From what people tell me, “Comedy Writing for Sales Teams” is the first of it’s kind, and I’m pretty proud of that. Not being able to be uber-unique is part what I disliked about being a sales rep.

That said it hasn’t been easy launching something new. They say the first one through the wall always gets bloody. Roadblocks of all kinds have popped up. Some of those roadblocks have even ghosted me (not cool, roadblocks!).

Thankfully, I’ve been fortunate enough to have some smart people in my corner rooting for me. They’re successful sales trainers and consultants and leaders at companies. They’ve seen my videos, read my blogs, and get the value of what I’m up to. They’ve given me brilliant advice and tried to help as best they could. I’ve taken and implemented much of it.

Some suggested to me when marketing myself or speaking to prospects, that sales leaders don’t like hearing the words “comedy” or “jokes”  associated with “sales training”.

They advised I replace both words with ‘humor’”.

This sound advice comes from a good place – “numor” is a much safer word.

And that’s why I’m not taking it.

I can see how those who feel comfortable discussing “cadences”, “scaling”, and “ramp-time” with peers, in-laws, and themselves could be loath to adopt the idea of using “comedy” or “jokes” as a way to help their reps to stand-out when prospecting or making impactful points. I can also see how these people will not take what I do seriously, because they’re serious about being serious – and stressing their entire team out.


Unless you sell oxygen, prospects’ attention needs to be captured and it’s an ongoing challenge. Playing it safe will rarely work and is harder work to begin with. Unless you’re Warren Buffett (please note: he’s not in sales).

Telling people that I bring best practices and skills from stand-up comedy to sales teams is what’s gotten ME attention, and has helped separate me from everyone else in the absurd sales bubble in which anyone reading this inhabits (wink).

On the other hand, the word “humor” itself is one of the most boring, clinical, drab, lame words in the world.  There’s nothing funny – or thought provoking – about it.

No one says “I want to be regaled with delightful humor”.

Seinfeld & Chappelle don’t perform at “humor clubs”. If those existed, they’d be home to stuffy men with various facial hair configurations, wearing three-piece suits, smoking curved pipes and guffawing at each other’s haiku-ed wit – while the audience rolls their eyes wondering if anyone’s posted videos on Instagram of turtles rescuing dogs. When done well, the best reaction that humor elicits are wry grins.

Well-crafted jokes highlight truths, absurdities – or both – and trigger an emotional reaction called “laughter” – a gateway drug that leads to conversations. Making prospects laugh about something a unique, day-to-day professional struggle is also memorable, thought-provoking, and conversation-starting.

More proof:

When I was selling Oracle software and services, people would ask me what I do. I’d tell them. Eyes glazed over because no one goes to “Database Festivals”.

Since I began writing and performing – and even when I totally stunk – stand-up comedy’s been my secret life weapon. And it’s not because I’m super-hysterical and have the power of hilarity on my side – but because the idea that I get up on stage BY MYSELF to entertain paying customers seems to fascinate people and leads to a LOT of questions that come without even seeing me perform.

“You do stand-up?? Really? Tell me more! Where do you perform? When? How often? What’s it like? Do you get scared? Isn’t it hard??? Where do you get the courage? Where do you get your material? How do you deal with hecklers? Am I asking too many questions? I’m SO ending up in your act, aren’t I???”.

If I hadn’t been in sales, I could never have dealt with the trauma that bombing inflicts on a newbie comic’s soul. Both teach resilience, iteration, and persistence. Sales prepared me for stand-up, and now aspects of stand-up have made me a better salesperson and communicator.

Buzzwords and the pressures of salespeople hitting BS metrics to please managers who are trying to please leadership who are trying to please investors who are trying to please themselves – have done a number on a sales pro’s ability to be authentic. We live in an age where everyone’s working hard to to show their authenticity. Some succeed, some fail.

Making a prospect – aka a fellow human being – laugh is part of that, and my authenticity. Life’s too short for me to not laugh and make other’s laugh.

Irony’s funny, but I don’t want to be ironic by masking the core inspiration for what I do out of fear of turning off people likely to never be attracted to what I do in the first place.

You can’t please all the people all the time – but you can lean on old-timey cliches to make your point.

My new my monthly live class, “The Writers’ Room” helps handfuls of colleagues find new ways for their entire team stand-out and be memorable.

If your team needs memorable openers for cold outreach & demos, b) a process to create some, or c) some new team members need a process that will  get them explaining what problems you solve for who in really simple English, team up with a small group colleagues and get my full training & workshop (classes start first Wednesday of every month).

Have questions? Let’s talk it out.