How this course works
Six sessions, 45 minutes each, and one message you rebuild in every one of them. Not six example messages. One, six times, until it works.
★ What you walk out with tonight. A named reader, a written ask that starts with a verb, a one-sentence version of your message, and an honest count of how much of somebody's attention you are about to spend.
LiveThe message, and why it keeps failing2 min▶
You are the data lead at Daybreak, the coffee-subscription company. The subscription redesign - the one from learn-product-design-with-phoebe - is three weeks late. The founder needs to know, and needs to choose between shipping a smaller version on time or shipping the whole thing later.
You have sent three updates about it. None of them got a reply. Then in Thursday's steering meeting the founder said "why is this the first I am hearing about the delay", in front of eight people.
The updates were accurate. They were not short, but they were not unreasonable. Every one of them was read. Here is what none of them had: a sentence telling the founder what to do.
Self-studyThe artifact: one message, in six rebuilds2 min▶
| Session | What the message gains |
|---|---|
| 1 · tonight | A named reader and an ask that starts with a verb |
| 2 | What the reader actually needs, found by asking rather than assuming |
| 3 | A skeleton, with the ask at the top of it |
| 4 | The written version, measured: 5 out of 100 becomes 100 |
| 5 | The spoken version, and what has to be cut to survive a room |
| 6 | The version where it is bad news and somebody pushes back |
If you only do three, do 1, 4 and 6. Session 1 is whether there is an ask, session 4 is whether it can be found, session 6 is whether you can say it when it is uncomfortable.
An update with no ask is a file, not a message
6 min liveGo and look at the last five updates you sent. Count how many contain a sentence that names something the reader should do. The honest answer for most people is one, and it is usually the one that got answered.
LiveFour tests for whether you have an ask4 min▶
- Does it start with a verb? Approve, decide between, confirm, send me, choose. "Thoughts" is not a verb, and neither is "visibility".
- Could they do it wrong? A real ask can be done incorrectly. If there is no way to fail at it, it is not an instruction, it is a feeling.
- Is it theirs to do? The most common failure after "no ask" is an ask pointed at someone who cannot authorise it. Two minutes on an org chart saves a fortnight.
- Is there a date? An ask with no date is a request to be deprioritised, and it will be, correctly, by a reasonable person with other work.
If the honest answer is that you do not want anything - it is genuinely information they asked to receive - then say that in the first line: "No action needed, this is the monthly number." That is also an ask. It asks them to stop reading, which is a gift.
"Following on from the last steering committee, I wanted to circle back and provide a holistic update on the state of play regarding the subscription workstream and the various dependencies identified across the wider ecosystem..."
163 words. Accurate. Nine corporate abstractions. The thing you want is in the last sentence, phrased as "it would be appreciated if you could let us know in due course". Read, understood, filed. Nobody did anything, because nobody was asked to do anything by a date.
"I need a decision from you by Thursday: ship on 18 September with pause only, or hold until 9 October and include skip and frequency."
24 words. Starts with a verb. Two options, both real, both costed. A date. It can be got wrong, which means it can be got right. The rest of the message exists to support that sentence, and it comes after it.
Who is reading, and what does it cost them
6 min liveYou are not writing to an audience. You are writing to one person, on a specific day, who has other things happening. Everything about the message follows from taking that seriously.
LiveThe one-sentence test4 min▶
If they read one sentence and nothing else, what is it? Write that sentence. Then check three things about it:
- Is it the ask, or is it context? If the sentence you wrote describes the situation rather than the decision, you have written a headline for a report, not a message.
- Would it survive being forwarded with no other text? Messages get forwarded constantly, stripped of everything around them. A sentence that only makes sense in place is a sentence that will be misread by somebody two hops away.
- Does it contain a number or a date? Not always necessary. Usually the difference between a sentence somebody can act on and one they have to reply to in order to act on.
Report headline: "Update on the subscription redesign timeline." Nothing to do.
Message: "I need a decision by Thursday: ship 18 September with pause only, or hold to 9 October for the full scope." Survives forwarding, contains two dates, can be answered in four words.
The seeded paragraph is Daybreak's real opening. It is 46 words, it takes about 14 seconds to read aloud, and it contains no information at all - every clause is a description of the fact that an update is happening. Session 4 will count its abstractions by name. Tonight, just notice what it spends.
Find the ask, or admit there is not one
★ 22 min · everyone buildsFive short blocks, and you write them about your own message, not Daybreak's. Daybreak is here so you have a worked example to check yourself against.
Reader. One person, named. What they know, what they fear, what they can authorise, and when they will read it. Four lines, one each.
Ask. One sentence starting with a verb. Test it: could they do it wrong? If not, it is not an ask yet.
Options. If it is a decision, give exactly two or three, each real and each costed. One option is an announcement. Five is homework.
Date. When you need it, and what happens if it does not come. "By Thursday, otherwise we default to shipping the smaller version" is a complete ask, and the second half is the part people leave out.
One sentence. The version that survives being forwarded alone. Write it last, because now you can.
Take out a real message you sent that got no reply. Not a hypothetical one. The friction of using a real message is the entire value of the exercise.
Find the ask in it. Highlight the sentence that names something the reader should do. If there is no such sentence, write "no ask" at the top - that is the most useful finding available tonight and it applies to more messages than people expect.
Write the reader's four lines. Knows, fears, can authorise, reads-when. Where you do not know, write your guess and mark it as a guess - session 2 is about going and finding out.
Write the ask as one sentence starting with a verb. Then apply the could-they-do-it-wrong test. "Let me know your thoughts" fails it. "Confirm the 18th or the 9th by Thursday" passes.
Add the default. What happens if they do not reply? Writing that down converts a request into a decision that gets made either way, and it is often the sentence that finally produces the reply.
Do the reader-cost arithmetic. Use the counter above on your own message. Words, and read-aloud seconds. Then ask whether the ask is worth that spend - sometimes the honest answer is that this should have been two lines, and sometimes it is that it should have been a meeting.
Write the one-sentence version. Read it to somebody with no context. If they can tell you what you want, you are done for tonight.
Notice the trap. Adding background is the most reasonable request in professional life and it is the only line here that makes the number worse. Session 4 shows what it does to the score: a finished message drops from 100 to 64, not because the background is wrong, but because it goes in front of the ask.
Before session 2
20 min- Audit five sent messages. How many contain a sentence naming something the reader should do, by a date? Write the fraction down. It is usually one in five and it is usually the one that got answered.
- Rewrite one ask so it starts with a verb. Send it. This is the only homework in the course that produces a result the same week.
- Add a default to one open request. "If I do not hear back by Friday I will proceed with X." Watch how often that produces the reply that three polite follow-ups did not.
- Find your "let me know your thoughts". Everybody has one. Look at what you actually wanted and write that instead.
- Write down one thing you are guessing about your reader. Session 2 is about going and asking, and having the guess written down first is what makes the answer useful.
Three questions
Clear all three and session 1 gets stamped in your passport.
1 · Your update was read by everyone and answered by nobody. What is the most likely cause?
Length and distribution are real problems and they are downstream of this one. A message with a clear ask survives being long and survives a wide distribution list. A message with no ask cannot be answered, because there is no question in it - only information, which people file.
2 · Which of these is a real ask?
Apply the tests: starts with a verb, could be done wrong, is theirs to do, has a date. A and B fail all four - they ask a busy person to invent the question, answer it, and own both. C can be answered in four words, which is why it will be.
3 · Why write down what happens if nobody replies?
A default removes the option of doing nothing quietly. It also does something for the reader: it tells them the cost of not answering, which lets them make a real choice rather than deferring one. The record is a side effect, not the reason.
What this session teaches, and where it came from
Daybreak, the founder and the message are a teaching scenario, stated as such in the course's source map. The measurement code in session 4 is real.
Session 1 cheat sheet · pin this
Tonight's reader block is built out of what you assume. Session 2 goes and checks: the two questions to ask before drafting anything, what a non-reply is actually telling you, and the uncomfortable possibility that your beautifully structured update has been answering a question the founder stopped caring about a month ago.