How to Ace a CIO Job Interview

CIOs seeking new jobs: Time to shine your shoes, press your suits and prepare for interviews. The CIO job market is strong, say executive recruiters. Companies have shifted their focus from cost-cutters and are now looking for visionary IT leaders who can partner with the front office, are focused on external customers, speak the language of business and can use data to drive revenue or uncover new business opportunities, says Katie Graham, managing partner of executive search firm Heidrick & Struggles’ global information officers practice.

As strong as the CIO job market is, competition for these positions is fierce. “There are fewer tables and fewer seats at those tables,” says Shawn Banerji, a recruiter with Russell Reynolds Associates’ information officers practice. “You don’t have Bear Stearns. You don’t have Lehman Brothers. There’s huge consolidation in the healthcare and media industries, as well, so competition for these roles is much steeper than in the past.”

Consequently, CIOs who become contenders for these jobs face an arduous interview process full of potential pitfalls. To help you prepare for CIO job interviews, CIO.com explains what to expect at each round—from the questions you should ask and the ones you’ll need to answer, to mistakes that will crush your chances of landing the job.

Mutual Goals

When companies interview potential CIOs, they’re trying to ascertain three fundamental things:

1. Whether the candidate can help them achieve a particular business goal, e.g. to turnaround a failing project, help with a merger or acquisition, or use technology to better connect with customers.

2. Whether the candidate possesses certain key competencies, such as leadership, business acumen, strategic thinking, relationship building and the ability to get things done.

3. Whether the candidate is a good match with the rest of the leadership team.

Keep in mind that everything the hiring company asks or does during the interview process is designed to obtain answers to these questions. Your goal, then, is to prove that you can help them achieve their objectives, possess the competencies they’re seeking, and that you’ll fit in with the senior management team by drawing on current and previous work experiences.

Understanding what an employer is trying to achieve when interviewing potential CIOs ought to focus your preparation for the interview and guide your thought processes and responses during the interview.

For example, when David Starmer interviewed for his position as the senior director of store solutions and services with Vancouver, Wash.-based pizza chain Papa Murphy’s International, he knew that two of the company’s strategic initiatives were its rapid expansion and helping its franchisees be more successful. So he talked about a business process reengineering effort and a point of sale deployment he had led in the past.

“You need to show them that you’re that rare mix of person who can build the picture of where the organization needs to go, then help it get there,” says Starmer.

How CIO Job Interviews are Structured

While there’s no single interview process for CIO jobs, knowing how CIO job interviews are typically structured, along with what to expect at each round of interviews, will make the interview process less intimidating and help you prepare for the big event.

Candidates for CIO jobs can expect, on average, three to five rounds of interviews, say executive recruiters. The quantity of interviews is driven by the number of people with whom the candidate needs to meet. Because the CIO role touches so many parts of an organization, candidates often have to meet with a number of stakeholders inside the company, says Russell Reynolds’ Banerji.

Round One

The hiring company’s aim with the first round of interviews is to winnow down its pool of candidates—say, from five to three. The executives involved in the first round of interviews are usually the hiring manager, a senior HR leader and a key internal business partner.

You can expect the hiring manager to discuss the specific tactical and strategic challenges and opportunities the company is facing and to ask you for details about your work experiences that can help them. For example, says Heidrick & Struggles’ Graham, if the company is looking for a CIO to lead an ERP implementation, the hiring manager may want you to talk through the ins and outs of ERP projects you’ve previously spearheaded and the returns from those efforts.

As you enter this first round, and subsequent rounds of interviews, your goal is to understand the company as if you were already working there, says Starmer. Reaching this understanding of the company goes beyond studying its financial statements, SEC filings and financial analyst reports, he adds. It requires treating the job interview as a conversation.

Starmer notes that interviews for senior-level position are generally candid affairs that emphasize dialog over canned interview questions. In these conversations, he says, the candidate and the hiring team dive straight into the company’s challenges and the ways you can make a difference.

To encourage dialog—and impress your interviewer—ask questions. Starmer asks why the position is open because the answer might spur a revealing conversation about the cultural impediments the candidate might face. Similarly, Marc Lewis, CEO of executive search firm Leadership Capital Group, recommends asking what made the person who used to be in the CIO role successful or less than successful. Starmer also asks about the relationship between the C-suite and the board of directors.

“Asking probing questions shows a sincere interest in the company and intellectual curiosity, which is an important aspect of a C-level position,” says Starmer.

Adds Lewis, “The best way to make a great impression is to ask great questions.”

As previously noted, it’s not enough to know about the company’s mission, financials and strategic goals going into the interview. Candidates should also have a good sense of the company’s culture, says Graham. Before the interview, seek out current and former employees who can give you the scoop on the company’s challenges, opportunities and culture. The better you understand the softer side of the company, the better you can demonstrate your fit by drawing parallels to organizations where you’ve worked in the past.

One trap to avoid during a CIO job interview are the inevitable hypothetical questions your interviewers will ask to find out how you might handle specific situations, such as working with a difficult customer. Rather than proffering a hypothetical answer to a hypothetical question, bring up an experience similar to the hypothetical situation your interviewer is presenting, advises Graham. The danger in giving a hypothetical answer is that you can’t get into details and you miss an opportunity to highlight the strengths you want to emphasize, she adds.

Another trap that catches many candidates is the executive assistant. “You don’t know it, but you’re being interviewed by the executive assistant, too,” says Graham. “I’ve seen candidates blow up as a result of what they’ve said to those individuals. A lot of organizations use their executive assistants for feedback. It counts much more than anybody would think.”

In fact, one of Graham’s clients pulled a candidate from the final stages of its interview process after three executive assistants overheard the candidate take a business call while he waited for his next interview. The candidate was rude to the person on the other end of the line, and the assistants shared that information with the hiring manager.

CIOs would be wise to treat everyone they encounter with respect. Graham says that in Richard Branson’s book, Losing My Virginity: How I Survived, Had Fun, and Made a Fortune Doing Business My Way, the Virgin Group tycoon shares a story of how he once masqueraded as a limo driver to test a candidate who was interviewing for a job with his company. As the limo driver, Branson tried to make conversation with the candidate on their way from Heathrow Airport to Branson’s office, but the candidate wanted no part of it and was dismissive to the driver. The “driver” promptly took the candidate back to the airport, whereupon Branson revealed himself.

Round Two

Having reached a shortlist of their top two to three candidates, the hiring organization uses the second round of interviews to determine which candidate they want to move forward with, says Graham. If any concerns about your candidacy came up during the first round of interviews, says Leadership Capital Group’s Lewis, the company will address them in the second round.

The second round of interviews usually includes a larger group of executives and may include senior managers in the IT organization.

Graham says to expect these interviews to be less tactical and more relationship-focused. If you spent the first interview talking about your experience implementing an ERP system, during the second round of interviews, when you speak with specific functional executives (such as the CFO or head of supply chain), you’ll want to talk about how you built relationships with each of those functions during previous ERP implementations, adds Graham. You’ll also want to discuss how each of those functions benefitted from ERP.

When you meet with other functional executives, know that they’re trying to find out what you can do for them if you join the organization, says Starmer, even if they don’t ask you that point blank. He says you have to ask these executives about their pain points so that you can tell them how, based on your previous experience, you’ll help them be more effective. To uncover their challenges, Starmer asks the following questions: What keeps you up at night? What do you see as the most significant, unexploited opportunity in the company, and what’s preventing you from getting there?

Banerji recommends asking whether technology is helping these executives achieve their goals or if it’s an impediment. He also says CIOs should try to find out how these executives get rewarded. “Are they rewarded on top line revenue growth? Are they rewarded on profitability? Are there events that need to take place, like an M&A or regulatory compliance?” says Banerji. “As you learn their goals, bring out things you’ve done that have achieved those goals.”

The trick to acing a CIO job interview is being quick on your feet. You need to be able to swiftly process all the information your interviewers are giving you so that you can pull comparable work experiences out of your memory bank, says Banerji.

You also need to look for patterns in what your interviewers tell you, advises Starmer. Hearing a certain theme, challenge or opportunity reiterated throughout your interviews with different executives should indicate the importance of that topic, and you should look for ways to speak to it.

The Final Round

During the final round of interviews, the CIO candidate will typically interview with the CEO and/or a board member, says Graham. At this point, you need to know what keeps the CEO up at night, what’s important to the board, and what the customer thinks, she says. The mistake she sees CIOs make going into interviews with the CEO or board is getting too focused on technical details and not thinking at a strategic level.

“The CIO has to go into these meetings not thinking about the CIO job but about what’s going on at the CEO level, the board level,” adds Graham.

The good news is that if you’ve made it to a meeting with the CEO or board, chances are good that you’ll be offered the job. “If you make it this far, it indicates that the rest of the organization and hiring manager agree that you are the individual they would love to work with, and they want the CEO’s or board’s blessing,” says Graham.

But don’t let that fact make you overly confident. Even after you’ve received a job offer, you can’t let down your guard. “If you accept an offer, then go to dinner with key executives before you start, you better treat that as an interview,” says Banerji.

Banerji shares the story of a CTO whose jocular attitude killed his chances of starting a new job. The CTO was in his soon-to-be new employer’s office one day before he officially started to take a drug screening test and meet with the head of HR. The head of administrative services came by and mentioned that the company was pressed for space and that he wasn’t sure where the CTO’s office was going to be. According to Banerji, the CTO said to the head of administrative services, “I don’t care where you put me as long as I have a bigger office than the people who report to me.” The flip remark got back to the hiring manager, who rescinded the CTO’s job offer.

Even when all the interviews are complete, and an offer is made, “you’re still on stage and you’re still being evaluated,” says Banerji.

Meridith Levinson covers Careers, Project Management and Outsourcing for CIO.com. Follow Meridith on Twitter @meridith. Follow everything from CIO.com on Twitter @CIOonline and on Facebook. Email Meridith at mlevinson@cio.com