What a CEO Should Reasonably Expect from Technology Today (And what to do when those expectations aren’t being met.)
Technology is shifting faster than most organisations can absorb. AI is creating pressure and noise. Systems are becoming more interconnected and more fragile. Leaders are being asked to make major decisions with information that is often incomplete, overly technical, or shaped by competing internal agendas.
In this environment, the most important thing a CEO should expect from their technology landscape is clarity.
If you’re not getting that today, it’s not a failing — it’s a sign that the landscape hasn’t been translated into business terms yet.
Here are five core expectations every CEO should be able to rely on.
1. Technology Should Be Explained in Your Business’s Language
A CEO shouldn’t need to interpret technical jargon or architectural diagrams.
You should expect explanations framed around:
the realities of your sector
the commercial model of your business
the operational pressures you face
the decisions you are accountable for
the outcomes that matter most to you
If discussions sound technical, abstract, or disconnected from the work your business actually does, the problem isn’t your understanding — it’s that the explanation hasn’t been contextualised for your world.
What to do next:
Ask for the explanation again, but tied directly to your revenue model, your customers, your risks, or your operations.
If that connection can’t be made, clarity is missing at the source.
2. You Should Know What Actually Creates Value
Every organisation has a small number of systems or capabilities that truly drive performance — and a much larger set that simply keep things running.
You should expect a clear picture of:
where value is created
what differentiates your business
which systems are strategic, and which are supporting
what would materially impact the business if it failed
If everything feels equally important, you’re working without the map you need.
What to do next:
Ask for a simple, business-first view:
What are our value-driving capabilities, and what is foundational infrastructure?
Even a basic map changes the quality of every decision.
3. Investments Should Make Sense Without Persuasion
When technology aligns with business strategy, the case for investment tends to speak for itself.
You should expect clarity on:
why a particular investment matters
what it enables
what alternatives were considered
what the impact will be if nothing is done
how the business benefits — not just the technology
If a decision relies on selling, pressure, or complex technical reasoning, it’s a sign the value hasn’t been articulated clearly.
What to do next:
Use one grounding question:
What changes for the business if we proceed — and what stays the same if we don’t?
This cuts through noise quickly.
4. Risk Should Be Visible and Understandable
Most operational risk today is technology risk in disguise. CEOs cannot be expected to spot:
fragile systems
single points of failure
legacy dependencies
cyber vulnerabilities
knowledge gaps
integration weaknesses
But you should expect a clear and honest view of these risks, expressed in business terms and prioritised by real-world impact.
If risk feels vague or technical, it’s likely not being surfaced properly.
What to do next:
Ask for the top five risks, described plainly — with emphasis on business impact, not technical detail.
5. Advice Should Be Objective and Commercially Grounded
Technology decision-making should be led by commercial rationale, not:
vendor agendas
individual preferences
legacy habits
personal interpretations
“how things have always been done”
You should expect advice that is unbiased, strategic, and rooted in the realities of your business model.
If you’re hearing conflicting views or navigating noise, it’s usually a sign no one is providing that objectivity.
What to do next:
Ask:
What is the commercial case for this decision?
This instantly exposes whether advice is grounded — or not.
If any of the above feels familiar, it’s a sign your technology landscape may not be giving you the clarity you need.
If you’d like an objective view of where you stand — and what to focus on next — I’m always happy to talk.
