What Leaders and Managers Can Learn from On Writing
Marcus reread the performance review he'd drafted for a struggling report and winced. Three paragraphs in, he still hadn't said the actual problem: missed deadlines were hurting the team. Instead he'd written about "opportunities for growth" and "areas of alignment," phrases that let him avoid the uncomfortable part while feeling like he'd done his job. He imagined his report reading this and understanding nothing actionable. So he deleted it and started again: "You've missed three deadlines this quarter. Here's what needs to change, and here's how I'll support it." It felt blunter than he was used to writing. It also felt, for the first time, like something the person could actually act on.
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
Strip your emails and feedback down to honest, plain language
A manager avoiding a hard conversation writes a review full of qualifiers — "somewhat inconsistent," "could potentially improve" — that let both writer and reader off the hook. The employee leaves the meeting unsure whether there's actually a problem, and the issue resurfaces next quarter unchanged.
Before sending any piece of difficult feedback, find the one sentence that states the actual issue and the one sentence that states the actual ask. Put those first, then cut every hedge word — "somewhat," "kind of," "maybe" — from what surrounds them.
Protect a consistent block of time for writing that matters
A leader only writes team updates or strategy memos in the gaps between meetings, so the writing is rushed, inconsistent in tone, and often skipped in a busy week, leaving the team to guess at priorities from whatever fragments reach them.
Block a fixed, recurring 30-minute slot — before your first meeting, say — for the writing that shapes how your team understands direction: the weekly update, the project memo, the note that sets expectations. Treat that block as non-negotiable as a client meeting.
Read your team's and peers' writing as management education
Leaders read other managers' emails and documents only for content, never noticing why one manager's updates get read carefully while another's get skimmed, so they never learn what actually earns attention on a busy team.
Pick three emails or documents from leaders you find genuinely clear and three you find frustrating to read. Identify the specific sentence-level habits — length, structure, directness — that separate them, then check your own next memo against that list.
Your own hard experiences as a manager are material, but craft decides if they land
The mistakes you've made leading people — the layoff handled badly, the feedback given too late — are legitimate material for mentoring others and for your own writing about leadership. But sharing that experience helps a reader only when it's told with the same clarity and discipline you'd bring to a status report, not as an unstructured confession that leaves the lesson buried.
Protected writing time can feel like a luxury when an urgent email needs an instant reply, and plain, direct language can feel risky when a hard conversation tempts you toward softening it. Reading other people's management writing critically takes time too, time that competes with both of those habits on any given week. Resist trading one for the other by treating them as unequal in urgency, not importance. Use your protected block for the writing that sets direction and expectations, let urgency shorten a reactive message rather than making it vaguer, and save critical reading for a slower moment when you can actually absorb what you notice.
Name one thing, honestly
Which recent piece of feedback or direction you gave would your team have understood faster if you'd cut it by half?
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
Pick three emails or documents from leaders you find genuinely clear and three you find frustrating to read. Identify the specific sentence-level habits — length, structure, directness — that separate them, then check your own next memo against that list.