Exercises — Chapter 19: Emails That Get Read and Get Results

Writing is learned by writing. Almost every task here asks you to rewrite or produce an email, not pick an answer. Where a task is open-ended, a self-assessment rubric follows. All emails below are anonymized composites—fictional but realistic—of the kind that fill real inboxes. Fuller solutions to starred items live in appendices/answers-to-selected.md.

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

Part A — Analyze This ⭐

Diagnose what's working or broken. Name the principle; don't fix it yet.

A1. A subject line reads: "Quick question." The email under it is a 400-word request for budget approval due Thursday. Name two distinct failures of this subject line and what each one costs the sender.

A2. An email opens: "Hi Jordan, I hope you're having a wonderful week! It's been so lovely seeing the spring weather finally arrive. I wanted to reach out about something that's been on my mind…" The actual purpose appears in sentence five. What's the principle being violated, and what should the first sentence have done?

A3. A teammate replies-all to a 60-person project thread with: "Thanks, looks good!" Is reply-all the right choice here? Explain the cost, and state the question they should have asked before clicking.

A4. Read this close to a request email: "So anyway, if you happen to get a chance at some point and it's not too much trouble, it would be really great to maybe hear your thoughts. No rush at all though!" Identify three things that make this ask easy to ignore.

A5. An email delivering bad news ends with its only mention of the new timeline: "…so realistically it might slip a bit, possibly into next week sometime, but we're doing everything we can." What does the reader actually need here that they're not getting, and where in the email should it have appeared?

A6. A "no" email reads, in full: (no reply was ever sent). The asker waited eight days, nudged twice, and eventually gave up. Why is silence the worst of the available options for declining? Name what a thirty-second reply would have prevented.

A7. ⭐⭐ Here is a subject line and opening from a real-pattern email. Decide whether the channel choice (email) is right, and whether the structure serves a scanning reader:

Subject: Re: Re: Re: thoughts? "Hey, just following up on the thing from earlier — did you see my last message? Let me know." (Consider: would the recipient know what "the thing" is, or what's being asked? What does the subject line tell them?)

A8. ⭐⭐ This email is complete—it contains every relevant fact—but it fails. Explain why "complete" and "effective" are different here, using the chapter's threshold concept.

Subject: project status "Hi team, wanted to give everyone a full rundown of where the migration stands. We've completed the schema design, the staging environment is provisioned, QA has done a first pass, there are three open bugs (one minor, two we think are edge cases), the rollback plan is drafted but not yet tested, marketing has been told the launch is 'around mid-month,' legal still needs to review the new ToS, and we're waiting on a final cost estimate from the cloud vendor. Also the offsite is next week. Let me know if anyone has questions!"

Part B — Revise This ⭐⭐

Rewrite the email. Give the improved version, subject line included.

B1. Fix the subject line. Rewrite each of these throw-away subjects to state the topic and the action/urgency. Invent plausible specifics. - Following up - Update - Meeting - Quick one - Important!!!

B2. Purpose first. Rewrite this opening so the purpose leads, while keeping it warm (not cold).

"Hi Marcus, hope you're doing well and that the new quarter is off to a good start! I've been meaning to email you for a while about the reporting dashboard. There's been a lot going on and I keep meaning to bring it up. So I guess what I'm getting at is that I think there might be an issue with how the revenue numbers are being calculated and I was hoping we could look into it."

B3. The buried request. Rewrite this whole email so the ask is first, specific, and deadlined, and friction is removed. The sender needs the design files to start development.

Subject: hello! "Hi Sana, I hope your week is going great! I know the design team has been swamped with the rebrand so I really appreciate everything you've all been doing. I'm getting ready to start building the new settings page and I realized I don't think I have the latest design files — or at least I'm not sure if what I have is current, because I know there were some changes after the last review. Anyway, if there's any chance you could point me to the most recent versions whenever you get a moment, that would be super helpful and I'd really appreciate it. Thanks a million!"

B4. The over-apologetic no. Rewrite this into a clean "no" with the four moves (acknowledge → clear no → brief reason → door open). Cut the guilt.

"Oh wow, thank you SO much for asking me to speak at the team lunch-and-learn, I'm genuinely so flattered you'd think of me!! I really really want to say yes because I think it's such a great idea and I love that we're doing these. But I feel awful because I'm just buried right now with the release and I have a few deadlines stacking up, and honestly I'd be so stressed trying to prepare something good that I don't think I could do it justice, and the last thing I'd want is to give a bad talk and waste everyone's time, so I think — though I really wish I could — I probably have to say no this time, but PLEASE ask me again, I promise I'll do it next time, I'm so so sorry!!"

B5. The defensive bad-news email. Rewrite this so the news comes early, the context is owned in one sentence (not a paragraph of excuses), and the plan with a date leads. The sender is telling a client the report will be late.

Subject: report update "Hi Dr. Lin, I wanted to update you on the analysis report. This has honestly been a much bigger lift than we expected. The data we received from your team had some inconsistencies in the formatting that we had to clean up first, which took a few days, and then we discovered that two of the source files were actually duplicates, so we had to go back and reconcile everything. On top of that, one of our analysts was out sick this week. We've been working hard but it's been one thing after another. I'm not totally sure when it'll be ready but it probably won't be by Friday like we'd discussed, maybe early next week, we'll keep you posted."

B6. ⭐⭐ Reply-all repair. A colleague sent the following to the entire 80-person engineering list. Rewrite it so it goes to the right recipients with the right scope, and note who should actually receive it.

To: engineering-all@ Subject: Re: Friday's deploy "Hey, can someone remind me what time we're doing the deploy on Friday? Also Dana do you have the runbook handy? Thanks!"

B7. ⭐⭐⭐ Channel choice. Below is a 9-message email thread, summarized. Decide what should have happened, and write (a) the one email that should have ended the thread, and (b) the follow-up email that records the outcome.

Three engineers spent a morning emailing back and forth about whether to adopt a new testing framework. Message 1 proposes it. Message 2 raises a concern about migration cost. Message 3 answers but raises a new concern about CI integration. Message 4 adds a fourth person. Messages 5–7 go in circles on tooling specifics, two of them crossing in transit. Message 8 says "I think we're overcomplicating this." Message 9 says "per my earlier email…". No decision has been reached.

B8. ⭐⭐ Tone calibration. This reply is technically fine but reads cold and could damage the relationship. Rewrite it to be clear and warm, without becoming gushy.

"Received. The numbers in section 3 are wrong. Fix them and resend."

Part C — Write This ⭐⭐–⭐⭐⭐

Produce the email from scratch. Apply the chapter's structures deliberately.

C1. ⭐⭐ The request email. You need a colleague in another department to review a two-page document by Wednesday so you can submit it Thursday. They are busy and you don't report to each other. Write the full email (subject + body, under 130 words) using the five-part request anatomy: ask first and specific, brief why, real deadline with a reason, friction removed, easy out.

C2. ⭐⭐ The subject-line set. You're about to send five emails today: (1) asking your manager to approve a Friday deploy; (2) telling a client a delivery will slip to next Tuesday; (3) an FYI that a migration finished successfully; (4) declining a meeting invitation that conflicts with a deadline; (5) asking three teammates to confirm attendance at an offsite by Friday. Write only the five subject lines—each specific, action-signaling, and deadline-bearing where relevant.

C3. ⭐⭐⭐ The bad-news email (full scenario). You lead a small team. A feature you promised a stakeholder for this Friday will not be ready until the following Thursday because of a problem your team should have caught earlier. Write the full email to the stakeholder using the four-move bad-news structure (news early and framed → owned context in one sentence → the plan with a concrete date and a checkpoint → what you need / offer to talk). The stakeholder has a customer expecting it Friday. (This is the centerpiece writing task — give it real care; it's the kind of email that defines a reputation.)

C4. ⭐⭐⭐ The "no" email. A respected senior colleague asks you to join a committee that meets weekly for the next quarter. You genuinely can't take it on. Write the full "no" email using the four moves, and make sure you leave a real door open (an alternative person, a future timeline, or a smaller contribution you can make). Under 120 words.

C5. ⭐⭐ The channel-switch email. You and a coworker have traded five emails about a customer issue and aren't converging; the tone is fraying slightly. Write the short email that switches channels gracefully (proposes a call, sets a time, and commits to recording the outcome) without making anyone feel blamed for the thread.

Part D — Synthesis and Critical Thinking ⭐⭐⭐

Integrate across chapters; argue, don't just answer.

D1. Translate-for-audience. Take one finding—"the checkout page is failing for any cart over $1,000, blocking roughly 8% of high-value orders"—and write the first sentence and the ask only of an email about it, three times: (a) to the on-call engineer who must fix it, (b) to the engineering manager who must reprioritize, (c) to the head of sales who must decide what to tell affected customers. Then explain in two sentences how audience (Chapter 2) determined the first sentence and the ask each time.

D2. The "so what?" test, at email scale. Chapter 3 taught the sentence-level "so what?" test. State the email-level version, then apply it: take a real (or invented) four-paragraph request email and cut it to its load-bearing core. Show the before length and the after, and name what you cut and why.

D3. Find the flaw. A colleague argues: "Putting the ask first is rude and transactional. Building rapport first—asking how someone's doing, acknowledging their work—is what makes people want to help you. Diving straight into what you want treats people like vending machines." Write a two-paragraph response. Where is the colleague partly right, and where is the argument wrong? (Use the idea that warmth can ride alongside purpose rather than in front of it, and the cost of a buried ask to a scanning reader.)

D4. ⭐⭐⭐ The channel-decision framework, defended. For each message, name the right channel (email / chat / call / meeting) and defend it using the three properties (speed, permanence, emotional load): (a) telling a teammate their code broke production overnight; (b) confirming a 2pm meeting is still on; (c) getting five stakeholders to agree on a launch date; (d) documenting a decision the team already reached verbally; (e) giving an employee difficult performance feedback. One is a trap—identify which and why.

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

These mix this chapter with earlier ones. Decide which principle is actually being tested before you act.

M1. A request email is both bloated (Chapter 3) and badly structured (Chapter 4): the ask is buried under nominalizations and windup. Diagnose both problems separately, then rewrite. Which do you fix first—the structure (move the ask up) or the bloat (cut the words)—and why?

Subject: regarding the matter we discussed "Pursuant to our earlier conversation regarding the implementation of the new onboarding process, and following the completion of an initial assessment of the various considerations involved, it has become apparent that the obtaining of input from your team would be of significant value to the undertaking, and as such, the scheduling of a meeting at a mutually convenient time would be appreciated."

M2. You're told to "make this email shorter." On inspection, the sentences are already tight—but the email is twice as long as it needs to be because it answers a question the reader didn't ask and includes three paragraphs of context they don't need to act. Explain how a structural/audience problem (not a wordiness problem) makes an email too long, and name the fix. (Ties Chapter 2 + Chapter 4.)

M3. An email has a perfect purpose-first opening and a clear ask—but it's aimed at the wrong reader: it asks the project manager to make a technical decision only the lead engineer can make. Which chapter's principle is the real failure here—Chapter 2 (audience) or this chapter (email mechanics)? Defend your answer. (Careful—this is a trap; think about how they interact.)

M4. Choose the right approach for each, and name the structure: (a) a one-line request to confirm a meeting time; (b) telling your manager a deadline will slip; (c) declining a vendor's sales pitch; (d) an email that must serve as the permanent record of a decision three people reached on a call. For each, state: which channel? which of the chapter's email structures (request / bad-news / no / FYI-record)? what goes in the first sentence?

M5. ⭐⭐⭐ Recall Dana Whitfield's churn analysis (Chapter 2). She must email two people about the same finding: the Ops analyst who needs to pull more data, and Renée Okafor (the VP) who must decide on the discount budget. Sketch the structural difference between the two emails: what's the first sentence of each, and what's the ask of each? Connect this explicitly to Chapter 4's inverted pyramid (which fact tops each email) and Chapter 2's audience analysis (why they differ).

Part E — Extension ⭐⭐⭐⭐ (optional; Deep Dive track)

E1. Build your personal email templates. Design three reusable skeletons you'll actually use—a request template, a bad-news template, and a "no" template—each as a fill-in-the-blanks structure (subject-line pattern + the ordered moves). Justify each move by the reader's need. This is a genuinely useful artifact; keep it.

E2. Audit a real thread. Find a real email thread you were part of (sanitize names). Reverse-engineer where it went well or badly: Was the ask clear? Did the subject line survive triage? Did it stay in the right channel, or should someone have called? Did tone problems creep in? Write a one-page diagnosis and the two changes that would most have improved it.

E3. The "reply-all" culture proposal. Imagine your team has a reply-all problem and a vague-subject-line problem. Write the short, friendly email you'd send proposing two lightweight team norms (a subject-line tag convention and a reply-all guideline). Note: this email must itself model everything it preaches—purpose first, scannable, one clear ask. That's the real challenge.

Self-Assessment Rubric (for open-ended items C, D, E)

Rate each dimension 1 (weak) – 4 (strong):

Total ≥ 24/28: ready to send. 17–23: revise the lowest two dimensions. < 17: re-read §19.2–§19.4 (anatomy, subject line, request) and redo with the ask written first.

Back to: Chapter 19 · Quiz · Key Takeaways