10 things CIOs wish they knew from the start

“Life can only be understood backwards but it must be lived forwards,” wrote Danish philosopher Søren Kierkegaard. That’s true, but what if by some stroke of magic we could go back in time and give a pep talk to our younger selves. What would we say? To provide some indirect counsel for first-time CIOs, we asked IT leaders to have a quiet word with their younger selves when they first took on a senior IT leadership role.

Give yourself the gift of time

Some CIOs pondered how they managed that most precious resource: time.

“I wish I’d have told myself to buy myself more time, setting out a three-year, step-by-step plan, and not try and get everything right on day one and solve everything in the first year,” says David Henderson, chief technology and product officer at music and entertainment group Global.

Gregory Morley, CIO at services provider United Living Group, says he’d say to the younger Morley: “Stop and take more breaths,” and many others we spoke to agreed, adding that going 100 miles per hour was at best counterproductive and at worst a recipe for burn-out and making yourself unpopular.

Speak up

A tendency to bottle up thoughts is a regret for some who felt cowed or overwhelmed by bosses, fellow execs, or their own teams when they were new to the IT leader role.

“I wish I focused on talent and culture over strategy,” says Henderson. “The right team with the right culture can do anything, and early on, I wasn’t courageous enough to deal with the cynics, time wasters, and the toxic few that affect the majority.”

Similarly, Caroline Carruthers of global data consultancy Carruthers and Jackson recommended being true to yourself.

“It’s something I tell a lot of younger people at schools,” she says. “Don’t limit yourself based on other people’s expectations. I felt I had to be like other people at that level and say certain things and behave in a certain way. When I freed myself and said, ‘That’s not right,’ my career really took off.”

Several CIOs say they wished they had more gumption.

“Once you take the hot seat, don’t second-guess yourself,” says Lenovo global CIO Arthur Hu, with the benefit of hindsight. “There’s a difference between being cautious and being too tentative, and there were times when I could have been more confident. The company puts you in the chair because they trust you.”

Nic Bellenberg, an experienced CIO at publisher Condé Nast and elsewhere, had some practical advice.

“I’d say be fearless,” he says. “I bit my tongue so many times in the first year in my first CIO job [and] I regret not saying to company directors, ‘No, you’re wrong. That’s not the way to do things. What we need to do is…’ I remember being ambushed by two of the owners, who knew that they had underinvested in tech and the tech team for many years. Their opening line was, ‘Well, things aren’t really all that bad, are they?’ I should have said, ‘Worse than you can possibly imagine.’”

Interim CIO at TDS Consulting Tony Healy added: “The most significant risk you can take is not taking any risks, getting bogged down in analysis paralysis and not making a decision.”

It’s not (just) about tech

CIOs were at pains to stress they sometimes overly focused on the tech aspects of the job.

Richard Steward, CTO of UAE real estate company Nakheel, offered a simple formula. “Think and talk business first, technology second,” he says. “There are thousands of technology investments that can be applied to improve a business, but to make the right decisions, you need to understand what your business really needs next and get aligned with your CXO colleagues on that.”

Healy concurred.

“Make a concerted effort to meet the business stakeholders on day one,” he says. “Show them you aren’t just a techie but someone who can make technology work for them. Read the business strategy, understand it, and make it your mission to help deliver it. Focus on how technology can work better for external and internal customers.”

Bruna Pellici, CTO at law firm Linklaters, agreed. “It’s not all about the tech. It’s as much about the people, creating an equitable and diverse team, keeping people motivated and laying the path for development and growth.”

Build bridges

Similarly, fostering deep relationships with others within the organization is something many IT leaders wished they learned earlier.

“I’d tell myself to spend way more time with the board, execs and non-execs, educating them about the true value of tech, rather than it being largely seen as PCs on desks, printers and servers, and periodic upgrades to application software,” says Jerry Fishenden, an experienced IT leader and expert on government digital strategy. “I’d aim to be better at challenging and educating them about some of their most basic assumptions of how the organization operates, how it connects with those it’s there to serve, and where it will be in the future.” 

Healy also had some advice for his younger self.

“Building relationships with your peers, colleagues, and stakeholders is critical to your success as a CIO,” he says. “Take the time to understand the needs and concerns of different departments and build relationships based on trust and collaboration. Focus on outcomes rather than outputs. Don’t get bogged down in the technical details. Instead, focus on how your IT initiatives can help the business achieve its goals.”

Get some training

Today, all CIOs need to think about having a culture of continuous improvement and lifelong learning for themselves and their staff. And they certainly recognize the value of training for new CIOs.

“Get some formal leadership training,” says Keith Baxter, head of IT and InfoSec at Carlow, College, St Patrick’s, in Ireland. “I did my MSc in leadership a little later and it really added a great toolset of frameworks and knowledge to my roles, allowing me great outcomes in various areas.”

Others said a grounding in the nuts and bolts of business operations would have been valuable.

“I think the one thing I would have told myself when starting as a CIO was to get training in understanding balance sheets, EBITDA and finance,” says David Ivell, group chief product and technology officer at edutech company Team Teach. “Often as CIOs, we come from a tech background and then we advise organizations on M&A, accelerating growth, and business restructures, and it’s not just about the tech anymore. I have gained that experience over time, but I could have short-cut that journey.”

Be a storyteller

Today’s CIOs need to translate what’s happening with tech for others who may not understand its nuances and implications. But many are going further and trying to be true storytellers in order to be in a better position to persuade and cajole.

Phil Brunkard, a former CIO and CTO at telecoms giant BT, emphasized the importance of psychology and the power of narrative.

“Stakeholder engagement and how you influence and get people on board is critical to their perceptions of you, and around technology and the IT team,” he says. “If they are protective and change- or risk-averse, that affects initiatives. When you think about implementing change, it’s all about how you speak to the little voice in people’s head. Think about storytelling in films, identify a hero, be aware, and definitely get some training.”

Healy agreed.

“Nobody in a boardroom is going to be interested in technical details,” he says. “Tell a story they can understand. Read and subscribe to magazines, understand the latest trends, follow other CIOs on LinkedIn and look at what they follow or read.”

Invest in your team

Several CIOs stated the importance of teambuilding and team development, including giving people the guidance, resources and tools they need.

Lenovo’s Hu said he was influenced by business writer Jim Collins, author of Good To Great: Why Some Companies Make The Leap… And Others Don’t, who argues that even if circumstances change, having the right people with you makes a huge difference to the success of the organization.

“One of his books talks about who’s on the bus and who’s off that bus,” he says, adding that following that guidance and figuring out the team made a big difference to eagerness and tangible results.

But sometimes, managing teams needs to have a ‘get tough’ component too.

“Don’t underestimate the effort needed to get your team performing and onside,” warns Bellenberg. “You need to be fearless in dealing with weaker team members, dissidents and the generally two-faced. I remember trying to be encouraging, supportive or diplomatic, rather than just telling staff straight that they were not doing well enough or that they were simply out of order. It’s all about managing change and that’s a bigger subject than you can ever be prepared for until you’ve been through it at an organizational level. But if you can cultivate enough fearlessness, you’ll make progress.”

Balance work and life

The CIO role has high levels of responsibility, but some leaders would like to go back and remind themselves that work, and speed of work, isn’t everything.

“One of the things I didn’t have was patience, so I was pushing hard on the people around me,” says Federal Reserve System CIO Ghada Ijam. “I used to be very hard on myself too: ‘Why aren’t you making the progress you said you were going to make?’ I was super-focused on outcomes. So be kind to yourself. Be realistic in your expectations and the pace of your output and the people around you. Bring people along by touching their hearts and minds, not just with objectives and incentives. ‘A’ was the only grade I would accept for myself, and that meant very long hours so there were family sacrifices from that. Running at that pace takes its toll eventually.”

Ijam adds that the Covid lockdown also changed attitudes and made people more attuned to dissatisfaction with working conditions and culture.

“The most fascinating thing that happened to the workforce in the pandemic is it forced us to step back and come back home, find time for hobbies and to enjoy nature,” she says. “That’s one reason why we saw so many job transitions in corporate America.”

Think about equality, D&I, and be kind

United Living Group’s Morley said knowing what he knows today, he would have pushed harder and earlier for diversity. A lot of progress has been made to promote ED&I in the CIO community, he says, but adds that it’s also important to recognize the contributions of people whose work often get overlooked.

“Have a greater appreciation for the many unsung heroes in each business,” he says. “These are the diligent and patient PAs and the administrators in HR, finance, legal, etc. who quietly grease the wheels and make a CXO’s role that much easier.”

Global’s Henderson said bringing outsiders in can provide a valuable perspective too. “I wish I’d embedded more people in the business,” he says. “Getting ambassadors and experts in among the wider business always pays off.”

Enjoy it

Speaking to a range of CIOs uncorked lots of memories, a few regrets, but also laughter and reminiscences. One CIO said that if they could go back, then taking a job at Apple or Microsoft could have been a smart move in terms of share options renumeration. But lots of CIOs said that no matter how many instructions or warnings they would have liked to give their younger selves, one thing is clear: the CIO role is a great career path so, whatever you do, don’t forget to enjoy the journey.