What Sales and Customer-Facing Professionals Can Learn from On Writing
Angela stared at the proposal she'd just finished for a prospective client, six pages built almost entirely from a template: "Our best-in-class solution empowers organizations to unlock transformative outcomes." She'd sent versions of this exact paragraph to a dozen prospects this year. Reading it now, she couldn't picture the actual person who'd receive it or say what problem it solved for their specific situation. She deleted the boilerplate opening and wrote two sentences about the exact issue the client had mentioned on their call, in their own words. It felt riskier, more exposed, than hiding behind polished corporate language. It also felt, for the first time in months, like she was actually talking to someone instead of at everyone.
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 proposals and emails down to honest, plain language
A salesperson sends a proposal built from a reused template full of phrases like "best-in-class" and "transformative outcomes" that could apply to any client. The prospect reads generic confidence instead of evidence that their specific problem was heard, and the proposal blends into every other one in their inbox.
Before sending any proposal or follow-up, replace the generic opening with one sentence that names the prospect's specific problem in their own words from your conversation. Cut every phrase in the rest of the document that would still make sense if you swapped in a different client's name.
Protect a consistent block of time for writing that isn't a template
A salesperson only writes original, tailored messages when there's unusual downtime, which is rare, so nearly every proposal and follow-up defaults to the template because there's never a moment set aside to write something better.
Block 20 minutes before or after your daily calls, every day, reserved only for writing one genuinely tailored piece — a proposal opening, a follow-up, a note to a stalled prospect. Protect that time the same way you protect a scheduled call, even when the pipeline feels calm.
Read proposals and pitches you receive as ongoing craft education
A salesperson receives cold emails and proposals constantly as a buyer of other services but deletes them without a second thought, missing an easy, low-cost source of insight into what actually earns a reply versus what gets ignored.
The next five sales emails or proposals you receive, before deleting them, note the one line that made you want to keep reading or the one that made you stop. Apply whatever you find to the next proposal you send.
Your experience with hard customer conversations is material, but craft decides if it lands
The tough objections you've navigated, the deal that fell apart and what you learned from it, are legitimate material for case studies and conversations with prospects. But that material only builds trust when it's told with specific, honest detail rather than smoothed into a generic success story that could describe any vendor's win.
Protected writing time and tailored language both take longer than reusing a template, and reading other people's pitches for craft takes time that feels better spent prospecting. Don't let volume pressure push every message back toward the template. Reserve your protected block for the messages that matter most — the stalled deal, the high-value prospect — and let the template handle only the lowest-stakes routine replies.
Name one thing, honestly
Which proposal or email you sent this week could have gone to any client with the name changed, and what would it take to make it unmistakably about this one?
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
The next five sales emails or proposals you receive, before deleting them, note the one line that made you want to keep reading or the one that made you stop. Apply whatever you find to the next proposal you send.