After enough years working across organisations and industries, patterns become easier to recognise. You know what a struggling program looks like. You recognise an executive team that has agreed on the strategy but not on what any of them are actually going to do differently on Monday morning.

That pattern recognition is part of what organisations pay experienced leaders and advisors for. The benefit of experience is that you have seen a lot before. So is the risk.

We see something familiar and reach for the approach that worked last time: the framework, the sequence, the workshop. We know how another organisation solved something remarkably similar. The problem is that remarkably similar is doing too much work in that sentence.

Underneath this sits a persistent norm in leadership: the belief that experience means you have already seen the answer. It is a comfortable belief because it rewards the years we have put in. It is also the one worth rewriting.

I once worked with a large government agency on a transformation and went in with my own version of the 80/20 rule: 80 per cent of what had worked elsewhere would be repeatable, and only 20 per cent would need to change. I was wrong. From the outside, the issues looked familiar. Underneath, the agency was different enough that it needed a different operating model altogether. It cost us rework and credibility until we rebuilt the approach from what that organisation needed.

Since then I have seen the same thing in other forms: a commercial organisation that can make a decision in weeks that a government agency would quite properly take months to work through, or an architecture that looks elegant on paper until it meets the legacy estate it has to coexist with. The technical answer might be correct. That does not make it the right answer.

AI is making this harder to see, because much of the advice about what organisations can do with it may well be technically true. Imagine an advisor fresh from a successful AI pilot recommending the same approach to another company. The company automates its intake and processes requests ten times faster, but the same one person still triages everything that comes through. The technology delivered what it promised, and the organisation is no faster, because the bottleneck has moved to the one place nobody redesigned.

The more useful leadership question is what any of it means here. What problem are we solving in this organisation? How does work happen today, including the slightly ridiculous parts everyone has learned to live with? Where does accountability sit, and what happens if we get a decision wrong?

Those questions require context, and context is inconvenient. It can turn a beautifully designed roadmap into a conversation about procurement rules, workforce agreements, data quality, or the fact that three parts of the organisation use the word "customer" to mean entirely different things. That conversation is where you find out what adoption will require.

The longer I work in transformation, the less interested I am in whether an organisation can adopt a new technology, operating model, or way of working. Usually, it can. What I want to know is what adopting it will take: what the organisation has to absorb, what has to change around it, and whether the capability exists to execute.

Experience should help us see possibilities faster and recognise patterns earlier. It should never give us permission to skip the work of understanding where we are. The value of experience is not having seen the answer before. It is knowing enough to understand why the answer might be different this time.

— Cindy Schwartz

Founder, Executive Excellence Group | Rewriting Leadership Norms