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š The lost art of "asking for the sale"
People are terrified of asking direct questions when it comes to closing time. Here's why this is awful for performance and why we need a resurgence now!
IN THIS EDITION
The second month of 2026 is upon us.
If youāre feeling quota creep, we got you.
The lost art of "asking for the sale"
What to do after a record commission hits
Steve Jobsā idea of a āsuper salespersonā
And moreā¦
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BOS PODCAST
This week on the Because of Sales Podcast:
Excalidraw beats boring decks, buyersā love for dynamic visuals, 10/10 urgency, the hardest part of sales, asking for the sale, GTM engineers are cool but banging phones still pay the bills, execution > fancy tools.
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SELLERāS SECRETS
The lost art of "asking for the sale" and why we need a resurgence now
Asking for the sale used to be the entire point.
And a recent post on X reminded us just how far weāve strayed away from best practices over the years.
Lately, it's treated like something you're supposed to avoid. Like if you just nurture the relationship long enough, add enough value, stay top of mind, the buyer will eventually close themselves.
They won't.
Somewhere along the way, we lost the ability to just ask directly. People are scared of it now. Scared they'll sound pushy. Scared they'll blow the deal. Scared the buyer will think less of them for actually trying to close something.
So instead, they dance around it. Send follow-ups that sound like apologies. Wait for the buyer to bring it up first. Drop hints and hope the prospect figures it out on their own.
You know what that looks like: "Just circling back to see if you had a chance to review the proposal." Or "No pressure, but wanted to check in."
Or worse, complete radio silence while you're waiting for them to tell you they're ready.
That's not selling. That's waiting.
Good sellers just ask. Not in a pushy way. Not desperately. Just clearly.
"Does this make sense for you?"
"Are we doing this?"
"What needs to happen for us to move forward?"
These aren't gotcha questions. They're fair when someone's been sitting in your pipeline for weeks or months.
The fear is that being direct kills deals. But the reality is the opposite. Buyers respect clarity. They're juggling ten other things. If you're not creating a decision point, the deal just sits there. And time kills all deals.
We know you know what weāre talking aboutā¦
The seller who's too afraid to ask ends up with a CRM full of "warm leads" that go nowhere.
The seller who asks straight up gets a yes or a no, and both are way better than maybe.
You can still be human about it. You can still actually care about solving their problem. But at some point, you've got to stop performing and start closing.
If asking for business feels uncomfortable, you're probably just not doing it enough. It's like anything else. Feels weird at first, then it just becomes part of how you talk.
Stop apologizing for wanting to close deals.
That's the job.
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