional." If a reference truly believes in the candidate, he or she will return the call quickly. If you do not hear back from them, you can read into that, too.
"I work hard to find someone who worked with the particular person, but who wasn't their recommended reference," says Ellen Rudnick, the executive director of the Polsky Center for Entrepreneurship at the University of Chicago Booth School of Business. "Through one or two phone calls, you can usually track somebody down to get an unbiased opinion."
When you have an ideal candidate with whom you can agree on a salary and benefit package, begin the on-boarding process as quickly as possible, because helping the new executive become acclimated to your business, its culture, and its standard procedures can be a lengthy process.
In order to ease the transition, because an executive-level hire will likely not have a training program to go through in entering the company, some veterans suggest pairing the new hire with a project manager from the start. The project manager can help the CTO navigate some of your company's intricacies and cultural elements.
Despite that you'll be working closely with your new CTO day in and day out, don't forget to maintain new-employee HR standards, including having a formal progress assessment two or three months after their start date. Take time every few months at least for the first year to allow for questions from them on expectations and review any problems they might be having on projects or in the position.
Dig Deeper: Working with an Executive Search Firm
Hiring a CTO: Additional Resources
Breakthrough! Exploding the Production of Experienced Recruiters, by Steven M. Finkel. 2008.
Hire With Your Head: Using Performance-Based Hiring to Build Great Teams, by Lou Adler. Wiley, 2007.
The CTO Handbook/Job Manual: A Wealth of Reference Material and Thought Leadership on What Every Manager Needs to Know to Lead Their Technology Team,by Mark D. Minevich. Aspatore Books, 2004.
Adventures of an IT Leader, by Robert D. Austin, Richard L. Nolan and Shannon O'Donnell. Harvard Business Press, 2009.
