Four Things 2026 Taught Me

They say poverty breeds character. But I have enough character.

I am beginning to feel much the same way about lessons.

Some of the most useful lessons come from things that didn’t go according to plan: the question that wasn’t asked, the assurance that wasn’t quite as reassuring as everyone thought, or the information that reached the board later than it should have.

When that happens, the first question is typically “who was responsible?” Accountability matters, but another question can be more useful: what could I have done differently?

Looking back over 2026, four things in particular have stuck with me.

1. AI has made judgment more valuable, not less

This was the year when AI became something almost everyone used.

It can analyse information extraordinarily quickly, summarise enormous documents and produce work in minutes that once took hours.

It can also produce complete nonsense with extraordinary confidence.

Air Canada discovered this when its chatbot told a customer he could buy a normal ticket and subsequently apply for a bereavement fare. The airline’s actual policy said the opposite, and a Canadian tribunal ultimately held Air Canada responsible for its chatbot’s incorrect advice.

Google’s AI search feature famously suggested using glue to help cheese stick to pizza. Lawyers have submitted court documents citing cases that didn’t exist because AI invented them.

The obvious nonsense is the least worrying. Nobody is likely to put glue on a pizza. The danger is the answer that is wrong but sounds right.

AI can also create work. A client can feed a document into AI and generate 20 questions for their lawyer in seconds. Some may be excellent. Others may be irrelevant or based on a misunderstanding. The lawyer still has to deal with them and, if charging by the hour, AI may have achieved something remarkable: increasing the client’s legal bill.

The easier it becomes to produce answers and questions, the more important judgment becomes.

2. A risk register is not risk management

Risk reports have become increasingly sophisticated. Heat maps, arrows, risk scores and pages of commentary can tell a board a great deal about what might go wrong.

But identifying a risk achieves very little by itself.

Every significant risk should connect to what is actually happening in the business. There should be clear ownership, agreed actions and responsibility for making sure those actions are implemented. The danger is that producing the risk report can itself start to look like the job has been done. The risk has been identified, assessed, given a rating and reported to the board. The report looks good and the process appears complete. But unless someone is actually doing something about the risk, all that has really been done is to document it.

Some risks simply can’t be mitigated.

War is an obvious example. Putting geopolitical conflict in a red box doesn’t make it less likely. What matters is whether management has thought about what happens if it occurs, who will lead the response and which customers, employees, suppliers and operations could be affected.

Sometimes managing risk means reducing the likelihood that it happens. Sometimes it means being ready when it does.

3. Beware the Knowing Gap

The third lesson concerns what I have come to think of as the Knowing Gap: the gap between when an issue becomes known somewhere inside an organisation and when the board finds out about it.

That doesn’t necessarily mean anyone has done anything wrong. Someone may know there is a problem but reasonably believe it will be fixed, work itself out or never become significant enough to trouble the board. Most of the time that judgment may be right.

The problem is when it isn’t.

Weeks or months can pass before it becomes clear that the issue isn’t going away. By then, the board discovers not only that there is a problem, but that people within the organisation have known about it for some time.

Materiality can make this worse. There is no material financial impact, regulatory consequence or reputational damage.

Not yet.

A project may be falling behind schedule while remaining within budget. A control may not be operating properly but may not yet have caused a loss. Neither may be financially material, but both may be something a director would reasonably want to know.

Perhaps that is the better test.

The objective isn’t to swamp the board with every operational problem. It is to avoid an issue being repeatedly judged not quite important enough to escalate until suddenly it is.

The Knowing Gap is the time between when the board could usefully have known and when it actually did.

That can be a very expensive gap.

4. Be careful of the comfortable answer

Problems don’t necessarily survive because nobody notices them. Sometimes they survive because there is a perfectly reasonable explanation for not looking any further.

A question may have been asked and the answer comes back that it is correct, that it is market practice or that it has already been checked. Sometimes management simply believes pursuing it further would be a waste of time. And most of the time they may be right.

The danger is that a confident answer can close down curiosity too quickly.

“It’s correct” isn’t quite the same as explaining why it is correct. “Market practice” doesn’t necessarily mean it is the right practice. And the fact that something has been checked doesn’t mean the person checking it was looking for the problem that eventually emerged.

This isn’t about second-guessing management or endlessly reopening matters. It is about going one step further when something doesn’t quite make sense.

Nobody wants to be the person asking the stupid question. But appearing foolish for 30 seconds isn’t much of a corporate risk. Discovering six months later that everyone had accepted the same incorrect assumption is.

And into 2027…

These four lessons don’t fit neatly together, and perhaps they don’t need to.

Technology will get better. Risk frameworks will become more sophisticated. There will be more information and no shortage of external advice.

But judgment, curiosity and common sense are unlikely to become obsolete.

And when something does go wrong, asking who was responsible is important. Asking what we could have done differently may teach us more.

I am sure 2027 will provide a few more lessons. I just hope fewer of them are character building.

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About the Author: Jon Brett

Jon Brett has spent more than three decades in senior executive and board roles as CEO, CFO, Chair, Audit and Risk Chair, non-executive director, founder, and adviser.

His career has included leadership roles with Techway Limited, a pioneer of internet banking in Australia, Investec Wentworth Private Equity and Investec Bank (Australia). He has also served on the boards of numerous ASX-listed companies.

He created and hosted The Taking of Vocus, a podcast series examining the rise of Vocus Group from start-up to a market capitalisation of more than $5 billion, and the turbulence that followed the acquisition of M2 Telecommunications. It was subsequently adapted into a book.

The Taking of Vocus is available on Kindle.

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