Billions of commission dollars die from unqualified deals, never reaching their true home – a salesperson's bank account.
Simply because no one asked the hard-hitting questions upfront.
But it doesn’t have to be that way.
You can avoid wasting time on dead-end deals by spotting them early.
Here are 3 questions that will help you do exactly that.
Help me understand - if this is a top priority, why hasn't it been fixed already?
Asking this exposes the “priority paradox”.
If something is truly critical, why has it been ignored so far? What’s changed now?
This question reveals whether there’s a true catalyst.
It also uncovers past attempts and failures.
If they’ve tried solving this before, dig into why it failed. Then assess whether you are positioned to succeed where others couldn’t.
Pro Tip
The strongest catalysts are time-bound with someone accountable for the outcome.
Why do this now instead of waiting 6 months or a year?
This reverse-psychology question challenges the prospect to defend this project.
You're testing how severe the consequences of inaction really are.
Why?
Because inertia is real – in physics and in business.
Projects at rest stay at rest unless acted on by a compelling force.
The larger the consequences the bigger the force.
So you’d rather have the physics of business working for you than against you.
What are the reasons this may not go live by {Target Date}?
Every deal has hidden landmines.
But most reps ask for a timeline and never challenge it.
This question flips the script and forces prospects to think through the barriers.
By asking upfront, you uncover hidden obstacles before they derail momentum.
Budget approvals. Competing priorities. Lack of exec buy-in. Legal reviews.
Get everything on the table. Address each risk head-on.
And if they can’t articulate any potential roadblocks…
The timeline is still untested.
