· Letter
The Question Before the Pitch
Why the best salespeople surface objections on purpose, before they even start selling.
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What would be the reasons we're not going to move forward?
That's the question one of our Outgrow Certified Advisors opened with on a pre-proposal call last month.
Not "let me walk you through what we do." Not "here's how we've helped companies like yours." Not even "what are your goals this quarter?"
Just that one line. Before the pitch. Before the deck. Before anything.
And the room went quiet for about five seconds. Then the prospect said something no one expected.
"Honestly? We've been burned before. We hired a consulting firm last year that promised transformation and disappeared after 90 days. So my biggest concern is that this is going to be another one of those."
Four minutes into the call, the real blocker was on the table. Not budget. Not timing. Not "we need to talk to our board." The actual thing that would have quietly killed the deal three weeks later came out in the first conversation.
Here's why this works.
Most salespeople treat objections like obstacles. Something to overcome. Something to handle. They prepare scripts for "too expensive" and "we're happy with our current provider" and "send me some information." They rehearse comebacks.
But the best salespeople don't handle objections. They invite them.
When you ask someone why they wouldn't move forward before you've even started selling, two things happen.
First, the prospect feels safe. You're not pushing. You're not pitching. You're asking them to be honest, and you're doing it before they have any reason to put their guard up. That changes the entire energy of the conversation.
Second, you get to build your entire proposal around the thing that actually matters. Instead of guessing what matters, instead of leading with features and hoping something sticks, you know exactly what to address. Your pitch becomes a direct answer to their deepest concern.
The advisor on that call didn't panic when the prospect said "we've been burned before." He didn't rush to differentiate. He just said, "Tell me more about what happened." And for the next ten minutes, the prospect told him everything. The bad experience. The broken trust. The specific things that would need to be different this time.
By the time the advisor started talking about Outgrow, he wasn't selling anymore. He was responding to a specific problem with a specific solution. The prospect had already told him exactly what to say.
This is what proactive selling actually looks like. It's not about being pushy. It's not about volume. It's about asking better questions earlier than anyone else is willing to.
Most people wait for objections to surface on their own. They hope they won't come up. And when they do, usually in week three of the sales cycle when the deal is about to close, everyone scrambles.
The question before the pitch eliminates that scramble. It pulls the future into the present. It lets you deal with reality instead of assumptions.
Try it on your next call. Before you open your deck, before you share your screen, before you do anything, ask: "What would be the reasons we wouldn't move forward?"
Then be quiet. Let them answer. And build everything that follows around what they tell you.
Hit reply and tell me the objection you keep hearing too late. I'll tell you the question that surfaces it in the first five minutes.
Originally published on Substack (opens in a new tab). Subscribe (opens in a new tab) for the next letter.