“Are you ready to move forward?”
I hate that question.
If you’ve done your job correctly, you shouldn’t have to dramatically ask for the sale. The customer should already be moving toward it.
One of the most underrated ways to get them there?
Make them laugh.
Not constantly. Not with rehearsed jokes. And definitely don’t walk into a sales meeting thinking you’re suddenly a stand-up comedian.
The secret is using just the right amount of humor at exactly the right time.
More importantly: READ THE ROOM.
People know when they’re being sold. The second they feel the pitch coming, the walls start going up. They analyze your words differently. They question your motives. They start waiting for the close.
Humor can completely change that dynamic.
Get someone genuinely laughing with you and, for a moment, the salesperson/customer relationship disappears. You’re simply two people having a conversation.
That’s powerful.
Because people tend to do business with people they like, trust, and feel comfortable around.
But humor can also kill a sale.
If someone is discussing a serious business problem, losing money, dealing with a deadline, or explaining something important to them, shut up and listen.
That’s reading the room.
The best salespeople I’ve known have an instinct for when they can push, when they should listen, when they should challenge—and when they can make someone laugh.
And here’s where it gets interesting.
Humor can be incredibly effective when you’re approaching the end of a sales conversation.
Everyone knows why you’re there. You know it. They know it.
So why suddenly turn into a stereotypical salesperson?
Don’t change personalities just because it’s time to close.
Keep talking. Keep listening. Keep the conversation comfortable. Then naturally transition into what happens next:
“When do you want this delivered?”
“Who should we work with on implementation?”
“Let’s get the paperwork started.”
Notice what’s missing?
You never asked them to buy.
You created enough trust, confidence, and comfort that moving forward became the natural next step.
That’s selling.
Humor didn’t close the deal.
You did.
Humor just helped the customer forget they were being sold.
So use it.
Just remember the most important rule:
Read. The. Room.
