by John Edwards

7 questions CIOs should ask before taking a new job

Dec 18, 2019
CareersCIOIT Leadership

Will your new job be a dream come true or a career cul-de-sac? Asking the right questions before you sign is the best way to ensure an IT leadership role is right.

A group of business leaders / board members surrounded by question marks.
Credit: FangXiaNuo / Melpomenem / Getty Images

IT leaders seeking a new job must be prepared to answer plenty of questions on various technology, business and personal topics. Yet before any employment meeting ends, it’s always a good idea to toss a few decisive questions back to the interviewer. After all, as the potential employer seeks to ensure that you’ll be able to perform professionally and productively, you’ll be risking nothing less than your reputation and future career path on commitments made during the interview.

Here are 7 carefully crafted questions you should consider asking before accepting any new IT leadership role.

1. Will I be leading an IT department that’s an equal partner with business, helping to drive innovation and revenue?

Enterprises that don’t include IT in planning and other business-focused activities generally view the department as a cost center that’s little more than a necessary drain on resources. Such organizations are typically less willing to give IT the time and budget needed for exploration and innovation, observes Matt Mead, CTO of technology consulting firm SPR.

“It’s important to be at an organization where IT is viewed as a critical part of the business,” he explains. “You will benefit personally and professionally as the organization will value you and your department more.”

2. What are the attributes you valued most in your previous CIO?

It can be a telling sign — a red flag — if the interviewer has trouble defining what he or she most liked about their enterprise’s last IT chief.

“They may have legitimately never worked with a qualified CIO, but there should be some level of realistic expectations,” says Joe Olson, vice president of the technology and financial practices executive search firm ON Partners.

If the interviewer simply parrots a series of bland CIO attributes, such as “reliability,” “knowledge” and “frugality,” while omitting more salient characteristics such as “leadership” and “innovation,” it may be an indication that the organization is resistant to change and views its CIO as little more than an IT administrator.

“Any [CIO] is going to need advocates within the broader organization to ultimately be successful,” Olson says. “This [question] is a great way to flesh out those biases.”

3. How do you define long-term IT department success, and what methods do you use to measure overall performance?

This question is designed to help you understand the enterprise’s view of IT and the department’s role in contributing to business success. The interviewer’s response will also provide insight into the goals the new CIO is expected to achieve.

“Probing here allows you to discover what their priorities are [in] expense optimization, refreshing team talent, driving strategic change, and determining how well [everything] matches the skills and interests you bring,” says Art Hu, senior vice president and global CIO of Lenovo. “If the company is aspirational, it should be able to articulate clearly the overall company strategy and then link it to what you can deliver as an incoming CIO.”

Shayne Sherman, CEO of IT support service TechLoris, believes that this question will also help you determine how highly the enterprise values its CIO. “While some employers may look at you as leading the way in technology, others may see you simply as the head IT guy,” he notes. “See what the company’s expectations are and if they line up with what you have in mind.”

4. A few years from now, how will you know that I am a successful CIO?

You can use this question to reveal the type of CIO the organization is searching for. Enterprise expectations are as diverse as CIO candidate’s personalities, observes Mikhail Papovsky, CEO of Abraic, an IT management consulting firm. “If the organization is trying to run a tight IT ship and you’re a frugal-style CIO, it’s a great match,” Papovsky says. “If you’re a strategic thinker and the organization is looking to stabilize its current technology, [you’re] doomed.”

5. What’s the size of your organization’s IT budget?

This is a potentially touchy, but critical question. “Make sure they’re not going to have you running the department on a dollar a day,” warns Jon Hill, CEO and chairman of energy industry management consulting firm The Energists. “You’ll need people and resources to keep the department running, so you have the right to know that [budget size] before you commit to the position.”

As a current or aspiring CIO, you probably already have at least a general idea of how much money it takes to run a specific type of IT department. Apply this knowledge to the position you’re interviewing for.

“You’ll have to look at the size of the organization and run the numbers to see if they add up,” Hill says. “That’s going to have a huge impact on your effectiveness and your happiness.”

If you’re hesitant to ask this question outright, Hill advises discussing the types of challenges the department is currently facing. “Often, this will lead to a discussion about budgetary limits,” he notes. “Then you can segue into the money question by saying something like: ‘If you don’t mind me asking, what type of budget would I be working with?'”

6. How would you define your organization’s vision and culture?

Chances are, you’ve already done your due diligence by learning all you can about your potential future employer, including its focus, financial status and competitive stance. You’ll also want to further validate what you’ve discovered by asking the interviewer to describe the enterprise’s fundamental vision and culture.

“I suggest asking questions about major programs and how the organization structured itself to achieve these programs,” says Carlos Sanchez, CIO of SUEZ Water Technologies & Solutions, a water treatment and disposal company. “Also, ask how operations, finance and systems work together to achieve success.”

It’s also important to ask questions that will help you determine whether the enterprise’s vision and culture match your own personal beliefs and goals.

“At the end of the day, vision and culture is what attracts you to a company,” Sanchez observes. “Success is a byproduct of something you like — passion for what you do.”

7. How much power will I have to make changes, and will you always support my decisions?

As a C-level executive assuming control over an essential enterprise department, it’s generally assumed that you’ll be instituting new and updated IT approaches and practices. Yet some enterprise leaders may be tempted to second-guess your decisions, thereby eroding your ability to make IT a force for sustained enterprise growth. To minimize the likelihood that your IT strategy will be unwound by a meddlesome CEO, COO, board member or anyone else, it’s important to receive a firm commitment that your IT decisions will be respected.

Many CIOs will simply refuse to join an organization that doesn’t give them undisputed control over their department. Promoting weak IT leadership is also a sign that management doesn’t respect the department’s essential value. “My preference is to work at a company where IT is considered essential to the company’s product and existence,” Mead says. “The companies that embrace this idea are able to best differentiate themselves from the competition.”

If the enterprise requires your decisions to meet specific performance metric goals, ensure that the metrics to be used are still valid.

“Many times, older businesses may still rely on metrics that are outdated and should be changed,” explains Jason David, CEO of software review publisher Software Portal. “Determining how often [they are] revisited … will help you defend any plans you come up with that may disturb these metrics.”

The question not to ask

Don’t inquire about salary or benefits. “If you’re at the table and having the interview, they value what you could bring to the organization,” Sanchez notes. Just as you’ve done your research and set your compensation expectations, enterprise management will also generally know what it plans to offer you.

“Unless the interviewer asks you about it first, I wouldn’t bring it up,” Hill advises. “There will be time to discuss that later on, after you’ve received an offer.”