A host says he has learned not to try humor until the other party makes a humorous comment, because that opens the door. He permits self-deprecating lines earlier, but warns that misreading the room with a joke can backfire. When the prospect jokes first, the salesperson can safely join in.

Attempting humor in a professional context is like sales; you fail more than you succeed. Embracing and sharing these imperfect attempts creates an authentic connection. It shows others that it is normal to fail on the path to success, which helps combat widespread imposter syndrome.

When a prospect gives a nasty or absurd objection (e.g., "I'm in a meeting"), don't be defensive. Counter with a ridiculously hilarious response that breaks the tension, calls out the absurdity, and reveals the human behind the phone.

When a prospect gives a knee-jerk objection like "not interested," respond with self-deprecating humor ("Wow, is my voice that bad?"). This shatters the typical salesperson-prospect dynamic and forces a more authentic, human-to-human interaction.

In response to Corina in Newport Beach, who fears saying the wrong thing, the hosts say excessive formality can make people feel disconnected. They recommend starting small and trying humor with existing clients who will forgive a misstep. Her fear, they add, suggests she is focused too much on her own performance.

The hosts contrast an elaborate joke with a quick line about a price being 'never more than a million dollars.' They say good humor comes from the immediate situation, while planned or canned material does not work. The price line is offered as a spontaneous example that lowers pressure.

The hosts say humor plays differently depending on the country. One says he avoids jokes with German clients but can use humor with South American clients, so salespeople must know the environment before trying a line. They tie this directly to adjusting style rather than assuming a joke travels.

Successfully telling a joke, especially one that pushes boundaries slightly, is the ultimate demonstration of comfort and control in a social setting. However, it's a high-risk maneuver; a joke that falls flat can be disastrous. Use humor sparingly and with a strong read of the room.

Striving for perfection on a cold call can make you sound robotic. Occasionally stumbling over a word and acknowledging it with humor can break the script, lower the prospect's guard, and result in a better reaction than a flawless delivery.