Hey Reader quick one,

Here’s something you’ll hear on almost every sales floor:

“When do you plan to decide?”

“What’s your timeline for rolling this out?”

These questions sound smart.

They feel logical.

But they rarely get you a real answer.

Why?

Because people don’t buy on your timeline.

But only when staying the same costs them more than changing.

That’s why timeline questions so often land flat.

So when you ask, they say:

“Not sure, we’re just exploring for now.”

End of conversation. No urgency. No next step.

When I coach AEs, we replace “timeline talk” with something better: framing risk.

Here’s how this works.

Instead of asking:

“When are you planning to move forward with this?”

Try showing what happens if they don’t:

“A lot of teams push security until the last sprint, then pay double fixing rushed code after launch. Curious, how are you planning to handle that overlap?”

Or:

“We’ve seen companies stall at this stage because they rely on manual checks. What’s the risk for you if this slows down your rollout?”

This works because it flips the spotlight:

You’re not begging for a date.

You’re helping them see what waiting actually costs.

One AE I worked with made this shift on a fintech deal.

He stopped asking, “When do you plan to decide?”

Instead, he asked,

“Out of curiosity, if this slips by another quarter, what does that mean for the revenue targets you just mentioned?”

The prospect paused.

Then admitted they’d be short $800k.

That’s urgent.

Not forced, but real.

Planted by making the cost of inaction clear.

Next time you’re tempted to ask,

“When will you decide?”

Stop.

Plant a risk instead.

Help them see that staying still hurts.

Then tell me how it goes.

Stay curious,
​

Charles Muhlbauer​
​Find me on LinkedIn​