That complication does not arrive with any warning. It does not announce itself as a problem to be managed or a boundary about to be crossed. It begins in much smaller ways. A longer conversation than usual. A shared frustration about something unrelated to the work at hand. A sense of understanding that extends beyond the numbers and into the person sitting across from you.
WHAT THE ACCOUNTANT SAW
CHAPTER 1 Introduction – Handle With Care
This is a dangerous book, although not in the way that might first come to mind. It is not dangerous because it exposes secrets, nor because it names names or pulls back curtains that were meant to stay firmly drawn. In fact, quite the opposite is true. The people in these pages do not exist in any identifiable sense. They are shadows, composites, fragments of moments that have been observed, remembered, reshaped and, where necessary, softened around the edges so that no single person could point and say, “That’s me.” If anything, the danger lies not in who might be recognised, but in who might feel uncomfortably familiar.
It has been my habit over many years to sit in rooms where decisions are either being made or, more accurately, justified. That distinction took me some time to appreciate. Early in my career, I held the naive belief that people came to an accountant for advice, that they arrived with questions and left with answers, and that somewhere in that exchange better outcomes were created simply because the right conversation had taken place. There are certainly moments where that still holds true, and they are satisfying when they occur. But more often than not, what unfolds is something altogether different. By the time someone is explaining a course of action, the decision has already been made. What they are seeking, whether they realise it or not, is alignment.
It took me longer than it should have to recognise that subtle shift, because on the surface nothing appears out of place. The questions are asked. The documents are produced. There is a tone of inquiry, sometimes even a hint of caution. But if you listen closely, not to the words themselves, but to the way they are delivered, you begin to hear something else. The answer is already sitting there, just beneath the surface, waiting to be confirmed. The conversation is not an exploration; it is a test. Not of the idea, but of the adviser.
You can almost feel the moment it happens.
A proposal is laid out, often with impressive detail, sometimes with numbers that appear to have been carefully considered, occasionally with references to something someone else has done or said that lends it credibility. Then comes the pause. Not a pause of uncertainty, but one of expectation. A small, almost imperceptible lean forward. This is the point where the role you thought you occupied begins to shift.
Because if your response aligns with what they already believe, the conversation flows easily. There is agreement, momentum, even a sense of shared purpose. You are, in that moment, seen as insightful, pragmatic, someone who “gets it.” The decision feels validated, strengthened by professional endorsement, and whatever doubts may have lingered are quietly put to rest.
But if your response doesn’t align, if you introduce friction, if you question an assumption, if you suggest that perhaps the path being taken is not quite as sound as it appears, then something else happens entirely. The conversation doesn’t necessarily stop, but it changes. The energy shifts. The same person who was moments ago seeking your input begins, often unconsciously, to defend their position. Additional information is produced. The emphasis moves from inquiry to persuasion. What was framed as a question reveals itself as something closer to a conclusion looking for support.
And that is when you begin to understand that the advice itself is not always the point.
Over time, this becomes less surprising and more… instructive. You start to see that people don’t always come for answers. Sometimes they come for reassurance. Sometimes they come to test whether their thinking holds up under scrutiny. And sometimes, perhaps more often than any of us would comfortably admit, they come looking for someone to agree with them so that they can proceed with a clearer conscience.
The advice, in those moments, is almost secondary.
Which leads, inevitably, to a quieter, more uncomfortable question that sits just beneath the surface of the profession, rarely spoken out loud but frequently felt.
Why bother?
Why go through the exercise of analysis, of explanation, of carefully laying out risks and alternatives, when there is a strong chance that the outcome will remain unchanged? Why invest the time in providing advice that may be acknowledged, even appreciated in the moment, only to be set aside once the conversation ends and the original course resumes its place?
It is not a question born of frustration so much as recognition.
Because as you will see throughout this book, the issue is not that advice is wrong, nor that it lacks value. The issue is that by the time advice is sought, the decision has often already moved beyond the point where it can be easily influenced. The thinking has settled. The narrative has formed. The role of the adviser becomes less about shaping the outcome and more about intersecting with a process that is already in motion.
And alignment, when it occurs, is rarely accidental.
Once an idea has taken hold, it begins to organise the world around it. Facts that support it are welcomed, given weight, repeated. Those that don’t are questioned, softened, or quietly set aside for later consideration that rarely comes. It is not done maliciously, nor even consciously in most cases. It is simply how the mind protects its own conclusions. Over time, I stopped being surprised by this and started paying attention to it, because it didn’t seem to matter whether the conversation involved a modest local business or a much grander venture. The pattern was the same. The language changed, the numbers grew or shrank, but the underlying rhythm remained remarkably consistent.
And once you see that rhythm, you start to realise that the real story is not in the advice that is given.
It is in the decision that was already made before anyone walked into the room.
It would be comforting, I think, if this behaviour were limited to those who lacked experience or understanding. If mistakes were the domain of the uninformed, then the rest of us could take quiet refuge in our knowledge and believe ourselves immune. Unfortunately, that has not been my observation. Some of the most spectacular missteps I have witnessed have come from people who would describe themselves, quite reasonably, as capable and informed. They were not guessing. They were not careless. In many cases, they were confident to the point of persuasion, able to articulate exactly why what they were doing made sense. And for a time, sometimes a long time, it did.
That is the part that makes this subject so difficult to pin down. Mistakes rarely feel like mistakes at the time they are made. They feel like progress. They feel like solutions. They feel like clever interpretations of a system that perhaps wasn’t designed with enough flexibility in mind. Occasionally, they even feel like courage, dressed up as a willingness to do what others are too hesitant to attempt. It is only with the benefit of distance, usually accompanied by consequence, that the shape of the decision changes. What once appeared logical begins to look strained. What felt certain becomes, in hindsight, improbably optimistic. And yet, if you were to rewind the moment and stand again at the point where the decision was made, you would likely find it just as persuasive as it was the first time.
Somewhere along the way, after seeing this play out more times than I could reasonably count, I stopped thinking of these situations as isolated events and began to see them as something else entirely. Not as failures of intelligence or even of judgement in the traditional sense, but as natural outcomes of a process that most of us move through without ever really examining. A thought forms. It gathers support. It becomes a belief. And then, almost without noticing the transition, it becomes something we feel compelled to act upon. By that stage, the decision is no longer being tested. It is being defended.
That is the space this book explores.
It is not a technical discussion of business structures, although those will make appearances where they are relevant. It is not a guide to avoiding risk, nor a collection of rules that, if followed carefully, will keep you safely on course. There are plenty of books that attempt to do those things, and some of them do it very well. This is something a little less structured and, perhaps, a little more confronting. It sits in the periphery of decision making, in that quiet, often overlooked moment where something begins to feel right for reasons that are not entirely clear.
You will find stories here, although even that word may be giving them more form than they deserve. They are better thought of as reflections, built from conversations that may have happened across a desk, over a phone call, or in those informal settings where people speak more freely because it doesn’t feel like a meeting. The characters that move through these pages are not real in the sense that you could identify them, but they are entirely real in the way they think, in the way they justify, and in the way they arrive at conclusions that, to them, feel entirely reasonable.
No clients were harmed in the making of this book. That is the official position, and I am comfortable standing by it. The unofficial position is that a number of lessons were learned along the way, some more expensive than others, and it would be a shame not to make use of them. If there is any discomfort in what follows, it should not come from recognising a particular individual, but from recognising a way of thinking that is far more widespread than we might like to admit.
It would also be misleading to suggest that I am standing outside all of this, calmly observing from a position of detached objectivity. That may have been the case once, or at least I might have believed it was. Experience has a way of softening that illusion. Spend enough time watching how decisions unfold, and eventually you begin to notice the same patterns in your own thinking. Not always in ways that lead to the same outcomes, but close enough to understand that the difference between observer and participant is not as fixed as it first appears. It shifts, depending on the moment, and sometimes without warning.
Which brings us, in a roundabout way, back to where we started.
This is a dangerous book, not because it exposes others, but because it quietly removes the protection of distance. It asks the reader to sit not as a spectator, but as a participant in the same process that is being described. It suggests, without insisting, that the decisions we find easiest to critique from the outside are often built on reasoning that would feel entirely acceptable if we were standing inside them.
This isn’t a book about mistakes.
It’s a book about how easily mistakes are made, and how, with just enough confidence, justification, and timing, they can take on a shape that feels not only acceptable, but inevitable. And if that is the case, then the stories that follow are not really about the people who appear in them at all.
They are about something much closer to home.
Handle with care. Because what follows is not meant to sit on you like a weight. It was never intended to be that kind of book. If anything, it is an attempt to walk a line that most of us recognise but rarely acknowledge out loud, the line between seeing something clearly and seeing it too late, between laughing at a situation and realising, perhaps uncomfortably, that we might not have acted so differently ourselves.
There is, deliberately, a sense of humour running through these pages. There has to be. Without it, the subject matter becomes too sharp, too exposed, and perhaps a little too honest for its own good. Many of the moments that sit behind these stories, when viewed from a safe distance, are genuinely amusing. Not because anyone set out to be amusing, but because there is something inherently human in the way we justify our thinking, in the way we construct logic around what we want to believe, and in the confidence with which we carry that logic forward.
It would be easy to strip that humour away and present everything as cautionary tales, neatly packaged with lessons and conclusions, but that is not how these moments occur in real life. They arrive with a sense of normality. They feel reasonable at the time. It is only later, often much later, that their shape changes and the consequences begin to define them differently. By then, of course, the moment itself has long since passed, leaving behind only the reflection, and sometimes, if you are fortunate, the ability to laugh at it.
That is part of the agreement I am offering here. There is a promise, if you like, that while the stories may at times feel pointed, they are not intended to wound. The people within them are not targets. They are not examples held up for criticism or judgement. They are, more accurately, reflections of a way of thinking that appears far more often than we might expect, and in far more places than we would comfortably admit.
And if I am honest, and I think that is required here, those reflections do not stop with others.
Many of the anecdotes that follow are drawn from conversations and experiences that I have been part of over a long period of time, but they are not separate from me. They are not observations made from some elevated position of clarity, neatly packaged and delivered from a safe distance. They sit much closer than that, uncomfortably close at times, because the truth is you do not spend a lifetime around decision-making without, in some way, becoming part of the same machinery you are observing. There are moments where I have watched, moments where I have advised, and moments where, despite knowing better—or at least believing that I did—I have found myself moving in step with the very patterns I now describe.
It would be far too easy, and far less confronting, to present these stories as though they belong entirely to others. To cast myself as the steady hand in the background, the one who saw it coming, the one who quietly understood what was unfolding while others pressed on regardless. There are certainly moments where that version of events holds true, and they are tempting to lean into. But they are only part of the picture, and not even the most interesting part. Because alongside those moments sit others where the lines are far less defined, where familiarity begins to soften judgement, and where the role of adviser becomes something more complicated than it first appears.
That complication does not arrive with any warning. It does not announce itself as a problem to be managed or a boundary about to be crossed. It begins in much smaller ways. A longer conversation than usual. A shared frustration about something unrelated to the work at hand. A sense of understanding that extends beyond the numbers and into the person sitting across from you. Over time, these small moments accumulate, and what was once a clearly defined professional relationship starts to take on a different shape. It feels natural enough at the time, even beneficial, because trust is being built and communication is easier. But with that ease comes a subtle shift, one that is rarely noticed when it happens.
Nowhere is that shift more apparent than in what will unfold in Chapter 2—Clients Are Not Friends. It is a statement that reads cleanly on the page, almost too obvious to warrant discussion. Of course clients are not friends. Of course there are boundaries. Of course professionalism requires a certain distance. All of that is true, right up until it isn’t. Because in practice, those lines are not drawn with the clarity we imagine. They are negotiated, quietly and incrementally, through repeated interactions that feel entirely reasonable in isolation.
The difficulty is not in understanding the principle. The difficulty is in recognising the moment where it no longer applies in quite the way you thought it did. When a conversation that should be direct becomes slightly tempered. When advice that should be firm is delivered with a little more flexibility than it deserves. When the desire to maintain the relationship begins, almost imperceptibly, to compete with the responsibility to provide clear guidance. None of this feels significant at the time. In fact, it often feels like good practice, like being approachable, like building rapport. It is only later, with the benefit of hindsight, that the shift becomes visible for what it was.
And that is where these stories begin to sit closer to home than is entirely comfortable. Because they are not distant examples drawn from textbooks or exaggerated for effect. They are built from moments that were, at the time, entirely real and entirely understandable. The decisions made within them did not feel reckless or ill-considered. They felt appropriate, given the circumstances. That is precisely what makes them worth examining, because the gap between what feels right and what is right is rarely obvious when you are standing inside it.
Which brings with it another layer of complexity, one that became increasingly difficult to ignore as these reflections took shape. The question of naming, or more accurately, the question of whether naming serves any real purpose at all. It might seem straightforward at first. After all, every story has its central figure, someone whose decisions drive the outcome. But the more closely you look, the less clear that becomes. Rarely does a single person carry the full weight of what has occurred. Decisions are shaped by conversations, by influences, by the quiet reinforcement of others who may not even realise the role they are playing. What appears, on the surface, to be one person’s mistake is often the product of a much broader set of interactions.
There is also the more personal reality that some of these moments do not sit entirely outside my own experience. Not in a way that allows for clean separation, not in a way that would make naming comfortable even if it were appropriate. Because once you acknowledge that the same patterns exist within your own thinking, even if only in part, the idea of assigning ownership to someone else begins to lose its meaning. The behaviour is not unique. It is shared, repeated, and, perhaps most importantly, recognisable.
So what you are left with are not individuals, but impressions. Not names, but patterns that move through different situations wearing different faces. The people in these stories are deliberately indistinct, not to avoid responsibility, but to ensure that the focus remains where it belongs. This is not about identifying who did what. It is about understanding how easily it can be done.
As you move into the chapters that follow, and particularly into the territory where professional relationships begin to blur into something more personal, it is worth holding onto that perspective. The value of these stories does not lie in the detail of who was involved or the specifics of the situation. It lies in recognising the thinking that sits beneath them, the small shifts that occur long before anything outwardly goes wrong, and the ease with which those shifts can take place.
Especially when you believe you are aware of them.
Because if there is one thread that runs quietly through all of this, it is that awareness on its own is rarely enough. The patterns do not disappear simply because you can see them. They remain, waiting for the right combination of circumstance, confidence, and justification to make them feel entirely reasonable once again. And when that happens, the distance between observing a situation and being part of it is not nearly as great as we might prefer to believe.
Not always in the same way, and not always with the same outcomes, but close enough to recognise that the distinction between observer and participant is not as clean as we might like it to be. It shifts, often quietly, and sometimes without us noticing until the moment has already passed.
So as you move through what follows, it may help to think of this less as a collection of stories about others, and more as a shared space where certain behaviours are allowed to play out without the need for names or ownership. The situations are real enough to feel familiar, but distant enough to remain unclaimed. If you see someone you recognise, that is coincidence. If you see something of yourself, that is where the value sits.
In that sense, consider this a simple understanding between us.
No harm, no foul.
No names, no claims.
No intention to expose, only to explore.
If you find yourself entertained, then the book is doing its job. If you find yourself pausing, reflecting, perhaps even reconsidering something you had previously been certain about, then it is doing a little more than that. And if, somewhere along the way, you begin to sense that the difference between the stories on these pages and the decisions in your own life is not as great as it first appeared, then the purpose of the exercise will have quietly taken hold.
It is, after all, not a book about mistakes.
It is a book about how easily they are made, and how, with just enough confidence, justification, and timing, they can feel entirely reasonable in the moment they occur.
And if that is true, then none of us are quite as far removed from them as we might prefer to believe.
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