More often than not CEOs are expected to lead technological change, drive efficiency through automation, and make fast decisions on complex IT matters. The problem? Most of them aren’t technologists, and they shouldn’t be.
CEOs are strategists, visionaries, and problem solvers. But when it comes to technology, many find themselves flying blind, forced to rely on gut feel, internal teams who may be overstretched, and vendors who speak in jargon. It’s no wonder tech transformation can feel like walking a tightrope with a blindfold.
This article is for the business leaders who know technology is important, but who may feel overwhelmed, under-resourced, and unsure where to start.
The CEO’s Dilemma: You Don’t Know What You Don’t Know
One of the most common challenges CEOs face is knowing who to trust when making tech decisions. Is your operations manager really equipped to manage a system overhaul? Are your developers thinking strategically, or just tactically? Is that low-cost vendor proposal too good to be true?
Because you’re not in the weeds, it’s hard to assess whether your team’s confidence is grounded in skill, or bravado. And unlike sales or finance, where performance can be tracked with numbers, IT progress is often invisible until something breaks.
Common Pain Points for CEOs Managing Tech Projects
Inconsistent Advice
One expert says rebuild, another says integrate, a third recommends off-the-shelf. Who’s right?
Misjudged Internal Capacity
Teams often say “we can handle it”, until scope expands, deadlines are missed, or quality suffers.
Scope Creep and Budget Blowouts
Without strong architecture or technical governance, small projects become monsters.
Hidden Risks
Security holes, poor data handling, or fragile integrations that aren’t apparent until go-live.
Vendor Dependence
Getting locked into a single provider due to poor planning or lack of internal knowledge.
Why It’s Not Your Fault (And What to Do About It)
You weren’t hired to write code or architect cloud platforms. But you are responsible for making smart, strategic decisions, and that starts with getting visibility into what you’re really working with.
Here’s how to regain control:
Test Your Internal Capability
Start with a frank audit of what your current team can deliver.
Ask:
- Have they managed a project of similar size and scope before?
- Do they understand the long-term technical implications (not just implementation)?
- Can they articulate risks and explain trade-offs in plain language?
- What is their track record on deadlines, budget, and delivery?
If the answers raise concerns, it’s not a failure, it’s a flag that you need extra support.
Bring in Independent Technical Advisors
Think of it like a second opinion. An external consultant or tech strategist can help you:
- Perform skills due diligence on your internal team or vendors.
- Run a feasibility and risk review before committing to a build.
- Translate business outcomes into system requirements and user journeys.
- Align your tech roadmap with commercial goals, without the sales pitch.
The best advisors don’t replace your team, they strengthen them by adding experience, structure, and oversight.
Look for Early Warning Signs
If your tech project is already underway, here are red flags that things might be veering off-track:
- Deliverables keep shifting or are vaguely defined.
- Dependencies are unclear or undocumented.
- Communication is inconsistent between tech and business teams.
- You’re not receiving regular updates in language you understand.
- People are busy, but nothing seems finished.
Build a Culture of Transparency and Learning
You don’t need to micromanage every ticket. But you do need a culture where:
- Questions are welcome.
- Failures are surfaced early.
- Non-technical staff feel comfortable asking for help.
- Technical staff feel safe admitting limitations.
This allows you to spot issues early and make proactive decisions.
The Cost of Getting It Wrong
According to the Australian Cyber Security Centre, the average cost of a cyber-attack on an SMB is $276,000. Meanwhile, failed IT projects commonly result in:
- Operational downtime
- Data loss or corruption
- Staff turnover and burnout
- Erosion of customer trust
- Long-term reputational damage
And often, these costs stem not from bad intentions, but from underestimating the complexity of the work at hand.
It’s OK to Not Be the Tech Expert
As a CEO or founder, your job isn’t to be the most technical person in the room. Your job is to make good decisions, and that starts with being honest about what you don’t know.
When it comes to tech transformation, success isn’t just about building the right solution. It’s about assembling the right mix of people, oversight, and strategy to ensure it delivers lasting value.
So, if something doesn’t feel right, or you’re unsure whether your team can handle the challenge, don’t wait. Ask the hard questions. Seek a second opinion. And lead with clarity, not guesswork.