What Sales/Customer-Facing Professionals Can Learn from Show Your Work
Sales and customer-facing professionals often present only the finished pitch or the resolved outcome, hiding the research, false starts, and iteration that went into getting there. That habit can make prospects and customers see only a polished performance, missing the chance to build the kind of trust that comes from watching someone actually work through a problem on their behalf.
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
Share your process and work-in-progress regularly, not just the polished result
Letting a customer see the work behind a recommendation — the options considered, the reasoning applied — builds more trust than delivering a polished answer with no visible reasoning behind it.
A salesperson prepares a proposal entirely behind the scenes and presents only the final recommendation, with no view into why other options were ruled out. The customer, unable to see the reasoning, treats the recommendation with more skepticism than it deserves.
In your next proposal or recommendation, briefly walk the customer through one alternative you considered and explain why you didn't go with it.
Be generous with what you're learning — teach and share it, not just the finished outcome
Sharing useful, non-confidential insight from your work — a pattern you've noticed, a common pitfall — often does more to build a relationship than any pitch.
A customer-facing professional notices the same avoidable mistake tripping up several customers, keeps the observation to themselves, and only mentions it reactively after a customer has already run into the problem.
The next time you notice a pattern that could help customers avoid a common problem, turn it into a short, proactive piece of guidance and share it before anyone asks.
Share thoughtfully, adding real value rather than promoting yourself relentlessly
Outreach and updates that teach something useful build a relationship; outreach that's only ever a pitch tends to get tuned out.
A salesperson's regular check-ins with a customer consist entirely of upsell attempts with no genuinely useful content, and the customer starts screening the messages rather than reading them.
For every message that asks a customer for something, send at least one that simply offers something useful with no ask attached.
Handle criticism and stay consistent over the long haul
Being visible about your reasoning invites customers to push back on it, and the professionals who do best treat that pushback as a normal part of building a recommendation the customer will actually trust, not as a rejection of their expertise. Consistency is what turns a single good interaction into a durable relationship — a customer who sees steady, honest effort across many interactions trusts that far more than one exceptional pitch. Staying reliably present, especially through the routine and less exciting moments, is what actually retains relationships over time.
Projecting confidence can feel at odds with being open about tradeoffs or uncertainty in a recommendation. In practice, customers generally read honest acknowledgment of tradeoffs as more credible than blanket confidence — so stay confident about your process and effort, while being straightforward about genuine uncertainty in the specifics.
Name one thing, honestly
Think about your last major customer interaction — how much of your actual reasoning did the customer get to see, versus just the final recommendation?
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
For every message that asks a customer for something, send at least one that simply offers something useful with no ask attached.