Exercises — Chapter 20: Proposals and Business Cases

Writing is learned by writing. Most of these ask you to produce or revise a persuasion document, not pick an answer. Where a task is open-ended, a self-assessment rubric follows it. Fuller solutions to starred items live in appendices/answers-to-selected.md.

Difficulty: ⭐ warm-up · ⭐⭐ revision · ⭐⭐⭐ production/synthesis · ⭐⭐⭐⭐ extension.

Part A — Analyze This ⭐

Identify what's working or broken in these persuasion documents. Name the principle; don't fix it yet.

A1. An executive summary opens: "In today's rapidly evolving business landscape, organizations must continually adapt their operational infrastructure to remain competitive." What is this sentence doing for the reader, and what should the first sentence of an executive summary do instead?

A2. A proposal's "Solution" section appears on page 1; its "Problem" section appears on page 4. Using §20.5, predict the reader's reaction to the solution and explain why the ordering fails.

A3. A business case compares two options: "Adopt Vendor A" and "Adopt Vendor A with the premium tier." A reviewer says the analysis isn't really an options analysis. Why are they right? What's missing?

A4. A proposal's qualifications section reads: "Our firm is a recognized industry leader with deep expertise and an unwavering commitment to client success." Identify why a skeptical client wouldn't be persuaded, and name what would persuade them.

A5. A proposal lists this benefit: "Our platform will dramatically increase productivity and deliver substantial cost savings." What's wrong with it as a benefit, even though it's framed as an outcome rather than a feature?

A6. A proposal ends: "We are confident this solution will meet your needs and look forward to discussing it further at your convenience." What did the writer forget, and what would the last sentence look like if they'd remembered it?

A7. ⭐⭐ A business case for a $3,000 software subscription runs 18 pages, with a full financial model, a competitor matrix, and an appendix of vendor reference calls. Separately, a proposal for a $2M data-center migration is a single page. Diagnose both using §20.3's "match depth to stakes."

A8. ⭐⭐ Here is a risk section. Identify why it weakens the proposal rather than strengthening it, and which §20.7 principle it violates.

"Risks: This project carries some risk. Implementation could be complex. There may be unforeseen challenges. Timelines in projects of this nature can be uncertain. As with any initiative, success is not guaranteed."

Part B — Revise This ⭐⭐

Rewrite for persuasion. Produce the improved version.

B1. Lead with the ask. Rewrite this buried-ask opening so the recommendation is the first sentence and the hedging is gone.

"Over the past several months, our team has been examining the challenges associated with our current expense-reporting process, which many employees have found cumbersome and time-consuming. After evaluating several alternatives, we believe it may be worth considering the adoption of a tool called ExpenseFlow, which could potentially streamline this process at a cost of approximately $40,000 per year."

B2. State the problem in the reader's currency. Rewrite this writer-centric problem statement so a non-technical executive feels the consequence.

"The legacy CRM runs on an unsupported database version, the codebase has high cyclomatic complexity, and integration points are tightly coupled, making the system brittle and difficult to maintain."

B3. Price the "do nothing." A business case recommends migrating off an aging server but never states what happens if the company waits. Invent a plausible, quantified cost-of-inaction paragraph (you may make up reasonable numbers) that you could insert as the "do nothing" option.

B4. Turn the pitch into an options analysis. This is a one-sided recommendation. Rewrite it as a genuine options comparison (you may invent reasonable figures) using a small table, including a "do nothing" row.

"We should buy the AnalyticsPro suite. It's the best tool on the market and will transform how we use our data. At $120,000 per year, it's an investment that will more than pay for itself."

B5. Cut the throat-clearing. This 70-word summary opening contains roughly 50 words before its first useful fact. Rewrite it to lead with the fact, in under 30 words total.

"As you are likely aware, given the discussions that have taken place over recent quarters across various teams and at several leadership meetings, there has been a growing recognition, shared by many stakeholders, that our onboarding process for new engineers is slower than we would like it to be."

B6. Right-size the risk list. Take the weak, anxiety-inducing risk section from A8 and rewrite it as a proper risk–mitigation table with three real, material risks (invent plausible ones for a software-migration project) and a concrete mitigation for each.

Part C — Write This ⭐⭐–⭐⭐⭐

Scenarios → produce the document.

C1. Write the executive summary. ⭐⭐⭐ You are proposing that your company replace its manual, spreadsheet-based inventory tracking with a barcode-scanning system. Facts you may use (and quantify further if you like): the current process takes two employees ~15 hours/week; stockouts caused by tracking errors cost an estimated $90,000 in lost sales last year; the new system costs $55,000 up front plus $12,000/year; in a pilot, scanning cut counting time by 80% and eliminated stockout errors. Write a stand-alone executive summary (≤ 180 words) following §20.4's five moves (situation, ask, justification with a number, cost, dated next step). Then apply the finished-test: could a reader approve it from the summary alone?

Self-assessment rubric (C1): - Leads with the ask? The recommendation is in sentence 1, not buried under context. (Pass/Fail) - Stands alone? A reader needs nothing else to decide—problem, ask, justification, cost, and next step are all present. (Pass/Fail) - Quantified? At least two concrete numbers (e.g., 80% time cut, 11-month payback, $90K avoided). (1 point each, target ≥ 2) - Hedging removed? No "we believe it may be worth considering"; uses "we recommend." (Pass/Fail) - Dated next step? A single, specific action with a deadline. (Pass/Fail) - Length discipline? Under ~180 words and readable in under a minute. (Pass/Fail)

C2. Turn these features into benefits. ⭐⭐ For each feature below, run "so what?" until you reach a benefit a specific named reader cares about. Write the benefit as a sentence. (The reader differs per item—match the benefit to them.)

Self-assessment rubric (C2): A benefit (not a restated feature) names an outcome the reader feels—saved time, saved money, reduced risk, less hassle, peace of mind. Test each one: would this reader say "yes, that matters to me"? If your sentence still describes what the product is rather than what changes for them, run "so what?" one more time. Bonus: note where the same feature would yield a different benefit for a different reader.

C3. Write a problem statement two ways. ⭐⭐ Pick a real annoyance at your work, school, or a project (a slow process, a flaky tool, a manual task). Write the problem statement (a) the way you naturally would—in your own terms—and then (b) translated entirely into a decision-maker's currency (cost, risk, time, missed opportunity). Label them "before" and "after," like the book does.

C4. Write a one-paragraph "next step." ⭐⭐ You've just delivered a strong proposal verbally and the executive said, "Send me something." Write the closing paragraph of your proposal email: a single, specific, dated ask that makes it easy for them to say yes. Avoid "let me know your thoughts."

C5. Draft a risk–mitigation table. ⭐⭐⭐ For a proposal to migrate your team from one project-management tool to another, write a risk–mitigation table with the three or four risks a smart skeptic would actually raise (data loss, adoption resistance, downtime, cost), each with a concrete, convincing mitigation.

Part D — Synthesis & Critical Thinking ⭐⭐⭐

D1. Find the flaw. A colleague's proposal has a flawless executive summary that leads with the ask, quantifies the ROI, and ends with a dated next step. But the body opens with five pages of background before the problem statement, and the recommendation in the body contradicts the summary's (the summary says "Vendor B," the body's conclusion says "Vendor B or C"). Name both problems and explain which one is more dangerous and why.

D2. Translate for three readers. You're proposing a $200,000 investment in automated testing infrastructure. Write the one-sentence core pitch three times: (a) for the VP of Engineering, (b) for the CFO, (c) for the product team whose features ship faster as a result. Show how the same investment yields a different benefit per audience (theme 2).

D3. The persuasion-vs-honesty line. §20.6 warns that benefits must be provable, and Chapter 38 (Ethics) treats clarity as a responsibility. You're writing a proposal and your best benefit ("cuts processing time 60%") is true in the pilot but you're not certain it'll hold at full scale. How do you state it honestly without gutting its persuasive force? Write the sentence.

D4. Diagnose the genre mismatch. Leadership asks for a "quick business case" to choose between three already-approved vendors. The author submits a document that spends its first three pages re-arguing why the company needs the tool at all. Using §20.1, explain the genre error and what the author should have led with instead.

D5. Reverse-engineer the structure. Take a real proposal, sales page, or pitch you've received (an email, a vendor PDF, a grant call). Identify: Where's the ask? How long until you reach it? Are features or benefits foregrounded? Is there a cost-of-inaction? Write a one-paragraph structural critique using this chapter's vocabulary.

Part M — Mixed Practice (Interleaved) ⭐⭐–⭐⭐⭐

These mix this chapter with earlier ones, so you have to choose the right tool.

M1. (Ch 19 + Ch 20) You need to send a proposal and a cover email. The email shouldn't repeat the proposal—it should make the recipient open it. Write the cover email (Chapter 19: specific subject line, purpose-first opening, one clear action) whose body is essentially a three-sentence version of your executive summary. What goes in the email vs. the attached proposal?

M2. (Ch 4 + Ch 20) Apply a reverse outline (Chapter 4) to the buried-ask "before" summary in §20.4 of the chapter: write down the single point of each sentence, in order. What does the reverse outline reveal about why the ask is buried, and how does it confirm the §20.4 diagnosis?

M3. (Ch 3 + Ch 20) Take your executive summary from C1 and run Chapter 3's conciseness pass on it: cut nominalizations, kill "it is/there are" expletives, and remove empty intensifiers. How many words did you save, and did cutting strengthen the persuasion or weaken it?

M4. (Ch 2 + Ch 20) The same project proposal must go to two readers: a technical lead who'll scrutinize the approach, and a CFO who only cares about ROI. You can't write two documents. Using audience analysis (Chapter 2) and the executive-summary logic (§20.4), describe how one document serves both—what each reader reads, and what structural feature makes that possible.

M5. (Ch 17 + Ch 20) A grant's Specific Aims page (Chapter 17) and a business proposal's executive summary do the same job for different readers. Take a Specific Aims page you've seen or drafted (or invent one in two sentences) and rewrite its opening as if it were a business executive summary for a funder who thinks in ROI rather than scientific significance. What transfers, and what has to change?

Part E — Extension ⭐⭐⭐⭐ (optional)

E1. Full mini-business-case. Choose a real decision you'd like your organization (or household, or a club) to make that involves spending money. Write a complete one-to-two-page business case: current state, desired state, at least three options (including "do nothing," priced), an analysis table comparing them on cost and one other axis, and a recommendation. Then write the executive summary that goes on top. Apply every test in the chapter.

E2. Win an RFP. Find a real, public Request for Proposal (many governments and nonprofits post them). Read its required structure and evaluation criteria. Write a two-page response to its format—not your preferred format—and reflect in a short note on how answering the RFP exactly (§20.9) constrained and shaped your writing.

E3. The unsolicited proposal. Write an unsolicited proposal: pitch an improvement to an organization that didn't ask for one. The hard part (§20.9) is that you must first convince the reader they have a problem worth solving. Make the problem–solution structure (§20.5) carry that weight, and note where an unsolicited proposal is harder than a solicited one.

Selected solutions and rubrics live in appendices/answers-to-selected.md. For open-ended writing tasks, use the self-assessment rubrics above; the strongest signal you've succeeded is that a real reader, given only your executive summary, can make the decision.