Unclear and unpersuasive legal writing often comes from undeveloped analysis and undisciplined organization. This webinar explores best practices for structuring and organizing briefs, including how to most effectively frame and sequence arguments, use authority, and find a winning theme. It also takes a fresh look at an old law school war horse -- : I(ssue) R(ule) (A)nalysis C(onclusion) – one of the few rules in life from which there’s virtually never cause to deviate. Part of the webinar series: PERSUASIVE BRIEF WRITING 2022 See more at https://www.financialpoise.com/webinars/

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Practical and entertaining education for
attorneys, accountants, business owners and
executives, and investors.

3. Disclaimer
The material in this webinar is for informational purposes only. It should not be considered
legal, financial or other professional advice. You should consult with an attorney or other
appropriate professional to determine what may be best for your individual needs. While
Financial Poise™ takes reasonable steps to ensure that information it publishes is accurate,
Financial Poise™ makes no guaranty in this regard.
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Thank You To Our Sponsors

5. Meet the Faculty
MODERATOR:
Robert Michaels - Environmental Law & Policy Center
PANELISTS:
Hon. Maureen Hannon – Circuit Court of Cook County
Adam Hirsch - Roetzel
Rob Kelter – Environmental Law & Policy Center
Susan Valentine - Valentine Austriaco & Bueschel, P.C.
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6. About This Webinar
Unclear and unpersuasive legal writing often comes from undeveloped analysis and
undisciplined organization. This webinar explores best practices for structuring and organizing
briefs, including how to most effectively frame arguments, use authority and find a winning
theme. It also takes a fresh look at an old law school war horse -- : I(ssue) R(ule) (A)nalysis
C(onclusion) – one of the few rules in life from which there’s virtually never cause to deviate.
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7. About This Series
Especially in federal district court, pre-trial litigation occurs almost entirely “on the papers,” with few, if
any, oral arguments or courtroom presentations. If litigators want a claim to survive or be dismissed,
discovery to be permitted or denied, or evidence to be admitted or barred, they must persuade the court
in writing. But mastering the craft of persuasive legal writing can take decades and require shedding
ingrained old habits and defying some common expectations. Join a panel including seasoned litigators,
two former legal writing instructors, and a sitting judge discuss the structure, substance and style of
effective brief-writing. This series will help new and more experienced litigators sharpen a set of crucial
skills that can, and should, continue developing throughout their careers.
Each Financial Poise Webinar is delivered in Plain English, understandable to investors, business owners, and
executives without much background in these areas, yet is of primary value to attorneys, accountants, and other
seasoned professionals. Each episode brings you into engaging, sometimes humorous, conversations designed to
entertain as it teaches. Each episode in the series is designed to be viewed independently of the other episodes so that
participants will enhance their knowledge of this area whether they attend one, some, or all episodes.
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8. Episodes in this Series
#1: Structure and Organization
Premiere date: 9/14/22
#2: Style
Premiere date: 10/12/22
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9. Episode #1
Structure and Organization
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10. Before Writing Anything
• Determine exactly what you want to achieve
✓ If you’re the movant, what do you want the court to do?
✓ If you’re opposing, how, exactly, do you want to the court to dispose of the matter?
✓ Consider objective in light of whole case; what will happen if you lose?
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11. Before Writing Anything
• Complete all necessary research and become fluent in relevant law; this will guide
structure
✓ (Almost) always: take path of least resistance
✓ Invoke the least-demanding standard
✓ Assume the lightest/easiest burden
✓ Give the court the simplest, easiest route to give you what you need
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12. Overview of Brief Structure
• Introduction or Preliminary Statement
• Factual/Procedural Background
• Argument
• Conclusion
• NOTE: for appellate briefs, court rules will prescribe required sections that roughly track
the above
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13. Introduction
• At least one paragraph; up to 2-5 pages in longer briefs
• Provide sufficient factual and procedural context for the court to find its bearings; court has
tons of cases and likely remembers nothing about yours
• Clearly state desired outcome
• For reply briefs, no need to entirely re-frame the whole case; can get right into the core
fights
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14. Introduction (cont’d)
• Create some expectation of what’s to come;
• Can range from one “as explained in detail below” sentence to a bullet-point roadmap
• No need to overdo it or present entire argument; in longer briefs, table of contents serves
this role and in appellate briefs, the summary of argument will provide an intermediate level
of detail
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15. Introduction (cont’d)
• If possible, establish primary theme, including, potentially, that your desired outcome:
✓ is clearly required by precedent/rule,
✓ serves judicial economy, or
✓ is otherwise fair and reasonable (see Theme slides infra)
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16. Introduction (cont’d)
• Themes: Your Opponent’s Argument
• Confusing/unduly complicated
• Poorly supported
• Unfair
• Unpredictable
• Inconsistent with standard, other cases, and related law
• Promotes bad policy/creates bad incentives
• Inconsistent with record
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17. Background
• Follow chronological approach; use non-argumentative headings to separate events
• Cite carefully to ECF documents or evidence you’re attaching; accuracy is paramount
• Avoid unnecessary detail but be sure story is complete for reader new to the matter
• Freely quote key passages but don’t go overboard
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18. Background (cont’d)
• Slanted, but not silly; again, accuracy, and credibility, are essential
• On motions to dismiss or for judgment on the pleadings, factual background typically
limited to summary of allegations and responses
✓ Documents referenced in pleadings can occasionally be attached and used in motion,
but it risks converting motion into one for summary judgment
✓ Check local rules and cases to stay on right side of line
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19. Background (cont’d)
• Procedural history/posture typically woven into chronological recitation of entire story
• As with factual background, use non-argumentative headings to separate key events
✓ E.g., “The Second Amended Complaint” (followed by explanation of allegations) or
“The District Court’s Summary Judgment Opinion” (followed by summary of opinion)
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20. Argument: Structure
• Logical, and, if possible, symmetrical (i.e., no “A” w/out at least a “B”, etc.), outline-based
structure
• For longer briefs, table of contents should provide complete summary of argument
• For dispositive motions, typically organize by count or claim (I, II, etc.), element of claim (A,
B, etc.), and arguments re: element (1, 2, etc. and smaller)
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21. Argument: Structure (cont’d)
• In responses and replies, no obligation to follow opponent’s structure, but don’t ignore it
either:
✓ Opponent typically leads with point they consider strongest; if you delay addressing it,
you may appear afraid
✓ Once you’re in the guts of any argument, you have more room to deviate from
opponent’s structure
✓ If you need to delay reaching opponent’s lead argument(s), you can preview or give
notice in introduction to brief or introduction to section
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22. Argument: Structure (cont’d)
• For each major point, use IRA(C): Issue, Rule, Analysis and, if necessary, Conclusion
• Just about NO reason to deviate from this approach; it captures how reader understands
and applies legal rules and ensures reader will know why information is being presented
• Following IRA(C) can be harder than it seems, especially when opponent’s argument
requires extensive set-up/explanation; even then, however, it almost always helps to have
rule stated up front
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23. IRAC: Issue
• Ideally, the “issue” will be stated in your argument heading, e.g., “Corpco Is Vicariously
Liable for Its Agent’s Misconduct.”
• Keep headings to one-two lines if possible
• Consider a sentence or two right under heading to fully set up the fight, especially if the
argument has sub-parts e.g., “Corpco says it can’t be vicariously liable on Counts I-III. In
fact, as explained below: (a) Corpco is vicariously liable under Illinois law; (b) RICO
imposes no additional barriers to vicarious liability.”
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24. IRAC: Rule
• Typically state right below heading or right after sentence(s) that set up the fight
• Quote authority often; use as few of your own words as possible; mold case/statute
language into your articulation of rule [using brackets] if needed
• Include at least one sentence as to why rule makes sense, again with quote from authority
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25. IRAC: Rule (cont’d)
• No clear rule to apply? Carefully synthesize one, based on authority
• The rule/legal standard is the touchstone or anchor of the entire argument. At all times, you
should be arguing about which standard/rule applies or how it applies. If you find yourself
doing anything else, you need to find your bearings.
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26. IRAC: Analysis
• Closely apply authority, w/frequent factual comparison to your case (but w/out needless
details from cited cases like dates or parties’ names); need to explain similarities to your
case and demonstrate why they matter
• Avoid citing authority without providing either a short discussion of holding or parenthetical
• Use crisp case parentheticals that get to the heart of the fight; typically start with a present-
tense verb, e.g., “sustaining RICO conspiracy claim against employer based on employee
misconduct”
• Unless necessary, don’t rely on cases w/bad outcomes
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27. IRAC: Analysis (cont’d)
• Accurately summarize opponent’s argument; understand what they mean, or ought to
mean, not just what they say
✓ You can’t understand how silly your opponents’ arguments are unless and until you
take them seriously
• Don’t be afraid to quote opponent’s language; ideally, find phrase(s) you can turn back
against them
• Rebut ALL of opponent’s arguments and distinguish ALL of their authority
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28. IRAC: Analysis (cont’d)
• Concede NOTHING unless it’s absolutely essential; you never know what’s going to
happen next
• Structure fallback arguments accordingly, e.g., “In any event, even if the Caremark
standard applied (which it doesn’t), Plaintiffs state a claim.”
• Explain why your victory serves purpose of rule or otherwise makes sense in terms of
judicial economy, fairness, predictability, etc.
• Be careful with absolutes, e.g., “no court has held,” “defendants never indicated,” etc.
• Use footnotes wisely to separate primary from ancillary points but be aware of local and
court rules to avoid waiver
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29. IRAC: Analysis (cont’d)
• Carefully consider whether to preemptively rebut anticipated counter-arguments
• Especially if you’ll have a chance to reply, it’s often better to wait and let opponent raise
counter-argument, especially if they have the burden of proof
• If you hold your fire, frame your affirmative argument to preserve full opportunity to reply
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30. Conclusion
• Typically, keep it short; no need to rehash entire argument – “For the reasons above,
Plaintiffs respectfully ask the Court to deny Defendants’ motions to dismiss.”
• Clearly reiterate exactly what you want the court to do; be very precise
• Attach proposed order if local rules require it or it would otherwise be helpful
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31. About the Faculty
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32. About The Faculty
Robert Michaels - rmichaels@elpc.org
Rob Michaels is a Senior Attorney working to protect clean water, wildlife, biodiversity and
forests in the Midwest. Mr. Michaels is an experienced plaintiffs-side litigation attorney with 30
years of federal court complex litigation experience as a Partner at the Robertson, Curley &
Clayton law firm and the Goldstein & McClintock law firm. He previously was a Staff Attorney
and Project Director at the Environmental Law & Policy Center; University of Chicago Law
School Bigelow Fellow; and Associate at the Mayer Brown & Platt law firm following a federal
court clerkship with Judge Robert Hall (N.D. Ga.).
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33. About The Faculty
Hon. Maureen Hannon
Judge Maureen O. Hannon was elected as a Cook County Circuit Court Judge and sworn in December 2016. She
currently sits in the County Division where she hears real estate tax matters, election law, adoption, and mental
health cases. Prior to this assignment, she was assigned to the municipal division hearing contract disputes,
evictions, and traffic cases. Prior to taking the bench, Judge Hannon was a practicing attorney for over 25 years
with a wide breadth of experience. In addition to 5 years in private practice, she was a Cook County Assistant
State’s Attorney in the Civil Actions Bureau for 20 years. Judge Hannon has practiced in federal court and most of
the divisions of the Circuit Court of Cook County including chancery, probate, county, law, and the municipal
division and as well as defended the County from constitutional claims in litigation in federal court. When she left
the Office of the State’s Attorney, she was the Supervisor of the Conflicts Counsel Unit.
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34. About The Faculty
Robert Kelter - RKelter@elpc.org
Robert Kelter is a senior attorney at ELPC, leading the Energy Efficiency Program. Rob
advocates for stronger energy efficiency programs and implementation strategies in the Midwest
and on national policies. He is an experienced energy and public utilities regulatory attorney,
who served as the litigation director of the Illinois Citizens Utility Board handling a wide array of
electricity and natural gas rate and rulemaking cases and issues. Before that, he worked at
Environmental Action and the Office of the People’s Counsel in Washington, D.C.
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35. About The Faculty
Hon. Maureen Hannon
Judge Maureen O. Hannon was elected as a Cook County Circuit Court Judge and sworn in December 2016. She
currently sits in the County Division where she hears real estate tax matters, election law, adoption, and mental
health cases. Prior to this assignment, she was assigned to the municipal division hearing contract disputes,
evictions, and traffic cases. Prior to taking the bench, Judge Hannon was a practicing attorney for over 25 years
with a wide breadth of experience. In addition to 5 years in private practice, she was a Cook County Assistant
State’s Attorney in the Civil Actions Bureau for 20 years. Judge Hannon has practiced in federal court and most of
the divisions of the Circuit Court of Cook County including chancery, probate, county, law, and the municipal
division and as well as defended the County from constitutional claims in litigation in federal court. When she left
the Office of the State’s Attorney, she was the Supervisor of the Conflicts Counsel Unit.
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36. About The Faculty
Adam Hirsch - AHirsch@ralaw.com
Mr. Hirsch focuses his practice on commercial and business litigation, representing a wide
variety of clients ranging from individuals to small business owners to large corporations. He
has a particular focus on investment disputes and business fraud claims, and has
represented investors and investment companies as plaintiffs and defendants in lawsuits
around the country. Mr. Hirsch regularly writes and presents on current issues relating to
business fraud. He also has extensive experience litigating contract disputes, and has argued
and tried multi-million dollar contract issues before judges and juries nationwide. Mr. Hirsch
also has experience in advising clients in employment disputes relating to matters such as
separation, severance, non-solicitation, and non-compete agreements.
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37. About The Faculty
Susan Valentine - svalentine@vablawfirm.com
Susan Valentine is a founding partner of Valentine Austriaco & Bueschel, P.C. For more than
30 years, Susan has handled disputes, and when necessary, actively litigated a wide range of
matters. From 1997- 2000, she served on the full-time faculty of IIT Chicago-Kent College of
Law, teaching Professional Responsibility and Legal Research and Writing and serving as the
Faculty Adviser to the Moot Court Honor Society. Susan advises clients on a variety of
sensitive business issues, and her clients appreciate her practical, timely, and cost-effective
approach to their issues. She has extensive experience litigating disputes that involve insured
depository institutions and in representing business entities in commercial matters, ranging
from breach-of-contract issues to internal investigations that involve fraud and other
misconduct. She has also represented receivers, liquidators, and trustees in the investigation
and litigation of matters involving professional liability, contracts, fidelity bonds, insurance,
and reinsurance.
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38. Questions or Comments?
If you have any questions about this webinar that you did not get to ask during the live
premiere, or if you are watching this webinar On Demand, please do not hesitate to email us
at info@financialpoise.com with any questions or comments you may have. Please include
the name of the webinar in your email and we will do our best to provide a timely response.
IMPORTANT NOTE: The material in this presentation is for general educational purposes
only. It has been prepared primarily for attorneys and accountants for use in the pursuit of
their continuing legal education and continuing professional education.
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41. About Financial Poise
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