Hey Niepodam,

Let’s kill the myth right now: Asking “curious questions” doesn’t make you sound smart.

It usually makes you sound like every other seller fishing for a reply.

I reviewed 87 outbound sequences last month. Same pattern kept popping up:

• Vague probes
• Fake curiosity
• Questions that sound insightful 

But go nowhere

If you're doing this in 2026, you're not starting conversations. You're ending them.

Here’s what to stop — and what to send instead:

#1: “What’s keeping you up at night?”

This isn’t empathy.
It’s laziness.

You're asking a stranger to do your job for you.

✅ Replace with: “You just launched [X], guessing [Y problem] is now creeping up?”

Make a bet.
Use a real trigger.
Now they don’t have to “think”, they just react.

#2: “Is [problem] a priority for you?”: Translation: “Please tell me if this is worth my time.”

It screams commission breath.

✅ Replace with: “Are you actively solving [X], or punting to H1?”

It’s casual. It respects their agenda.
And it sets you up for either answer.

#3: “Open to a quick chat?”: Still asking this in your first email?

You’ve already lost.

✅ Replace with:  “Happy to share what [competitor] changed to cut churn 19%, want the quick version?”

Now you’re trading value. Not begging for time.

Here’s the real problem: Most reps ask questions like they’re writing a blog post.

But buyers don’t want philosophical prompts. They want relevance. Speed. An actual POV.

2026 Rule: Don’t ask a question unless it hits one of these:

• It shows you did research.
• It makes a specific assumption.
• It’s dead easy to answer.

Otherwise, it’s noise.

Full Template Example:

"Hey [FirstName], saw you're hiring 4 AEs and rebuilding GTM under your new CRO.

Guessing ramp speed is on your radar, especially if you’re pushing to hit full productivity before Q2.

We just helped [Company] cut the new hire ramp from 94 days to 48 without changing headcount or process.

Want the quick version?"

Take this into your next sequence:

Stop writing cold questions for thought leadership.
Start writing cold questions for real people, in real jobs, with real pressure.

That’s how you book meetings in 2026.

Alan "Modern Seller" Ruchtein.

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