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The Art of Start-Up Business Lawyering: Excellence in Writing

By George Grellas, Esq.

In the start-up business context, excellence in writing matters – a lot.

What are its attributes?

Good writing will reflect good thinking. A smart lawyer may lack writing strength, but a lawyer who writes well will also know how to think well. The one is not possible without the other. Feeble writing will often lack not so much style as thought. Lawyers are taught to present their materials in a certain way: set out facts, apply law, draw conclusions. A poor lawyer will mimic this process without offering anything sound to a client: logic will be disjointed, tough points ignored or glossed, and analysis lacking. This is nothing more than faking it. And clients see this all too clearly. Good writing must always have sharp, crisp thought behind it.

Good writing will reflect a right attitude. Nothing makes a founder wince so much as a lawyer who is patronizing, condescending, officious, or arrogant. Folksy is no better at the other extreme. Writing that reflects such attitudes will harm client relations and will harm negotiations, among other things. Good writing will be direct, down-to-earth, and professional because the attitude underlying it will be that way as well.

Good writing will be apt for the client’s needs. Start-up clients have no desire to pay for writing as art, and even technical excellence in writing is misplaced if it simply amounts to undue word-fiddling or other activity that adds substantially to a client’s bill without furthering a legitimate client purpose. And so the dash-off item ought to be dashed off, the heat-of-battle item treated accordingly, and the complex item edited with proper purpose in mind. Aptness also means fit in two critical senses: it excludes the “paper as an end in itself” goal of a certain rigid style of business lawyering, and it excludes the churning that can occur if product is generated primarily to allow an inexperienced lawyer to learn on the job. Start-up clients have no desire to pay for a lawyer’s stuffiness or for a lawyer’s greenness. Good writing will always be apt and to the point and done by a lawyer who is prepared and rightly focused to meet a client’s true needs.

Good writing will reflect versatility. The legal needs of a start-up business are typically complex but not ultra-specialized, and the niche-focused writing style of departmental specialists often misses the practical point of a problem faced by such a client. Being niche-based, and expensive, such ultra-specialists will feel a need to parade their expertise. The result is often an unwieldy written product that will kill by its sheer exhaustiveness. Great work but ill-fitted to the problem at hand. For the start-up, good writing will reflect the versatility of a hand that can shift easily from accuracy in contract drafting to apt tone for deal-making to vigorous advocacy for disputes.

Good writing will reflect traditional good-writing principles aptly applied. Both parts of this are important. It is good to be simple, direct, brief, and clear. But simple, short, and active can become simplistic, monotonic, and rigidly unnatural. A bad writer may ignore good-writing rules, but an equally bad one will apply them one-dimensionally in arty or mechanical fashion. A good writer will do neither. Thus, while ill use of passive voice can lead to stylistic pomposity, a categorical exclusion of passive voice can lead to a staccato and unnatural style. The same can be said of any arbitrary attempt to use exclusively short words or sentences. Good writing must be down-to-earth and natural, never stilted or stuffy, and writing style must reflect this.

Good writing will draw from rich, deep resources. Excellence in writing is not developed in a day. In lawyering, the core of writing excellence is not even developed on the job. A lawyer who writes well will have developed the core part of the needed depth and discipline for this craft long before passing the bar exam. Opinions may vary on what form this may take, but one might suggest disciplined studiousness, a systematic approach to having exercised oneself continually in writing over many years, and depth in understanding of language. It matters that a lawyer can demonstrate excellent academics, preferably with honors: this is part of a deep reserve of right habit, knowledge, and craft from which excellence derives during a legal career. And, because writing is craft, it also matters that a lawyer will have exercised the faculties needed to build strength over the years: one learns to write by doing the hard work of writing, often and well.

Depth of language study is best understood by analogy to a toolbox: one may be a good or even excellent carpenter without having a broad mix of sophisticated tools to use on a job, but having such tools increases immeasurably what a skilled carpenter can do. So too with a lawyer who seeks to be well-equipped. Ancient language study in particular allows one to gain a deep knowledge of word families, a rich vocabulary, and a strong understanding of how words are best ordered to achieve clarity, interest, and power. One can write well without this, just as one can code well without being skilled at designing the architecture of a complex software program, but one who can do both is optimally prepared to attack the whole.

In advocacy, good writing will reflect muscularity, pulling a reader from first to last by force of logical inevitability. This style requires a firm grasp of subject. It requires solid, understated control so as to convey a feel of assured confidence. And it avoids key flaws: it does not strain, or vaunt, or table-pound, or attack the person. It is professional. It has class. It works like a powerful engine under the hood: it does not show itself, but anyone who hears that quiet hum will immediately sense its power. Done right, it projects quintessential vigor: it races along and even leaps off the page on the strength of its own power alone.

Writing well is critical to start-up business lawyering – whether in the sharpness of a contract, the force of a demand letter, the tone of a negotiating position, the power of an argument, or the clarity of strategic advice. A client can tell if writing is lively or lies dead on a page, if it makes sense or sounds ill-defined or incoherent, if it is a source of pride or embarrassment. So too can an adverse party, a lawyer on the other side of a deal, a judge deciding a case, or a board of directors seeking advice on a matter. Though writing strength as such does not define good lawyering, a client will sorely feel its lack no matter what the remaining skills.

A well-equipped start-up business lawyer will display superior writing skill, will not be self-conscious about style and technique, and will be able to execute complex writing tasks quickly, intelligently, and effectively for the task at hand. Start-up clients appreciate a lawyer who does this consistently and well. It is absolutely critical to start-up business lawyering.