Of all the misconceptions – this one’s mah fave. I hear 2 common variants of the above title from sales leaders:

“Our prospects deal with serious issues. Making them laugh is TOTALLY inappropriate.”

There’s no shortage of subjects that a sales rep should avoid joking about, particularly when dealing with industries that deal with victims of unfortunate circumstances like healthcare (pharma, medical equipment, insurance, etc.), emergency services, law enforcement, and more.

In my experience when I tell the professionals in the aforementioned industries that I’m a stand-up comic, they begin cracking jokes I would NEVER make onstage or off. Frankly, I’m terrified to know what they say amongst themselves at company happy hours.

Turns out they use humor as a coping mechanism to deal with the daily darkness they’re subjected to. They’re fully aware of how serious the issues are and are sensitive to it, but if they succumb to the sadness they won’t be able to perform their duties. These are emotionally resilient people. The challenges they deal with are an accepted to part of their job and their success requires them to be numb to it.

Sales leaders targeting companies addressing serious problems underestimate, ignore or forget that their prospects have emotions, and can use a distraction from such seriousness.

There’s no shortage of topics/premises which these prospects in these industries that can be mined for humor without seeming insensitive. Your objective should be to find them.

A key topic I cover in my workshops, is “The line”. We discuss what is it and how to not cross it – don’t tell joke that belittle anyone’s ethnicity, culture, religion, sexual identity, political views, and don’t “punch down” on marginalized groups in society (the disabled, the poor, etc.).

Good comedy doesn’t lean on the easy and obvious – it surprises by taking us places we never thought of, and does it in a way that is harmless yet impactful.

“Our prospects won’t take our company seriously if my reps try to be funny”.

Apparently artificial intelligence has taken a greater hold than imagined, because there are a select group of sales leaders whose prospects are robots.

Or these sales execs are cyborgs who traded their souls for a sweet comp plan, fancy job title, and a cool tech stack.

Hey sales leader who feels this way: your last name must be “BENQ”, “Sony”, or “3M”,  because you’re projecting.

Yes, Sales Leader, your job is stressful. Someone employs you and has tasked you with growing their top line by managing a disparate group of personalities and technologies. You definitely need to mitigate risk wherever possible, and you run things based on your own experiences as sales rep.

I suggest shelve your fears of how your prospects will perceive your reps. Never overlook that humans make decisions partly based on their interactions with other humans, and the fun ones are the memorable ones.

Emotional triggers need to be part of those interactions, and you can’t win ‘em over with seriousness, fear, uncertainty, doubt, and cold, impersonal email blasts. In fact, some prospects repel reps’ seriousness and buy from people they jive with.

If your reps have the right, repeatable, insightful, tasteful bit of humor that they can make their own, they’ll trigger your prospects into the right kind of conversation, and appreciate that they’re different from other reps trying to reach them.

Let’s summarize, Sales Leader: Your prospects are people with (hopefully) unsuppressed emotions. Given the hundreds of vendors trying to reach them, your reps need to stand out. they’re also stressed. They also have objectives they’re trying to achieve, and – shocker – may not care about their job as much as you do yours. Your reps’ job is to help them get through it all.

When two humans are interacting with one another, there’s always room for tasteful humor that makes a key point.  When used properly, humor mitigates way more risks than it creates. It sets the buyer at ease, makes the rep a pleasure to deal with, galvanizes conversations, makes the experience feel less like a buying process, and more like two people trying to see if they can work together and help each other out.

First time here? Season 1 of my Saturday morning cartoon is now streaming. Binge it in just 60 seconds to learn why and how the comedy writing process can help your reps start more and have better conversations. Get in touch if you’d like to learn more!