ideas

The trouble with knowing what you're doing

30 October 2026

I've recently found myself back at university at the age of 46, studying for a master's in Creativity and Innovation at the University of Malta. It's been an interesting few weeks, particularly as many of the subjects we're exploring are things I've spent much of my professional life dealing with. Leadership, innovation, critical thinking and organisational change. All fairly familiar territory, although I'm discovering that familiarity doesn't necessarily make something easy to explain.

One of the things I'm enjoying is being asked questions that initially seem quite straightforward. What is leadership? What makes something an innovation? How do we know whether somebody has made a good decision? They're the sort of questions you can answer quite confidently until somebody asks you to explain your reasoning. Then things can become a little more complicated.

During one of our Critical Thinking sessions, we were presented with an exercise involving two managers, A and B, and asked which we preferred. I initially chose B, largely because of their disposition. There was something about the description that appealed to me, and I could quite comfortably explain why I'd made that choice.

Then we were given some additional information. Manager B's recommendations had resulted in costly mistakes, while Manager A had demonstrated better reasoning and made more effective decisions.

I changed my answer, which seems entirely reasonable given the new evidence. What interested me more was why I'd been drawn to B in the first place. I'd recognised something of myself in that description, and I suspect that influenced my judgement more than I'd initially appreciated.

I've been thinking about that since, particularly in relation to experience and professional confidence. I've spent a good part of my career working with technology, data and organisational change. I've seen plenty of things work well and a fair few go badly wrong. Over time you develop instincts about what makes sense, where the problems are likely to be and whether somebody has properly thought through what they're proposing.

Those instincts are valuable. Experience should count for something, otherwise what's the point of accumulating it? But there's an interesting distinction between recognising a familiar problem, having confidence in your judgement and actually being right about what should happen next.

I don't have much difficulty challenging my own assumptions. That's learning, and I rather enjoy it when somebody presents an argument that makes me reconsider something. In fact, one of my frustrations in professional life is the absence of that challenge. Too often we seem happy to agree with each other, particularly when the person making the argument occupies a sufficiently senior position or the proposal sounds broadly sensible.

It's something I've been noticing again recently in conversations about organisational change. Words like capability, transformation and governance get used quite freely, and there's often an assumption that everybody shares the same understanding of what they mean. Yet asking relatively simple questions about the evidence, the intended outcome or how we would know whether something had worked can expose some fairly significant differences.

I've been close enough to some of these conversations to understand the reasoning behind what's being proposed, and I've become increasingly frustrated by how much of it appears to rest on assumptions. Sometimes the supporting evidence simply isn't there, or at least it hasn't been demonstrated. Yet the argument can be presented with considerable confidence, and that confidence seems to carry its own authority.

I don't expect every decision to come with a mountain of data. I've worked with data long enough to know it rarely provides a complete answer anyway. Judgement, experience and intuition all have a place, and sometimes you have to make a decision without knowing everything you'd like to know. What troubles me is when we don't distinguish between what we know, what we believe and what we're assuming.

I've put forward some alternative proposals of my own recently, and they've been received positively, described as good, well thought out and worthy of consideration. That's encouraging, although I'm increasingly doubtful that they'll make much difference. My impression is that the important decisions may already have been made, which leaves me wondering what the opportunity to challenge them was really intended to achieve.

Of course, there's a possibility that my proposals simply aren't the best option. I'm comfortable with that, particularly if somebody can demonstrate why. I'd welcome the opportunity to have them properly tested. What I find less satisfying is the possibility of an argument being accepted as reasonable without having any meaningful opportunity to influence the outcome.

There's a wider question here about authority and credibility. We tend to associate seniority with experience, experience with competence and competence with sound judgement. They can certainly be related, but I don't think one automatically guarantees the next. Somebody can be experienced, articulate and entirely convincing while still having missed something important. Equally, somebody without the title or the polished presentation might be asking exactly the question that needs answering.

And I have to include myself in that. I have my own ambitions, strongly held views and a fair amount of confidence in what I can contribute. I'd be disappointed if my experience counted for nothing, but I don't expect it to be accepted as evidence that I'm right. If I want my ideas to be taken seriously, I have to be prepared for them to be challenged, including by people who might know less about the subject but have noticed something I've missed.

Perhaps that's why I've found the university discussions so refreshing. There's an expectation that you explain your reasoning, consider alternatives and recognise the limits of what you know. I'm enjoying bringing my experience into those conversations, but equally I want it to be challenged. Otherwise, I could spend a considerable amount of money finding academic explanations for things I already believe.

I'm only a few weeks into the course, and I don't want to pretend I'm having some great intellectual awakening every time I attend a lecture. Much of what we're discussing reinforces things I've believed for a long time. Some of it challenges them. Occasionally I'm finding that academic theory gives me a useful way of understanding something I've encountered in practice, which is part of what I hoped to get from the experience.

Coming back to Managers A and B, the exercise worked because we were given new information and allowed to reconsider our decision. Nobody had a particular interest in defending the original answer, and there was nothing to lose by changing it.

I wonder how often that remains true once we leave the classroom.