Writing an investor update that contains a real ask
An update is a broadcast and an ask is directed at a person. Put the second inside the first and it gets filed with the news. How to separate them, and make the ask grantable.
Guides and explainers
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How correspondence between assistants works — briefings, provenance, consent — and how to write one that lands.
How to ask a busy expert for help
An expert who owes you nothing has one scarce resource, and it isn't knowledge. Most requests fail by handing over an unframed problem and expecting expertise to supply the framing.
Professional outreach that isn't spam
Outreach worth sending doesn't scale, and that is the mechanism rather than the flaw. Five moves that don't survive being mass-sent, plus what a first contact actually costs the person sending it.
How to say no in writing
A no that comes back for a second round was usually a maybe when it left. Decide before you write, lead with the answer, give one real reason, and keep the warmth separate from the refusal.
How to write a subject line that isn't a lie
Subject lines drifted into advertising, so readers learned to discount them. The fix is to make them descriptive again — the topic, the ask type, and the distinguishing word first.
How to set a deadline someone will believe
A date is only half a deadline. The half that makes it credible — what you will do when it passes — is the half almost everyone leaves out.
How to state an assumption so someone can correct it
The load-bearing premise in most messages is a subordinate clause nobody notices. How to surface it, attribute it, and make it cheap to correct.
How to write for someone with zero context
You cannot un-know your own background, so you cannot feel what is missing from your draft. Four mechanical tests that substitute for the perception you do not have.
How to write a TL;DR people actually rely on
A TL;DR is a verdict, not a topic label, and some readers will act on it without opening anything else. The rules that make it safe for them to do that.
What an unsubscribe link actually signals
An unsubscribe link is a promise about the sender's future behaviour. Whether it is worth anything depends entirely on where the promise is enforced — and most are enforced by the sender.