Jokers Can Kill Deals

Jokers Can Kill Deals

My high-school class voted me “wittiest” in the senior superlatives. That’s a label that I’ve tried to live up to my whole life, to my detriment.

It meant that I joked around when I should have been serious. I went for the laugh instead of the trust. Big mistake.

I’ve blown key executive relationships because I was cutting up instead of customer focused. They just quit returning my phone calls.

It’s not just a matter of being politically incorrect, insensitive, or telling -ism jokes. Where was I putting the spotlight — on me, or on them?

Don’t get me wrong, humor is important and shows cognitive ability. It’s best used judiciously.

Here’s the real issue:

When you sell complex, high-consideration products, you’re selling up the executive chain of command by two to three levels, sometimes more.

An executive will never engage with someone who they believe will embarrass them or be risky. It’s not worth their career. Cutting up made me risky.

Does your sales team have the skills, insights, vocabulary, and image to be invited to converse at those levels?

If not, you’re losing sales to a more well regarded competitor, regardless of your product quality.

Do your team have the demeanor of a real sales professional, one who can sell high in an organization?


Let’s have a conversation about your experiences and what you want to change about how your team goes to market. If there’s a fit, I’ll design an approach that matches your culture and develops the right methods for a sustainable, scalable, and profitable operation. Using our joint insights, your experiences, and market research, I’ll adapt the sales model to select strategies and tactics that your sales team can intuitively use to do the right things at the right time to speed the deal and disrupt your market.

Find a mutually agreeable time at or contact me.

Get more great ideas like this from my weekly podcast, the Selling Disruption Show.

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