10 ways to ace the IT executive interview

You’ve worked hard advancing your career and are ready to make the shift to leadership. You’ve landed an interview for an IT executive position at a company you like. Like every step that got you to this moment, how you perform is vital for achieving the results you want.What kind of research should you do to ace this interview? What should you wear? What questions should you be prepared to answer? What questions should you ask of your potential future employer?To help you nail the interview, I spoke to IT executives who have hired people for roles like this one, career coaches who counsel IT leaders on landing their next role, and other experts to find out what you should — and should not — do.Here are 10 tips to help you prep.Know what makes the executive interview stand apartAn executive role is more about managing people, communicating with leadership, and thinking strategically than it is about technology itself. That’s what this interview is all about.The IT executive interview is a gauntlet of conversations with high-level management because they want to know whether you can communicate with leaders — including non-technical ones — at the highest level of the organization. “You will need to collaborate with all the stakeholders,” explains Vishal Grover, CIO at apexanalytix. “I look for an individual in this role who can do crisis management. How comfortable are you in a situation you haven’t faced before?”You will also need to be a strategic thinker and be able to grasp and work toward company goals.“I look for people who are intellectually curious and will challenge the status quo,” says Stephen Franchetti, CIO at Samsara. “By the time interviewees get to me, their technical capabilities and skills have been vetted. I’m looking for someone who will come in with a new perspective and be curious to learn.”Understand where each interviewer is coming from to know where to lead themEvery interview is different, so there is no way to truly predict how it will evolve. But for an executive position, you will certainly meet the leadership team, and that will likely mean several conversations. Each person will have their own criteria and questions. Some might want to evaluate your technical abilities, for example. Others might not.“Some companies don’t need you to be technically savvy or knowledgeable,” says Kyle Elliot, founder and tech career coach at CaffeinatedKyle.com. “Other companies, like an Apple or Google for example, will want you to share your technical know-how.”Research will help prepare you, either way. “Use Reddit, the company website, or your recruiter to learn how technically savvy they want you to be,” says Elliot. And check, as you go through the interview, to make sure you are operating at the right technical level. “Allow the interviewer to guide you as to how far into the weeds they want you to go,” he says.However technical you get, you are also likely to be asked to explain how you solved a difficult problem, failed at something, recovered from a disaster, made important decisions, and where you want to be in five years.You don’t have to make yourself look like the hero in every situation. At a high-level interview, they want to know you can learn, admit your mistakes, and take responsibility. Franchetti asks candidates to describe a situation where they tried to solve a hard problem and failed. “I’m looking for people to fess up,” he says. “I also want them to describe what they learned. Everyone makes mistakes. But what did you learn from it?”Research, research, research — and have your talking points downEveryone I spoke to said that interviewers expect candidates to research the company and know its products, goals, mission statements, and more.“Candidates need to understand the top-level company goals and financials,” says Wendi Zhang at Egon Zehnder, an executive search and leadership advisory firm. “Learn what’s been said in the press. Read the website. If you have friends in the industry or that company, ask what’s going on. You should know the greater purpose and priorities for the company.”You should also know yourself and what you want from this role.“Sometimes people at this level feel they don’t need to prep,” says Elliott. “This is a mistake. I encourage people to prep like a politician. Have your talking points down. It’s impossible to prepare for every potential interview question. Instead, prepare the points you want to get across and weave those into the conversation.”Get the balance right on social mediaIt’s easy to track down company executives on social media, read what they have posted, connect with them, and attempt to make friends. But should you?“You have to do that thoughtfully,” says Zhang. “There’s plenty of publicly available information.” Some of that will be in social media.“LinkedIn is powerful,” says Elliott. “Especially for cross-functional partners. If you’re an IT leader, talking to product, UX, or sales and learning what’s important to them can be helpful.”Again, though, be thoughtful about who you connect to, what you discuss, and what information you bring into the interview. There is a fine line between researching a company and coming off as creepy and invasive.“You don’t want to say, ‘Oh, you took a fun trip a year ago!’” says Elliott. “But it can be helpful to know people’s background, if they came from engineering, or if you worked at similar companies. This interview is about seeing how you communicate, how you collaborate.” How you use social media is part of that.Prepare your storiesEffective communication by and large finds its roots in storytelling. When you are preparing, develop some stories about your leadership experiences and have them ready. Recall examples of how you responded to a disaster, solved a problem, overcame an obstacle, or collaborated with a team. Curate your stories before the interview.“Oftentimes, people tell me, ‘I’m strategic; I’m great at leading,’” says Elliott. And when he asks for examples, they are not ready. You don’t want to walk away from the interview and, only then, remember a story that demonstrates your quick, thoughtful decision-making skills. “They will want to see examples and hear stories. Have them ready,” he says.Those stories should be largely pulled from the workplace, not your personal life — however adventurous or compelling. Keep examples pulled from your extreme sports or wilderness adventures to a minimum and, if you use stories like this, make sure you relate them back to the role at hand in ways that reflect well on the kind of leader you will be at their company.Unlearn previous ways of interviewingFor lower-level interviews, and technical ones in particular, searching for typical interview questions and asking an AI for the answers might pass muster. But at this level, the usual tricks around question preparation will backfire.“This can be difficult,” says Elliot, “when you’re used to a right or wrong answer.”Elliot’s clients often ask not only for the most common questions but also the best answers to them. “There isn’t a right or wrong answer,” he says, when it comes to the executive interview. “It’s more about strategy, business value, and the impact you can deliver.”The IT leaders I spoke to agree.When interviewing others for executive roles, they will ask questions or for a story, but they aren’t looking for boilerplate answers. They want to hear your talking points and ascertain how well you communicate.“I’m tuned into their ability to communicate effectively at an executive level,” says Franchetti. “That’s going to be the difference between success and failure in their role. In addition to being able to do the fundamentals like get the job done and lead the team, I’m looking for them to be able to communicate with impact.”So rather than prepping for a particular question, know what you want to say and how you want to say it. Focus on your goals. Prepare your stories. And use these questions as an opportunity to demonstrate your skills.“As you climb in your career, it’s less about right or wrong, less about technical knowledge, and more about that high-level strategy and how you communicate,” Elliott says. “You have to unlearn earlier ways of interviewing.”Practice, practice, practiceYou should absolutely practice. Get an executive coach. Work with your recruiter. Practice with a friend or spouse. This is a performance, and you want to be ready for it.Elliott works with clients before an interview to help them do this.“We develop their talking points,” he says. “And I’ll throw random questions at them. I find questions they haven’t prepped for to see how well they can answer these curveball questions using those talking points.”This will be much easier to do in the interview if you practice beforehand.Ensure your dress reflects how you will show up for the roleAccording to everyone I spoke to, the way you dress matters. But the fashion question doesn’t have a simple answer. Once upon a time, you could put on a suit and, as long as you weren’t dressed for a black-tie gala, never be overdressed. That’s not true anymore.Franchetti, who is CIO of a tech company serving physical operations and based in San Francisco, expects candidates to dress for an interview. “I would expect someone to put effort into how they present themselves,” he says. “That reflects how they’re going to show up to the rest of the organization.” But it is possible to go too far. “If they turned up in a suit and tie, though, that might be over the top,” he says.This can also vary from company to company. For example, in the financial or legal industry, that level of dress formality might be just what the situation calls for.“Do your due diligence,” says Zhang. “Go on social media and try to get a sense for how they’re dressed at that company. Certain companies are more formal. If you show up there dressed in Silicon Valley clothes, there might be a culture shock — similarly, if you go into a casual environment wearing a full-on suit.”Recognize the value of the questions you askThere will come a point, often at the end of the interview, where you will be given the opportunity to ask questions. This is your chance to close on a strong note.“What’s your goal?” asks Elliott. “What do you want them to learn about you? Start there and work backwards to develop your questions.”Franchetti says, if you want to end strong, “Ask great questions. Have three really strong questions. You may not get them all in depending on the length of the interview. But ask insightful questions.”Perhaps one of your questions is about the company culture. Don’t ask the interviewer to describe it. Ask a question that shows you have done your research.“In other words,” says Franchetti, “Don’t ask, ‘What’s the culture like?’ Get more specific. Demonstrate that you know about this company, and you know what you’re talking about.”Perhaps you researched the company’s culture on the website, social media, or news. “Tell them what you know about the culture,” says Franchetti and ask a specific question about it. “It would be great if someone asked me, for example, ‘Your operating principles really speak to me. Tell me how you put them into practice.’”Follow up to underscore fit and interestSending a follow-up note might seem old-fashioned but everyone I spoke to agreed it’s a good idea. This doesn’t have to be long or complex. It can be a simple thank-you email. But you could also use it as an opportunity to drive home one of your goals or to reiterate a talking point.“Follow up,” says apexanalytix CIO Grover. It shows that you are motivated, interested, hungry even, for this role at this company. “This is a good thing. Checking on something, following up, is never a negative. You don’t want to be a pest. But following up tells me that you want this.”