What Leaders and Managers Can Learn from On Writing Well
Marcus reread the reorg announcement his HR partner had drafted for his signature. It talked about "rightsizing organizational structures to better align with evolving strategic priorities," and he knew exactly what it meant because he'd lived through the decision meetings. His team wouldn't have that context. He imagined a report on his team reading this over lunch, trying to figure out whether her job was safe, and finding only a wall of careful, evasive phrasing built to survive legal review rather than to tell her anything. He picked up a pen and crossed out the second paragraph entirely, then the third. What remained was three plain sentences: what was changing, who it affected, and when they'd know more. It felt too blunt at first, almost unprofessional next to the language he was used to signing off on. Then he remembered how many status updates he'd skimmed past for exactly the reason he was about to inflict on someone else.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
Clutter is the enemy in your team communications
A manager sends a project update full of phrases like "circle back," "bandwidth," and "socialize this with stakeholders" because that's the register the rest of leadership uses. The team spends the meeting decoding what's actually being asked of them instead of doing it. Nobody admits they're confused, because the language sounds too authoritative to question. Practice: Draft the update, then rewrite the first paragraph as if explaining it to someone outside the company who has never heard the internal shorthand. Send that version. If a term wouldn't survive being said to a stranger, either define it once or cut it.
Draft the update, then rewrite the first paragraph as if explaining it to someone outside the company who has never heard the internal shorthand. Send that version. If a term wouldn't survive being said to a stranger, either define it once or cut it.
Clarity of writing requires clarity of thought about the decision itself
A leader writes a message announcing a new process before fully deciding how exceptions will be handled, so the message is vague exactly where people need it to be specific. Questions flood in immediately, and the leader realizes the plan was less finished than the announcement implied. Practice: Before writing any policy or decision message, write down the three hardest questions a skeptical employee would ask, and answer them in plain sentences first. If you can't answer one, the decision isn't ready to announce yet.
Before writing any policy or decision message, write down the three hardest questions a skeptical employee would ask, and answer them in plain sentences first. If you can't answer one, the decision isn't ready to announce yet.
Revise ruthlessly, even in a routine status update
A manager writes a weekly update in one pass between meetings and sends it unedited, so it opens with three throat-clearing sentences before reaching the one fact people actually need. Readers skim past the real news because it's buried on the second line. Practice: Put the most important sentence first, then cut everything before it. Reread once looking only for sentences that restate something already said, and delete them before sending.
Put the most important sentence first, then cut everything before it. Reread once looking only for sentences that restate something already said, and delete them before sending.
Personality survives simplicity in leadership writing
Once the hedges and buzzwords are stripped away, a leader's writing usually sounds more like how they actually talk in a good one-on-one — direct, a bit warmer, willing to say "I'm not sure yet" instead of dressing uncertainty up as strategy. People trust plain language from someone with authority precisely because it's rarer than it should be, and it signals respect for their time rather than a retreat into hiding behind position.
Legal and executive caution often pushes toward hedged language exactly when a team needs plain speech most, so cutting clutter can feel like it's cutting protection. The workable middle is to keep necessary caveats but write them as one clear sentence instead of scattering qualifiers through every line — precision about risk doesn't require vagueness about everything else.
Name one thing, honestly
Which recent message to your team would your direct reports have understood faster if you had written it the way you'd explain it to them in person?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
Put the most important sentence first, then cut everything before it. Reread once looking only for sentences that restate something already said, and delete them before sending.