Assumptions: The silent assassin of good legal strategy

In this article, Wessel sets out the first of the firm’s rules of practice: assumptions are the silent assassin of good legal strategy. Drawing on nearly three decades in disputes work, he explains why lawyers and clients must resist the urge to move too quickly to conclusions, and why the best outcomes usually begin with disciplined fact finding, structured digital systems, and the judgement to understand what the real problem is before trying to solve it.

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My first rule of practice is simple: assumptions are the mother of most errors. Everyone knows the rougher version of that line. The wording is not the point. The warning is. In legal work, assumptions are costly. They distort strategy, waste time, increase fees, and sometimes send a matter in entirely the wrong direction before anyone has properly understood what the problem is. They are also dangerous precisely because they are often silent. They sit in the background as passive positions, untested and unchallenged, until much later when they surface as a flaw in the strategy, a gap in the evidence, or a costly surprise in the case.

That is why I have always taken the view that assumptions are tested, not trusted. We work from detail upward. Facts are checked, documents are interrogated, the chronology is rebuilt and the commercial setting is understood. Only then should one begin to speak confidently about strategy.

A lesson taught to me early in practice has also stayed with me throughout my career. The bad lawyer tells you what you cannot do. The good lawyer is the one who tells you what you can do. That is not a call for easy optimism. It is a call for better thinking. The lawyer who starts with prohibition often starts too high up the ladder, at fear, habit, or abstract principle. The better lawyer starts lower down, in the facts, the documents, the sequence of events, and the options the real world still leaves open.

This article makes a simple point at the outset: Before lawyers start charging heavily for strategy, they should first understand the matter properly. Before clients ask for solutions, they should help unpack the problem properly. That applies across jurisdictions and across matter types. It applies in litigation, transactions, investigations, labour disputes, regulatory matters, restructurings, shareholder fights, and health and safety incidents. Facts before theory. Context before confidence. Understanding before strategy.

Now that you have the point, I unpack it in more detail for those whose curiosity has been piqued. What follows explains why assumptions are so dangerous in legal work, why the problem is becoming more acute in modern practice, and why better systems, especially digital systems, are now essential if lawyers are to get to sound judgement quickly enough for clients to afford it.

The problem is not lack of information. It is too much of it

Neil deGrasse Tyson, the American astrophysicist and science communicator, often describes a progression from data, to information, to knowledge, and finally to wisdom. The language comes from science, but it fits legal work exactly. Data is the raw material, emails, contracts, meeting minutes, WhatsApp messages, reports, timelines and witness accounts, which on their own are only fragments. Information is what emerges when that raw material is organised and placed in context, so that one can see what happened, when it happened, and who was involved. Knowledge is the next step, where that information is analysed and applied, allowing the lawyer to understand how the matter works, where the risks lie, and which issues are likely to matter most. That is where most people stop their thinking. Wisdom goes further. It is the distilled essence of knowledge, the disciplined judgement to understand why the detail matters, which parts of it are truly decisive, and what should be done next. In the end, that is what the client is really paying for.

That movement from raw material to wisdom has become harder, not easier. The data of disputes is getting bigger every year. Email chains are longer, and informal communications are more frequent. Meetings are recorded and notes are generated instantly. Drafts multiply. Messaging platforms add another layer of evidence. AI tools now generate summaries, transcripts and working notes at speed, which can be useful, but which also increase the amount of material surrounding a matter. The legal problem is no longer simply that important facts are hidden. It is that they are often buried.

This is one of the central modern pressures on legal practice. Lawyers and clients alike must adapt to the reality that the volume of material to be assessed at the start of a matter will continue to increase. That is not a trend that is going away. It is the new environment. Any legal method that still assumes a manageable paper file and a few lever arch bundles is already behind the problem.

And yet the legal world remains, in many respects, traditionalist and slow to adapt. That is a mistake. Law is full of ritual, hierarchy and habit. Some of that has value. Much of it does not. The idea that one proves seriousness by drowning in paper, or that only slow and manual review is properly careful, belongs to another era. Care remains essential. Discipline remains essential. But the systems by which we handle detail must modernise, because the volume and complexity of modern information demand it.

Why does this matter to clients?

Clients often want strategy immediately. That is understandable. Something has gone wrong. There may be operational pressure, commercial exposure, board attention, reputational risk, threatened proceedings, or a regulator asking hard questions. Speed matters, but speed is not the same thing as haste. The quickest way to waste money in legal work is to act with great confidence on partial understanding.

That is why assumptions are so dangerous at the beginning of a matter. The first version of the problem is often incomplete, and sometimes wrong. What arrives as a breach of contract may in truth be a breakdown in authority. What looks like misconduct may turn out to be incapacity. What appears to be a commercial deadlock may in fact be a regulatory problem. A safety incident turns out to involve a broader systems failure. A threatened claim turns out to be leverage in a wider commercial contest. When lawyers classify too early, they often reach too early for familiar tools.

This is where Abraham Maslow’s famous observation is so useful. If the only tool you have is a hammer, it is tempting to treat everything as if it were a nail. The same danger exists in legal work. The litigator wants to litigate. The transactional lawyer wants to draft around the problem. The labour lawyer sees misconduct. The regulator sees compliance failure. The restructuring lawyer sees distress. Familiar tools are useful, but they can become traps if they arrive before understanding.

Good legal work is therefore not merely about finding answers. It is about asking better questions at the right time. As Peter Drucker explained in The Effective Executive, effectiveness begins with identifying what really matters. In legal work, that means understanding the real problem before rushing to solve it. That is precisely what happens when strategy is built too early, on assumptions that have not yet been tested. The lawyer may be working hard, the client may be spending heavily, but both may be solving the wrong problem.

The answer is not endless delay, but rather structured understanding. Read the documents. Build the chronology. Test the narrative against the record. Separate what is proved from what is asserted, work out what is missing and identify what really matters commercially. Only then should the strategy begin to settle.

What experience taught me about records and memory

In the first three years of my career, I worked on one matter with a record of more than thirty five thousand pages. That was before Microsoft Word became what it is now. It was before searchable PDFs. It was before AI. The only way to master that record was to live inside it. In time, I became a kind of walking index to the papers. Even opposing counsel, in the middle of cross examination, would sometimes ask me where a particular document was in the record.

That experience taught me two things: The first is that detail matters more than people think. Cases are not won only by eloquence or by broad principle. They are often won in the record, in the sequence of events, in the overlooked document, in the inconsistency between what is now said and what was then written. The second is that there is a better way than relying on one person’s memory. In those days, if one person knew the record and the others did not, that was simply how large matters were often carried. That may once have been understandable. It is no longer acceptable. Knowledge trapped in one person’s head is not a system, it is a risk.

One digital bundle. Collective knowledge.

That leads to what I regard as a central practical point. The detail must be mastered, but it must also be mastered efficiently. Lawyers charge by the hour and if the process of getting to the facts is disorganised, repetitive, or dependent on a single individual carrying the file in his or her head, the client pays for confusion. This is why I regard system as part of legal judgement.

Over the years, we have developed a paperless method built around one digital bundle, one evolving chronology, and one shared body of knowledge. After an initial review, the team is already working on a living chronology that grows as the matter develops. The key documents sit in a structured digital record. The material is searchable, organised and accessible across the team. The point is not technology for its own sake but to shorten the road from raw material to judgement.

That has practical consequences. It means the next person on the matter can orient themselves quickly, the chronology can be tested and refined in real time and counsel can be briefed on a structured record rather than a panic assembled bundle. It means that when a new development arises, the team can place it into an existing framework immediately. It means that legal knowledge is cumulative rather than fragile and most importantly, the client is not paying repeatedly for the same learning curve.

That is where modern legal systems start to matter commercially. Good systems do not replace legal judgement. They make good judgement affordable, reduce duplication,  preserve context and improve continuity. They allow teams to work from the same organised body of information instead of from private memory, scattered emails or personal notebooks. In a world of expanding data, that is no longer optional. It is part of competent practice.

What should clients expect before they pay for strategy?

Clients are entitled to expect more at the outset of a matter than fast reactions and clever sounding summaries.

They are entitled to expect questions before opinions. If the lawyer is not asking for the key documents, the sequence of events, the missing context and the commercial objective, that lawyer is probably moving too quickly.

They are entitled to expect a distinction between facts and narrative. Most legal problems arrive as stories told under pressure. Those stories matter, but they are not the same thing as proof. A good lawyer should be able to say what is established, what is arguable, what still needs verification, and what assumptions are being made along the way.

They are entitled to expect the lawyer to understand the business problem, not merely the legal issue. That is where the better lawyer earns his or her keep, not by listing obstacles, but by identifying the routes through the problem once the real terrain has been mapped.

They are entitled to expect that early legal costs are being spent on understanding. There is a place for forceful drafting and tactical speed but before that comes the quieter work that makes the force meaningful. Good legal work is often won in the reading, sorting, checking and thinking that nobody sees.

They are also entitled to expect system. If the lawyers have no coherent way of organising the matter, the client will pay for repetition. If the bundle is disorderly, the chronology absent, the documents unstructured, and knowledge trapped in individual inboxes or private notebooks, the matter will become more expensive than it needs to be. That is not administrative trivia. It goes directly to value.

How is wisdom built?

There comes a point when fact gathering must become judgement. One can drown in paper, or in digital material, if one has no sense of what matters. Good lawyers therefore do not merely collect detail. They organise it, identify patterns, and work out which facts are load bearing and which are noise. That is where experience, commercial sense and discipline begin to matter most.

This is also where many lawyers stop too early. They reach knowledge and call it strategy. They have understood the documents, the legal issues and the broad risks, and they think the work is done. But clients are not really paying for knowledge alone. They are paying for wisdom, for the distilled essence of that knowledge, for the judgement to say what matters most, what can be done, what should be done, and what is not worth spending money on.

That is the final movement in good legal work. Not from ignorance to information, but from information to judgement. Not from paper to confidence, but from tested detail to disciplined direction.

What is the rule that should shape the start of every matter?

If I had to reduce this article to one practical rule for clients and lawyers alike, it would be this: before deciding what to do, decide what the problem really is.

That requires more discipline than many people think. It means resisting the urge to classify too early. It means sitting with the detail long enough for the matter to clarify itself. It means identifying the assumptions underneath the first version of the story and testing them one by one. It means asking what the client is actually trying to achieve, not merely what legal rights can be asserted. It means keeping more than one tool in the box until the right one is clearly called for.

For clients, the takeaway is straightforward. When you brief lawyers, do not start with the answer you want. Start with the facts you have. Give them the uncomfortable material as well as the helpful material. Ask them to test the assumptions in the matter before they build strategy on them. Expect chronology, verification and judgement. Expect system. Be wary of anyone who sounds too certain before they have engaged properly with the detail.

For lawyers, the takeaway is equally simple. Do not confuse speed with value. Do not confuse instinct with analysis. Do not charge heavily for strategy before you have done the work required to understand the problem. Read more. Ask more. Structure more. Test more. Then advise.

Good judgement does not begin with brilliance. It begins with discipline; it begins in the detail, and if the detail has not yet been properly understood, the wisest thing a lawyer can say is not what the client most wants to hear, but what the matter honestly requires: we need to test the assumptions first.

Written By: Wessel Badenhorst

Date: April 2026