By: Adam Eckart

Despite the challenges of the COVID-19 pandemic, many legal writing courses like Legal Practice Skills finished this past semester on-track and on-topic by discussing persuasion, submitting persuasive memoranda, and presenting oral arguments. Often overlooked by students, one important skill developed in a persuasive semester is learning how to draft advocacy letters – for both litigation and transactional practices.

Although legal writing courses often discuss the types of advocacy letters litigators write to courts (motions), to counterparties (demand letters), and even to governments (petitions), transactional attorneys in a variety of practices write advocacy letters too. By transferring the litigation-based principles of writing advocacy letters learned in a persuasive semester, students can learn to write effective advocacy letters for transactional matters as well.

In my former transactional practice at a global law firm, we often sought advice from the Federal Trade Commission regarding the interpretation of Federal regulations governing mergers and acquisitions. Attorneys in other practice areas regularly do the same. In labor and employment, investment management and tax practices, among others, attorneys must regularly seek advice from Federal regulators at the Department of Labor, the Securities and Exchange Commission, and the Internal Revenue Service, respectively. Seeking advice regarding Federal regulations involves carefully drafting an advocacy letter to the relevant agency, not simply writing a simple letter to ask a question.

A well-crafted advocacy letter written in a transactional context effectively utilizes the skills learned in a litigation-styled persuasive legal writing semester and requires a lawyer to:

1. Consider the audience and purpose: Ensure to use an appropriate tone given the intended recipient, remembering to be deferential and professional, and appropriately frame the inquiry at the outset of the letter;

2. Use precedent: Like in a litigation context where advocates use statutes and case law to persuade judges, transactional lawyers likewise use precedent – often published and anonymized opinion letters, no action letters, or informal interpretations – to show favorable precedent for the answer sought;

3. Apply appropriate legal reasoning: Like in a litigation context where advocates use legal reasoning, such as analogical reasoning, to employ fact to fact comparisons and apply precedent cases, transactional lawyers likewise use analogical reasoning with transactional precedent to show fact to fact comparisons and apply transactional precedent; and

4. Present the letter in the most favorable light: Don’t just ask the regulators a question hoping for a good result – ask the question in the light most favorable to your client, using transactional precedent and facts most favorable to your client, to lead the regulator to the answer sought.
By considering the above factors and transferring litigation-based persuasive writing instruction to transactional contexts, one can craft effective and impactful advocacy letters for transactional matters.

Adam Eckart is an Assistant Professor of Legal Writing at Suffolk University Law School. Prior to joining Suffolk, Professor Eckart practiced at Ropes & Gray LLP as an associate in the antitrust mergers and acquisitions practice and taught in the Lawyering Program at Boston University Law School.