top of page

5 Principles for Sales Messaging & Costume Contests

Every year some very good friends of ours host a Halloween party where costumes are mandatory and they give out cash prizes for the best costumes. Naturally, with my competitive nature, I play to win. After all, if you are going to do something, you should do it well, right? Go big or go home, as they say.

Well, after this year’s party, it occurred to me that, believe it or not, sales best practices are very similar to coming up with the perfect contest-winning costume:


The first rule is you must know your audience. We have a very good idea about what the party attendees like, what wows them, and what may get “Ooohs and Ahhs.” We know what they’ve seen before and what the competition is likely to be. That informs what costumes we choose. 

From a sales perspective, you need to know your customer. This is so fundamental to succeeding in a meeting, but Salesforce reports that a whopping 82% of salespeople are out-of-sync with the buyer. You need to know who you’re meeting with - what’s their background? What positions have they held? What companies have they worked with? What are their likely biases? 


Our costumes are always fun, but we specifically choose certain costumes because of the audience’s biases or what we think might resonate with the crowd. It’s not just enough to know your audience, but then you must tailor your approach accordingly. If you’re showing up to an all-adult Halloween party vs. a party with all kids, your costume will be very different.

In sales meetings, we have to tailor our conversation, our sales messaging, to our audience. We have to ensure our discussion relates to their objectives and priorities. You should have a very different dialog if you’re meeting with a CMO versus a CIO. But it’s not only about tailoring your messaging that’s important – it’s the approach as well. Senior level audiences like business dialogs, where a whiteboarding approach may be more appropriate than PowerPoint slides that can often come across as a “sales pitch.” 


My favorite response to our costumes is "How did you even think of that?" or "I couldn't believe that was your wife under there!” We could show up as zombies, which are very popular these days, but that wouldn’t challenge anyone or make them ask “How did they achieve that look?” Our goal every year is to catch the crowd off guard – go with something no one will expect. As we were thinking through last year’s Forrest Gump costume, it would’ve been easy to choose the obvious Forrest and Jenny couple costume. In fact, my wife would’ve preferred that because she initially didn’t want to dress up as a guy! But that wouldn’t have caught anyone off guard. So we came up with the idea of disguising my wife as Lieutenant Dan – my wife as a guy, with a beard, and no legs. That got some attention. 

The same thing goes for sales messaging. It’s our goal to get our customers to think differently or provoke them. And that can be a challenge these days because buyers are much more educated before we meet with them. They’ve done their homework. But if we are going to be compelling in our meetings, we must tell our audience something they don't know. We can do that by challenging them to think differently about their current state or about their planned approach to solving a problem


There are high expectations now. We've been going to this costume party for 5 years, and it's getting tough to set ourselves apart. Others are seeing what we do, and they’re trying to come with great costumes, so we have to continually challenge ourselves to think outside the box to set ourselves apart. 

Similarly in sales messaging, we need to make sure we don't sound like everyone else. If you go into a situation with fierce competition ‘dressed up’ like everyone else, you’re not going to fair well. Not only does our value proposition need to be uniquely differentiated, but even our selling approach. So what are we doing to drive a compelling and differentiated sales experience with our customers? 


Finally, at the end of the party we need to leave the audience wanting more. I love hearing "Man, I can't wait to see what you guys are going to think of next year."

In sales, you don’t show up and throw up in a meeting – saying everything you know. You show up and have a business level conversation, establishing credibility, so that you’ve earned the right to have the next conversation. A bleak Forrester study reported that only 7% of surveyed executives say they would probably schedule a follow-up meeting. How many initial meetings result in a lost opportunity because your sales team wasn’t compelling? In sales, we should strive for our meetings to be so insightful that the customer would've been willing to pay for that meeting. We want to leave them thinking "This dialog has been so valuable; I can't wait to meet with these guys again."


Sales Plays

Creating Focus Through Sales Plays

bottom of page