What Sales/Customer-facing Professionals Can Learn from Being Mortal
Janelle had a client renewal coming up that she knew, privately, was not a great fit for the upgraded package she had been assigned to sell. The client had mentioned twice that their team was overwhelmed and mostly using a fraction of what they already paid for. Instead of asking directly what the client actually needed, Janelle kept the conversation focused on the upgrade's features, hoping enthusiasm would carry the sale the way it usually did. The client signed, mostly out of trust in the relationship, then churned entirely four months later, citing a tool they had paid for and never used as the reason they no longer trusted the vendor's judgment. Janelle realized, going back over her notes, that the client had told her exactly what they needed, and she had simply never asked the one honest question that would have surfaced it.
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
Ask what the client actually needs before the renewal forces the truth out
It is tempting to let a pitch or a renewal conversation stay focused on features and enthusiasm, especially when a client seems ready to say yes. Asking directly what problem they are actually trying to solve, and whether what you are offering solves it, takes more nerve but avoids a much harder conversation later, after they have already paid for something that does not fit.
A rep closes a deal a client was not sure they needed, and the mismatch surfaces months later as a churn conversation instead of an honest one upfront.
In your next client conversation, ask directly what success would actually look like for them before recommending anything.
Chasing the bigger deal can cost you the client's trust
Pushing for the larger package or the faster close can come at the cost of the client's trust in your judgment, especially if it becomes clear later that the fit was not right. Naming the tradeoff honestly with the client, this bigger option costs more and may be more than you need right now, tends to build more durable trust than optimizing for the biggest number today.
A rep upsells a client into a package that does not match their actual use, and the client's next conversation with the company is a cancellation.
Before recommending the larger option, ask yourself honestly whether it is the best fit for the client or the best number for your quota.
Sell to the whole account, not just the open opportunity
A client account is more than the open deal in front of you. It includes their team's workload, their internal politics, and their longer-term goals, all of which shape whether a purchase will actually stick. Focusing only on closing the immediate opportunity while ignoring the account's whole situation tends to produce short-term wins and long-term churn.
A rep hits their number for the quarter by closing deals that do not account for a client's real capacity to use what they bought.
Ask an existing client what has changed in their broader goals lately, not just about the specific product conversation at hand.
Shape the deal together, and keep checking in
The strongest client relationships are built through ongoing, honest conversation about what the client actually needs, revisited at each renewal or check-in rather than assumed once and left unexamined. A rep who treats each interaction as a chance to re-confirm fit, rather than defend a past decision, earns a kind of trust that outlasts any single deal.
Being honest that a smaller package fits a client better can conflict with hitting your own sales targets. Resolve this by playing the longer game deliberately: a right-fit recommendation that keeps a client for years is worth more than a larger deal that churns within a year, and naming that math to yourself, and sometimes to your manager, makes the honest choice easier to justify.
Name one thing, honestly
What has a client told you they actually need that you have been quietly working around instead of directly addressing?
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
Ask an existing client what has changed in their broader goals lately, not just about the specific product conversation at hand.