Sales is a Serious Business.  Without sales, your business doesn't exist.

But what if it didn't actually have to be so... serious?

Even though sales is a serious job, you work for a serious company, and you sell a serious product... sometimes not being serious all the time becomes a way to stand out.

Quick aside: I don't want to try to tell you how to be funny (here's a fantastic resource for that), but when I looked around to see what other people had already contributed to this topic I found a lot of advice that seemed to aimed at people who missed out on basic human decency lessons somewhere along the way.

So, if we can just start this with the assumption I don't have to tell you not to use racist or bigoted jokes, how can we instead use humour effectively as part of the sales process?

Using humour in cold outreach

I get emails every day from people listing the 3,000 unique features and benefits of their SEO service, offshore Android development, or AI product. I bet you get them - or something like them - too.

Here are a couple of recent offenders:

Offender #1

Hey Millie,

I'm Darren, the Partnership Lead at [name redacted, I'm not that mean!]. We curate, craft, and deliver 50 verticalized and topical newsletters to over 500,000 opt-in subscribers covering all things business, tech, finance and more!

... very long list of features...

Do you have time for a quick chat this week or next?

I look forward to speaking.

Offender #2

Hi Millie,

We specialize in working with software and technology companies in a recruiting capacity.

Simply put, [NAME REDACTED] is a white-glove fractional talent acquisition solution for recruiting top marketing and sales talent.

Please let me know if you would be open to having a conversation.


Sorry Darren and Tyler.


A "white-glove fractional talent acquisition solution"?  

On the other hand, here's a LinkedIn message I got recently that actually got my attention:

Hey hey Millie,

Nice to ‘meet’ you. I have a weird skill that means I can book meetings with just about anybody.

If you’re at all curious, click ‘accept’. :)

If not, send me your most cutting insult. :(

Fingers crossed,


Why does this work?  A couple of reasons:

  • It's unexpected. We're all so used to the generic cold outreach email "templates" that people use, something different immediately stands out.
  • It shows personality. I already kind of like Heather just from this outreach. It might not work on all prospects, in all businesses, but it worked on me.
  • It's self deprecating. Making fun of yourself (instead of those marginalised groups we've been warned off) is almost always a safe space to play with humour.

Another great way to work some humour into your cold outreach is to make it personalised to the recipient and then work that into the pitch.  Ten minutes researching your prospect on Facebook, Twitter or LinkedIn should give you all that you need, and then work the details into the email.

Here's a Showcase example:

Hey Stefanie,

Based on your Twitter feed, I can see you're a fan of Beyonce — and who isn't?

What would Bey be without her team?  Well, probably still fabulous... she's Beyonce... But her team does do a lot to make her life easier.

Showcase Workshop is the Beyonce of sales tools!  It provides real-time insights into your sales team's most engaged prospects, offers detailed reporting to managers, and streamlines the distribution of sales and marketing materials to your entire team.

Plus, it works on any device, making your reps more efficient and effective in any sales situation — giving them everything they need to go on tour (much like Beyonce).

Would you have a few minutes to connect to talk about how Showcase can get your team to Queen B's level?

Let me know and I'll set up a free demo.


Of course, this only works if you've done your proper research. But if you can make a connection and a funny metaphor in one go? You've definitely got your foot in the door.

Using humour in sales meetings

I've come to accept that I'm often just a bit awkward. Lucky for me, I sell a software product and for the most part I think people brush it off as part of the territory.

But I've also found that keeping the mood light to begin with and inserting some humour helps cut tension and puts people at ease — probably by making them feel like the least awkward person in the room. And I'm fine with that.

Being able to take yourself lightly and joke around also makes you appear more relaxed and confident — because uptight nervous people mostly don't make jokes.

In this episode of the Modern Selling Podcast, the guest, Jon Selig, suggests treating objections the same way a stand up comedian might anticipate hecklers. A stand up comedian is always prepared — they're never just winging it. So as salespeople, we pretty much always know what kind of objections are going to be raised in our sales meetings before the client ever opens their mouth, so they present a really good opportunity for us to be prepared with some witty answers that cut any aggression about the objection, make us look authoritative and put us back in control of the conversation.

In fact, a great sales presentation can predict objections and address them in advance. Humour is an excellent way to do so in a non-confrontational manner.

Try brainstorming with your sales team to both identify objections and some lighthearted responses. (Some adult beverages might facilitate the process.)

Do you have other ideas for using humour effectively in sales? I’d love to hear your thoughts.