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❓ You’re Asking the Wrong Questions

  • April 20, 2026
  • 1 reply
  • 4 views

Jonathanmf17

“You’re asking the wrong questions.”

Here’s something that looks like good communication…
but quietly limits your impact:

“How’s everything going?”
“Any issues on your side?”
“Do you need anything from us?”

Now—those sound fine.

But most of the time?

They don’t create insight.

They create surface-level answers.

And that leads to 3 problems:

👉 you get vague responses
👉 you miss real risks
👉 and you stay reactive

Because weak questions…

Drive weak conversations.

Strong CSMs don’t just ask more.

They ask better.

They shift to:

👉 “What’s changed since last time?”
👉 “Where are things slowing down?”
👉 “What’s blocking your team right now?”

That’s the difference.

From checking in… to uncovering value.

If your questions are too general…
your insights will be too.

💬 Your turn: What’s one question you ask today… that you know isn’t actually helping you get real insight?

🔚 Monday Reset

“Better questions create better outcomes.”

1 reply

Jonathanmf17
  • Author
  • Known Participant
  • April 20, 2026

I’ll go first 👇

One question I used to ask all the time:

“How’s everything going?”

It felt natural…
but it almost always led to:

“Everything’s fine.”

No insight.
No signal.
No direction.

Now I replace it with:

👉 “What’s changed since we last spoke?”

And suddenly the conversation opens up.

Because better questions don’t just get answers…

They reveal what actually matters.

What’s a question you could upgrade this week?