Memoirs of a CIO: Observations from the Trenches of Tech Leadership

If I ever retire (and that's a big?if because retirement for a CIO inevitably means becoming the family's 24/7 tech support), I think my memoirs could practically write themselves. After years in the trenches of IT leadership, I've gathered enough oddities, challenges, and triumphs to fill a book or at least an amusing LinkedIn post.

Here are some chapters that will make it into?Ctrl-Alt-Del: Tales from the IT Frontlines.

Every C-Level Exec is a Technology Expert

When someone earns a "C" in their title, they seem to gain an honorary degree in IT, which is a fascinating transformation.

The CFO, for instance, often dabbles in cloud migration strategies. "Why don't we just move everything to the cloud by next quarter?" they'll ask as if untangling decades-old legacy systems is like switching broadband providers.

The CMO is a visionary. "We need AI," they'll declare. When asked?what kind?of AI, the response is a thoughtful pause followed by, "You know… the kind that makes things smarter."

And let's not forget the CRO, who has brilliant ideas about system integrations: "Why can't everything

just talk to everything else?" Oh, it can if you've got a spare year and a budget the size of a small country's GDP.

Here's the thing: I deeply respect my peers. They're incredible at what they do, and I value their insights. But you don't see me walking into the finance team's office, pointing at a balance sheet, and saying, "Why not just fudge the margins?" Let's all agree to trust each other's expertise.

The Miracle of Systems That Solve Everything

It happens like clockwork: a vendor delivers a dazzling presentation, and suddenly, a chorus of "This system will fix?everything!" echoes across the boardroom. This software apparently has answers to all the questions, from productivity issues to global warming.

The excitement often wanes around the fourth implementation delay when it becomes clear that the system isn't solving the problems it's exposing them. A bad process is still bad, even if you automate it.

Systems are enablers, not saviours. The sooner we accept that, the smoother our "digital transformation journeys" will be.

The Data Reporting Fallacy

"Data is the new oil," they say, and I agree, except when it's full of impurities.

Despite this, there's a belief that the right dashboards can make bad data look good. I've seen reporting tools so sophisticated they could be displayed in a modern art gallery. Unfortunately, those dashboards often end up displaying errors, omissions, or the infamous placeholder text: "Error: #DIV/0."

Good data reporting starts with good data governance. Otherwise, you're just shining a spotlight on problems you'd rather keep in the dark.

The "Technology Will Replace Humans" Myth

I occasionally hear someone proclaim that automation, AI, or other innovations will eliminate entire departments.

"Will this system mean we don't need a finance team anymore?" someone once asked me. The irony is that the same people think their desktop PCs are broken when the monitor is unplugged.

Here's the truth: technology doesn't replace humans. It amplifies them. The magic happens when people and tech work together, blending expertise with efficiency. A system is only as good as the people behind it.

The Email Multiplication Phenomenon

Have you ever sent a short, clear email only to watch it spiral into chaos? It starts simply enough: a concise query sent to a small group. Then, one person decides to cc their entire team "for visibility," who then adds more people for "input." Before long, the thread resembles a reality show reunion, noisy, dramatic, and going nowhere.

The kicker? When it's over, someone will inevitably say, "Let's summarise offline." Spoiler alert: we never summarise offline?

Meetings: The Black Hole of Productivity

If email threads are chaotic, meetings are their bigger, meaner sibling.

There's a specific type of meeting that every CIO dreads, the one that could've been an email. You join, only to realise the agenda is so vague it could double as a horoscope, and the discussion is 90% rehashing last week's conversation. After an hour, the group decides to "take it offline," which is corporate-speak for "let's have another meeting."

The solution? Clear agendas, shorter time blocks, and, frankly, fewer meetings.

The Password Paradox

Let's discuss password policies. On the one hand, we enforce rules so strict that they might as well require hieroglyphs. On the other hand, we are surprised when users reuse the same password everywhere or write it on a sticky note stuck to their monitor.

Here's the truth: people hate complexity. The answer isn't stricter policies but more innovative tools, like password managers and multifactor authentication, that make security effortless.

Shadow IT: The Hidden Ecosystem

Shadow IT, the unsanctioned apps and tools employees adopt without informing IT, is as old as the internet.

When we discover that the sales team has been running their workflows on an unapproved app, I'll ask, "Why didn't you tell us you were using this?" Their response? "It was easier this way."

Translation: easier for them, a nightmare for IT. The fix? Build trust and involve employees early in selecting tools. It's not about control. It's about preventing chaos.

The CIO's Balancing Act

Being a CIO is often about managing competing priorities. Marketing wants the new CRM to go live yesterday, operations need a data centre upgrade, and the board demands airtight cybersecurity, all on a budget that seems to shrink by the day.

The art is in balancing today's needs with tomorrow's growth. It's triage, strategy, and diplomacy rolled into one.

What Keeps Me Going

For all its quirks and challenges, I love being a CIO. It's not just about managing technology; it's about solving problems, enabling innovation, and translating complexity into simplicity.

The modern CIO's role is evolving. We no longer manage servers and software; we shape business strategies, bridge departments, and ensure the organisation stays competitive in an ever-changing landscape.

If I ever write that memoir, it will celebrate not just the frustrations but also the rewards of this role. Ultimately, being a CIO isn't about the tech but the people.