What Sales and Customer-Facing Professionals Can Learn from Designing Your Life
A cold stretch of numbers can feel like proof that you're simply having a bad run, or worse, that you're not cut out for the work — rather than a specific, investigable pattern in what's actually happening in your conversations. Designing Your Life's habits translate well here: get curious about what's actually not landing with customers, test a new approach small before overhauling your whole pitch, and keep some contact with what matters to you beyond the number on the board. None of this promises better results, but it gives you a steadier way to work the problem than grinding harder on autopilot.
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
Get curious about what's actually not landing
Instead of writing off a slump as just a tough market, look closely at what's actually happening in the conversations themselves.
A sales rep hits a rough quarter and assumes it's simply a slow season, so he keeps running the same pitch harder and more often. He never notices that a specific new objection about a competitor's pricing has started coming up in nearly every call in the last six weeks — something a closer look at his own call notes would have surfaced immediately.
After each of your next ten customer conversations, jot down the exact moment interest dropped or an objection appeared, then look for a pattern across all ten before assuming you already know what's wrong.
Test a new approach on a few calls before changing everything
Before overhauling your pitch, sequence, or outreach strategy across your whole territory, try the change on a small, contained set first.
After one promising webinar, a sales manager rewrites the entire team's outbound script and rolls it out to every rep the same week. Response rates drop across the board, and it takes weeks to untangle whether the new script or something else caused it, time that testing with two reps first would have saved.
Before rolling out a new pitch or approach broadly, try it on a small batch of calls or accounts first, and compare the results against your usual approach before deciding to switch fully.
Get clear on what matters to you beyond the number
Hitting quota matters, but it's rarely the only thing that makes the work worth doing, and it helps to know what else is actually on your list.
A rep pushes hard for a promotion into management mainly because it's viewed as the obvious next step up, and a year in realizes the part of the job he actually loved — direct client conversations and solving a customer's specific problem — is exactly what the new role removed from his days.
Name one or two things beyond quota that make a work day feel good to you — a kind of client, a kind of problem you enjoy solving, direct contact versus oversight — and weigh your next role or account decision against that list too.
Imagine a few different shapes your client-facing career could take
Rather than assuming the only path forward is either staying exactly where you are or moving into management, it's worth picturing a few different directions — specializing in a particular kind of account, moving into a role that blends sales with product or support, or staying client-facing but in a different market — and noticing which one actually appeals to you before treating the usual next rung as the only option.
Testing a new approach takes a few calls' worth of results that might dip before they improve, while quota pressure wants proven methods right now. Hold both by running small tests on a portion of your pipeline while keeping your reliable approach running on the rest, so you're never betting the whole quarter on an untested idea.
Name one thing, honestly
What's one thing about your current pitch or process you've assumed is fixed that you've never actually tested against a real alternative?
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
Name one or two things beyond quota that make a work day feel good to you — a kind of client, a kind of problem you enjoy solving, direct contact versus oversight — and weigh your next role or account decision against that list too.