Why the greatest difficulty in legal practice lies not in understanding the rules, but in understanding the people subject to them

There is something profoundly legal in the story of Adam and Eve. At the beginning of the human story, there is a rule and a boundary that is not to be crossed. Adam and Eve enjoyed abundance, yet a clear limit was placed before them. The prohibition was neither technically complex nor difficult to understand. It required no lawyer, no elaborate interpretation and no competing schools of jurisprudence. There was, quite simply, something they were told not to approach. Yet the clarity of the rule did not extinguish the desire to cross it. The Qur’anic account describes Adam and his spouse as being permitted to enjoy Paradise while being prohibited from approaching a particular tree. Temptation followed, the boundary was crossed, and repentance came afterwards.[1]

For a lawyer, that ancient account contains an important proposition about human conduct. A person may know the rule, understand its authority and appreciate the consequences of breaching it, yet still persuade himself to act contrary to it. If knowledge of a rule necessarily produced obedience, much of law would be unnecessary. Between the rule and the act stands the human mind, influenced by fear, ambition, pride, conscience, desire and self-interest. What makes the matter more difficult is that people rarely experience their own conduct as a straightforward pursuit of self-interest. We possess a remarkable ability to reconstruct what we want until it begins to appear reasonable, principled or even just.

A contracting party seldom says to himself, ‘I no longer wish to honour my obligation because performance has become expensive.’ He is more likely to conclude that the other party failed first, that circumstances have changed, or that strict enforcement has become commercially unreasonable. A director attracted to a corporate opportunity may genuinely persuade himself that he discovered it in his personal capacity or that the company would never have pursued it in any event. The internal justification often precedes the external act. This is one reason legal disputes become so difficult: the person on the wrong side of an obligation does not necessarily arrive there believing himself to be in the wrong.

Long before I came to understand any of this through practice, my father had begun teaching it to me in a very different way. My late father, Abdallah Nassar Al Qaissi, one of Jordan’s distinguished lawyers, used to tell me at the beginning of my career that if I genuinely wanted to become a lawyer, legislation and judgments would never be enough. He insisted that I read and memorise the Qur’an, and he was equally insistent that I read philosophy. To him, these were not separate intellectual disciplines. He believed that a lawyer who understood rules but made no effort to understand people would always be missing something essential.

I still remember sitting in front of him as he placed a book by Hegel, Descartes or another philosopher in my hands and told me to read. I would sometimes tell him, quite honestly, that I did not understand what I was reading. His response was usually simple: read it anyway; understanding will come later. At the time, I did not appreciate being made to work through books whose connection with the everyday practice of law seemed remote. Today, I am grateful that he insisted. He was not trying to make me memorise philosophical theories. He was teaching me to think about motive, judgement, power, money, self-deception and the contradictions that can exist within the same person.

He also repeatedly told me: ‘Every system carries within it the seeds of its own destruction.’ I heard that sentence many times before I understood what it meant in practice. Years later, after watching successful companies descend into internal conflict, partnerships move from friendship to litigation, families divide over money and property, and highly intelligent people convince themselves that an inconvenient rule should somehow apply differently in their particular circumstances, I began to understand his point. A system may be impeccable on paper and yet remain dependent upon the people operating it, the interests influencing them and the decisions they make once circumstances change. The same is true of contracts, corporate structures and governance arrangements.

Those early lessons affected the way I eventually learnt to practise law. Philosophy did not teach me how to draft a Shareholders’ Agreement, and reading the Qur’an was never a substitute for legislation, case law or professional training. What they gave me was another way of looking at people. I became more attentive to what was not being said, to inconsistencies between words and conduct, and to changes in expression, reaction and behaviour. With time, a lawyer begins to notice that a person’s real concern may be quite different from the legal position he advances, and that what is said in a meeting does not always reveal everything taking place in the mind of the speaker. I also learnt, sometimes uncomfortably, that the darker and better aspects of human nature do not divide themselves neatly between opposing parties. After almost two decades in practice, I have come to believe that a substantial part of the difficulty of law begins there.

Law Is Difficult; People Are More Difficult

Oxford Royale places Law second, after Aerospace Engineering, in its list of the most difficult degree subjects, referring to the volume of reading and the demands of legal analysis and interpretation.[2] It is important to be precise: this is an Oxford Royale ranking, not an academic study conducted by the University of Oxford itself. Whatever one may think of such rankings, there is no doubt that law is intellectually demanding. Legal provisions interact with other provisions, words take their meaning from context, judgments and precedents must be weighed carefully, and a seemingly minor drafting choice may produce consequences that a non-lawyer would never immediately anticipate.

Professional practice, however, introduces a difficulty that cannot be resolved simply by deeper legal research. Texts can be revisited, compared and analysed; people do not remain fixed. The same individual who negotiates calmly over a multimillion-pound or multimillion-dollar transaction may lose all sense of proportion once a dispute touches his pride, reputation or control. A person who appears entirely rational while interests are aligned may behave very differently once those interests begin to diverge. Lawyers see this particularly clearly because we rarely encounter people at neutral moments. We meet them after a shareholder feels excluded, after money has disappeared, after an employee has been accused of betrayal, or after spouses who once shared a life begin constructing competing accounts of that same life.

This is also where a lawyer begins to understand the distinction between the sincerity of a narrative and its accuracy. A client may be completely sincere in what he says and still be wrong. He may not be attempting to mislead his lawyer at all; he may simply have lived with his own interpretation of events for so long that interpretation and fact have become difficult to separate in his mind. This can be a difficult lesson early in one’s career because loyalty to the client is easily confused with agreement. It took me time to appreciate that identifying weaknesses in a client’s position may serve him far better than strengthening every argument he wishes to make.

René Descartes wrote in Discourse on Method that ‘it is not enough to have a good mind; the main thing is to use it well’.[3] I find the observation more relevant to legal practice today than I could have appreciated when my father first placed philosophy before me. Intelligence is undoubtedly valuable, but it does not protect a person from poor judgement. At times, it may simply provide more sophisticated tools with which to defend a conclusion already reached for other reasons.

This is particularly apparent when advising highly successful businesspeople. A founder may understand his market and industry far better than his lawyer and may have spent decades building a business, assuming risks and making decisions that proved correct. That history deserves respect, but it may also make disagreement more difficult. Success in one field does not automatically guarantee sound judgement in every other field, particularly once emotion, pride or fear of loss enters the equation.

What the lawyer may possess is not superior intelligence but a different collection of experiences. He has seen what partnerships look like after they collapse. He has watched courts examine evidence the parties once considered insignificant. He knows that a seemingly casual sentence in an agreement can acquire enormous importance five years later because he has seen it happen before. In that sense, experience is a memory of consequences.

Contracts Are Also About People

A young lawyer tends to read an agreement clause by clause. With experience, those clauses begin to look different. They are not merely legal language; they are attempts to anticipate future human behaviour.

Reserved Matters provisions exist because authority that appears harmless during periods of harmony may later become contentious. Information Rights exist because access to information can become a source of power. Warranties address inequalities of knowledge between parties. Indemnities matter because, once a loss has occurred, the parties may remember very differently who agreed to bear it. Deadlock and exit mechanisms exist because commercial relationships cannot sensibly be built upon the assumption that people who agree today will continue to agree indefinitely.

For that reason, I have never regarded detailed contracting as an expression of bad faith. A carefully drafted Shareholders’ Agreement does not mean that the parties distrust one another. It acknowledges that circumstances change and that friendship, goodwill and memory should not be required to perform the work that properly belongs to a legal document.

The Egyptian commercial-law scholar Dr Samiha Al-Qalyubi discusses the concept of affectio societatis, the shared intention to participate and cooperate as partners, as an important element distinguishing the company relationship from ordinary contractual arrangements.[8] What interests me about the concept after years in practice is not merely the existence of that common intention at incorporation, but its capacity to weaken over time. Partners who began with complete trust may view their respective contributions very differently once the venture succeeds and the value of what is being divided becomes substantial.

I have seen relationships in which percentages seemed almost irrelevant at the beginning and, years later, every contribution was being recalculated. Time, relationships, capital, managerial effort and even personal sacrifices suddenly acquired retrospective monetary values. Eventually, the history of the venture itself became disputed.

This does not necessarily mean that anyone is lying. Human memory tends to preserve the context and justification surrounding our own actions while retaining the consequences of other people’s actions. When I fail to perform an obligation, I remember every difficulty that prevented me from doing so. When someone else fails to perform the same obligation, I may remember only the failure.

Litigation magnifies this tendency. Tolstoy’s observation that people are often more concerned with changing others than examining themselves becomes uncomfortably familiar to anyone who has spent enough time around disputes.[4] A shareholder can explain in detail every act of disloyalty committed by his partner. The employee remembers injustice; the employer remembers betrayal. Far less common is the person whose first instinct is to ask what he himself contributed to the breakdown of the relationship.

We experience ourselves from within our own motives, while we see others primarily through their conduct. We know why we acted as we did, and we know our fears, frustrations and explanations. The inner life of the other party is unavailable to us, so his conduct appears stripped of much of its context. By the time a dispute reaches the lawyer, a complete trial may already have taken place in the mind of each party. Each has selected the evidence that supports his account, accepted his own explanations and, more often than not, acquitted himself before the real trial has begun.

Wealth, Power and the Absence of Contradiction

Long practice also changes the way one views successful people. Many self-made entrepreneurs are genuinely exceptional, and it would be foolish to undervalue the judgement and experience that enabled someone to build a substantial business merely because he is not a lawyer. Repeated success can, however, create a particular vulnerability: the assumption that excellence in one field necessarily implies superior judgement in others.

The greater problem may lie not within the individual, but in the environment that forms around him as his influence grows. The more powerful a person becomes, the more costly disagreement can become for those around him. Employees learn which observations are welcome and which are better left unsaid. An adviser who depends heavily upon one relationship may become gentler in expressing an uncomfortable view. Friends may stop challenging certain conclusions simply to avoid friction. None of this need be deliberate, and the successful individual himself may be entirely unaware that it is happening.

Eventually, the volume of information reaching him may increase while the amount of genuine contradiction decreases. That is a dangerous combination. Without realising it, a person may begin to interpret silence as agreement, respect as endorsement, and reluctance to challenge him as evidence that he must be right.

This is where the independent lawyer sometimes has a role that is not particularly comfortable. Clients do not always need someone to reformulate their position in more authoritative legal language. There are occasions when the most valuable advice is precisely the advice they did not wish to hear.

A client who knows very little law may sometimes be easier to advise because he understands the limits of his knowledge. The more complicated situation arises where the client is highly intelligent and commercially experienced, and understands leverage, ambiguity, cost and enforcement well enough to ask not, ‘What does the law require?’ but rather, ‘How far can I go without technically crossing the line?’

There may be a legal answer to that question, but it is rarely the only answer worth considering. How will the conduct look once it becomes evidence before a court? Will the explanation remain persuasive when narrated by an opponent rather than by the client? Does the decision still make commercial sense after reputational and relational consequences are taken into account? Sometimes conduct can be structured lawfully and still remain a poor decision.

Fraud Does Not Always Announce Itself

Experience also changes a lawyer’s understanding of dishonesty. Early in one’s career, it is tempting to assume that fraud will look suspicious when encountered. The reality is often far more complicated.

Improper conduct can arrive in a perfectly organised file containing contracts, invoices, board resolutions, legal opinions and properly executed documents. Each document, considered separately, may be entirely genuine, while the deception lies in the overall picture created when those documents are assembled.

The lawyer must therefore look beyond form. Does the chronology make sense? Did the parties behave at the relevant time in a manner consistent with the legal position they later advanced? Who actually received the economic benefit? Why was a particular document created at that particular time? Occasionally, a small inconsistency in an apparently minor fact reveals more than the dramatic issue that initially attracted everyone’s attention.

The deeper difficulty is that self-deception can coexist with deliberate conduct. A person may manipulate a situation to his own advantage and still construct an internal explanation that permits him to regard himself as justified. For that reason, I have become more reluctant to divide people too readily into the honest and the dishonest. Human beings are capable of carrying substantial contradictions within themselves, sometimes for many years.

Hegel’s famous observation that ‘the owl of Minerva begins its flight only with the onset of dusk’ has particular relevance to legal practice.[5] Wisdom frequently arrives after the event. The weakness of a Shareholders’ Agreement becomes apparent after the shareholders fall out. The importance of Information Rights becomes obvious once information has been withheld. An ambiguous governance structure may function without difficulty for years and then become disastrous as soon as control is contested.

Transactional lawyers are often expected to imagine those failures while everyone in the room remains optimistic. This can make sound legal advice appear unnecessarily pessimistic when it is given, only for the same advice to appear obvious several years later.

What the Profession Can Do to the Lawyer

There is another side to all of this that lawyers do not always discuss openly. Constant exposure to broken promises, manipulation and disputes can affect the person who spends much of his professional life dealing with them.

A synthesis review of 145 publications concerning lawyers’ well-being identified research in which difficult client work was associated with detachment, distrust and negative changes in worldview.[6] A separate qualitative study involving defence lawyers representing sex offenders reported increased wariness and erosion of trust among some participants.[7]

I would not overstate what such studies prove, but the experience underlying them will be familiar to many lawyers who have practised for long enough. One begins to recognise patterns and becomes less surprised by certain types of conduct. The danger is that pattern recognition gradually becomes assumption, and professional scepticism develops into a harsher view of people.

Over time, I have come to appreciate the importance of resisting that tendency. Legal practice exposes us to the darker aspects of human conduct because disputes naturally bring them into the room, but it also exposes us to the opposite. I have seen people honour commitments they could probably have avoided, businesspeople accept financial losses because they had given their word, and executives accept responsibility when denial would have been easier.

Those examples matter because, without them, experience may teach the wrong lesson. The lesson is not that people are bad. It is that human beings are capable of both good and bad conduct, and that particular circumstances may reveal aspects of character that years of ordinary dealings never expose.

This brings me back to what my father was trying to teach me before I had enough experience to understand him. When he insisted that I read the Qur’an and philosophy, he was not giving me a method for predicting people. No reliable method of that kind exists, and I have become increasingly cautious of anyone who claims to be able to read another human being perfectly. What those books taught me was to continue asking what may lie beneath the obvious explanation.

With time, that altered the way I listened to clients and opponents. I became more attentive to faces, reactions and silences, to the answer that arrives unusually quickly, to the subject a person repeatedly avoids, and to the distance that may exist between the legal position being advanced and the conduct that preceded it. None of these things is evidence in itself, nor should a lawyer ever treat it as such, but it may indicate where the next question needs to be asked.

From Adam and Eve to the Modern Boardroom

Civilisation has changed beyond comparison with the world in which the story opening this article took place. Human beings now organise themselves through companies, boards of directors, regulatory systems, complex agreements and governance frameworks that would have been unimaginable in earlier times. Yet the underlying relationship between rule, temptation and choice remains recognisable.

The forbidden tree has simply assumed different forms. It may be a corporate opportunity that attracts a director personally, confidential information that can be monetised, an undisclosed related-party transaction, or an obligation that appeared entirely reasonable when signed and became burdensome several years later.

This is one reason governance exists. It does not rest on the assumption that every director will behave improperly. An audit right does not mean management is presumed dishonest, and a written agreement does not demonstrate that trust has disappeared. These mechanisms are ways of creating institutions capable of continuing to function when the people within them are angry, afraid, ambitious or simply no longer in agreement.

The Egyptian jurist Dr Abd El-Razzak El-Sanhuri, one of the principal architects of modern Arab civil law, approached the function of law in terms of establishing rights, defining their limits and requiring respect for them.[9] I find that conception particularly useful because it does not burden law with the task of reforming human nature. It gives law a more practical function.

Law can establish a boundary, determine responsibility when that boundary is crossed, prescribe consequences and provide a process for resolving the resulting dispute. What it cannot do is remove from the human being the desire, fear, ambition or sense of entitlement that may cause him to test the boundary in the first place.

Perhaps this is the deeper meaning of my father’s statement that I did not fully appreciate at the time: ‘Every system carries within it the seeds of its own destruction.’ In the end, a system is tested by the people operating within it, not merely by the words through which it was created.

The Real Subject

When I began my career, I believed that becoming a better lawyer meant, above all, learning more law. I wanted to understand legislation, judgments, procedure and contractual structures, and I still regard all of these as essential. What changed was my understanding of what comes after them.

The books my father made me read gradually began to connect with what I was seeing in practice. Descartes’ distinction between possessing a good mind and using it well became visible in highly intelligent people making poor decisions. Hegel’s wisdom arriving only at dusk appeared in transactions whose weaknesses became apparent only after relationships had collapsed. Tolstoy became familiar in the moral certainty with which litigants described one another. These thinkers did not give me legal answers, but they gave me language through which to understand things I had begun to observe across the table.

I am grateful today for those occasions when my father sat me in front of him and made me read something I did not understand. I doubt that he expected me to remember every philosophical theory, and I certainly did not. What remained was the habit of looking beyond the first explanation and resisting the easiest narrative.

That habit has probably influenced my practice more than I realised. I learnt to look at the shareholder seeking control and ask why control had suddenly become so important. I learnt to listen differently when a partner’s conception of fairness changed after the business became more valuable. I learnt that sophisticated wrongdoing may look entirely respectable, and that intelligence may make rationalisation stronger rather than weaker.

I also learnt that faces, silences and conduct can sometimes tell a part of the story that legal language does not. Not always, and never with the degree of certainty that the law properly requires of evidence, but sometimes enough to make the lawyer ask one more question. Perhaps the clearest test of character I have encountered during my years in practice is also one of the simplest: what does a person do when doing the right thing becomes costly?

I would not have understood that question when my father first placed Hegel or Descartes in my hands. I understand it better now.

After almost two decades in the profession, I still spend a substantial part of my working life reading legislation, judgments and contracts. Yet these are no longer the things that surprise me most. The difficult part is usually the human being: the client, the opponent, the partner, the witness, the director and, sometimes, even the lawyer himself. The law can be researched, its provisions revisited, its judgments analysed and its rules compared. The human being sitting across the table still has to be understood afresh each time.

References

[1] The Qur’an, Surah Al-Baqarah 2:35–37.
[2] Oxford Royale, 15 Hardest Degree Subjects.
[3] René Descartes, Discourse on Method and Related Writings, Penguin Random House.
[4] Leo Tolstoy, Three Methods of Reform.
[5] Hegel Society of America, The Owl of Minerva.
[6] Towards a Context-Specific Approach to Understanding Lawyers’ Well-Being: A Synthesis Review and Future Research Agenda, PubMed Central.
[7] From Their Angle: A Look at the Emotional World of Defense Attorneys Who Represent Sex Offenders, PubMed Central.
[8] Samiha Al-Qalyubi, Commercial Companies (الشركات التجارية), Dar Al-Nahda Al-Arabiya, on the concept of affectio societatis in the company contract.
[9] Abd El-Razzak El-Sanhuri and Ahmad Hishmat Abu Sittet, Usul al-Qanun (The Foundations of Law).