How to know it’s time for a new CIO gig

It’s no secret that the labor market has been volatile in recent years, with workers moving positions in record numbers.

But it’s not just lower-level staffers making moves: Plenty of CIOs have been shuffling jobs during the past few years, too.

In its 2022 Global Leadership Monitor survey, executive search firm Russell Reynolds Associates reported that 56% of technology executives moved to a different company during the prior year — a higher percentage than their peers in finance, human resources, legal, risk & compliance, and operations.

The same survey revealed that 50% of technology executives, which includes CIOs as well as CTOs, CISOs and chief digital officers, said they’re willing to change employers for the right opportunity. Half of that cohort further expressed “a strong desire to leave their current employer.”

But how do CIOs know it’s time to make a move — particularly when there are no real problems driving them out the door?

There are both telltale and personally-felt signs that indicate the time is right to move on — even if everything is going well in a current job, according to experienced CIOs, career coaches, and executive advisers.

“Jobs often have a natural ending,” says Trevor Schulze, who became CIO of analytics software company Alteryx in 2021 after three years as senior vice president and CIO at RingCentral.

Schulze, who says he has some strategies for knowing when to make a move, is thoughtful about what he wants to do for work, acknowledging that he has “a passion for building.” As such, he looks for roles at companies “that I really feel passionate about” and are looking to transform.

The Monday morning test

Even if he’s in a position that meets his transformative criteria, Schulze still keeps an eye out for signs that it’s time to depart. Here, the “Monday morning test” can be a key indicator for making that call.

“First, I’m honest [when asking myself]: Are you energized or deflated on Monday morning going into that workweek? Am I fulfilled in my role? With fulfillment for me meaning I’m learning and growing. Or have I hit a ceiling?” he explains, noting that he has mentored others to use such questions as they make career choices.

Schulze developed this litmus test early in his career when heading to work one Monday following a particularly tough stretch of days. Going into his office, he knew that he and his colleagues would be challenged with fixing some issues that had surfaced.

“So I tested myself by asking: Is this something I wanted to do?” he says. “I said, ‘Absolutely.’ I wanted to be a change agent. I saw exciting things ahead of me.”

Schulze has used this test ever since to help guide decisions on whether to stay in a current role — a practice that is particularly helpful for making the right call when he’s approached by recruiters.

“It’s human nature when you find something dangled in front of you to want to pursue it. But if you are doing a great job at a good organization and you are changing the organization, that’s a great thing and not something that I’d walk away from,” he says. “Technology leaders get approached constantly with new opportunities, and I’m no exception. But if I’m still energized with driving my [current] company’s agenda I say, ‘No thank you.’”

He adds: “I pass opportunities onto other people constantly, and I think more people need to do that. They need to have the courage to say ‘Not now.’”

On the other hand, there have been times when Schulze’s response to that test question has helped him realize it’s best to consider new opportunities. The tipping point? “When too many Monday mornings you feel you don’t want to do this anymore.”

Breaking points

There are, of course, many circumstances that would prompt a CIO to leave. CIOs are sometimes pushed out, something they may recognize is evolving when they’re excluded for strategy sessions or sidelined to special projects. In such cases, advisers say most CIOs can read the tea leaves and know it’s time to put themselves back on the job market.

But veteran CIOs, executive advisers, and recruiters say it may take some introspection and good observation skills to understand other scenarios that might indicate that it’s time to exit a position on a high note.

For example, CIOs who find that they’re transforming elements that they already transformed at least once before often see that as a good time to break away.

“Some CIOs can start again, but others, or even more CIOs, say, ‘I’ve done this and I’ve had a good run.’ And once they get through one transformation, they may not want to do it again there,” says John-Claude (JC) Hesketh, the London-based CEO of global executive search and leadership advisory firm Marlin Hawk.

Coming to such realizations takes time and attention.

“There’s no one clear ‘That’s it, this happened, that’s the linchpin, it’s time to go,’” says Kristen Lamoreaux, president and CEO of Lamoreaux Search, who has seen plenty of CIOs opt for graceful exits by departing while they’re still effective in their roles.

In many cases, she says, CIOs who leave on a high note recognize that the role or its mission are changing in ways that they don’t want or aren’t suited for. A CIO who excels at growth, for example, may see the company — and thus IT — heading into maintenance or cost-cutting mode and, being self-aware about their strengths and interests, see that as a good time to start looking.

“They know it’s not going to be a good fit,” Lamoreaux says, adding that some CIOs have told her that they recognized a need to move on when they started to feel stunted or worn down in their current role, rather than energized.

Still other CIOs decide to leave once they’ve accomplished what they set out to do, she says.

“When you hit certain stage gates, when you can say, ‘I did this. It’s going well. Wow, look at what I did.’ When you’re crafting those bullet points to go your resume and you say, ‘I don’t think I’m going to top that,’ then it may be time to look,” she adds.

Establishing the exit signs in advance

Raj Iyer had an approach like that when it came to his position as CIO for the US Army. Iyer accepted that post in late 2020, after working nearly six years at Deloitte Consulting first as senior manager for Technology Strategy, Defense and National Security and then managing director for Government and Public Services.

Iyer says he decided to take the Army CIO job because it “was a tremendous opportunity to serve our nation and give something back and to help shape its future.”

But he adds: “I also knew I wasn’t going to spend the rest of my career there.”

Iyer says he took the position with a transformation mandate, one that would require “running at 200% all the time every day” to create a “future-ready” organization that he outlined in his Army Digital Transformation Strategy.

He set objectives and deadlines, saying that having these in place motivated everyone to get the work done quickly and on time. And he gave himself a deadline of three years, aiming to hit the markers he had established for himself as CIO and then transition out.

“I knew I had to drive a sense of urgency, and to do that, I knew I had to put time limits on myself so I could pull everyone at a quicker pace than they were used to,” he says, noting that “the sooner I worked myself out of the job, the better for the Army and the nation.”

He further explains: “When you want to be a transformative leader and a change agent, there’s a certain lifespan you have. You can come in as an outsider, question the status quo, make changes. But the longer you stay, you become the status quo, and someone else then has to come in. And so I told myself when we got to a point where we had critical mass, where we built irreversible momentum, it was going to be time for me to leave.”

Iyer stepped down as Army CIO in March 2023 and joined ServiceNow as head of its Global Public Sector business.

Iyer says he has not set deadlines for himself in this new role, noting that his work and the sense of urgency are different at ServiceNow than they were at the Army. He says he’ll stay “as long as I’m challenging myself and I’m in positions where I am learning and can grow and work in a bigger scale than I was before.”

Seeking more challenges

The desire for growth is, in fact, a common refrain among CIOs as they talk about their career decisions and their decisions about whether to stay or leave.

It’s a big part of Mojgan Lefebvre’s story and her three-decade tech career. Lefebvre has been CIO at four companies, explaining that she decided to leave each role despite all their positive aspects for the chance to tackle new challenges.

“I knew I was ready to move,” she says, noting that they were calculated even if they weren’t easy to make.

As an example, she points to her decision to move in 2010 from her job as corporate vice president and global CIO of the French company bioMerieux to work as SVP and CIO of Commercial Insurance Business at Liberty Mutual Insurance.

“That was a tough call for me,” she says.

She had to weigh what she was getting versus what she was giving up, explaining that she would head up IT for a division that was bigger than bioMerieux but would no longer be reporting to a CEO but instead Liberty Mutual’s global CIO.

Lefebvre made the call to leave bioMerieux after a mentor advised her the move to Liberty Mutual “would be the best move you could make” if she aimed to someday be CIO of a large organization.

In fact, she credits that move for putting her on the path to Travelers. She left her position as senior vice president and CIO of Global Risk Solutions at Liberty Mutual in 2018 to become CIO at Travelers. She is now Traveler’s executive vice president and chief technology and operations officer.