“Give me six hours to chop down a tree and I will spend the first four sharpening the axe.” —Abraham Lincoln, 16^th U.S. President

One of the more common misconceptions about professional writing is that strong writers simply sit down and produce clear, polished thinking in a single pass. In reality, most high-quality M&A writing is not the product of spontaneous brilliance. It is the product of disciplined preparation.

The strongest deal professionals rarely begin by writing sentences. They begin by organizing thoughts. This distinction matters because most writing problems are not writing problems at all; they are thinking problems.

When a CIM feels unfocused, an IC memo feels bloated, or a diligence report feels difficult to synthesize, the root issue is often not grammar, sentence structure, or formatting. More commonly, the team never fully clarified:

• The investment thesis,
• The central investment levers,
• The hierarchy of issues,
• The audience’s priorities, or
• The narrative structure needed to connect the analysis into a coherent whole.

As discussed in the first installment of this series, strong M&A writing is ultimately about interpretation and judgment. But before a professional can communicate judgment clearly, they must first organize it coherently. In practice, planning is where much of the real writing work occurs.

Most Weak Writing Begins with Weak Planning

One of the defining characteristics of inexperienced deal writing is the tendency to begin drafting before determining what the document is actually trying to accomplish.

This often manifests in familiar ways, such as:

• The IC memo that becomes a chronology of diligence findings rather than an investment recommendation,
• The CIM that feels like a collection of disconnected sections instead of a cohesive positioning narrative,
• The diligence report that summarizes analyses but never clarifies their implications or demonstrates their interconnectedness,
• Or the board update that contains information without communicating priorities.

In each case, the underlying issue is usually the same: the writing began before the thinking was fully organized.

Experienced professionals understand that writing quality is heavily influenced by preparation quality. Before drafting begins, strong deal teams typically have already formed views on:

• The investment thesis,
• Key supporting themes,
• Major risks and potential mitigants,
• Likely questions from stakeholders,
• And the relative importance of competing points.

This preparation does not eliminate iteration or revision; it creates direction. Without direction, writing tends to expand indiscriminately. Everything begins to feel equally important, and supporting details overwhelm central conclusions. Deliverables become technically comprehensive but strategically unfocused. The purpose of planning is not rigidity, but clarity.

Thus, it is critical to create an outline. But even before creating an outline, it is helpful to bullet point out the deal’s key themes. Key themes are the short statements of the key issues, diligence findings, or other critical deal considerations. It should focus on the short list of main considerations impacting:

• The deal’s go/no-go decision,
• Its valuation or pricing,
• The deal’s structure,
• Its risks and mitigants, and
• The probability of achieving the targeted return given identified value levers.

Keeping a key themes list throughout diligence and the deal process is a way to continually focus efforts on the most critical elements impacting the transaction. Items are likely to be added and fall off the list throughout the process, as well as move up or down the list in terms of priority. When it comes time to create a more formal outline, the key themes list provides the starting point and usually saves time and mental effort, as you have already been focused on the key issues rather than mere topical categories.

The First Draft is Supposed to be Imperfect

Many professionals struggle with writing because they attempt to draft and edit simultaneously. They search for perfect phrasing too early. They revise individual sentences before fully developing the broader argument. They mistake rough drafting for poor writing ability. This is a costly habit in M&A environments, where speed and iteration are essential, but so is accuracy and precision of thought and messaging.

Experienced writers understand that first drafts are not supposed to be polished. Their purpose is not perfection; their purpose is momentum. A blank page creates psychological pressure because it represents infinite possibilities and no structure. Once ideas exist on paper, however imperfectly, they can be refined, reorganized, challenged, compressed, and improved. This is particularly important in deal environments where information is incomplete, timelines are compressed, and investment views evolve as diligence progresses. By design, writing in M&A is iterative—not a one and done drafting session.

Strong writers therefore separate:

1. Idea generation,
2. Structural organization,
3. Refinement, and
4. Editing.

Attempting to perform all four simultaneously often leads to paralysis. The blank page is rarely defeated through inspiration. It is usually defeated through iteration.

For an M&A perspective, the separate functions look like this:

1. Idea generation => synthesizing your diligence and deal underwriting into prioritized key themes,
2. Structural organization => turning your key themes document into a formal outline,
3. Refinement => sharpening your IC memo, CIM, FDD report, or other M&A document, and
4. Editing => attempting to make more concise and remove errors or clumsiness.

Outline by Conclusions, Not Topics

One of the most effective disciplines in M&A writing is learning to outline by conclusions (i.e., key themes) rather than categories or topics.

Less experienced professionals frequently structure outlines around procedural sections. For the investment banker this might be the templated sections of a CIM, such as the executive summary, investment highlights, growth opportunities, business overview, industry overview, and financial overview. For the FDD professional, structured thinking and writing is commonly organized around quality of earnings, net working capital, and debt and debt-like items, along with industry-specific analyses. When followed mechanically, this structure often produces writing that feels descriptive rather than analytical.

Experienced professionals instead organize around investment implications and thematic conclusions.

For example:

• Revenue durability appears stronger than historical growth rates suggest;
• Customer concentration risk is mitigated by switching costs and embedded workflows;
• Margin expansion opportunities are credible but operationally dependent;
• Integration complexity may create execution risk post-close.

Notice the distinction. First, these examples make connections between critical issues and considerations rather than treating sections and their concepts as discrete or unrelated. Second, it immediately communicates judgment and prioritization (usually M&A writing is a form of persuasive writing). This matters because senior decision-makers do not simply want information categorized. They want information synthesized into actionable conclusions. They want to be persuaded by your thinking and diligence, but they will read it skeptically. In practice, this means the outline itself should already reflect the emerging investment narrative.

A useful test is simple: If someone reviewed only the outline of the document, would they understand the central conclusions? If the answer is ‘no,’ the thinking likely requires further refinement before drafting begins. 

The Pyramid Principle and Hierarchical Thinking

One of the most useful frameworks in professional writing—particularly in advisory and investing environments—is the pyramid principle. At its core, the concept is straightforward:

• Lead with the answer or conclusion,
• Support with key arguments by presenting the most compelling arguments first,
• Then provide the underlying evidence.

This approach mirrors how senior professionals naturally process information. Experienced decision-makers generally do not want to work upward from raw data toward conclusions. They expect the deal team to perform that synthesis first.

Yet many professionals write in the opposite direction. They begin with process:

• What was analyzed,
• Which data was reviewed,
• How diligence was conducted, or
• Which workstreams were completed.

Only after several pages do the actual conclusions emerge. This structure forces the reader to perform unnecessary analytical work. Strong M&A writing typically reverses this sequence.

Instead of: “We analyzed customer retention across the top twenty accounts…”  A stronger approach may be: “Customer retention appears materially stronger than initial concerns suggested, supported by long-tenured enterprise relationships and historically low churn.” The conclusion appears first. The supporting analysis follows afterward.

This principle becomes especially important in CIMs, FDD reports, investment committee memos, lender presentations, board materials, fairness opinions, and executive summaries. Senior audiences operate under severe time constraints and often have short attention spans. They prioritize clarity, hierarchy, and speed of comprehension. Well-structured writing respects and caters to those constraints and it is more persuasive.

Audience and Context Shape the Writing

One of the more underappreciated aspects of deal writing is that different audiences require different forms of persuasion. The underlying facts may remain identical, but the framing, emphasis, and structure often change depending on the reader.

For example:

Strong writers therefore constantly ask: “What does this audience need to understand, believe, or feel comfortable with?” This does not mean altering facts. It means prioritizing the information most relevant to the decision-maker sitting across the table and presenting it accordingly.

The medium itself also matters: a CIM is not written like an IC memo, an executive summary is not written like a detailed diligence report, and a board deck is not written like an internal workstream update. Sophisticated deal professionals understand that writing is contextual; effective communication requires both analytical rigor and situational awareness.

Writing is Often Clarification, Not Documentation

One of the more valuable realizations in professional writing is that the act of writing itself frequently sharpens the underlying investment view. Many professionals have experienced the following dynamic during live deals:

• An idea initially feels persuasive in discussion,
• But becomes difficult to defend once written clearly,
• While another issue initially viewed as secondary emerges as central once the narrative is organized.

This is not accidental. The writing process forces prioritization and precision of thought. Writing exposes gaps in logic and reveals unresolved assumptions, especially in the early stages of articulating key themes and consolidating thoughts. In this sense, writing is not merely documenting conclusions after analysis is complete. Writing—including planning, theme identification, and outlining—is part of the analytical process itself. Strong deal teams are constantly writing and revising throughout a deal so that the product becomes a reflection of their analysis rather than a summary of it.

While good writing is commonly iterative, it is important to think of it as a process to refine and clarify the team’s thinking rather than rework. Experienced deal professionals frequently add and subtract key themes, revise outlines, reorganize sections, and rewrite investment theses multiple times during a process. The investment narrative itself evolves alongside the team’s understanding of the business. Good writing is therefore not evidence that thinking is finished. It is evidence that thinking has become clearer.

Final Thoughts

In M&A, strong writing rarely begins with sentence construction. It begins with disciplined thinking and structured preparation.

The quality of a deliverable is heavily influenced before drafting ever starts:

• By the clarity of the investment thesis,
• The priority of the themes,
• The hierarchy of conclusions,
• The structure of the outline,
• And the writer’s understanding of the audience.

Experienced professionals understand that writing is iterative. Strong first drafts are rarely perfect. What matters is establishing a coherent structure that allows analysis, judgment, and narrative to develop together. The best deal writing does not emerge from improvisation. It emerges from organized thinking.

In the next installment, we will examine the tactical side of writing effective slides and reports in M&A, including “So What?” headlines, slide density, narrative flow, visualization, and how strong deliverables guide readers toward conclusions rather than merely presenting information.