Hey Niepodam,

A Head of Sales once told me: “Our reps freeze when buyers push back. It’s like their brain reboots.”

I get it. Objections feel personal.
But the best sellers? They invite them.
And here’s my cheat code:

When I prep for key calls, I drop the deal context into GPT and ask it to play the most skeptical buyer possible.

It turns me into a counterpunching machine.

How it works

I feed GPT a full call summary or note set:

• 30-rep team, just hired new VP Sales
• Pain: low meeting-to-opportunity rate
• Interested in improving rep ramp and conversion

Then I prompt: “Act like a skeptical VP Sales. List the top 5 objections you'd raise about buying this product.”

What comes back? Gold.

• This sounds like something we could build internally
• I don’t know if reps would actually use this
• We just bought a tool for this last year

Now I’m armed before the first punch is thrown.

Then I prep responses like this

Objection: “We already bought a tool for this.”

Response: “Totally fair. Most teams we speak with aren’t lacking tools, they’re lacking adoption and consistent execution. Mind if I ask how you’re measuring impact from the tool you bought?”

Objection: “Feels like something we could build ourselves.”

Response: “Honestly, I’d agree if this was just about dashboards or data. But the real value’s in the behavior change — getting reps to actually adopt the system and adjust in real-time. That’s where most internal builds flatline.”

The mindset shift

You’re not blocking objections.
You’re preloading for them.

And when you respond with calm confidence,
you flip the dynamic from defensive to consultative.

Buyers don’t want to win the argument.
They want to trust that you’ve thought about the risk more than they have.

GPT helps you simulate that. Fast, smart, and on your terms.

Want to make it even tighter?

Try role-playing live with GPT during call prep:

“Act as a CFO who’s skeptical about this spend.”
“Act as a founder who’s just cut budget.”
“Act as a Head of Sales who’s seen five tools like this fail.”

Then answer. Out loud. In your pitch voice.
It’s like sparring before the real match.

Takeaway
Objections aren’t something to avoid.
They’re your chance to show control, confidence, and preparation.

Feed the fear to GPT.
And walk in ready for anything.

Here are 2 ways I might be able to help:

→ 1:1 Coaching: If you’re doing “everything right” but still not booking or closing like you should be, I’ll help you pinpoint the problem and fix it fast. Book your free strategy call

→ Team Workshops: No fluff. No lectures. Just tactical coaching that makes your team sharper, faster, and better at moving real revenue. Book your free strategy call

PS: Every training I run includes real AI tools, workflows, and use cases—so you’re not just learning sales, you’re learning how to sell smarter with AI.

Alan "Modern Seller" Ruchtein.

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