Hey Reader,

A good question is a given for reps.

But many still hesitate when the question might feel too direct.

So they water it down.

Or skip it.

Or hope the prospect brings it up first.

I see this every week when coaching teams:

The best question is on the tip of their tongue… but fear kicks in.

Here’s the simple fix: ask permission first.

“Would it be okay if I asked you something a bit direct?”

“Would it be out of line if I asked why this hasn’t been tackled yet?”

This does two things:

1. It lowers the other person’s guard.
2. It gives you confidence to ask what matters.

One AE I coached used this line on a CFO last week:

“Would it be a bad idea if I asked how this is affecting your team right now?”

The CFO paused. Then shared three blockers no one knew about.

Same question. Better timing. Zero pushback.

A reminder:

Good discovery is about trust first, questions second.

When you make people feel safe, they tell you the truth.

So next time you feel a question is too blunt.

Don't drop it.

Wrap it in with permission. See how the tone shifts.

Last week I sent you a training video on this.

If you missed it:

​Watch it here​

Stay curious,

Charles Muhlbauer​
​Find me on LinkedIn​