Day one as CIO can mean opening up a box of leftover IT nightmares. Whether you’re an experienced or first-time CIO, getting started in a new post will be a challenge. To make matters worse, it turns out that the previous leader didn’t only drop the ball but left behind a total shambles that threatens to degrade or destroy IT performance. It’s now your turn to set things right.
Start the rebuilding process by understanding the full scope of the situation, advises Ravi de Silva, founder of compliance advisory firm De Risk Partners. “This means reviewing systems, vendors, policies, and personnel,” he explains in an online interview. It’s important to look at what’s broken, as well as what still works and why. “Before making changes, take a step back and assess the landscape,” de Silva says. “Decisions made without that context can do more harm than good.”
The assessment phase is your reconnaissance mission, says Zaira Pirzada, an IT leader at security threat exposure management services firm Hive Pro, and a former Gartner security and risk management analyst. “You can’t fix what you don’t understand, and assumptions will kill you faster than any zero-day exploit,” she warns in an email interview.
Seek and Study
Begin the reconstruction process with a comprehensive asset inventory — not just the obvious servers and workstations, but every device touching the network, Pirzada suggests. “I’ve seen CIOs get blindsided six months-in by discovering critical systems they didn’t know existed.” She adds that it’s imperative to extend research beyond configuration management databases (CMDB) and asset management tools. Pirzada also recommends extending the inquiry into security functions. “Cyber asset attack surface management (CAASM) tools will give depth and breadth to the digital asset landscape.”
Pirzada advocates running comprehensive vulnerability scans. “Don’t just look at patch levels,” she says. Examine configurations, access controls, and the network architecture. “I’ve found domain admin privileges scattered like confetti across user accounts more times than I can count.”
Evaluate each system on four basic criteria: security supportability, business criticality, integration complexity, and replacement cost, Pirzada says. “A system handling customer data that hasn’t seen a security update in three years is a different problem than an isolated HR application used only during performance reviews,” she explains.
The new CIO should listen to IT teams, business stakeholders, and end-users to uncover pain points and achieve quick wins that will build credibility, says Antony Marceles, founder of Pumex, a software development and technology integration company in an online interview. Whether to rebuild or repair depends on the architecture’s integrity. “Sometimes, patching legacy systems only delays the inevitable, but in other cases smart triage can buy time for a thoughtful transformation.”
Build Support
Connect with your immediate peers — the CFO, COO, CISO, and legal counsel, de Silva suggests. “They’ve likely experienced the pain points and can give you a grounded view,” he says. “It’s also helpful to lean on internal audit or trusted outside advisors who can help pressure-test your early assumptions.”
Establish trust and clarity, de Silva advises. “People inside the organization will be watching closely to see how you lead, especially if the last CIO left things in disarray,” he says. Set expectations, listen to your teams, and communicate priorities clearly. “Focus on small but meaningful wins early to build momentum.”
Support can often come from unconventional corners, such as high-performing team leads, finance partners, or external advisors, all of whom may have experienced their own transitions, Marceles says. “The biggest mistake is trying to fix everything at once or imposing top-down change without context,” he notes. “A new CIO needs to balance urgency with empathy, understanding that cleaning up someone else’s mess is as much about culture repair as it is about tech realignment.”
Your existing IT and security staff will be invaluable, even if they’ve been operating under poor leadership, Pirzada says. “They possess institutional knowledge about system dependencies, workarounds, and hidden issues that no documentation captures.” She also advises creating safe spaces for unlocking truth-telling. “Your team knows where the bodies are buried, but they need to trust that sharing problems won’t get them blamed for creating them.”
Final Thoughts
When you inherit a messy situation, it’s both a technical and leadership challenge, de Silva says. “The best thing you can do is lead with transparency, make thoughtful decisions, and rebuild confidence across the organization.” People want to see steady hands and clear thinking, he observes. “That goes a long way in these situations.”
Remember, too, that every inherited mess is also an opportunity, Pirzada says. “It’s a chance to build something better, establish new standards, and demonstrate the value that thoughtful IT leadership brings to an organization.” The key, she suggests, is approaching the challenge with the right combination of urgency, patience, technical expertise, and business acumen.