What Coaches and Mentors Can Learn from On Writing
After a session with a client who was clearly avoiding a hard truth about her business, Reuben sat down to write his follow-up notes. His draft read: "Explored various dynamics around growth mindset and potential blockers to forward momentum." He stopped and read it back, and realized he was doing to his notes exactly what his client did in the session — dressing up an avoidance with language that sounded thoughtful but said nothing. He deleted it and wrote what actually happened: "She changed the subject three times when I asked about her pricing. Next session: name that pattern directly." It felt less polished. It also gave him, and eventually her, something real to work with.
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 session notes and feedback down to honest, plain language
A coach writing follow-up notes reaches for professional-sounding but vague phrases — "explored dynamics," "potential blockers" — that describe the session without naming what actually happened. The client reads generic encouragement instead of a specific, actionable observation, and the pattern that needed addressing goes unaddressed again.
Write your session notes as if a specific event, not a theme, has to be named: what exactly did the client say or do that mattered. Cut any phrase that could describe five different clients equally well, and replace it with the detail that could only describe this one.
Protect a consistent block of time for writing between sessions
A coach writes notes and program materials in five-minute gaps between back-to-back sessions, so early clients get thoughtful, specific follow-ups while later ones get a rushed line dashed off before the next call, without the coach ever noticing the pattern.
Block 15 minutes immediately after each session, before the next one starts, reserved only for writing that session's notes while it's fresh. If your schedule doesn't allow that, protect a single longer block at day's end instead, but protect it the same way every day so quality doesn't depend on how the day went.
Read client writing and other coaches' materials as ongoing education
A coach reads client journals and check-ins purely to track progress, never noticing which of their own past prompts or feedback produced real reflection and which produced surface-level answers, so the same weak prompts get reused without anyone questioning them.
Once a month, review five of your own past prompts or pieces of written feedback against how clients actually responded. Keep the ones that produced specific, honest reflection, and rewrite or drop the ones that only produced polite agreement.
Your own path is material, but craft decides if it lands
The setbacks and false starts on your own way to becoming a coach or mentor are legitimate material to share with clients, especially when they're stuck in a similar place. But that material only serves the client when it's told briefly, specifically, and in service of their situation, not as an extended story that shifts the session's attention from them to you.
Protected writing time and specific, honest notes both take more effort than a quick generic summary between calls, and studying client writing for patterns takes time that feels better spent on the next session. Don't let a full calendar push you toward vaguer notes. A short, specific note written in five protected minutes serves the client more than a longer, softer one written in a rush.
Name one thing, honestly
Whose notes from your last week of sessions would embarrass you if the client read them, because they say nothing specific?
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
Once a month, review five of your own past prompts or pieces of written feedback against how clients actually responded. Keep the ones that produced specific, honest reflection, and rewrite or drop the ones that only produced polite agreement.